Vacation Home Rentals By Owner In Anna Maria, FL

$520.74

Shell We Dance Charming Bungalow with Fabulous Location and Private Pool!

Anna Maria, Florida, United States

Like so many homes on Anna Maria Island, our home was severely flooded. Professional photos are coming, but until they are in, we thought you may enjoy a sneak peek!br We made a few needed changes in the floor plan, and believe it is at its best ever! We cannot thank those who reached out to us and wished us well, and those understanding guests whose vacations were upended by the storm and its toll on our humble home. It is with much gratitude that we thank you for your kindness, understanding, prayers, and love. Shell We Dance is back and better than EVER!! br Sweet vintage 1950's bungalow/cottage with all the charm of the island! Beautifully decorated, fully fenced back yard with private pool, (second building is the original garage where bikes and beach gear are stored). Located on the island's much sought after north end, it is a short walk to Bean Point Beach, Bay Front Beach and Park. Crystal clear waters of the gulf, white sands, and island breezes await!brbr2 bedrooms, 2 baths. Cozy living room with queen sized foldout sofa, screened in lanai, kitchen, and laundry room. With full sized washer and dryer included in the home and complimentary bikes to explore the island. Other items at the home for your use during your stay are beach towels, pool toys, beach chairs, a cart to roll all your gear to the beach, and pack-n-play for baby. Many accoutrements included! brbrRelax, unwind, and dance like no-one is watching!brbrShell We Dance

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$690.24

/ Nightly

Private Vacation Home

Waterfront house with pool - bring boat and rod - close to Gulf and Bay Beaches

Anna Maria, Florida, United States

This beautifully spacious home sits on a very large waterfront lot on the northern tip of AMI. The house is embedded in a natural landscape.brThe fully air-conditioned house has two air conditioners and parking spaces in front of the house. It was completely renovated in 2015. You have 4 bedrooms with 2 baths, large open kitchen, French doors from nearly all rooms to the pool area, TV in the living room and in the two master bedrooms, free WIFI and short walking distance to Bay and Gulf Beaches.brTerrace dining table for 8 people, pool lounge chairs and outdoor chairs, charcoal barbecue, pool- and beach equipment - everything for your personal convenience to make the most beautiful days of the year as pleasant as possible.

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$1311.24

/ Nightly

Private Vacation Home

Pine Avenue next door!~Heated pool~Steps to Beach

Anna Maria, Florida, United States

Summary:brbrAMI Oasis is a luxurious 4-bedroom retreat steps from Pine Avenue and a 5-minute walk to the beach. Enjoy a private heated pool, backyard putting green, ping pong table, and outdoor dining area. Inside features a bright open layout, gourmet kitchen, and four king suites with spa-like ensuite baths. Owner managed and perfectly located, this Anna Maria gem delivers the ultimate island getaway. ️✨brbrbrbrThe Space:brbr AMI Oasis | Next to Pine Ave • Heated Pool • Steps to Beach ️brbr 94 N Shore Dr, Anna MariabrbrbrbrWelcome to AMI Oasis, your luxurious island retreat just steps from Pine Avenue and only a 5-minute walk to the breathtaking Gulf beaches ☀️ Perfectly located in the heart of Anna Maria, you can stroll to boutique shops, charming cafés, and waterfront dining—then return to your own private backyard paradise.brbrbrbrInside, modern elegance meets coastal comfort. The bright and stylish living space offers plush seating, a large TV for cozy nights in , and an open layout that flows seamlessly into the gourmet kitchen. Home chefs will love the stainless-steel appliances, full cookware set, and oversized granite island with bar seating—perfect for gathering after a day in the sun ️✨brbrbrbrEach of the four king suites is thoughtfully designed with beautiful décor, ample storage, and French doors that invite in natural light. Every bedroom features a spa-like ensuite bath with double vanities, a soaking tub, walk-in glass shower, and private water closet—bringing true luxury to your stay brbrbrbrStep outside to your tropical outdoor oasis Enjoy the heated pool, unwind on the covered patio, fire up the grill for dinner , or spark some friendly competition on the putting green and ping pong table ⛳ The fun and relaxation never end at AMI Oasis!brbrbrbrOwner managed for a seamless, elevated vacation experience ✨brbrbrbr✨ Highlightsbrbr• ️ 5-minute walk to the beachbrbr• ️ Steps to Pine Avenue shops & restaurantsbrbr• Private heated poolbrbr• ⛳ Backyard putting greenbrbr• Ping pong tablebrbr• Outdoor dining & BBQ areabrbr• ️ 4 King Suites with ensuite bathsbrbr• Owner managedbrbrbrbr ️ Bedrooms (4 King Suites)brbr• Primary Bedroom: King bed, ensuite bath with soaking tub & walk-in showerbrbr• Second Bedroom: King bed, ensuite bath with soaking tub & walk-in showerbrbr• Third Bedroom: King bed, ensuite bath with soaking tub & walk-in showerbrbr• Fourth Bedroom: King bed, ensuite bath with soaking tub & walk-in showerbrbrbrbrAll bedrooms include double sinks, enclosed glass showers, soaking tubs, and private toilets for ultimate comfort.brbrbrbrGuest Access:brbrGuests have full access to the entire home, including a private heated pool/spa and a fully fenced backyard—perfect for relaxing, entertaining, and enjoying your own secluded space.☀️brbrbrbrOther Things to Note:brbr ️ Beach-Ready Convenience brbrTo make your stay effortless, the home is fully stocked with beach chairs, a beach cart, and a beach umbrella, plus all bath towels, beach towels, and linens—just pack your bags and enjoy island time ☀️ brbrbrbr Parking InformationbrbrParking is available for up to 4 vehicles maximum. Please plan ahead and coordinate with your group accordingly.brbrbrbr Friendly Island ReminderbrbrThis home is located in a residential neighborhood. We kindly ask guests to be respectful of our neighbors by keeping noise at a considerate level day and night. Thank you for helping preserve the peaceful island atmosphere brbrbrbrInteraction with Guests:brbrIf you need anything during your stay, I’m always here to help! You can call or text me directly on my cell anytime. I’m available 24/7 to answer questions, share local tips ️, or assist with anything that comes up. Your comfort and peace of mind are my top priority! ✨

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$228.0

/ Nightly

Private Vacation Home

La Casita Beautiful, Elegant Florida Cottage, 1 Minute Walk to the Beach!

Anna Maria, Florida, United States

Nestled in beautiful tropical landscaping, this 2 bed, 2 bath beach cottage vacation rental blends simple elegance with a prime location, just steps from the gorgeous Gulf sands of Anna Maria Island!brbrWhile the décor sets a soothing tone from the minute you step foot inside, there are surprising and colorful touches throughout the home. It’s the perfect place to relax and unwind from the demands of the day-to-day, with two sitting areas, a shady outdoor seating space, and a screened lanai. brbrBut the best part just might be around the corner, a one-minute walk away – the famous white sand beaches of Anna Maria Island! Positioned North of Pine Avenue, these beaches are the least crowded and, in our humble opinion, all the more beautiful for it. brbrBack at the house, you’ll have all the necessities for a comfortable stay, including WiFi, cable TV, beach towels, and cozy bed and bath linens. There are two bedrooms - one with a king bed and en-suite bathroom with shower, the other with two twin beds – plus a queen sleeper sofa, allowing up to six guests to decompress and reset by living the Island life.brbrYou’ll want to return to this La Casita sooner than later, just try it and see!brbrLa Casita is owned by a family of Island-lovers, excited for others to fall in love just as they have. The current photos were taken in 2022 to showcase the hard work they put in to polish and update this adorable beach cottage, inside and out. The kitchen was updated in August 2023 and now includes a dishwasher and full size smooth top electric range. brbrPlease note that pets are not allowed in this rental.brbrSpecial thanks go to the Anna Maria General Store, where you can purchase the LOLA wine used for staging in the photos, and Hometown Desserts, who provided those gorgeous cookies used in the kitchen photos. Both are located on Pine Avenue, not far from La Casita.

