Vacation Condo Rentals By Owner In Anna Maria, FL

Sunrise Garden #2brbrOur 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.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

Bath

Sleeps

$285.64

Sunrise Garden #8brbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrWelcome back to your favorite island getaway—now better than ever! This beautifully remodeled ground-floor suite in Anna Maria offers the same soothing ocean breeze and peaceful charm you love, with fresh new furnishings and thoughtful upgrades to elevate your stay.brbrInside: fully equipped kitchen (no dishwasher), dining space, living area with TV, and complimentary Sarasota-roasted coffee to start your mornings. Free WiFi included.brbrAmenities: access to shared swimming pool, grills, and on-site laundry. Multiple units are available on the property (16 in total) for larger groups traveling together who want to stay together but also have their private space.brbrEnjoy the perfect blend of convenience, comfort, and coastal charm just steps from the Gulf of Mexico..brbrDiscover the Magic of Anna Maria IslandbrLet this hidden gem melt your stress away with its postcard-perfect beaches, small-town charm, and endless opportunities for ocean adventures. Whether you're into deep-sea fishing, paddleboarding, or simply soaking up the sun, you'll find it here.brbrHungry You’re surrounded by fantastic local restaurants in every direction—perfect for when you want to skip the cooking and treat yourself. Just half a mile away is Bayfront Park, a family favorite thanks to its incredible views and relaxed vibe. And just three miles away, Manatee Public Beach awaits with soft white sands, volleyball courts, picnic areas, grills, gift shops, and plenty of space for the whole family to play.brbrYour dream beach escape starts here—book your stay and experience all that Anna Maria has to offer!brbrbrWe will not be accepting payments for pool heat for the months of May through October.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

Bath

Sleeps

$250.09

Sunrise Garden # 17brbrOur 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: VR20-000083brbrYou 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

Sleeps

$294.71

Welcome to The Bayou 5C! With a prime location the north side of Pine Avenue on Anna Maria Island. The Bayou 5C is the perfect location for a relaxing Island getaway. This two-bedroom/ one-bath condo features updates throughout and has been designed for a family or romantic vacation in mind. The floor plan takes advantage of the water views from the living, dining and kitchen area. The balcony off the living area allows for morning coffee and provides direct access to your own private fishing or kayaking pier where you can launch from each morning to explore the waterways of Anna Maria. Shared washers and dryers.br br HIGHLIGHTS br br br Two kayaks (waiver signature required)br br br Private fishing/ kayak dockbr 822 sq ftbr Televisions in every bedroombr Fully equipped kitchen br br BEDROOMS br Sleeps 4br Primary Bedroom: King br Second Bedroom: Two twinsbr br BATHROOMSbr Primary bathroom: Shower/Tub Combobr br EXTERIORbr The Bayou 5C is located within The Bayou community. This community is located off Pine Avenue and is approximately 0.1 mile from the Anna Maria City Pier and the Bayview Plaza with coffee and ice cream shops. Coconut Bayou offers the use of 2 kayas that can be launched at its own private dock #7. br If you are interested in fishing off the dock during your visit, a saltwater fishing license would be required if you are over 16 or under 65. To obtain a Fishing License, you may go to the local bait and tackle shops, some marinas, or any tax collector office (3340 East Bay Dr, Holmes Beach, FL 34217).br br There is one allocated parking space assigned to the unit along with extra guest parking spots. This Condo Association does not permit motorcycles, trailers, large trucks, or RV parking. This property does not accommodate golf carts.br br Please keep in mind that 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.br Amenities Include:br - Bedroom 1 Kingbr - Bedroom 2 2 Twinsbr - Bathroom 1 Shower /Tubbr - Hot Waterbr - Water View Ybr - Canal Viewbr - Canal Accessbr - Central A Cbr - Cental Heatbr - Sqft under a c 822br - Free Parkingbr - Parking Spots 1br - Assigned Parkingbr - Self Check Inbr - Keyless Entrybr - Bath Towelsbr - Beach Towelsbr - Quality Linensbr - Hair Dryerbr - Hangersbr - Refrigeratorbr - Stovebr - Cookwarebr - Toasterbr - Blenderbr - Keurigbr - Drip Coffee makerbr - Dishwasherbr - Microwavebr - Dining Tablebr - TV 3br - Cable Channelsbr - Shared Laundrybr - Ironbr - Ironing Boardbr - Cleaning Kitbr - First Aid Kitbr - Fire Extinguisherbr - Smoke Alarmbr - Balconybr - Fishing Dockbr - Kayakbr - Exterior Outlet No - Golf carts not allowedbr - Duncan Emerald Club

