Vacation Home Rentals By Owner In Anna Maria, FL

HIBISCUS HAVENbr✨ Luxury 4-Bed Coastal Retreat • 3 King Suites • Bunk Room • Heated Pool• Water Views • Steps to the Beach • Pet Friendly brbrWelcome to Hibiscus Haven, your upscale tropical escape on Anna Maria Island! brThis beautifully designed coastal home sits directly across from the water and just steps from the white-sand Gulf beaches. Relax in your private heated pool, unwind in the spa, enjoy water views, and bring your furry family members along — this home is pet friendly with a non-refundable pet fee. ✨brbr Why Guests Love Hibiscus Havenbrbr✨ Pet Friendly — Non-refundable pet fee applies br✨ 3 King Bedrooms + Bunk Room (Sleeps up to 9)br Private Heated Poolbr Water Viewsbr Walk to the Beach in secondsbr Quiet, upscale island neighborhoodbr Beautiful modern kitchenbr Open coastal-chic living spacebr Walk to Free Island Trolley stopsbr Professionally managed by Flota’cal Vacation Rentalsbrbr Coastal-Chic InteriorsbrbrThe open layout brings natural light and island charm into every room.brRelax in the inviting living space featuring:brbr Comfortable coastal décorbr Smart TV for streamingbr Bright beachy tonesbr Pet-friendly spacesbrbrPerfect for relaxing after a day on the sand.brbr Bedrooms (Sleeps 9 Comfortably!)br Primary King SuitebrbrPlush King bedbrbrPrivate ensuite bathbrbrSerene, spacious, and relaxingbrbr King Bedroom #2brbrBright coastal charm + comfortable King bedbrbr King Bedroom #3brbrSoft bedding + peaceful décor + King bedbrbr Bunk RoombrbrQueen bed (bottom bunk)brbrTwin bed (top bunk)brPerfect for kids, teens, or adultsbrbrAll bedrooms include premium linens, comfy mattresses, and room to unwind.brbr Fully Equipped KitchenbrbrCook, entertain, and enjoy the good life with:br✔ Stainless appliancesbr✔ Coffee maker ☕br✔ Cookware & utensilsbr✔ Bar seatingbr✔ Dining table for group mealsbrbr Outdoor Oasis – Private Pool & SpabrbrYour own tropical retreat awaits:brbr Heated Poolbr Spa / Hot Tubbr Lush landscaped surroundingsbr Loungers & outdoor seatingbr Water Viewsbr Beach access just steps awaybr Pet-friendly outdoor areasbrbrEnjoy coffee by the pool, sunset soaks in the spa, or peaceful evenings outdoors.brbr Prime Location – Anna Maria IslandbrbrClose to everything you’ll love:brbr ‍♂️ Walk to the beach in secondsbr Steps to the free island trolleybr Ice cream shopsbr Pine Ave boutiquesbr Fishing & boat chartersbr☕ Cafés + waterfront restaurantsbr Paddleboard & kayak rentals nearbybrbr Amenitiesbrbr High-speed WiFibr Smart TVsbr Washer & dryerbr Fresh linens & beach towelsbr Central ACbr Keyless entrybr Free parkingbr Heated poolbr Spabr Pet Friendly (non-refundable pet fee required)br Water viewsbr Quick beach accessbrbr Booking NotesbrbrPets welcome with non-refundable pet fee (you can specify: e.g., $150 per pet)brbrNo smoking indoorsbrbrNightly, weekly & monthly stays availablebrbrMinimum age to rent: (Insert #)brbrProfessionally managed by Flota’cal Vacation Rentalsbrbr Book Your Stay at Hibiscus HavenbrbrYour perfect island getaway — sunshine, serenity, and luxury for the whole family (pets included!). ☀️

Hibiscus Haven Your perfect island getaway

ANNA MARIA, Florida, United States

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Sleeps

$544.98

Plan your next island vacation at this exception 4 bedroom, 2 bath home located at the north end of Anna Maria! Enjoy the short walk with easy access to the beautiful white sand beaches on the Gulf of Mexico. This unique floor plan with living area on the top floor allows you to take advantage of the cool sea breezes. This open floor plan allows the entire family to have space to enjoy separate activities while still being together. Enjoy dinner or a glass of wine on the large balcony situated just off of the kitchen and living area. The private, heated, saltwater pool is the perfect place to soak in the sun all year round! Pete's Blue Heaven offers serene, outdoor decks and a private, outdoor pool side shower, great to rinse off after the beach! A short walk to historic Pine Avenue with shops, restaurants, the Anna Maria City Pier, as well as easy access to the FREE Anna Maria Trolley!brbr*Please note: 4 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.brbr***OVERCROWDING CONSEQUENCES***brMaximum occupancy of rental homes on Anna Maria Island are set by the Cities and are strictly enforced. An occupant is any person staying overnight, regardless of the number of nights. Due to recent issues of overcrowding in the area, if maximum occupancy is exceeded during your stay, a $1000 (one thousand dollar) overcrowding fee will be charged to the payment method on file and your party will be immediately evicted. We appreciate your understanding and cooperation to keep Anna Maria Island enjoyable for everyone.