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Sleeps

$919.54

/ Nightly

Private Vacation Home

The Cottage on Pine - Charming Pine Ave Cottage w/ Heated Pool in Heart of AMI

Anna Maria, Florida, United States

Welcome to The Cottage on Pine!brOn Anna Maria Island (Anna Maria, FL)brbrThe SpacebrStep inside The Cottage on Pine and feel the ease of island life take hold. Gentle natural light, soft coastal hues, and thoughtfully curated details create an atmosphere that feels both uplifting and serene. Located directly on Pine Avenue, this home offers the best of both worlds — walkable access to shops and cafés, and a peaceful retreat just beyond the gate.brbrPerfect for: Couples, small families, or friends seeking peaceful simplicity, walkable charm, and restorative island living.brbrHighlightsbr- Located on charming Pine Avenue, steps to boutiques, cafés, and beachesbr- Private fenced backyard with heated pool, loungers, dining area, and outdoor showerbr- Pet-friendly with prior approval and paid pet fee (up to two pets under 65 lbs)br- Open-concept living and dining area for gathering and connectionbr- Covered front porch perfect for morning coffee or evening reflectionbr- Professionally designed interiors blending modern comfort with coastal charmbrbrInterior Spacesbr- Living Area: Bright and welcoming with comfortable seating, Roku-equipped TV, and soft natural lighting that makes every moment feel unhurried.br- Dining Area: A table set for shared meals and conversation, perfectly placed between the living room and kitchen.brbrBedrooms:br- King Bedroom: Features a king bed, TV, dresser, and French doors leading directly to the backyard and pool.br- Twin Bedroom: Two twin beds, TV, and ample storage — ideal for children or additional guests.br- Bathroom: Full bath with modern finishes, plush towels, and thoughtfully chosen amenities.brbrEach space reflects a sense of quiet care, from the crisp linens to the coastal textures and natural light that fills the home.brbrLayout OverviewbrSingle-Level Living:br- Open-concept kitchen, dining, and living areabr- One king bedroom and one twin bedroombr- Full bathbr- Front porch and private fenced backyard with poolbrbrThis layout makes the home easily accessible for all ages and perfect for those who prefer simplicity and flow.brbrOutdoor LivingbrStep into your own private sanctuary.brbrThe fenced backyard features a heated pool, loungers for sunbathing, and a shaded dining area for enjoying meals al fresco. An outdoor shower offers the perfect rinse after a beach day, while the grill invites slow, easy evenings spent under the island sky.brbrAt the front, a covered porch with comfortable seating provides another peaceful perch — the ideal spot to enjoy Pine Avenue's morning quiet or an evening breeze with your favorite drink in hand.brbrKitchen & DiningbrThe kitchen blends charm and functionality, with premium Café appliances and everything you need to prepare fresh meals or quick snacks.brbr- Stove, oven, and microwavebr- Refrigerator and freezerbr12-cup coffeemaker, Keurig, blender, and toasterbr- Fully stocked kitchenware for cooking and servingbrbrWhether you're creating a full breakfast before a beach day or reheating leftovers from one of Pine Avenue's local eateries, this space makes it easy to feel at home.brbrAdditional Amenitiesbr- Washer and dryer (off covered porch)br- A/C and heat for year-round comfortbr- Cable TV and wireless internetbr- Hair dryer, iron, and ironing boardbr- Professionally laundered linens and towelsbr- Beach gear rental credit for items like chairs, umbrellas, and bikesbrbrParkingbr- Private driveway with space for 1–2 vehicles.br- Please note: The home is located behind another property that serves as our Once Upon A Beach office. All areas designated for guest use — including the private driveway, entrance, fenced backyard, and pool — are completely separate and exclusively yours, ensuring peace and privacy.brbrWrite your vacation story at The Cottage on Pine — where calm meets connection, and every moment feels like coming home.brbrPoliciesbrbrPlease Remember: You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property. *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.brbrNO SMOKING.brbrPets are welcome with prior approval, provided they meet our pet policy guidelines. We allow a maximum of two pets, each weighing under 65 lbs. A pet fee applies based on the length of your stay: $100 for stays under 4 days, $200 for stays of 4-14 days, and $400 for stays of 15+ days, per pet.brbrBooking & Fee PolicybrInclude all guests and pets in your reservation request for accurate pricing. Additional fees apply for extra occupancy (over 2 guests per bedroom) or undeclared pets.brbrOptional Services (subject to approval)brEarly check-in/late departure, elevator access, and mid-stay cleaning for stays of 28+ days. Fees for approved add-ons are collected after booking.brbrReservations & Guest RequirementsbrMost stays are 7 nights, Saturday–Saturday, though flexible dates may be available outside peak/holiday weeks—confirm before booking, as changes are not always possible afterward. Guests must be 25+, provide valid ID, and remain for the full stay. Standard occupancy is 2 per bedroom; extra guests are $25/person/night up to the maximum allowed.brbrQuiet Hoursbr10 PM–8 AM. Maintain reasonable noise at all times to respect neighbors; excessive noise is not permitted.brbrCleaning & LinensbrHome is professionally cleaned and sanitized between stays. Starter amenities provided; daily service available for a fee. Stays of 28+ days require a mid-stay clean. Linens/towels are commercially laundered through our Professional Linen Program; no extra sets stored onsite.brbrGolf Cart RentalsbrExplore the island with ease! After booking, reserve a golf cart through our sister company, Once Upon A Beach Carts, and enjoy an exclusive discount available only to our vacation rental guests.brbrPool & SpabrPool heated year-round to 82–85°F; heating may be affected by cooler weather. Heaters/filters off during quiet hours (10 PM–8 AM). Spa, if available, is part of the pool, seasonal, not a commercial hot tub, and may be unavailable in summer. Guests may not adjust equipment; violations may result in fines or damages.brbrProperty SecuritybrExterior cameras may monitor entries, driveways, pool equipment, and backyard access for security, deliveries, and occupancy compliance. Cameras do not face private areas.brbrPayments & Cancellation PolicybrPolicies updated October 6, 2025 — see full Terms & Conditions for details.brbrPayment SchedulebrDepositbr- Reservations up to 20 days: 50% of total amount due at time of booking.brRemaining Balancebr- Reservations up to 20 days: Remaining 50% due 30 days prior to check-in.brbrCancellation PolicybrFor Reservations of 20 Days or Lessbr- More than 30 days before arrival: Full refund of deposit (including taxes) minus non-refundable booking administration fee.br- 14–29 days before arrival: Refund of 50% of total rental, fees, and taxes, minus non-refundable booking administration fee.br- Less than 14 days before arrival: Refunds only for base rental rate, fees, and taxes for nights we are able to rebook, minus non-refundable booking administration fee.br- Please note: While we make every effort to rebook, we cannot guarantee the same rate or number of nights. For any nights that cannot be re-rented, as well as for non-arrivals, late arrivals, early departures, or alterations resulting in lost revenue, no refunds or price adjustments will be made.brbrTravel InsurancebrCSA Travel Insurance is available to U.S. guests (except NY and HI residents) and is strongly encouraged to protect your trip from unforeseen events. No refunds are given for COVID-19, weather, or beach conditions outside our cancellation policy. Hurricane season runs June 1–Nov 30; insurance can safeguard your plans. In the event of a mandatory evacuation, home unavailability, or government order halting vacation rentals, guests receive a full refund of base rate, applicable fees (minus booking fee), and taxes.brbrAdditional TermsbrNo refunds for events beyond our control (weather, red tide, travel issues, etc.). Cancellation requests must be submitted in writing by the registered guest—phone/text not accepted.brbrMax Occupancy: 4 | Max cars: 2brInformation deemed reliable but not guaranteed; subject to change or withdrawal without notice.

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Sleeps

$405.79

/ Nightly

Private Vacation Home

North End Home, 5 Houses to Beach! Near Pine Ave!