Coconut Bayou by Duncan Real Estate

Anna Maria, Florida, United States

Bed

Bath

Sleeps

$103.03

South Bay Inn 4brbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrEscape to your perfect Anna Maria Island retreat at this charming romantic getaway just steps from the sparkling waters of the bay. Ideal for couples or solo travelers, this welcoming retreat offers the perfect blend of comfort, relaxation, and island charm.brbrLocated directly across the street from the bay, you’ll enjoy peaceful water views and easy beach access via a short sandy path. Spend your days strolling along the shoreline, relaxing under the Florida sun, or exploring the picturesque beauty of Anna Maria Island.brbrBack at the property, unwind in the shared heated pool, surrounded by lush tropical landscaping. Comfortable outdoor seating invites you to relax in the ocean breeze with your morning coffee or evening glass of wine. Inside, the space is thoughtfully designed to ensure a comfortable and stress-free stay.brbrThis rental is perfectly positioned within walking distance of Pine Avenue, home to local boutiques, cafés, and some of the island’s favorite dining spots. Bayfront Park is also nearby, offering picnic areas, sandy beaches, and great fishing. For those looking to explore further, the tranquil sands and stunning sunsets of Bean Point are just a short one-mile drive away.brbrWhether you’re seeking romance, relaxation, or quiet time near the water, this Anna Maria Island escape offers a charming and convenient base for your stay.brbrTHINGS TO KNOWbrbrAll guests occupying this property who are under the age of 25 must be accompanied by a parent or legal guardian.brF is available upon request for $22 per day plus tax. 24 hour advance notice is required. Heat may not be available if temperatures drop below 65 degrees.brbrParking notes: There is free parking available for 2 vehicles.brThis rental is located on floor 2.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 25 years of age to book. Guests under 25 must be accompanied by a parent or legal guardian for the duration of the reservation.

2nd-floor condo across the street from the beach with heated pool, balcony, W/D

Anna Maria, Florida, United States

Bed

Bath

Sleeps

$384.29

brThis rental is part of the Anna Maria Beach Cottages. More information on this charming property below!brbrCottage 109A is the perfect place for a small family or a couples’ getaway on Anna Maria Island! One of the charming Anna Maria Beach Cottages, this is a 1 bed/1 bath second-floor vacation home with a balcony surrounded by tropical landscaping and is just a few minutes walk to the white Gulf sands.brbrThis unit features a wrap-around balcony with outdoor dining, a full kitchen, a cozy living room, and a full bathroom with a walk-in shower. Enjoy meals al fresco on the deck surrounded by green palms and a blue sky overhead. Or curl up with a book in the nook of the bright entry porch. brbrThe master suite enjoys a sunny southern exposure and includes a queen bed and spacious ensuite bathroom with a large walk-in shower. And the comfy couch converts to a full sleeper sofa, providing sleeping space for two more guests.brbrYou’ll also have access to all the amenities the Anna Maria Beach Cottages has to offer, including a heated pool with a lounge area, assorted beach gear, bikes, picnic area with grills, onsite shared laundry and an on-site office for area information and support during your stay. Continue reading for more about this sweet and enchanting place!brbrbrPlease note that pets are not allowed in this rental.brbrbrABOUT ANNA MARIA BEACH COTTAGESbrbrBe whisked away to an Old Florida beach cottage experience! An Island vacation favorite, Anna Maria Beach Cottages preserves the charm of yesterday alongside modern conveniences. Snuggled just a few steps from the beach between Oak Avenue and Mangrove Avenue on Anna Maria Island’s gorgeous north-end, you’ll have the beach within reach, a cozy place to call home, and plenty of vacation adventures close by.brbrMade up of six buildings with eleven rental homes between them, Anna Maria Beach Cottages marries a homestyle atmosphere with resort-style service. The Cottages range from studio-size to three bedrooms, all including a kitchen. There is an on-site office, a heated pool, a picnic area with grills, beach chairs and umbrellas, bikes, onsite shared laundry and lovely landscaping along the paths from building to building. brbrGroup gatherings are welcome, including weddings, family reunions, and company getaways. And with a ground-level, ADA accessible unit, multi-generational families can include grandparents and great-grandparents to take part in family vacation memories that will last a lifetime.brbrFrom this prime location, you can walk, bike, or take the free Island Trolley to check out shops, art, restaurants, excursions, and more. Pine Avenue is the center of activity on the north end, just a few minutes away, with great food and fun shops leading up to the Anna Maria Island City Pier. The heart of Holmes Beach has a wide array of activities and sights for everyone in your group. And Bridge Street is located to the south in Bradenton Beach, home to a boardwalk-style, “walkable community.” brbrAlso well within driving distance for day trips to popular Florida destinations, it’s easy to check out theme parks in Orlando, the aquarium and zoo in Tampa, zip-lining in Bradenton, museums and culture in Sarasota, or getting close to nature at one of many nearby state parks.brbrWhether you’re looking for a quick trip to disconnect (perhaps a long one ), a fun-filled change of pace, or a romantic weekend, Anna Maria Beach Cottages has what you need for a memorable holiday. Reserve your memories today!