Pete's Blue Heaven: Steps to beach w/heated pool

Anna Maria, Florida, United States

Bed

Bath

Sleeps

$484.83

Sweet Melissa’s Beach House by AMI Locals brVR19-000057 brbrWelcome to Sweet Melissa’s Beach House, a cheerful and welcoming three-bedroom, three-bath retreat ideally located just across the street from the bay. With a private pool, vibrant coastal interiors, and a separate guest suite, this island gem is perfect for families or friends seeking the perfect mix of relaxation and fun. Located minutes from Pine Avenue's shops, dining, and the iconic Bean Point Beach, your Florida Gulf Coast getaway starts here! brbrHighlights br• Across the Street from the bay br• 12-minute walk to Bean Point Beach br• 3 Bedrooms / 3 Bathrooms br• 2 Kings, 2 Twins, 1 King Sleeper Sofa br• Private Pool with Sun Loungers br• Screened-in Lanai br• Outdoor Dining Area and BBQ Grill br• Washer and Dryer br• Separate Private Suite with Pool Access br• Near Pine Avenue br• Pet friendly with host approval br• 3 Parking spaces brbrThe private backyard is a true island oasis, with a refreshing pool, sun loungers, and an outdoor dining area with a BBQ grill for evening cookouts or relaxing days in the Florida sun. The screened-in lanai offers a shady escape with a dining table, perfect for enjoying morning coffee or cocktails in the island breeze. brbrStep into this island-style beach house through a breezy screened-in lanai, perfect for morning coffee or unwinding in the shade. The interior great room offers a spacious, open layout with a large sofa and TV; ideal for relaxing after a beach day. The fully equipped kitchen includes coastal cabinetry, appliances, and a large island with seating, making it easy to entertain and enjoy meals together. brbrThe home’s layout is ideal for families and small groups. In the main house, the primary bedroom features a king bed and ensuite bath with a shower/tub combo. The second bedroom has two twin beds and is perfect for children or extra guests. The third bedroom is a private suite, complete with a second king bed, king sleeper sofa, ensuite bath with walk-in shower. The private suite has a separate washer and dryer, direct access to the pool, and a separate entry from the front of the house. brbrRoom Details br• Primary Bedroom: King bed, ensuite bathroom br• Second Bedroom: Two Twin beds br• Third Bedroom (Private Suite): King bed, King sleeper sofa, ensuite bathroom br• Hall Bath: Tub/shower combination brbrThis home is packed with extras to make your stay easy and enjoyable. Inside, enjoy the convenience of a washer and dryer, TVs in every room, and plenty of space to gather and relax. You'll be close to top Anna Maria Island attractions, Pine Avenue nightlife, the trolley stop, and access to explore all 7-miles of the scenic island. brbrHead across the street to the calm waters of Tampa Bay or take a short walk or quick drive to the white-sand Gulf beaches. Whether you're fishing off the soft sands, exploring Pine Avenue, or lounging poolside with your favorite drink, Sweet Melissa’s Beach House by AMI Locals delivers the comfort, convenience, and charm of a true Anna Maria Island vacation. brbrBook now to experience the island lifestyle and make lasting memories at this unforgettable beach retreat! br br- br3 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 AMI Locals, 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 AMI Locals 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. brbrPlease see our AMI Locals 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 a refund.

Charming Island Escape with Private Pool and Screened Lanai!

Anna Maria, Florida, United States

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Bath

Sleeps

$1713.72

Villa Marisol, located at 797 North Shore Drive at the north end of Anna Maria Island and nestled on the shores of the Gulf of Mexico, offers breathtakingly beautiful views of the crystal blue waters of the gulf. This is unquestionably one of Anna Maria's loveliest homes and has recently completed major renovations inside as well as a new pool. This spectacular home features upscale furnishings and amazing attention to detail. Furnished with a Spanish flair, you will enjoy every moment of your stay. As you enter through a lush, tropical secluded courtyard accented with a fountain centerpiece, the beautifully Mexican tiled stairway leads to a gracious front foyer that leads you to the living area. Villa Marisol has a home theatre system and of course, free Wifi with expanded cable and free domestic long distance calling.brbrThe main level of Villa Marisol consists of a surprising large living area, dining room and family room. There is a large, well equipped kitchen with a commercial Wolf stove. There are two refrigerators, a dishwasher, and two sinks. All of these rooms face out to the white sandy beach and the Gulf of Mexico. There is a wonderful mix of elegance and simplicity. The family room is a fabulous retreat to relax and watch a movie after a day at the beach. This room features a 52 television with a DVD player. Off of the living and dining area there is an open deck facing the beach featuring a seating area and gas grill.brbrThe main level of the Villa Marisol also features three full bedrooms. The first bedroom is equipped with a full sized bed and an adjoining bathroom with a full walk in shower. This room also has a 32 television. The second bedroom has a queen size bed and features a 31 television. The third bedroom is geared toward younger guests and features a set of twin bunk beds and a trundle bed. This room also features a 31 television. There is a full bathroom on this level as well as a guest bathroom.brbrThe upper level of this beautiful home is unlike anything you've ever seen. This master suite features panoramic views of the Gulf of Mexico from every window. There is a very large private deck that is unparalleled. The beach views are spectacular and there is plenty of comfortable seating to sit back and enjoy the sunsets. This master suite also features a seating area, a desk area and a full size master bathroom suite which has separate sinks, a huge walk in shower with twin heads and numerous large closets. Did we mention the sauna There is a full sauna in the master suite as well.brbrThe outdoor space at Villa Marisol does not disappoint. The home offers beach chairs and a beach wagon for guest use. Spend the day at the beach and head back to the home and enjoy the gorgeous pool area and covered outdoor living space. The covered area boasts two large tvs, a sound system, comfortable seating and a space to dine or play games.brbrThis wonderful home will comfortably accommodate ten people. No pets or parties please! brGarage for owner's use only.br brOnce you visit Villa Marisol, you'll want to return year after year. It's that special!brbr**Outdoor Security Cameras in Use**brbrPlease note that the fireplace is not operational. brbr***OVERCROWDING CONSEQUENCES***brMaximum occupancy of rental homes on Anna Maria Island are set by the Cities and are strictly enforced. An occupant is any person staying overnight, regardless of the number of nights. Due to recent issues of overcrowding in the area, if maximum occupancy is exceeded during your stay, a $1000 (one thousand dollar) overcrowding fee will be charged to the payment method on file and your party will be immediately evicted. We appreciate your understanding and cooperation to keep Anna Maria Island enjoyable for everyone.

Villa Marisol: Beachfront, Mediterranean style, w/terrace, pool, hot tub!

Anna Maria, Florida, United States

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Bath

Sleeps

$620.93

The Hammock House, located on the North end of Anna Maria is a 3 bedroom, 3.5 bathroom spacious, contemporary home. The property features a large custom pool and spa as well as an expansive private yard! The open concept living space allows for plenty of space for the entire group to relax and regenerate! The main floor features two separate living areas, a large kitchen, dining room, half bath, and bedroom with a full bath. The remaining bedrooms and bathrooms are located on the third level. The Hammock House features a fantastic outdoor area with pool and hot tub! The pool area has the perfect mix of sunny and shaded spaces. Enjoy outdoor dining, a lounge area with tv, and two sun loungers for soaking in the warm Florida sun! Conveniently located just off of Pine Avenue, you can easily walk to shops, restaurants, and the beautiful Gulf beaches!brbrMain level: br2 living areasbrKitchenbrDiningbrHalf bathbrBedroom 1: King bed w/ tv and walk-in shower ensuitebrbr3rd Floor:brSmall sitting areabrBedroom 2: Queen bed w/ tv and ensuite w/ tub/showerbrBedroom 3: Queen bed w/ tv and ensuite w/ walk-in showerbrbr***OVERCROWDING CONSEQUENCES***brMaximum occupancy of rental homes on Anna Maria Island are set by the Cities and are strictly enforced. An occupant is any person staying overnight, regardless of the number of nights. Due to recent issues of overcrowding in the area, if maximum occupancy is exceeded during your stay, a $1000 (one thousand dollar) overcrowding fee will be charged to the payment method on file and your party will be immediately evicted. We appreciate your understanding and cooperation to keep Anna Maria Island enjoyable for everyone.