Anna Maria, Florida, United States

Sea Esta by Anna Maria Vacations brHome in Anna Maria, FL brVPR22-000085brbrWelcome to Sea Esta, a beautifully refreshed beach haven in the sought-after north end of Anna Maria Island. Just steps from the sugar-white sand and sparkling Gulf waters, this multi-level three-bedroom, two-bath home offers a spacious backyard, private outdoor seating, and a dog-friendly policy. Perfect for families or friends, enjoy sunrises and sunsets from your outdoor living areas, with easy access to the island’s best attractions, shops, and restaurants.brbrHighlights br• 1 block / 2-minute walk to Anna Maria Beachbr• 3 Bedroom / 2 Bathbr• 2 Kings, 2 Full Bedsbr• Outdoor patio and dining areabr• BBQ grill br• Short stroll or bike ride to Pine Avenue’s boutiques, restaurants, and lively downtown br• Dog friendly (prior approval and additional fee) br• Washer and DryerbrbrStep out to your private outdoor oasis with cozy lounge chairs and plenty of outdoor seating, perfect for sunbathing or cocktails. Create island-inspired meals straight from the BBQ grill or enjoy family dinners on the patio. The backyard creates a peaceful retreat, ideal for relaxing after beach days or water adventures while creating lifelong memories with family and friends.brbrInside, this spacious home features a main living area with a plush oversized sofa, flat-panel TV, and a contemporary decor style. The fully equipped kitchen includes upgraded stainless steel appliances, a gas range stove, and a large farmhouse sink. The grand kitchen island provides ample space for meal prep, while the modern butcher block dining table is perfect for serving island treats or intimate dinners. French doors lead to the outdoor patio and upstairs balcony.brbrRelax in the luxurious primary suite with a king bed and a private balcony, a stunning bathroom with a dual-head walk-in shower enclosed in brickwork completing the second floor. The second bedroom offers a king bed, plenty of natural light, and a TV, while the third bedroom has two full beds, French doors to the patio, and views of the lush backyard, both located on the main floor. The hall bathroom on the first floor includes a large walk-in shower with dual shower heads and beautiful tilework, providing a spa-like experience.brbrRoom Details br• Primary Bedroom (2nd floor): King bed, separate second floor bathroombr• Second Bedroom (1st floor): King bedbr• Third Bedroom (1st floor): Two full bedsbrbrExplore the island by bike, golf cart, or the free trolley that stops just minutes away. Walk to the nearby Spruce Avenue beach entrance, where you can swim, sunbathe, or cast a line at the historic Anna Maria City Pier.brbrBook Sea Esta today and enjoy a memorable Anna Maria Island vacation! With stunning Gulf views, outdoor amenities, and prime near-beach location, this home offers everything you need for a relaxing, fun, and unforgettable getaway. Reserve your dates now and start living your island dream!brbrbr-brThis home is managed by Anna Maria Vacations, an Anna Maria Island property management company. brbrWith host approval before check-in, this property accepts dogs only. Breed and weight restrictions apply. (No cats or other animals are allowed). An additional pet fee will apply. See our Anna Maria Vacations Rental Policies for full details. brbrWe do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age. Please see our Anna Maria Vacations Rental Policies for full details. brbrPlease Remember: You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property. *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.

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Sleeps

$585.54

/ Nightly

Private Vacation Home

Private Canal Front Home! Heated Pool and 24 ft Boat Dock! - Tarpon Pointe

Anna Maria, Florida, United States

Tarpon Pointe by Anna Maria Vacations brHome in Anna Maria, FL brVR16-000430 brbrWelcome to Tarpon Pointe, a beautiful canal-front retreat featuring four bedrooms and three bathrooms on the exclusive north end of Anna Maria Island. With a private dock, pool and hot tub, and a location just ten minutes from the beach, this home offers the perfect blend of relaxation and adventure. Guests will love being only two and a half blocks from Pine Avenue’s restaurants and boutiques, where you can shop, dine, and experience the best of island life. brbrHighlights br• Canal front with private dock (accommodates boats up to 24 feet) br•4 Bedrooms, 3 Bathrooms br• 2 Kings, 1 Queen, One Full Bunk, 1 Twin/Full Bunk br• Private pool and hot tub br• 10-minute walk to the Gulf beach br• 2.5 blocks from Pine Avenue restaurants and boutiques br• BBQ grill and outdoor seating br• Beach chairs, carts, kids books and toys br• Washer and dryer br• 6 Parking spaces brbrSpend your days soaking up the sunshine in your own private tropical oasis. Relax by the heated pool and spa, lounge in the poolside chairs, or enjoy a breezy outdoor meal using the BBQ grill and outdoor dining area. The private dock provides direct access to the water, perfect for boating, kayaking, or fishing. Whether you’re taking in the canal views or unwinding after a day at the beach, Tarpon Pointe offers everything you need for the perfect Anna Maria Island escape. brbrInside, Tarpon Pointe welcomes you with a relaxed coastal style and plenty of natural light. The living room features a large sofa, vibrant beach decor, and a TV for movie nights, along with a reading and game nook for quiet moments. Spark joy for young ones with our collection of books and toys for endless family fun and entertainment. The kitchen is fully equipped with stainless steel appliances, cookware, and a spacious island with seating, making it easy for guests to gather while meals are prepared. Step through the glass doors to enjoy the deck seating and grill area, ideal for morning coffee or evening cocktails. brbrThe primary bedroom is a tranquil retreat with a king bed, private balcony, and ensuite bathroom featuring a dual vanity and walk-in shower. The second bedroom, also on the upper level, has a king bed and plenty of storage, making it ideal for another couple or as a second primary. The third bedroom is perfect for kids, offering one full bunk bed and one twin/full bunk, while the fourth bedroom includes a queen bed for additional guests. The hall bathroom features a tub/shower combination, providing convenience for families. brbrRoom Details br-Primary Bedroom, Third Floor: King bed, ensuite bath with walk-in shower, private balcony br-Second Bedroom, Third Floor: King bed br-Third Bedroom, Third Floor: One full bunk bed and one twin/full bunk bed br-Fourth Bedroom, Second Floor: Queen bed brbrThis home includes a washer and dryer, beach chairs, beach carts, and ample parking for your stay. Guests can stroll just a few blocks to Pine Avenue to enjoy local boutiques, ice cream shops, and island restaurants, or head west for a ten-minute walk to Gulf beaches. Spend your mornings fishing off the dock and your afternoons lounging by the pool. brbrFrom fishing on your private dock to relaxing in the pool and exploring nearby Pine Avenue, Tarpon Pointe by Anna Maria Vacations delivers the ultimate island getaway filled with comfort, sunshine, and coastal charm. Start your Anna Maria Island vacation today and book your stay today!

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Sleeps

$666.29

/ Nightly

Private Vacation Home

Single Level Beach Home, Private Heated Pool! 6 Minutes to the Beach

Anna Maria, Florida, United States

Sunshine Reef by Anna Maria Vacations brHome in Anna Maria, FL brVR16-000425brbrExperience the perfect family getaway at Sunshine Reef, a beautifully updated four-bedroom, four-bathroom ground-level home nestled in the prestigious north end of Anna Maria Island. Recently refreshed with new kitchen and bathroom updates, this home is showcased with current photos that accurately reflect the space, so what you see is exactly what you’ll enjoy. Just two blocks from Pine Avenue’s family-friendly shops and dining and a short stroll to the island’s powdery Gulf beaches, this island oasis blends an unbeatable location with thoughtful upgrades. Relax by your private pool, take in peaceful water views, and create lifelong memories in a setting designed for comfort and coastal living.brbrHighlights br• 6-minute walk to Holmes Beach br• 4 Bedroom / 4 Bathbr• 2 Kings, 1 queen bed, 1 twin/ full bunkbr• Private poolbr• TVs in all bedroomsbr• BBQ grill br• Dedicated workspace br• Washer and dryer br• Short walk or bike ride to shops, waterfront restaurants, parks, and attractions br• 3 Parking spacesbrbrStep outside into your tropical paradise, with a private, heated pool, sun shelf, and swim-up Tiki table, perfect for relaxing, floating, or sharing meals with island breezes. The covered outdoor space features a poolside bar, ample seating, and a large TV, making every sunset or dinner all the more special. brbrInside, the home exudes coastal flair with beautiful furnishings throughout. The spacious living area flows seamlessly into the fully equipped kitchen and dining space, where family meals or lively conversations unfold. Large windows and sliding doors open to the backyard oasis, flooding the space with natural light and tropical vibes.brbrRetreat to the primary bedroom, featuring a king bed, a spacious ensuite with a walk-in shower, and a modern, relaxing atmosphere. The guest bedrooms include a range of beds from a king bed, a queen bed, and a twin-over-full bunk bed, each with their own ensuite bathrooms and premium linens. Everyone will find their perfect place to rest and recharge after days exploring or relaxing on the island.brbrRoom Details br• Primary Bedroom: King bed, ensuite with walk-in shower br• Second Bedroom: Queen bed, ensuite with walk-in shower br• Third Bedroom: Twin-over-full bunk bed, ensuite with walk-in shower br• Fourth Bedroom: King bed, ensuite with walk-in showerbrbrbrWith its resort-style outdoor space, luxurious interiors, and unbeatable location near Holmes Beach and Pine Avenue, Sunshine Reef is the perfect destination for your Gulf Coast vacation.brbrWhether you’re swimming, dining outdoors, or exploring Anna Maria Island by foot, bike, or trolley, this home has everything you need for lasting memories.brbrBook Sunshine Reef today and start planning your unforgettable Anna Maria Island getaway!brbrbr-brThis property participates in our Professional Linen Program. In Anna Maria Vacation's continuous effort to bring only the best quality experience to our guests, we are proud to offer a professional linen service at this property to better enhance your enjoyment while staying here. This luxury amenity provides you with high-quality linens; including bedding, bath towels, washcloths, and beach towels that are in place and ready for your use upon your arrival. These high-quality linens are washed in a commercial setting using the latest and best technology. brbrThis home is managed by Anna Maria Vacations, an Anna Maria Island property management company. brbrThis property does not allow pets of any kind. brbr3 cars maximum are able to park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles. brbrWe do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age. Please see our Anna Maria Vacations Rental Policies for full details. brbrPlease Remember: You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property. *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.