Charming beach cottage close to the beach with Pool, Bikes, Beach gear and Grill

Anna Maria, Florida, United States

Bed

Bath

Sleeps

$489.86

brThis rental is part of the Anna Maria Beach Cottages. More information on this charming property below!brbrCottage 110A is a beautifully beachy place to call home on your next Anna Maria Island vacation! One of the charming Anna Maria Beach Cottages, this is a 2 bed/2 bath second-floor vacation home, with a large deck and only moments from the beach.brbrFeaturing a full kitchen, spacious living room, two bathrooms, and a large balcony area for relaxing or dining, you’ll have everything you need for a memorable trip. Perfect for a small family, two couples, or a friends’ quick getaway, this vacation rental sleeps up to six guests. brbrUpdated plank floors and traditional cypress walls alongside refreshing, modern décor in the renovated kitchen and bathrooms give you the best of both worlds. The master bedroom includes a queen bed and a TV, with a walk-in shower in the ensuite bathroom. A double bed and twin bed occupies the second bedroom with the guest bathroom just outside. A full-size sleeper sofa is available for larger groups or alternate sleeping arrangements. The guest bathroom has double sinks and a shower/tub combination, perfect for families with small children.brbrYou’ll also have access to all the amenities the Anna Maria Beach Cottages has to offer, including a heated pool with a lounge area, assorted beach gear, bikes, picnic area with grills, onsite shared laundry and an on-site office for area information and support during your stay. Continue reading for more about this sweet and enchanting place!brbrbrPlease note that pets are not allowed in this rental.brbrbrABOUT ANNA MARIA BEACH COTTAGESbrbrBe whisked away to an Old Florida beach cottage experience! An Island vacation favorite, Anna Maria Beach Cottages preserves the charm of yesterday alongside modern conveniences. Snuggled just a few steps from the beach between Oak Avenue and Mangrove Avenue on Anna Maria Island’s gorgeous north-end, you’ll have the beach within reach, a cozy place to call home, and plenty of vacation adventures close by.brbrMade up of six buildings with eleven rental homes between them, Anna Maria Beach Cottages marries a homestyle atmosphere with resort-style service. The Cottages range from studio-size to three bedrooms, all including a kitchen. There is an on-site office, a heated pool, a picnic area with grills, beach chairs and umbrellas, bikes, onsite shared laundry and lovely landscaping along the paths from building to building. brbrGroup gatherings are welcome, including weddings, family reunions, and company getaways. And with a ground-level, ADA accessible unit, multi-generational families can include grandparents and great-grandparents to take part in family vacation memories that will last a lifetime.brbrFrom this prime location, you can walk, bike, or take the free Island Trolley to check out shops, art, restaurants, excursions, and more. Pine Avenue is the center of activity on the north end, just a few minutes away, with great food and fun shops leading up to the Anna Maria Island City Pier. The heart of Holmes Beach has a wide array of activities and sights for everyone in your group. And Bridge Street is located to the south in Bradenton Beach, home to a boardwalk-style, “walkable community.” brbrAlso well within driving distance for day trips to popular Florida destinations, it’s easy to check out theme parks in Orlando, the aquarium and zoo in Tampa, zip-lining in Bradenton, museums and culture in Sarasota, or getting close to nature at one of many nearby state parks.brbrWhether you’re looking for a quick trip to disconnect (perhaps a long one ), a fun-filled change of pace, or a romantic weekend, Anna Maria Beach Cottages has what you need for a memorable holiday. Reserve your memories today!