The Hammock House: Bright and modern pool home with outdoor living space

Anna Maria, Florida, United States

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$260.37

A Place in Paradise Unit A by Anna Maria Island Accommodations brDuplex in Anna Maria, FloridabrVR16-000529 brbrWelcome to A Place in Paradise Unit A, a charming two-bedroom, two-bath duplex located just a short walk from the sugar-white beaches of Anna Maria Island. Perfect for families or small groups, this coastal cottage offers the ideal blend of comfort, convenience, and Old Florida charm. Stroll to Pine Avenue’s boutique shops and local dining, hop on the nearby trolley to explore the island, and relax knowing you’re only steps from the Gulf beaches. brbrHighlights br-4-minute walk to Palmetto Ave Beach br-2 Bedrooms / 2 Bathrooms br-1 King bed, 2 Twin beds br-Screened-in lanai with seating br-BBQ Grill br-Shared washer and dryer br-Conveniently located near Pine Avenue dining, shops, and trolley stop br-Neighboring unit available for group rentals br-Dog friendly (with approval) br-Parking for 2 vehicles brbrGuests can take their morning coffee on the screened-in lanai, take a short stroll to the white-sand beaches, or fire up the BBQ grill for a family cookout. For beach days, the home provides convenient extras like a wagon and beach chairs, making it easy to pack up and go. This duplex is also pet-friendly, so your furry friend can join in on the island fun. brbrStep inside and find a bright and beach-inspired living room with cozy sofas and a TV, the perfect spot to relax after a day at the beach. The galley kitchen is stocked with cookware, utensils, and essentials so family meals are easy, whether you’re preparing breakfast before hitting the sand or a casual dinner together. brbrThe primary bedroom features a comfortable king bed for a restful retreat, while the second bedroom has two twin beds, making it great for kids or friends. Two bathrooms provide convenience for groups, both with walk in showers. brbrRoom Details br-Primary Bedroom: King bed br-Second Bedroom: Two Twin beds brbrThis property includes one designated parking space, washer/dryer combo, and offers the option to rent the neighboring Unit B for larger family gatherings. With its walkable location, guests can easily explore the Pine Avenue Shopping District, local seafood restaurants, and boutique shops. Plus, the Anna Maria Island trolley makes it easy to reach Coquina Beach and Holmes Beach without needing a car. brbrWhether you’re planning a family getaway or a couple’s retreat, A Place in Paradise Unit A by Anna Maria Island Accommodations delivers comfort, convenience, and true coastal charm. Book your stay today and enjoy the best of Anna Maria Island accommodations just steps from the beach! brbr- brPlease note this property does not feature a dishwasher. 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 Island Accommodations, 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 Island Accommodations Rental Policies for full details. brbrThis property does not feature a dishwasher.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.

Family-Friendly Duplex Near Beaches and Local Shops! - A Place In Paradise Unit

Anna Maria, Florida, United States

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Bath

Sleeps

$274.53

A Place in Paradise Unit B by Anna Maria Island Accommodations brDuplex in Anna Maria, FloridabrVR16-000529 brbrWelcome to A Place in Paradise Unit B, a delightful two-bedroom, two-bath vacation home located just two blocks from the shimmering Gulf beaches. This cozy retreat is ideal for couples or small families looking to enjoy the laid-back charm of Anna Maria Island accommodations. With shopping and dining on Pine Avenue just around the corner and Bean Point Beach a short stroll away, you’ll have everything you need for the perfect island escape. brbrHighlights br-4-minute walk to Palmetto Ave Beach br-2 Bedrooms / 2 Bathrooms br-1 King bed, 2 Twin beds br-Outdoor shower br-Beach wagon, and beach chairs included br-Shared washer and dryer br-Close to Pine Avenue shops, restaurants, and the trolley stop br-Neighboring Unit A can be rented for larger groups br-Dog-friendly with approval and additional fee br-2 parking spaces brbrThis charming island duplex makes vacationing simple and relaxing. After sun-filled days at the beach, rinse off in the outdoor shower, then grab the beach wagon and chairs provided for your next seaside adventure. The screened-in lanai is a great spot for enjoying your morning coffee, while the island trolley nearby makes exploring Anna Maria a breeze. brbrThe inviting living room welcomes you with cozy seating and TV, perfect for movie nights or winding down after a day in the sun. A fully stocked kitchen makes it easy to prepare quick snacks or casual meals, and a dining area offers a space to enjoy them together. For added convenience, this home also includes a washer and dryer, so you can pack light and keep beachwear fresh throughout your stay. brbrThe primary bedroom offers a serene retreat with a king bed and easy access to a bathroom featuring a step-in shower. The second bedroom has two twin beds, making it a versatile space for children, friends, or additional guests. The second bathroom includes a shower/tub combo, ensuring both comfort and convenience. brbrRoom Details br-Primary Bedroom: King bed, ensuite bathroom with step-in shower br-Second Bedroom: Two Twin beds, hall bathroom with step-in shower brbrGuests love the home’s prime location just minutes from Pine Avenue’s boutique shops, and local dining. Whether you’re fishing, kayaking, or simply soaking in the Old Florida charm, this vacation home makes it easy to experience all the best of Anna Maria Island. For larger groups, book both Unit A and Unit B to stay side by side. brbrFrom its walk-to-the-beach location to its thoughtful amenities like a washer and dryer, outdoor shower, and beach gear, A Place in Paradise Unit B by Anna Maria Island Accommodations is the perfect choice for a relaxed island getaway. Don’t wait, plan your stay today and enjoy the charm of Anna Maria Island with comfort and ease! brbr- brPlease note this property does not feature a dishwasher. 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 Island Accommodations, 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 Island Accommodations Rental Policies for full details. brbrThis property does not feature a dishwasher.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. brbr Please 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.