Bed

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Sleeps

$644.64

/ Nightly

Private Vacation Home

Beach Front Home with Direct Access to Beach and Beautiful Sunset Views

Anna Maria, Florida, United States

Shells and Sunshine by Anna Maria VacationsbrHome in Anna Maria, FL brVR16-000437brbrDiscover Shells and Sunshine, a family-friendly beach-front retreat on the prestigious north end of Anna Maria Island! This charming home features two levels with three bedrooms and two bathrooms, accommodating up to eight guests. Enjoy unobstructed views of the ocean from your private deck or take a scenic walk down the backyard trail to Bean Point Beach, known for its soft sands and turquoise waters. Perfect for families or groups, this home combines tranquility, waterfront beauty, and island adventure just moments from Pine Avenue’s shops and excellent eateries!brbrHighlights br• Direct Beach frontbr• Private walkway to Bean Point Beach br• 3 Bedroom / 2 Bathbr• 2 King beds, 2 twin-over-twin bunksbr• Newly updated interiorbr• Outdoor deckbr• Outdoor grill br• Short walk or bike ride to Pine Avenue's boutiques, restaurants, and local attractions br• 3 Parking SpacesbrbrEnjoy your private outdoor oasis on the furnished deck with water vistas or take a peaceful walk down the backyard trail to Bean Point Beach, your go-to spot for swimming, shelling, or relaxing on white sands. The outdoor space features a private gas grill perfect for island cookouts, while the lush landscaping creates a tranquil backdrop. Explore nearby shops, waterfront restaurants, and water activities like fishing and paddle boarding just minutes away.brbrInside, the open concept kitchen flows effortlessly into the living and dining rooms. The contemporary kitchen features new appliances, plenty of cabinets, and counter space perfect for family dinners or quick island snacks. The bright living room is furnished with comfortable seating and a large TV, ideal for relaxing nights or family movie time. Large windows and sliding doors open to the deck and outdoor area, bringing in water views and sunshine.brbrRetreat to the primary bedroom on the second floor, featuring a king bed, ample closet space, and an ensuite bathroom with a shower and tub combo, creating a relaxing sanctuary. The first-floor bedrooms include another king bed and two twin bunks, with access to a shared hall bathroom with a shower/tub combo. All bedrooms are decorated with fresh, coastal decor to ensure restful, tropical nights.brbrRoom Details br• Primary Bedroom (2nd floor): King bed, ensuite with shower and tub combo br• Second Bedroom (1st floor): King bed br• Third Bedroom (1st floor): Two Twin Bunksbr brBook Shells and Sunshine today and enjoy a luxurious, waterfront escape on Anna Maria Island. With private beach access, scenic water views, outdoor dining, and proximity to shops and dining on Pine Avenue, this home offers everything you need for a memorable Gulf Coast vacation. Reserve your dates now and start your island adventure!brbrbr-brThis home is managed by Anna Maria Vacations, an Anna Maria Island property management company. br brWe do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age. brbrPlease Remember: You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property. *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.

Bed

Bath

Sleeps

$371.08

/ Nightly

Private Vacation Home

Canalfront Retreat with Saltwater Pool and Private Dock

Anna Maria, Florida, United States

Palm Trees and Manatees by Anna Maria Vacations brHome in Anna Maria, FL brVR16-000462 brbrWelcome to Palm Trees and Manatees, a beautifully remodeled two-bedroom, two-bathroom canal-front home with a private saltwater pool, screened-in lanai, and private dock! All located just a short stroll from Bean Point Beach and Bayfront Park on the quiet north end of Anna Maria Island. Whether you're launching kayaks, soaking in the sun by the pool, or walking to your favorite waterfront restaurant, this tropical hideaway has it all for a peaceful island escape. brbrHighlights br• Canal Front Home and Private Dock br• 2 Bedrooms / 2 Bathrooms br• 2 Queens, 1 Twin over Full Bunk br• Saltwater Pool with Tanning Shelf br• 5-Minute walk to Bayfront Park br• 9-Minute walk to the Bean Point Beach br• Screened-in Lanai and Outdoor Shower br• Grill and Outdoor Dining Area br• Desk with Monitor for Remote Work br• Walkable to Pine Avenue Shops & Dining br• Professional Linen Service Included brbrEnjoy the best of Florida outdoor living in your private canal-front backyard. On one side, you’ll find a sparkling saltwater pool with a tanning shelf, surrounded by travertine pavers, lounge seating, and a convenient outdoor shower. On the canal side, a private dock awaits; perfect for launching kayaks or jet skis, casting a fishing line, or simply relaxing as gentle manatees drift by in the water. A screened-in lanai overlooking the canal sets the stage for peaceful mornings, while the grill and outdoor dining area make family BBQs effortless and fun. brbrStep into the spacious, sunlit living area and you’re immediately greeted by tranquil water views and relaxed island style. The open concept layout flows from the living room to the fully equipped kitchen, featuring island seating, a high-top dining table, and a formal canal-view table. Two comfy sofas and a large TV invite you to relax after a day in the sun, and a dedicated desk is perfect for remote work or planning your daily adventures. brbrThis single-level home comfortably sleeps up to seven guests. The primary bedroom features a queen bed, elegant floral decor, private patio access, and a spa-like ensuite bathroom with a tub/shower combo. The second bedroom is a flexible space, offering another queen bed and a twin-over-full bunk. Both bedrooms are equipped with Samsung Smart TVs, ample storage, and premium linens provided through the Professional Linen Program. brbrRoom Details br• Primary Bedroom: Queen bed and a bathroom with shower and tub combo br• Second Bedroom: Queen bed and Twin over Full Bunk br• Hall Bathroom: Walk-in shower brbrThis home also includes a washer and dryer, beach towels, and thoughtful extras to help you feel right at home. Located just four houses from the bay, this home is a short walk to Bean Point, Bayfront Park, and the local shops and restaurants on Pine Avenue. With easy access to fishing, beachcombing, paddleboarding, and dining. brbrBook your stay today and get ready for unforgettable sunsets, poolside relaxation, and true island living! brbr- brPools heated at request from Nov-April. brbrThis property participates in our Professional Linen Program. In Anna Maria Vacation's continuous effort to bring only the best quality experience to our guests, we are proud to offer a professional linen service at this property to better enhance your enjoyment while staying here. This luxury amenity provides you with high-quality linens; including bedding, bath towels, washcloths, and beach towels that are in place and ready for your use upon your arrival. These high-quality linens are washed in a commercial setting using the latest and best technology. brbrThis home is managed by Anna Maria Vacations, an Anna Maria Island property management company. brbrWe do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age. brbrPlease see our Anna Maria Vacations Rental Policies for full details. brbrPlease Remember: You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property. *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.