Charming Cottage with modern amenities close to beach w/ pool, beach gear, bikes

Anna Maria, Florida, United States

Bed

Bath

Sleeps

$379.04

This rental is part of the Anna Maria Beach Cottages. More information on this charming property below!brbrCottage 107A is the perfect place for a small family or a couples’ getaway on Anna Maria Island! One of the charming Anna Maria Beach Cottages, recently updated 1 bed/1 bath second-floor vacation home overlooking the beautiful pool deck and is just a few minutes walk to the white Gulf sands.brbrThis unit was lovingly redecorated to compliment and highlight the beautifully restored original heart of pine wood floors and the original cypress wood ceilings and walls to complete the modern beach cottage look. Main features include a balcony with outdoor dining, a full kitchen, a cozy living room, and a full bathroom with a walk-in shower. Enjoy meals al fresco on the deck surrounded by green palms and a blue sky overhead. Or curl up with a book in the nook of the bright entry porch.brbrThe master suite features a queen bed and spacious ensuite bathroom with a large walk-in shower. The overstuffed sofa in the living room isn’t just for sinking into after a long day of sun and sand, it’s also a sleeper sofa, providing sleeping space for two more guests. brbrYou’ll also have access to all the amenities the Anna Maria Beach Cottages has to offer, including a heated pool with a lounge area, assorted beach gear, bikes, onsite shared laundry and an on-site office for area information and support during your stay. Continue reading for more about this sweet and enchanting place!brbrbrPlease note that pets are not allowed in this rental.brbrbrABOUT ANNA MARIA BEACH COTTAGESbrbrBe whisked away to an Old Florida beach cottage experience! An Island vacation favorite, Anna Maria Beach Cottages preserves the charm of yesterday alongside modern conveniences. Snuggled just a few steps from the beach between Oak Avenue and Mangrove Avenue on Anna Maria Island’s gorgeous north-end, you’ll have the beach within reach, a cozy place to call home, and plenty of vacation adventures close by.brbrMade up of six buildings with eleven rental homes between them, Anna Maria Beach Cottages marries a homestyle atmosphere with resort-style service. The Cottages range from studio-size to three bedrooms, all including a kitchen. There is an on-site office, a heated pool, a picnic area with charcoal grills, beach chairs and umbrellas, bikes, and lovely landscaping along the paths from building to building. brbrGroup gatherings are welcome, including weddings, family reunions, and company getaways. And with a ground-level, ADA accessible unit, multi-generational families can include grandparents and great-grandparents to take part in family vacation memories that will last a lifetime.brbrFrom this prime location, you can walk, bike, or take the free Island Trolley to check out shops, art, restaurants, excursions, and more. Pine Avenue is the center of activity on the north end, just a few minutes away, with great food and fun shops leading up to the Anna Maria Island City Pier. The heart of Holmes Beach has a wide array of activities and sights for everyone in your group. And Bridge Street is located to the south in Bradenton Beach, home to a boardwalk-style, “walkable community.” brbrAlso well within driving distance for day trips to popular Florida destinations, it’s easy to check out theme parks in Orlando, the aquarium and zoo in Tampa, zip-lining in Bradenton, museums and culture in Sarasota, or getting close to nature at one of many nearby state parks.brbrWhether you’re looking for a quick trip to disconnect (perhaps a long one ), a fun-filled change of pace, or a romantic weekend, Anna Maria Beach Cottages has what you need for a memorable holiday. Reserve your memories today!

Anna Maria Beach Cottage 107A Pool, bikes, beach gear, moments from the sand!

Anna Maria, Florida, United States

Bed

Bath

Sleeps

$380.47

This rental is part of the Anna Maria Beach Cottages. More information on this charming property below!brbrCottage 110G is the perfect place for a small family or a couples’ getaway on Anna Maria Island! One of the charming Anna Maria Beach Cottages, this recently remodeled 1 bed/1 bath ground-level vacation home is close to the beautiful pool deck and only moments to the turquoise water of the Gulf beach.brbrThis cozy rental features a front patio, corner kitchen, dining area, living room, and private bedroom. A trellis over the patio and the surrounding hibiscus offers a sun-dappled and welcoming place to enjoy a meal or just relax in the fresh Florida air. brbrThe master suite includes a queen bed with a spacious en-suite bathroom, complete with a walk-in shower. The overstuffed sofa in the living room isn’t just for sinking into after a long day of sun and sand, it’s also a sleeper sofa, providing sleeping space for two more guests.brbrYou’ll also have access to all the amenities the Anna Maria Beach Cottages has to offer, including a heated pool with a lounge area, assorted beach gear, bikes, picnic and grilling area, onsite laundry and an on-site office for area information and support during your stay. Continue reading for more about this sweet and enchanting place!brbrbrPlease note that pets are not allowed in this rental.brbrbrABOUT ANNA MARIA BEACH COTTAGESbrbrBe whisked away to an Old Florida beach cottage experience! An Island vacation favorite, Anna Maria Beach Cottages preserves the charm of yesterday alongside modern conveniences. Snuggled just a few steps from the beach between Oak Avenue and Mangrove Avenue on Anna Maria Island’s gorgeous north-end, you’ll have the beach within reach, a cozy place to call home, and plenty of vacation adventures close by.brbrMade up of six buildings with eleven rental homes between them, Anna Maria Beach Cottages marries a homestyle atmosphere with resort-style service. The Cottages range from studio-size to three bedrooms, all including a kitchen. There is an on-site office, a heated pool, a picnic area with grills, beach chairs and umbrellas, bikes, onsite shared laundry and lovely landscaping along the paths from building to building. brbrGroup gatherings are welcome, including weddings, family reunions, and company getaways. And with a ground-level, ADA accessible unit, multi-generational families can include grandparents and great-grandparents to take part in family vacation memories that will last a lifetime.brbrFrom this prime location, you can walk, bike, or take the free Island Trolley to check out shops, art, restaurants, excursions, and more. Pine Avenue is the center of activity on the north end, just a few minutes away, with great food and fun shops leading up to the Anna Maria Island City Pier. The heart of Holmes Beach has a wide array of activities and sights for everyone in your group. And Bridge Street is located to the south in Bradenton Beach, home to a boardwalk-style, “walkable community.” brbrAlso well within driving distance for day trips to popular Florida destinations, it’s easy to check out theme parks in Orlando, the aquarium and zoo in Tampa, zip-lining in Bradenton, museums and culture in Sarasota, or getting close to nature at one of many nearby state parks.brbrWhether you’re looking for a quick trip to disconnect (perhaps a long one ), a fun-filled change of pace, or a romantic weekend, Anna Maria Beach Cottages has what you need for a memorable holiday. Reserve your memories today!