Dog-Friendly 4 Mins to the Beach and Pine Ave - A Place in Paradise Unit B

Anna Maria, Florida, United States

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Bath

Sleeps

$627.52

Welcome to Coconut Lagoon!brOn Anna Maria Island (Anna Maria, FL)brbrThe SpacebrStep into Coconut Lagoon, where generations of island charm meet easy, family-focused living. Nestled along the beloved Magnolia Avenue—lined with palms, bike paths, and the soft hum of island life—this pet-friendly home blends vintage character with thoughtful updates. It's a place made for gathering: where morning coffee turns into laughter, and afternoons by the pool stretch into unhurried evenings beneath string lights.brbrPerfect for: families, friend groups, and guests traveling with pets who love to share life's simple moments together.brbrHighlightsbr- Ground-level home on iconic Magnolia Avenuebr- 3 Bedrooms | 2.5 Bathrooms | Sleeps up to 6 guestsbr- Heated lagoon-style private pool with sun shelf & built-in tablebr- Covered outdoor cabana with Smart TV and bar seatingbr- Screened-in front porch for morning coffee & quiet conversationbr- Pet-friendly with prior approval (see policies below)br- Fully equipped kitchen & dining space for sixbr- Driveway parking for 2–3 vehiclesbr- Please note: There is no spa at this home.brbrInterior SpacesbrCoconut Lagoon carries the easy rhythm of an old Florida home—with wood accents, airy rooms, and natural light that dances across the floors. Inside, every detail feels intentionally designed for comfort, conversation, and togetherness.brbrThe open-concept living area invites guests to unwind after a day in the sun. Gather on the sofa for movie night, play a board game at the dining table, or curl up with a book while the island breeze drifts through the screened porch.brbrEach bedroom blends nostalgic charm with modern convenience: soft linens, cheerful colors, and space for everyone to rest and reconnect.brbrLayout Overviewbr- Main Living Area: Open-concept living, dining, and kitchen with Smart TV and plenty of seating.br- Primary Bedroom: Queen bed, Smart TV, dresser, and en-suite bathroom with shower/tub combination.br- Second Bedroom: Queen bed, Smart TV, dresser, and easy access to hall full bath.br- Loft Bedroom: Two twin beds (convertible to a king with advance notice), Smart TV, dresser, and half bath.br- Laundry Closet: Washer and dryer for guest use.brbrOutdoor LivingbrOutside, you'll find a backyard that feels like a story unfolding—lush greenery, a gently curving pool, and quiet corners meant for connection.brbrThe heated lagoon-style pool features a built-in dining table and a sun shelf for lounging. Spend the day swimming, laughing, and soaking up the Florida sunshine. When evening falls, gather under the covered cabana—complete with bar seating, a Smart TV, and soft ambient lighting—to share a meal, watch a game, or simply talk beneath the palms.brbrFrom the shaded front porch to the cabana's golden glow, every outdoor space invites time spent together—without hurry, without agenda.brbrOutdoor Highlightsbr- Heated lagoon-style pool (82–85°F year-round; weather dependent)br- Sun shelf with in-pool tablebr- Covered cabana with Smart TV, bar seating & string lightingbr- Outdoor dining area and lounge chairsbr- Propane grill & enclosed outdoor showerbr- Screened-in front porch with seatingbrbrKitchen & DiningbrThe kitchen brings everyone together. Its stainless-steel appliances and generous counter space make cooking feel effortless, whether it's breakfast pancakes or a family seafood feast.brbr- Stove, oven, and microwavebr- Refrigerator/freezerbr- Dishwasher and garbage disposalbr- 12-cup coffeemaker, blender, and toasterbr- Cookware, dinnerware, and utensilsbr- Dining table for sixbrbrPrepare meals while chatting with family nearby, then sit together and share the kind of stories that always seem better told on island time.brbrAdditional Amenitiesbr- Air conditioning & heatbr- High-speed Wi-Fi & cable televisionbr- Linens, bath towels & beach towelsbr- Washer & dryerbr- Hair dryer, iron & ironing boardbr- Beach gear rental credit (chairs, umbrellas, bikes, etc.; details sent after booking)brbrParkingbr- Driveway accommodates 2–3 vehiclesbr- Garage not availablebrbrCoconut Lagoon is more than a vacation home—it's a gathering place. Located just steps from Pine Avenue's shops, cafés, and ice cream stops, and a short stroll to the Gulf beaches, it embodies the best of island living: connection, community, and care.brbrHere, mornings begin with barefoot walks under swaying palms, and nights end with laughter echoing through the backyard. However you choose to spend your time, Write Your Vacation Story somewhere between the sunshine, the salt air, and the joy of being together.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.brbrPlease note: There is no spa at this home.brbrCity of Anna Maria Vacation Rental License: VR20-000090brMax Occupancy: 6 Guests | Max Vehicles: 3brInformation deemed reliable but not guaranteed; subject to change or withdrawal without notice.

Coconut Lagoon – AMI Pet Friendly Home w/ Heated Pool, Screened Porch & Cabana TV

Anna Maria, Florida, United States

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Bath

Sleeps

$397.73

The Wee CottagebrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrThe Wee Cottage | Charming Vintage Retreat in Anna Maria with Private Pool & SpabrbrWelcome to The Wee Cottage, professionally managed and supported 24/7 for your peace of mind. Nestled in the heart of Anna Maria, this charming 1-bedroom, 1-bath home comfortably accommodates up to 4 guests and offers a truly unique getaway experience.brbrA Rustic, Vintage Florida EscapebrStep into a timeless slice of Old Florida the moment you arrive. Built in 1926, this delightful cottage embraces a rustic, vintage Florida feel, filled with carefully curated antiques, classic books, and warm character that transport you to a simpler, more relaxed era. It’s the perfect blend of nostalgic charm and modern comfort.brbrOutdoor Paradise AwaitsbrYour private backyard is designed for relaxation and fun. Enjoy sunny Florida days lounging by the heated in-ground pool, unwind in the attached spa, or practice your swing on the authentic putting green. This serene outdoor space offers the ideal setting for both quiet mornings and memorable evenings.brbrPrime LocationbrJust steps from the beach and within walking distance to the shops, restaurants, and local charm of Pine Avenue, you’ll be perfectly situated to enjoy everything Anna Maria Island has to offer. The iconic Rod and Reel Pier and AMI City Pier are both less than a mile away.brbrComfort & ConveniencebrbrFully equipped kitchen for easy, home-cooked mealsbrCozy, thoughtfully designed living spacesbrSmart lock entry for seamless check-inbrParking available for up to 2 vehiclesbrThings to KnowbrCheck-in: 4:00 PM | Check-out: 10:00 AMbrQuiet hours: 10:00 PM – 8:00 AMbrNo smoking permittedbrNo pets allowedbrConstruction is currently taking place behind the homebrPool heat is included at 80°FbrOptional upgrade to 85°F available for $32/day + tax (48-hour notice required)brHeat may not be available if temperatures fall below 65°FbrPool heat upgrades not available May–Octoberbr*This house has a pool spa, not a Hot TubbrbrParking notes: There is free parking available for 2 vehicles.brbrbrbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 21 years of age to book. Guests under 21 must be accompanied by a parent or legal guardian for the duration of the reservation.