Bed

Bath

Sleeps

$747.01

/ Nightly

Private Vacation Home

Canal-Front Oasis with Private Dock, Pool, Near Beach and Shops - Aqua Cove

Anna Maria, Florida, United States

Aqua Cove by Anna Maria Vacations brHome in Anna Maria, FL brVR16-000429 brbrWelcome to Aqua Cove by Anna Maria Vacations, a beautiful canal-front vacation rental featuring 4 bedrooms and 3.5 bathrooms in the heart of Anna Maria Island, Florida. Perfect for families who love boating and beach adventures, this home offers a private pool with spa, boat dock, and game tables for hours of fun. Located just a 6-minute walk to Anna Maria Beach and the shops and restaurants along Pine Avenue. Aqua Cove blends Old Florida charm with modern comforts for the ideal Gulf Coast family getaway. brbrHighlights br• Canal front with private dock br• 6-minute walk to Anna Maria Beach br• 4 Bedrooms, 3.5 Bathrooms br• 2 Kings, 2 Twins, 1 Full-over-Full Bunk with Trundle br• 6-minute walk to Pine Avenue shops and restaurants br• Private pool with in-ground spa br• Pool table and ping pong table br• Elevator access br• 4 parking spaces br• Professional Linen Program included brbrStep into your own private tropical paradise. The backyard oasis features a heated pool and spa, surrounded by lush landscaping and sunny lounge areas perfect for relaxing or watching boats drift by. Launch your boat, kayak, or paddleboard from the private 26-foot dock for a day on the water. Afterward, enjoy a family cookout at the outdoor dining area with grill, or challenge friends to a round of ping pong or pool. Aqua Cove offers the perfect balance of relaxation and recreation. brbrInside, this home radiates coastal comfort with beach inspired decor and an open concept layout ideal for family gatherings. The living area includes plush recliner sofas and TV for movie nights. The fully equipped kitchen features stainless steel appliances, kitchen island seating, and everything you need to prepare home-cooked meals. A formal dining table and balcony seating provide options for both casual breakfasts and sunset dinners overlooking the canal. brbrRetreat to the primary suite, featuring a king bed, private balcony, and luxury ensuite bathroom with a double vanity, soaking tub, and walk-in shower. The second bedroom also includes a king bed and ensuite bathroom with a walk-in shower. The third bedroom offers two twin beds, while the fourth bedroom includes a full-over-full bunk bed with a trundle; perfect for kids or cousins. These two rooms share a hall bathroom with a tub/shower combination, ensuring comfort for every guest. brbrRoom Details br-Primary Bedroom: King bed, ensuite bath with walk-in shower, soaking tub, double vanity, private balcony br-Second Bedroom: King bed, ensuite bath with walk-in shower br-Third Bedroom: Two twin beds br-Fourth Bedroom: Full-over-full bunk bed with full trundle brbrGuests will enjoy the Professional Linen Program, providing premium bedding, bath towels, and beach towels for your stay. Additional conveniences include a washer and dryer, private elevator, and parking for four vehicles. Explore the island by foot, bike, or golf cart. Pine Avenue’s local boutiques, ice cream parlors, and waterfront restaurants are just minutes away. Spend your days at Anna Maria Beach or venture to nearby Holmes Beach and Bradenton Beach for more Gulf Coast fun. brbrWhether you’re relaxing by the pool, launching your boat for a day on the water, or walking to the beach for a sunset stroll, Aqua Cove delivers the perfect blend of comfort, adventure, and island charm. brbrBook your stay at Aqua Cove today with Anna Maria Vacations, your trusted source for family-friendly Gulf Coast vacation rentals! brbr- brThis home is managed by Anna Maria Vacations, an Anna Maria Island property management company. brbrThis property participates in our Professional Linen Program. In Anna Maria Vacation's continuous effort to bring only the best quality experience to our guests, we are proud to offer a professional linen service at this property to enhance your enjoyment better while staying here. This luxury amenity provides you with high-quality linens, including bedding, bath towels, washcloths, and beach towels that are in place and ready for your use upon your arrival. These high-quality linens are washed commercially using the latest and best technology. brbrThis property does not allow pets of any kind. brbr4 cars maximum are able to park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles. brbrWe do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age. Please see our Anna Maria Vacations Rental Policies for full details. brbrPlease Remember: You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property. *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.

Bed

Bath

Sleeps

$2359.86

/ Nightly

Private Vacation Home

Direct Beachfront Home, Steps to the Sand! Private Pool, Amenities for All!

Anna Maria, Florida, United States

The Big Yellow House on Pine by Anna Maria Vacations brHome in Anna Maria, FL brbrWelcome to The Big Yellow House on Pine by Anna Maria Vacations, a beachfront five-bedroom, four-bath home that captures the relaxed spirit of Anna Maria Island. Perfectly positioned along the Gulf, this charming coastal retreat offers spectacular beach views, a private pool and in-ground spa, and spacious living areas designed for family gatherings. Located right on Pine Avenue, guests are just steps away from local boutiques, coffee shops, and waterfront dining; making this the perfect home base for a classic Old Florida beach vacation. brbrHighlights br• Beachfront home with direct Gulf access br• 5 Bedrooms / 4 Bathrooms br• 2 King beds, 1 Queen bed, 4 Twin beds br• Private pool and in-ground spa br• Ping pong table and BBQ grill br• Recently updated first floor br• Washer and dryer br• Multiple living spaces and dining areas br• Steps from Pine Avenue shops and restaurants br• 5 Parking spots brbrEnjoy the ultimate island lifestyle at this family-friendly beachfront home. The covered patio and pool area overlooks the turquoise waters of the Gulf, creating an ideal space for morning swims, sunbathing, and sunset dinners. Fire up the BBQ grill, challenge the family to a ping pong match, or simply unwind in the bubbling spa as you listen to the waves roll in. With direct beach access, you can walk from your patio straight onto the soft white sand of Anna Maria Beach, making this one of the most desirable vacation rentals on Anna Maria Island. brbrInside, guests will find two spacious living areas, one on each floor; each featuring cozy seating, TVs, and dining tables perfect for shared meals. The main kitchen on the ground floor is fully equipped for home-cooked meals, while the second-floor kitchenette adds extra convenience for larger groups. Step out onto the upper balcony to take in uninterrupted Gulf views, the perfect spot for your morning coffee or an evening glass of wine. brbrEach bedroom has been thoughtfully designed for comfort and relaxation, offering soft linens, ample storage, and serene coastal touches. The home features two primary suites, each with a king bed and an ensuite bathroom with a walk-in shower. On the main floor, there are two additional bedrooms; one with a queen bed and one with two twin beds, sharing a hall bath with a shower and tub combination. Upstairs, a twin bedroom offers an ensuite bath with a walk-in shower, providing the ideal retreat for younger guests or friends traveling together. brbrRoom Details br-Primary Bedroom (1st floor): King bed, ensuite bath with walk-in shower br-Second Bedroom (2nd floor): King bed, ensuite bath with walk-in shower br-Third Bedroom (1st floor): Queen bed br-Fourth Bedroom (1st floor): Two Twin beds br-Fifth Bedroom (2nd floor): Two Twin beds, ensuite bath with walk-in shower brbrBeyond the beach, explore the best of Anna Maria Island right from your doorstep. Stroll along Pine Avenue to find local shops, bakeries, and restaurants, or spend your days exploring the island by bike or trolley. The home also features a washer and dryer, making it easy to keep beachwear fresh throughout your stay. brbrFrom its beachfront location to its private pool and spa, The Big Yellow House on Pine by Anna Maria Vacations offers a perfect mix of comfort, convenience, and coastal charm. Ideal for families and groups, this home captures the essence of island living with everything you need for a stress-free, sun-soaked getaway. brbrBook your stay today with Anna Maria Vacations and make unforgettable memories at The Big Yellow House on Pine! brbr- brThis property participates in our Professional Linen Program. In Anna Maria Vacation's continuous effort to bring only the best quality experience to our guests, we are proud to offer a professional linen service at this property to better enhance your enjoyment while staying here. This luxury amenity provides you with high-quality linens; including bedding, bath towels, washcloths, and beach towels that are in place and ready for your use upon your arrival. These high-quality linens are washed in a commercial setting using the latest and best technology.

Bed

Bath

Sleeps

$859.16

/ Nightly

Private Vacation Home

North End of Anna Maria Island! Private Pool and Spa, One Block to the Beach! -

Anna Maria, Florida, United States

Beach Paradise by Anna Maria Vacations brHome in Anna Maria, FL brVR17-000025 br brExperience the ultimate Florida getaway at Beach Paradise, a luxuriously designed home just seconds from Bean Point Beach and breathtaking views of the ocean! This home features four bedrooms, multiple balconies, a private heated pool and spa, elevator access, and a wealth of outdoor amenities. Located just a short walk or drive to Anna Maria’s top shops and restaurants, Beach Paradise is your perfect retreat for relaxation, water adventures, and unforgettable memories! brbrHighlights br• 1 minute/ 4 houses from Bean Point Beach br• 4 Bedroom / 4 Bath br• 3 Kings, 1 queen bed br• Private heated pool and spa br• Multiple balconies br• Outdoor TV, lounge, and dining area br• Ping pong table br• Elevator  br• In-home washer and dryer br• WiFi and cable TV included br• 3 Parking Spaces br brRelax outdoors in your private backyard oasis with a brand-new heated pool, spa, and in-water sundeck and bar seating. The patio is lined with numerous lounge chairs, armchairs, a dining table, and Adirondacks perfect for sunbathing or enjoying a tropical sunset. From here, it’s an easy walk to Bean Point Beach, with views of the Gulf, or a quick drive to local shops and waterfront restaurants, perfect for exploring Anna Maria Island’s scenic waterways and charming town. br brInside, the open concept living area combines modern elegance with comfort. Large windows and flood the space with natural sunlight, offering gorgeous water vistas. The fully equipped kitchen boasts brand new stainless-steel appliances, a large marble island with barstool seating, and an elegant dining area that comfortably seats eight, perfect for family gatherings or special occasions. The stylish living room, with a large flat-screen TV and cozy seating options, invites relaxation after a day at the beach. br brThe primary bedroom, located on the second floor, offers a king bed, balcony access, and an ensuite bathroom with walk-in shower, and double vanity, a luxurious retreat for restful nights. The second bedroom upstairs features a king bed and its own ensuite bathroom with a walk-in shower and balcony access. The third bedroom, on the main floor, features a king bed with an ensuite bathroom, while the fourth bedroom, on the same floor, has a queen bed and a nearby hall bathroom. All bedrooms feature premium linens ensuring comfort and privacy. brbrRoom Details br• Primary Bedroom (2nd floor): King bed, ensuite bathroom br• Second Bedroom (2nd floor): King bed, ensuite bathroom br• Third Bedroom (1st floor): King bed, ensuite bathroom br• Fourth Bedroom (1st floor): Queen bed br brBook Beach Paradise today and indulge in a luxurious, waterside Florida escape. With stunning Gulf views, outdoor entertainment, and proximity to the beach and local hotspots, this home offers everything you need for a relaxing, memorable vacation in paradise. Reserve your dates now and start creating lifelong beach memories! br brbr- brThis home is managed by Anna Maria Vacations, an Anna Maria Island property management company. brbrWe do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age. brbrPlease see our Anna Maria Vacations Rental Policies for full details. brbrPlease Remember: You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property. *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.