The Wee Cottage | House in Anna Maria

Anna Maria, Florida, United States

Bed

Bath

Sleeps

$570.52

Photos updated March 2025!brbrWelcome to Glad Tidings, a comfortable and well-appointed vacation home on Anna Maria Island. Designed with a boho-chic style, this home offers a laid-back and inviting space for your island getaway.brbrInside, you'll find two master suites, each with a king bed and ensuite bathroom, providing plenty of space and privacy. The third bedroom features a set of bunk beds and easy access to the shared hallway bathroom. The kitchen is fully stocked with essentials for preparing meals at home; however, please note that it does not have a full-size oven but includes a half-size microwave oven for convenient cooking.brbrStep outside to enjoy the private pool, perfect for cooling off or lounging in the sun. This home is just a 5-minute walk to Pine Avenue, where you’ll find local shops, restaurants, and island activities. Both the Gulf and Bay beaches are a short 10-minute walk away, making it easy to spend your days by the water.brbr**Please note: Property does not have a full oven.brbr*Please note: 2 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.brbr***OVERCROWDING CONSEQUENCES***brMaximum occupancy of rental homes on Anna Maria Island are set by the Cities and are strictly enforced. An occupant is any person staying overnight, regardless of the number of nights. Due to recent issues of overcrowding in the area, if maximum occupancy is exceeded during your stay, a $1000 (one thousand dollar) overcrowding fee will be charged to the payment method on file and your party will be immediately evicted. We appreciate your understanding and cooperation to keep Anna Maria Island enjoyable for everyone.

Glad Tidings: Heated pool, turfed outdoor lounge and dining area.

Anna Maria, Florida, United States

Bed

Bath

Sleeps

$488.67

Island Breeze by Anna Maria Life Vacation Rentalsbr119 Beach Ave, Anna Maria, FL 34216brbrWhat You'll Love About This Home:brLocation! 5 Houses to the Beach!br2 Bedrooms / 2 Bathroomsbr1 King Bed, 2 Twin BedsbrHeated Pool & Spa (Spa only heats to the temp of the Pool)brPool LoungersbrCovered Poolside Lounge with Adirondack Chairs & TVbrFenced YardbrCharcoal GrillbrVerandah with Rocking Chairs & Patio Dining Table for FourbrKeurig Coffee MakerbrProfessional Linen Service, Washer & DryerbrComplimentary WIFIbrBeach Towels, Beach Chairs, Beach WagonbrParking for 4 Cars (2 Driveway & 2 Covered Carport)brbrDetails:brIsland Breeze is our elevated beach house on Beach Ave located 5 houses to the beach! That's a lot of beach in one sentence! With such a great location, it's worth repeating.brbrThe perfect balance of indoor and outdoor spaces await your family vacation. The main living space is on level two and includes kitchen, dining area and living room and two bedrooms. Enjoy your morning coffee in one of the rocking chairs on the front verandah which also includes a patio dining table and chairs for four.brbrThe master bedroom features a king-sized bed and En-suite bathroom, and the guestroom has two twin beds and easy access to the hall bathroom. Each bedroom has a TV and includes crisp linens and plush towels from our professional linen company. Your guests will stay connected with complimentary WFI and enjoy all of the comforts of home, including a washer and dryer.brbrThe heated pool and spa are the highlights of the fenced in backyard. With pool loungers, Adirondack chairs,a charcoal grill and covered poolside lounger area with a TV, this is the place to enjoy the island breezes.brbrIsland Breeze is easy walking distance to many shops and restaurants, and to the free island trolley, which travels the entire length of the 7 miles of the island. Hop on and off at your leisure and explore shopping, dining and the beaches. The perfect location for your next beach vacation!brbrBedroom 1: King with TV and Ensuite Bath (Level 2)brBedroom 2: Two Twin Beds with TV (Level 2)brbrPlease note:brPets are not allowed in this home.brThe Spa only heats to the same temperature of the pool. brAmenities are subject to change.brbrYou 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.brVR16-000447brbrGolf Cart DEAL ALERT!!! brReserve now a street legal GOLF CART from Fun & More Rentals! 4, 6 or 8 passenger gas or electric carts to choose.brFUN way to explore the island for the entire family.brMention Anna Maria Life Vacation Rentals and receive this VIP deal!brwww.FunAndMoreRentals.combr941-462-2719brbrIMPORTANT INFORMATION: brbrYour booking is with Anna Maria Life Vacation Rentals. We will send you check-in instructions 14 days prior to your arrival date. We will send you our rental agreement in an electronic signature document. Please review and return to us by following the instructions.brbr** Your signed rental agreement must be returned in order to receive your check-in details. brbrVRBO BOOKINGSbrbrAnna Maria Life Vacation Rentals will charge your credit card for your deposit payment. You will also see a separate charge by VRBO for their service fee. brbrYour final balance is due 60 days prior to your arrival date. We will send you a final payment reminder 90 days prior to arrival. We do not automatically charge your card for your final balance. brbrThe instructions for making your final payment will be included in your final payment reminder.brbrPlease review the cancellation policy prior to booking. brbrGOOGLE VACATION RENTAL BOOKINGSbrbrYour payment is due in full at the time of booking and the final balance information above does not apply to your reservation.

Island Breeze: Steps to Beach, Heated Pool & Spa, Huge Verandah by Anna Maria Life Vacation Rentals