Bed

Bath

Sleeps

$533.49

/ Nightly

Private Vacation Home

Canal Front Home with Dock, Saltwater Pool, Ping Pong - Ama Maria

Anna Maria, Florida, United States

Ama Maria by Anna Maria VacationsbrHome in Anna Maria, FL brVR16-000113 brbrWelcome to Ama Maria! This three-bedroom and two bath canal front home has everything you need to have the best Anna Maria Island vacation ever. It has a private dock that can accommodate a boat up to 26 ft, a ping pong table, a screened-in patio with a saltwater pool, and plenty of seating to enjoy the gorgeous tropical views. brbrHighlights br• Canal front home with private dock br• Saltwater poolbr• Ping pong table br• Less than a 15-minute walk to Gulf beach br• Less than a 5-minute walk to Bay beach brbrEnjoy good times in the main living space of the house, which features a beach-themed seating area with recliner sofas, a TV, a fully equipped kitchen, and a dining table inside and on the balcony.brbrThe primary bedroom is perfect for getting some restful sleep. It has been decorated with light blue touches to create a serene atmosphere, and it also provides balcony access and an ensuite bathroom that features a walk-in shower and a soaking tub. The guest rooms are just as peaceful, with comfortable bedding, ample storage space, and TVs for your entertainment. The hall bathroom has a walk-in shower, and there is also a laundry room that guests can use, complete with a washer and dryer. brbrRoom Details br-Primary Bedroom: King bed, balcony access, and ensuite bathroom with walk-in shower and tub br-Second Bedroom: King bed and balcony access br-Third Bedroom: Twin over Full bed brbrWith the close proximity to Bayfront Park, AMI City Pier, Pine Ave’s restaurants and shops, and Rod n Reel Pier, you and your loved one’s will be having the time of your life at Ama Maria! brbr- brThis property participates in our Professional Linen Program. In Anna Maria Vacation's continuous effort to bring only the best quality experience to our guests, we are proud to offer a professional linen service at this property to better enhance your enjoyment while staying here. This luxury amenity provides you with high-quality linens; including bedding, bath towels, washcloths, and beach towels that are in place and ready for your use upon your arrival. These high-quality linens are washed in a commercial setting using the latest and best technology. brbrWith host approval before check-in, this property accepts dogs only (No cats or other animals are allowed). An additional pet fee will apply. See our Anna Maria Vacations Rental Policies for full details. brbr4 cars maximum are able to park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles. brbrThis home is managed by Anna Maria Vacations, an Anna Maria Island property management company. brbrWe do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age. brbrPlease see our Anna Maria Vacations Rental Policies for full details. brbrPlease Remember: You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property. *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.

Bed

Bath

Sleeps

$508.82

/ Nightly

Private Vacation Home

Family-Friendly Canal-Front Home with Pool, Dock, and Games! Close to Beach! - W

Anna Maria, Florida, United States

White Shell by Anna Maria Vacations brHome in Anna Maria, FL brVRC16-000161br brWelcome to White Shell, a charming canal-front Anna Maria Island vacation rental offering a perfect family retreat with modern amenities! This three-bedroom, two-bath home comfortably sleeps the whole family and your dog, featuring a seasonally heated private pool, a spacious outdoor bar and grill, and a private boat dock with two jet ski slips. Located just seven minutes from tranquil Bay beaches and a twelve-minute walk to Anna Maria Beach, White Shell puts you in the ideal spot near Pine Avenue to enjoy all of Anna Maria Island’s natural beauty, shopping, dining, and water adventures! brbrHighlights br• Canal front home with a private dock br• 3 Bedroom / 2 Bath br• 2 Kings, 2 Twin Beds br• 7-minute Walk to Bay Beach  br• Outdoor bar and grill br• Heated pool and spa br• Pool table, Ping Pong table and Foosball table br• Beach gear provided br• Dog friendly with host approval br• 4 Parking Spaces br brPlunge into Old Florida charm at this island gem! A dazzling, seasonally heated oasis pool and hot tub anchor in the lush backyard, packed with plush loungers and chic seating. Sizzle up feasts at the outdoor bar and BBQ, perfect for sunset cocktails. Launch water adventures from your private dock or dive into fun in the game room with pool table, ping pong, and foosball. Seamlessly blending indoor thrills with outdoor bliss, this retreat redefined vacation magic. br brInside, the vibrant and inviting interior seamlessly connects the living room, dining area, and fully equipped kitchen. The open layout encourages family gatherings and relaxed conversations, perfect for your vacation. The fully stocked kitchen features plenty of appliances, utensils, and gadgets, making meal prep effortless. Step out through the large screened-in lanai, with plush seating and a second dining table, to enjoy the tropical views of the pool and canal. br brThe primary bedroom, located on the third floor, features a king bed, luxurious linens, and a private ensuite with a soaking tub and walk-in shower, your peaceful sanctuary after a day on the water or at the beach. The second bedroom, on the second floor, offers another king bed and shares a hall bathroom with a walk-in shower. The third bedroom, perfect for kids, boasts two twin beds and is ideal for restful nights and fun sleepovers. The home’s layout ensures everyone has their own space to relax. brbrRoom Details br• Primary Bedroom (3rd floor): King bed, ensuite bathroom  br• Second Bedroom (2nd floor): King bed br• Third Bedroom (2nd floor): Two twin beds brbrUse the private dock and boat slips for fishing, kayaking, or boating excursions. With beach toys, a wagon, chairs, and umbrellas included, you’ll be ready for memorable days on the sand or adventures on the water. br brBook White Shell today and enjoy a perfect blend of relaxation, water fun, and island charm. Whether relaxing by the pool, exploring Anna Maria’s shops and restaurants, or boating on the bay, this home offers everything for a memorable family vacation. brbrReserve now and start creating lifelong memories on Anna Maria Island! br brbr- brThis property participates in our Professional Linen Program. In Anna Maria Vacation's continuous effort to bring only the best quality experience to our guests, we are proud to offer a professional linen service at this property to better enhance your enjoyment while staying here. This luxury amenity provides you with high-quality linens; including bedding, bath towels, washcloths, and beach towels that are in place and ready for your use upon your arrival. These high-quality linens are washed in a commercial setting using the latest and best technology. brbrThis home is managed by Anna Maria Vacations, an Anna Maria Island property management company. brbrWith host approval before check-in, this property accepts dogs only (No cats or other animals are allowed). An additional pet fee will apply. See our Anna Maria Vacations Rental Policies for full details. brbr4 cars maximum are able to park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles. brbrWe do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age. brbrPlease Remember: You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property. *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.