Anna Maria, Florida, United States

Bed

Bath

Sleeps

$448.9

**ASK ABOUT LAST MINUTE DEALS!brbrFamilies or groups of friends love this big open house with plenty of room and lots of amenities! A sprawling elevated home with three bedrooms and three en suite bathrooms, this is one of those places where everyone in your group will be able to find plenty to do, while enjoying a laid-back atmosphere and lots of room to relax.brbrLocated at the end of a deep water canal with direct access to Tampa Bay and the Gulf of Mexico beyond, boaters will welcome the ...opportunity to use the dock. Bring a boat from home, or rent one from a local marina. The dock is also a fun place for fishing, and if you're lucky, you'll catch sight of one of our local manatees and perhaps a brand new calf! They love swimming the canals in hopes of finding someone to visit.brbrThe living and dining areas, along with the kitchen, open onto the big front deck. In season, most guests like to keep all the French doors open for a real sense of outdoor living. The front deck is a great spot for dining al fresco while enjoying views of happy travelers out for a taste of the sun, and even a lovely view of Tampa Bay across the street. A heated pool and hot tub are perched canalside, with a large open patio that's the perfect place for a picnic. An upstairs deck overlooks this area, offering lovely views down the canal to Bimini Bay.brbrInside the house on the first level you'll find a bedroom that can be made up as two twins, or as one king-size bed. Tell us when you book which you'd like, and our housekeeping staff will take care of the setup. Another bedroom at the front of the house features a daybed with trundle, along with a built-in twin on the other side of the room, a large walk-in closet, and en suite bath with walk-in shower. This bedroom has French doors that open directly onto the large front deck, allowing refreshing breezes into every corner.brbrUpstairs you'll find the primary bedroom with a queen bed, en suite bath with walk-in shower, and a private deck boasting fabulous views over Tampa Bay and the Sunshine Skyway bridge. Be sure to watch for the big cruise ships on their way out to sea; it's fun to imagine where they might be traveling!brbrReady for a salt-water swim and the feel of sand between your toes The beautiful white-sand beach and crystal-clear waters of Tampa Bay are just across the street. The water here is shallow with a sandy bottom, so it's usually a great place to swim with children, or just float on the smooth waters. Fishermen love to wade out a distance from the shore and cast their lines, while shell-seekers know they're likely to find something special in this relatively unpopulated section of the beach. The charming Historic Anna Maria City Pier is just 200 yards down the beach.brbrWhen the shopping bug bites, or you feel like eating out, you can walk to Anna Maria's restaurants and shops, as well as the Historic Society Museum and Community Playhouse. Ready for something a bit further afield Catch the free Island Trolley to travel the length of the Island from 6 am to 10 pm. Get off anywhere to access the Gulf beaches, walk as far down the beach as you'd like, and then catch the trolley for a ride home...all you need is shoes to get on and off the Island's favorite mode of transportation.brbrSleeps 7. Stays of less than one week may be available depending on time of year.brbr*PET OWNERS: This property is dog friendly for one dog with a maximum weight of 25 pounds and a non-refundable pet fee of $150 for the first week. There is a $50 fee per week for any additional weeks booked. Also, certain breeds are excluded. It is necessary that you check with our office prior to your trip for details on weight and breed limitations.brbrA NOTE ABOUT POOL HEAT: If you book online, your reservation will automatically populate with a pool heat charge for one week. If your reservation is for a longer period, someone on our staff will adjust the pool heat rate to reflect the longer stay. We recommend pool heat at this property, regardless of the time of year, as pools near shady trees stay cooler, even in the summer.brbrOur Cancellation Policy: In order to protect our owners from loss of income, ALL MONIES PAID TOWARDS YOUR RESERVATION MAY BE NON-REFUNDABLE AFTER A CERTAIN DATE! FULL AND PARTIAL REFUNDS MAY BE GIVEN UNDER CERTAIN CONDITIONS. Ask our office for details, or check your rental agreement.

HEATED POOL & SPA ON CANAL, FREE WiFi & Trolley, Close to Beach & Bay!

Anna Maria, Florida, United States

Bed

Bath

Sleeps

$397.6

Escape to paradise at Lakeview Cottage, a beautifully updated island retreat just one block from Pine Avenue and the stunning Gulf beaches of Anna Maria Island. Perfect for couples or small families, this charming 2-bedroom cottage comfortably sleeps 4 with two king beds.brbrRelax in your private heated pool and spa, unwind on the spacious screened porch, or refresh in the outdoor hot-and-cold shower surrounded by lush tropical landscaping. Inside, enjoy vaulted ceilings, an open-concept living area, updated kitchen with island seating, wine fridge, and plenty of space to gather and relax.brbrWalk to restaurants, shops, the Anna Maria City Pier, beaches, museums, and moreor hop on the free Island Trolley nearby to explore the island with ease.brbrHighlights:brbrPrivate heated pool & spabrbr2 king bedroomsbrbrScreened porch & outdoor showerbrbrUpdated kitchen with wine fridgebrbrWalkable location near beach & Pine AvenuebrbrFree Island Trolley nearbybrbrDog-friendly (1 small dog allowed with fee)brbrYour perfect Anna Maria Island getaway awaits!brbr*PET OWNERS: This property is dog friendly for one dog with a maximum weight of 25 pounds and a non-refundable pet fee of $150 for the first week. There is a $50 fee per week for each additional week booked. Also, certain breeds are excluded. It is necessary that you check with our office prior to your trip for details on weight and breed limitations.brbrA NOTE ABOUT POOL HEAT: If you book online, your reservation will automatically populate with a pool heat charge for one week. If your reservation is for a longer period, someone on our staff will adjust the pool heat rate to reflect the longer stay. We recommend pool heat at this property, regardless of the time of year, as pools near shady trees stay cooler, even in the summer.brbrStays of less than one week may be available during the off-season and at the last minute; check with our office for details!brbrOur Cancellation Policy: In order to protect our owners from loss of income, ALL MONIES PAID TOWARDS YOUR RESERVATION MAY BE NON-REFUNDABLE AFTER A CERTAIN DATE! FULL AND PARTIAL REFUNDS MAY BE GIVEN UNDER CERTAIN CONDITIONS. Ask our office for details, or check your rental agreement.

Heated Pool & Spa, FREE WiFi, Near AMI Beach & Village, Dog* (See Note) Friendly!

Anna Maria, Florida, United States

Bed

Bath

Sleeps

$656.3

Welcome to Southern Belle Beach House located just steps away from the Gulf beaches of Anna Maria Island. Southern Belle is an elevated beach home with a patio surrounded by tropical landscaping where you can enjoy the outdoor shower, picnic table and Weber grill, as well as the heated pool located under the main floor. For a day at the beach, we have provided a beach wagon, chairs and umbrella.brInside the home located on the main floor you will find that the fully equipped kitchen has bar seating as well as a dining table for 8 and is open to the spacious living area. You can access the porch area through the sliding doors in the living area. Also located on the main floor is the half bath and laundry room, as well as the master suite with a king bed complete with 600 thread count prima cotton wrinkle free sheets.brUpstairs you will find the 2 other bedrooms, one with a king size bed, one with 2 twins and both have a private bathroom. Linens, towels and beach towels are included in the home.brbrLizzie Lu's Island Retreat is a full-service property manager on Anna Maria Island to ensure our guests enjoy some of the nicest, well stocked homes on the island. For an additional charge, we offer GEM cars among other services. Rest assured we are here to assist as needed in the most efficient manner possible. While vacationing on Anna Maria Island, please adhere to our local rules and regulations for our residential community which are included in our homes as well as our arrival information.

Beautiful Luxury Southern Style Home located in Anna Maria - Walk easily to Beach, Sleeps 6!

Anna Maria, Florida, United States

Bed

Bath

Sleeps

$435.32

**ASK ABOUT LAST-MINUTE DEALS!brbrWelcome to your perfect Anna Maria Island getawaya beautifully designed 4-bedroom, 3-bath ground-floor cottage ideally located just one block from the pristine sands of Bean Point Beach and the tranquil Bay Beach park.brbrFrom the moment you arrive, you'll feel at ease in this relaxed coastal retreat designed for comfort, gathering, and effortless island living.brbrStep outside to your private backyard oasis, where a full-length patio invites you to unwind in the ...sun or shade. Enjoy outdoor dining, grilling with family and friends, or lounging poolside under umbrellas. Take a refreshing dip in your heated private pool, the centerpiece of this serene outdoor space.brbrInside, the home is thoughtfully equipped for group stays. The open-concept kitchen is fully stocked and flows into a dining area with seating for eightperfect for shared meals, game nights, and planning your island adventures.brbrSleeping accommodations include:brbrPrimary suite with king bed, ensuite bath (dual sinks, walk-in shower), and private outdoor accessbrbrTwo guest bedrooms with queen bedsbrbrBunk room featuring a twin-over-full bunk plus twin trundleideal for kids or extra guestsbrbrAdditional conveniences include multiple bathrooms, comfortable gathering spaces, and modern amenities designed to make your stay seamless.brbrLocated in one of Anna Maria Island's most desirable areas, you're just steps from Bean Point Beach, bay-side sunsets, and scenic park areas. Explore seven miles of uninterrupted beaches, soft white sand, and crystal-clear waters. Catch unforgettable sunsets in the evening or sunrise views over the Tampa Bay Bridge from the Pier.brbrHop on the free island trolleyrunning from 6 a.m. to 10 p.m.for easy access to local shops, cafes, and restaurants, or spend your days exploring the charm of the island at your own pace.brbrAdditional Notes:brbrPool heat is recommended year-round and may be included automatically depending on booking durationbrbrDog-friendly with restrictions and applicable pet fees ($150 first dog per week, $50 per additional dog per week; breed/weight restrictions applyplease inquire before booking)brbrWhether you're gathering with family or escaping for a coastal retreat, this home offers the perfect blend of comfort, location, and laid-back island living.brbrOur Cancellation Policy: In order to protect our owners from loss of income, ALL MONIES PAID TOWARDS YOUR RESERVATION MAY BE NON-REFUNDABLE AFTER A CERTAIN DATE! FULL AND PARTIAL REFUNDS MAY BE GIVEN UNDER CERTAIN CONDITIONS. Ask our office for details, or check your rental agreement.

CHARMING COTTAGE | Steps to Bean Point Beach | Private Heated Pool | Family-Friendly Island Retreat | FREE WIFI /Trolley, Dog*(See Note) Friendly!

Anna Maria, Florida, United States

Bed

Bath

Sleeps

$431.6

Dock Holiday by Anna Maria Life Vacation Rentalsbr235 Chilson Ave, Anna Maria, FL 34216brbrWhat You'll Love About This Home:brLocation! 1.5 Blocks to the Beach! On a Canal!br3 Bed / 2 BathbrKing, Queen, 2 TwinsbrPrivate Heated Pool & SpabrOutdoor ShowerbrPoolside Patio Dining for 4brAdirondack ChairsbrCovered Poolside Patio Set brPing Pong TablebrPutting Green brGas GrillbrBoat Dock Space Available for 15' - 18' BoatbrDrip Coffee MakerbrProfessional Linen Service, Washer & DryerbrComplimentary WIFIbrFenced BackyardbrBeach Towels, Beach Chairs & Beach WagonbrParking for 4 CarsbrbrDetails:brWelcome to Dock Holiday, our canal front vacation home located 1.5 blocks to the sugar sand beaches of Anna Maria!brbrThe main living space includes the kitchen, dining and living rooms and is filled with natural light from the patio doors leading to the pool. Dining options include the dining room table which seats six and counter bar seating at the kitchen island for four.brbrThe master bedroom features a king bed with an ensuite bathroom. One of the guest rooms includes a queen bed and the other has two twin beds. Each bedroom includes a TV, and crisp linens and plush towels from our professional linen company.brbrYour guests will stay connected with complimentary WIFI and enjoy all of the comforts of home, including a washer and dryer.brbrA sparkling, heated pool and spa with an outdoor shower are highlights of the fenced backyard. A gas grill, outdoor patio dining table for four, Adirondack chairs and a covered lounge set lend to a relaxing afternoon poolside. Guests will also enjoy the putting green, and a ping pong table.brbrThe canal side dock provides an ideal spot to fish and enjoy nature. Be prepared to see a variety of native Florida birds and possibly a dolphin or manatee. Kayaks and paddleboards may also be launched from the dock for a relaxing paddle into Bimini Bay.brbrYou may bring a 15 - 18 ft boat to dock at the home. There is a boat docked on the dock but there is up to 18 feet of dock remaining available.brbrDock Holiday is easy walking distance to many shops and restaurants, and less than a block to the free island trolley, which travels the entire length of the 7 miles of the island. Hop on and off at your leisure and explore shopping, dining and the beaches. The perfect location for your next beach vacationbrbrYou 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. brbrBedroom 1 - King Bed, Ensuite Bathroom, TVbrBedroom 2 - Queen Bed, TVbrBedroom 3 - Two Twin Beds, TVbrbrPlease note:brAmenities are subject to change.brThe Owner's boat will be docked at the home year-round. Boat lifts and any motorized watercraft are not available for guest use. **brThis home is not dog friendly.brbrDISCLAIMER: Depth of the canals and channels vary depending on tides, weather, and other circumstances beyond our control. At times this can result in a water level that is too low to support watercraft. Additionally, the entrance to the canal has a bridge that may have limited access during high tide. It is the responsibility of the guest to review forecasts and make alternate arrangements for watercraft as necessary.brbrVR16-000175brbrIMPORTANT INFORMATION: brbrYour booking is with Anna Maria Life Vacation Rentals. We will send you check-in instructions 14 days prior to your arrival date. We will send you our rental agreement in an electronic signature document. Please review and return to us by following the instructions.brbr** Your signed rental agreement must be returned in order to receive your check-in details. brbrVRBO BOOKINGSbrbrAnna Maria Life Vacation Rentals will charge your credit card for your deposit payment. You will also see a separate charge by VRBO for their service fee. brbrYour final balance is due 60 days prior to your arrival date. We will send you a final payment reminder 90 days prior to arrival. We do not automatically charge your card for your final balance. brbrThe instructions for making your final payment will be included in your final payment reminder.brbrPlease review the cancellation policy prior to booking. brbrGOOGLE VACATION RENTAL BOOKINGSbrbrYour payment is due in full at the time of booking and the final balance information above does not apply to your reservation.