Bed

Bath

Sleeps

$1019.14

/ Nightly

Private Vacation Home

Bayfront Home with Amazing Water Views! Private pool! – Breakaway

Anna Maria, Florida, United States

Breakaway by Anna Maria Vacations brHome in Anna Maria, FL brVPR16-000458brbrEscape to Breakaway, a beautiful ground-level bayfront home with stunning views of the bay on Anna Maria Island! This stunning vacation home includes four bedrooms and two bathrooms, a private heated pool, outdoor lounge areas, and a cozy yet chic interior. This rental is perfect for families, couples, or groups seeking relaxation and adventure. Just a short walk to Bean Point Beach, Pine Avenue shops, and some of Anna Maria’s best restaurants, Breakaway is your ideal seaside retreat to unwind, explore, and create lifelong memories under the warm Florida sun!brbrHighlights br• 6-minute walk to Bean Point Beach br• 4 Bedroom / 2 Bathbr• 1 King, 2 Queens, 2 XL Twin/ Twin bunksbr• Private heated poolbr• Outdoor dining and loungebr• Outdoor showerbr• Gas grillbr• Water views of Tampa Bay and the Skyway Bridge br• Close to Pine Avenue shops, waterfront dining, and water sports rentalsbr• 3 Parking Spots br• 4-night minimum staybrbrEnjoy luxurious outdoor living with your private, and heated pool, complete with in-water seating and a sun shelf for kids or sunbathers. Relax in the lush, tropical landscaping around the large, paved deck, which features plenty of outdoor seating and a full-sized outdoor dining set perfect for outdoor meals. Marvel at the gorgeous water views from the second-story deck and outdoor spaces, perfect for sunsets and peaceful mornings. The outdoor lounge area with seating, and access to the water makes this backyard a true tropical oasis, and an ideal setting to relax, entertain, or enjoy nature’s beauty.brbrInside, enjoy an open-concept kitchen, dining, and living space designed for comfort and easy entertainment. The kitchen boasts stainless steel appliances, ample countertops, and a breakfast bar. The wooden dining table seats eight, while the living room with plush sofas and a large flat-screen TV is perfect for relaxing after a day at the beach or water adventures. Large windows and sliding doors frame water vistas, filling the space with natural light and a soothing coastal vibe.brbrRetreat to the primary suite featuring a king bed, a water-facing balcony, and an ensuite bathroom with a walk-in shower for a spa-like experience. The second and third bedrooms offers queen beds, while the fourth bedroom includes two twin-over-twin bunk beds, ideal for kids or additional guests. The hall bathroom features a walk-in shower and a stylish design, with a washer and dryer for added convenience.brbrRoom Details br• Primary Bedroom: King bed, ensuite with walk-in shower br• Second Bedroom: Queen bed br• Third Bedroom: Queen bedbr• Fourth Bedroom: Two XL twin over twin bunk bedsbrbrEnjoy your outdoor paradise, lounge poolside or soak in the sun while enjoying water views and sunsets. The lush, tropical landscaping surrounds the backyard, with plenty of seating for family and friends. Take a short walk to the beach, or hop on the boat or kayak in Tampa Bay, straight from your backyard. Explore Anna Maria Island’s shops, waterfront restaurants, parks, and water sports, making every day an adventure.brbrBook Breakaway today and enjoy a water-front retreat on the Gulf Coast. With stunning water views, outdoor amenities, and proximity to beaches, dining, and shopping, this home offers everything for a memorable getaway. Reserve now and start creating lifelong memories in paradise!brbrbr-brThis property participates in our Professional Linen Program. In Anna Maria Vacation's continuous effort to bring only the best quality experience to our guests, we are proud to offer a professional linen service at this property to better enhance your enjoyment while staying here. This luxury amenity provides you with high quality linens; including bedding, bath towels, washcloths, and beach towels that are in place and ready for your use upon your arrival. These high-quality linens are washed in a commercial setting using the latest and best technology.brbrThis home is managed by Anna Maria Vacations, an Anna Maria Island property management company. brbrWe do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age. brbrPlease Remember: You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property. *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.

Bed

Bath

Sleeps

$1036.26

/ Nightly

Private Vacation Home

Large Private Beach Home! Private Pool, Spa and Outdoor Lighting

Anna Maria, Florida, United States

Southern Exposure by Anna Maria Vacations brHome in Anna Maria, FL brVRC16-000065 brbrWelcome to Southern Exposure by Anna Maria Vacations, a five bedroom, four and a half bath luxury home perfectly located on the prestigious north end of Anna Maria Island. A 7-minute walk from the beach, this retreat combines coastal elegance with laid-back island comfort. Enjoy a private heated pool and hot tub, elevator access, and multiple balconies where you can unwind with your morning coffee or evening cocktail. Just one block from Pine Avenue’s shops and restaurants, Southern Exposure offers the perfect blend of relaxation and convenience for your next Anna Maria Island getaway. brbrHighlights br• 7-minute walk to the beach br• 5 Bedrooms / 4 Bathrooms br• 3 King beds, 1 Queen bed, 1 Twin-over-Twin bunk, 1 Queen sleeper sofa br• Private heated pool and hot tub br• Ping pong table and outdoor lounge area br• Elevator and multiple balconies br• One block from Pine Avenue’s shops and restaurants br• Washer and dryer br• Professional Linen Program included br• 4 Parking spots brbrDiscover outdoor living at its finest. The tropical pool area invites you to soak up the Florida sunshine or relax beneath the covered patio while the kids splash in the pool. The built-in bistro table is perfect for snacks and refreshments, and the hot tub offers the ideal way to unwind after a day on the sand. Challenge friends to a ping pong match or gather on the outdoor sectional for a family movie night under the island breeze. Every detail at Southern Exposure was designed to make guests feel at home in paradise. brbrStep inside and be greeted by a bright, open floor plan that flows seamlessly from the living room to the dining area and kitchen. The coastal decor and natural light set the perfect tone for a relaxing stay. The living room features plush seating, TV, and a wet bar with a wine fridge, creating an inviting space to unwind after exploring the island. The chef’s kitchen is fully equipped with stainless steel appliances, ample counter space, and barstool seating for casual dining. A colorful dining area and covered pool deck provide additional spots to enjoy meals together. brbrThe primary suite is a tranquil retreat featuring a king bed, balcony access, and a spa-inspired ensuite with a soaking tub, double vanity, and walk-in shower. Two additional king bedrooms and a queen bedroom each include ensuite bathrooms with walk-in showers, ensuring comfort and privacy for all guests. The fifth bedroom includes twin-over-twin bunk beds and a queen sleeper sofa, making it ideal as a playroom or flexible family space. brbrRoom Details br-Primary Bedroom: King bed, ensuite with soaking tub and walk-in shower br-Second Bedroom: King bed, ensuite with walk-in shower br-Third Bedroom: King bed, ensuite with walk-in shower br-Fourth Bedroom: Queen bed, ensuite with walk-in shower br-Fifth Bedroom: Twin-over-Twin bunk beds and Queen sleeper sofa brbrLocated between the Gulf and Bay, Southern Exposure offers easy access to both calm bay waters and the white sand beaches of Anna Maria Island. Spend your mornings beachcombing, afternoons paddleboarding, and evenings dining along Pine Avenue, just a short stroll away. For guests wanting to explore further, hop on the island trolley or rent a golf cart to experience all seven miles of island beauty. brbrWith its heated pool and spa, elevator, and prime location near the beach and Pine Avenue, Southern Exposure by Anna Maria Vacations is the ideal home for families and groups seeking the perfect balance of comfort and coastal charm. Book your stay today with Anna Maria Vacations and experience the best of Anna Maria Island living at Southern Exposure! brbr- brThis property participates in our Professional Linen Program. In Anna Maria Vacation's continuous effort to bring only the best quality experience to our guests, we are proud to offer a professional linen service at this property to better enhance your enjoyment while staying here. This luxury amenity provides you with high-quality linens; including bedding, bath towels, washcloths, and beach towels that are in place and ready for your use upon your arrival. These high-quality linens are washed in a commercial setting using the latest and best technology.

Bed

Bath

Sleeps

$339.03

/ Nightly

Private Vacation Home

Cozy Family Duplex with Pool! Close to the Gulf Beaches

Anna Maria, Florida, United States

Southern Breeze 1 by Anna Maria VacationsbrVR16-000199brbrWelcome to Southern Breeze 1, a chic ground-level vacation retreat located on the North end of Anna Maria Island! Just a short four-minute walk from Bean Point Beach, near Bayfront Park, this two-bedroom, one-bath home offers an ideal spot for families and friends to relax, explore, and soak up the Florida sunshine. Part of the Island 6-Plex community, this rental feature access to a shared pool, picnic areas, and convenient amenities, making it the perfect island escape.brbrHighlights br• 4-minute walk to Bean Point Beach br• 2 Bedroom / 1 Bathbr• 2 Kings, 1 Queen sleeper sofabr• Shared pool br• Updated interiors with tropical decor br• Picnic tables and BBQ grill br• 7-minute walk to Bayfront Park br• Close proximity to shops, restaurants, and Pine Avenue br• Shared laundry roombr• 1 Parking spacebrbrEnjoy the ultimate outdoor living experience with a shared pool, picnic area, and BBQ grill perfect for family cookouts after a day at the beach. Bask in the warm Florida sunshine on the loungers or unwind at the outdoor dining tables. Located on the north end of the island, this vacation retreat is near the pristine gulf beaches, restaurants, and shops on the famous Pine Avenue. brbrUpon entering, you are greeted by a relaxing living room decorated with tropical accents, a TV, and a large sectional sofa ideal for unwinding. The kitchen is equipped with all the essentials, including pots and pans for preparing meals. The open floor plan connects to the dining area for comfortable family gatherings, creating a welcoming atmosphere.brbrBoth bedrooms feature king-sized beds with cooling hybrid gel mattresses for a restful sleep, along with TVs and dressers for your convenience. The bathroom offers plenty of storage with cabinets, and a shower-tub combo for your comfort. The living room’s queen sleeper sofa allows extra guests to comfortably stay and sleep.brbrRoom Details br• Primary Bedroom: King bedbr• Second Bedroom: King bed br• Living Room: Queen sleeper sofabrbrGuests enjoy access to a shared laundry room, outdoor grills, a community pool, and close proximity to the best beaches and attractions Anna Maria Island has to offer. Perfect for extended stays or family reunions, Southern Breeze 1 offers both comfort and convenience in a prime location.brbrBook your stay at Southern Breeze 1 today and enjoy a Florida vacation filled with sunshine, sand, and sea. This inviting retreat provides everything you need for a memorable island escape. Reserve now and create lifelong memories with loved ones.brbrbr-brThis home is managed by Anna Maria Vacations, an Anna Maria Island property management company. brbrWe do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age. brbrPlease note: 1 car maximum can park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles.brbrThis property participates in our Professional Linen Program. In Anna Maria Vacation's continuous effort to bring only the best quality experience to our guests, we are proud to offer a professional linen service at this property to better enhance your enjoyment while staying here. This luxury amenity provides you with high-quality linens; including bedding, bath towels, washcloths, and beach towels that are in place and ready for your use upon your arrival. These high-quality linens are washed in a commercial setting using the latest and best technology.brbrPlease Remember: You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property. *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.