Dock Holiday: On Canal, Pool & Spa by Anna Maria Life Vacation Rentals

Anna Maria, Florida, United States

Bed

Bath

Sleeps

$227.46

Sunrise Garden #4brbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrFreshly Remodeled Island Suite w/ Pool | Pet-Friendly Paradise in Anna MariabrbrWelcome to your dream island getaway—beautifully remodeled and perfectly located just steps from the Gulf of Mexico! This bright and modern ground-floor suite offers everything you need for a relaxing, worry-free vacation on Anna Maria Island.brbrInside the SuitebrbrStep into a fresh coastal retreat featuring:brbrA fully equipped kitchen (no dishwasher) with everything you need to cook and dine in comfortbrbrA cozy living area with TV—perfect for unwinding after a day at the beachbrbrComplimentary locally roasted Sarasota coffee to start your mornings rightbrbrFree WiFi, so you can stay connected and share your favorite island momentsbrbrResort-Style AmenitiesbrbrYour stay includes access to a sparkling shared pool, outdoor BBQ grills, and on-site laundry facilities.brTraveling with family or friends There are 16 total units on the property—book multiple to enjoy time together while still having your own private space!brbrPet-Friendly EscapebrbrBring your furry family members—up to 2 dogs are welcome! Enjoy peaceful morning walks and sunset strolls with your pets by your side.brbrLocation, Location, LocationbrbrLocated just steps from the Gulf of Mexico’s white-sand beaches, this suite puts you right in the heart of Anna Maria’s charm.brbrBayfront Park – less than ½ mile away, perfect for picnics and incredible viewsbrbrManatee Public Beach – just 3 miles away, offering volleyball courts, grills, gift shops, and soft sandsbrbrSurrounded by local restaurants, boutique shops, and ocean adventures like paddleboarding, kayaking, and deep-sea fishingbrbrAdditional DetailsbrbrPool heat not available from May through OctoberbrbrFree parking for one vehiclebrbrSmart E-lock entry – unique code provided for each guest for easy, contactless check-inbrbrNo smoking inside the unitbrbrCome relax, recharge, and rediscover Anna Maria Island! Whether you're here for a romantic weekend, a family getaway, or a solo beach retreat, this freshly updated suite offers the perfect blend of coastal comfort and island adventure.brbrCity/town permit number: VR20-000078brbrYou must be 21 years or older to rent this property.brbrIf you are bringing a dog on your trip, the pet fee is already included in your quote when selecting ‘Yes’ to pets. If you would like to add more dogs, please contact us.brbrParking notes: There is free parking available for 1 vehicle.brbrbrbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 21 years of age to book. Guests under 21 must be accompanied by a parent or legal guardian for the duration of the reservation.

Freshly Remodeled Island Suite w/ Pool & Pet Friendly

Anna Maria, Florida, United States

Bed

Bath

4

Sleeps

$420.7

Tucked away on the coveted north end of Anna Maria Island, this charming 2-bedroom, 2-bathroom home offers the perfect blend of coastal comfort and laid-back luxury—just two blocks from the Gulf.brbrDesigned for easy island living, the home features a bright, open layout with inviting interiors and plenty of natural light throughout. Whether you're relaxing after a beach day or gathering with family and friends, the space feels both cozy and functional.brbrStep outside to your own private retreat, where a private pool and multiple outdoor living areas create the ideal setting for soaking up the Florida sunshine. A unique highlight of the property is the private putting green—perfect for a little friendly competition or unwinding with a fun outdoor activity.brbrLocated just a short stroll from the sugar-white sands and turquoise waters of the Gulf, this home offers both convenience and a peaceful island atmosphere. Whether you're planning a romantic escape or a small group getaway, this north end gem delivers a true Anna Maria Island experience.brbrBEACH DISCLAIMER: Please be aware that the beach and sand may differ from the photos due to natural processes like tides, weather, and erosion. The beach environment is dynamic and constantly changing, and we appreciate your understanding. Enjoy the beauty of our beachfront properties!brbrPETS: Please note this property does NOT allow pets. brbrPARKING: 2 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.brbr***OVERCROWDING CONSEQUENCES***: Maximum occupancy of rental homes on Anna Maria Island are set by the Cities and are strictly enforced. An occupant is any person staying overnight, regardless of the number of nights. Due to recent issues of overcrowding in the area, if maximum occupancy is exceeded during your stay, a $1000 (one thousand dollar) overcrowding fee will be charged to the payment method on file and your party will be immediately evicted. We appreciate your understanding and cooperation to keep Anna Maria Island enjoyable for everyone.brbrYou 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.br*Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.

Aloha House: beautiful north end pool home

Anna Maria, Florida, United States

Bed

Bath

Sleeps

$226.38

Sunrise Garden #15brbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrFreshly Remodeled Island Suite w/ Pool | Pet-Friendly Paradise in Anna MariabrbrWelcome to your dream island getaway—beautifully remodeled and perfectly located just steps from the Gulf of Mexico! This bright and modern ground-floor suite offers everything you need for a relaxing, worry-free vacation on Anna Maria Island.brbrInside the SuitebrbrStep into a fresh coastal retreat featuring:brbrA fully equipped kitchen (no dishwasher) with everything you need to cook and dine in comfortbrbrA cozy living area with TV—perfect for unwinding after a day at the beachbrbrComplimentary locally roasted Sarasota coffee to start your mornings rightbrbrFree WiFi, so you can stay connected and share your favorite island momentsbrbrResort-Style AmenitiesbrbrYour stay includes access to a sparkling shared pool, outdoor BBQ grills, and on-site laundry facilities.brTraveling with family or friends There are 16 total units on the property—book multiple to enjoy time together while still having your own private space!brbrPet-Friendly EscapebrbrBring your furry family members—up to 2 dogs are welcome! Enjoy peaceful morning walks and sunset strolls with your pets by your side.brbrLocation, Location, LocationbrbrLocated just steps from the Gulf of Mexico’s white-sand beaches, this suite puts you right in the heart of Anna Maria’s charm.brbrBayfront Park – less than ½ mile away, perfect for picnics and incredible viewsbrbrManatee Public Beach – just 3 miles away, offering volleyball courts, grills, gift shops, and soft sandsbrbrSurrounded by local restaurants, boutique shops, and ocean adventures like paddleboarding, kayaking, and deep-sea fishingbrbrAdditional DetailsbrbrPool heat not available from May through OctoberbrbrFree parking for one vehiclebrbrSmart E-lock entry – unique code provided for each guest for easy, contactless check-inbrbrNo smoking inside the unitbrbrCome relax, recharge, and rediscover Anna Maria Island! Whether you're here for a romantic weekend, a family getaway, or a solo beach retreat, this freshly updated suite offers the perfect blend of coastal comfort and island adventure.brbrCity/town permit number: VR20-000081brbrYou must be 21 years or older to rent this property.brbrIf you are bringing a dog on your trip, the pet fee is already included in your quote when selecting ‘Yes’ to pets. If you would like to add more dogs, please contact us.brbrParking notes: There is free parking available for 1 vehicle.brThis rental is located on floor 1.brbrbrbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 21 years of age to book. Guests under 21 must be accompanied by a parent or legal guardian for the duration of the reservation.

Freshly Remodeled Island Suite w/ Pool & Pet Friendly

Anna Maria, Florida, United States

Bed