Bed

Bath

Sleeps

$685.52

/ Nightly

Private Vacation Home

Antigua Bay! Rooftop Views and Private Pool!

Anna Maria, Florida, United States

Antigua Bay by Anna Maria Vacations brHome in Anna Maria, FL brVR16-000450 brbrWelcome to Antigua Bay, a stunning five-bedroom, four-bath luxury vacation home located on the prestigious north end of Anna Maria Island, just steps from the Gulf. Perfect for large families and groups, this dog-friendly retreat offers premium amenities including a rooftop deck with panoramic island views, a private pool and in-ground spa, and fun family entertainment with both a pool table and foosball table. With Pine Avenue’s charming shops and restaurants just around the corner. brbrHighlights br-3-minute walk to Anna Maria beach br-5 Bedrooms / 4 Bathrooms br-4 King beds, 2 Twin-over-Twin bunks br-Rooftop deck br-Private heated pool and in-ground spa br-Covered patio with foosball, pool table, and bar area br-Outdoor dining and BBQ grill br-Near Pine Avenue restaurants and shops br-Dog-friendly br-6 Parking spots brbrFrom sunrise coffee on the rooftop deck to sunset swims in the private pool, Antigua Bay is designed for memorable island living. Spend the day exploring Anna Maria’s pristine beaches, then return to tropical landscaping, lounge chairs for sunbathing, and a shaded entertainment area with a pool table, foosball, and bar. An outdoor dining space and BBQ grill to make breezy meals. brbrThe open living area welcomes you with plenty of natural light, plush seating, and a large TV. The fully equipped kitchen features stainless steel appliances, cookware essentials, and an island with seating, ideal for casual breakfasts or evening appetizers. A dining table provides ample room for family meals, while multiple balconies invite you to sip morning coffee with gentle Gulf breezes. brbrAntigua Bay offers two luxurious primary suites, one on each living floor, each featuring a king bed, furnished balcony, and ensuite bathroom with double vanities and walk-in showers. Two additional guest bedrooms also feature king beds, and the fifth bedroom is perfect for kids with two twin-over-twin bunk beds. Bathrooms are stylishly appointed, with walk-in showers and a shower-tub combination for added convenience. brbrRoom Details br-Primary Bedroom 1: King bed, balcony, ensuite bathroom with double vanity and walk-in shower br-Bedroom 2: King bed, balcony, ensuite bathroom with double vanity and walk-in shower br-Bedroom 3: King bed, balcony access br-Bedroom 4: King bed br-Bedroom 5: Two twin-over-twin bunk beds brbrThis property participates in Anna Maria Vacations’ Professional Linen Program, providing guests with premium-quality bedding, bath towels, and beach towels, all freshly laundered and ready for your stay. Other amenities include Wi-Fi, washer and dryer, and multiple entertainment options indoors and out. brbrSpend your days exploring nearby Pine Avenue with its boutiques, ice cream shops, and waterfront dining, or hop on the island trolley to discover the rest of the island. brbrAntigua Bay offers the perfect blend of luxury, location, and entertainment. Book your dream Anna Maria Island getaway today! br br- brWith host approval before check-in, this property accepts dogs only (No cats or other animals are allowed). An additional pet fee will apply. See our Anna Maria Vacations Rental Policies for full details. brbrThis property participates in our Professional Linen Program. In Anna Maria Vacation's continuous effort to bring only the best quality experience to our guests, we are proud to offer a professional linen service at this property to better enhance your enjoyment while staying here. This luxury amenity provides you with high quality linens; including bedding, bath towels, washcloths, and beach towels that are in place and ready for your use upon your arrival. These high-quality linens are washed in a commercial setting using the latest and best technology.

Bed

Bath

Sleeps

$708.44

/ Nightly

Private Vacation Home

Vacation Home with Private Pool and Cornhole! Short Walk to the Beach and Shops

Anna Maria, Florida, United States

Angelfish by Anna Maria Vacations brHome in Anna Maria, FL brVRC16-000003brbrWelcome to Angelfish, a ground-level sanctuary just a three-minute walk to the sugar-white sands of Anna Maria Beach. With three bedrooms, two bathrooms, a private pool, and an in-ground spa, this charming home is designed for relaxation and fun. Guests will love being just steps from Pine Avenue’s boutique shops, waterfront restaurants, and water activities, making it the perfect island escape for families, groups of friends, and pet lovers.brbrHighlights br• 3-minute walk to Anna Maria beach br• 3 Bedroom / 2 Bathbr• 1 King, 1 queen bed, 1 twin-over-queen bunkbr• Private pool with in-ground spabr• Outdoor seating and BBQ grillbr• Cornhole br• Outdoor shower br• Pet friendlybr• Washer and dryerbr• 2-minute walk to Pine Avenue’s shops, waterfront restaurants, and water activitiesbr• 2 parking spaces brbrRelax outdoors in your tropical backyard oasis. Splash in the private pool and spa, soak up the sun on comfortable loungers, or enjoy a meal at the outdoor dining table. Challenge friends to a game of cornhole or rinse off in the outdoor shower after beach or pool fun. brbrEnjoy a relaxed and inviting interior with an open layout designed for comfort. The main living area features plush couches, a giant TV for family movie nights, and a cozy ambiance. The fully equipped kitchen includes stainless steel appliances, a 2-in-1 Keurig, ample counter space, and a large island, perfect for quick bites or full family meals. Outdoor sliding doors lead to the patio, where you can bask in the sun or dine al fresco in the fresh island air.brbrRetreat to the primary bedroom, which offers a king-sized bed and ample dresser and closet space. The second bedroom exudes a beach vibe with a queen bed, and the third bedroom, featuring a twin over queen bunk bed, is ideal for kids or additional guests. Both bedrooms provide plenty of storage for beach gear and personal belongings. The hall bathrooms, each with walk-in showers, complete this comfortable retreat, ensuring everyone has a restful night’s sleep.brbrRoom Details br• Primary Bedroom: King bed, ensuite bathroom with walk-in shower br• Second Bedroom: Queen bedbr• Third Bedroom: Twin over Queen bunk bedsbrbrWith Pine Avenue’s shops and restaurants just two minutes away, and Anna Maria Beach only a short stroll from your door, Angelfish places you at the heart of everything. Whether you’re exploring, relaxing, or spending quality time with family and friends, this vacation home delivers the perfect balance of convenience and comfort.brbrBook Angelfish today and make your perfect beach vacation a reality. With its water views, outdoor amenities, and prime location near beaches and shops, this home provides everything you need for a relaxing, fun-filled escape. Reserve your dates now and start creating lifelong memories in paradise!brbrbr-brThis property participates in our Professional Linen Program. In Anna Maria Vacation's continuous effort to bring only the best quality experience to our guests, we are proud to offer a professional linen service at this property to enhance your enjoyment better while staying here. This luxury amenity provides you with high-quality linens; including bedding, bath towels, washcloths, and beach towels that are in place and ready for your use upon your arrival. These high-quality linens are washed commercially using the latest and best technology.brbrWith host approval before check-in, this property accepts dogs only (No cats or other animals are allowed). An additional pet fee will apply. See our Anna Maria Vacations Rental Policies for full details. brbr2 cars maximum are able to park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles. brbrThis home is managed by Anna Maria Vacations, an Anna Maria Island property management company. brbrWe do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age. brbrPlease Remember: You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property. *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.

3

Bed

2

Bath

8

Sleeps

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