Anna Maria Beach Cottage 110G Updated beach cottage, with pool and beach gear!

Anna Maria, Florida, United States

Bed

Bath

4

Sleeps

$373.53

Welcome to your exclusive slice of paradise: Serenity Beach Haven. Nestled on the coveted North End of Anna Maria Island, this 3-bedroom, 1-bath property is a true hidden gem—a sophisticated, European-Modern Island Retreat right on the tranquil waterfront. This is not just a rental; it's a meticulously designed luxury escape offering the rare combination of secluded tranquility and immediate, effortless accessibility to the island's charm. Whether you are a couple seeking a memorable, intimate escape, a family creating lasting memories, or a remote professional demanding a quiet, high-performance workspace, this retreat offers perfect harmony. Due to its unique location and limited availability, we highly recommend securing your preferred dates immediately. Book your exclusive waterfront escape today before the calendar fills up

Serenity Beach Haven: a Waterfront Luxury Condo

Anna Maria, Florida, United States

Bed

Bath

Sleeps

$441.83

Seashell is 3 bedroom 2 bath second story condo that is set up like a single family home. It features wood floors, a king size bed in the master bedroom, one queen bed in the second bedroom as well as two twin beds in the third bedroom. The master bedroom ensuite has a shower, bath tub, granite vanity top with double sinks. Each bedroom has its own flat screen television. brbrThe living area has a open floor concept with a breakfast bar. The kitchen entails granite counter tops which features a full range of stainless steel appliances. The fully stocked kitchen includes all your household items that make you feel like you are at home. brbrFrom the living room area you have access to the front and back porch. Indulge in the large flat screen TV in the living room that offers sports package and all local channels. Relax, as natural light will illuminate the whole living space. If you are hosting guests, the dining room table seat up to 8 people. brbrThe front porch faces south toward Pine Avenue. The back porch faces north overlooking the private fenced pool . Outdoor furniture and a gas grill complete the private pool oasis. Beach wagon and beach items are also available. One assigned parking. Bus stop of the free Island trolley is just in front of the house. At this location you could completely forget your car!brDogs are welcome. Pet fee is $200 per pet plus taxes, maximum of 2 pets unless otherwise approved by FDR. brbrFree Wi-Fi, linens & towels, etc. + beach equipment provided.brbrAccommodates up to 6 people. Minimum Stay Required: 1 Week. brMax. parking: 1brbrYou 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.brbr* Cancellation more than 90 days prior to arrival will receive a deposit refund less a $250 cancellation fee. Cancellation less than 90 days prior to arrival will forfeit all deposit received. Cancellation less than 60 days prior to arrival will forfeit all monies on account. Cancellations must be confirmed in writing.

3 bedroom on Pine in Anna Maria Island, private pool and PET friendly!

Anna Maria, Florida, United States

Bed

Bath

Sleeps

$307.29

Seeking a private piece of Anna Maria Island charm This Anna Maria rental is ideal for a small family, a romantic escape, or a long overdue, quiet catch-up with close friends. Palm Court is an updated villa which sleeps 4, making it perfect for smaller groups. But don’t let the small size fool you, Palm Court Villas has everything you need for the ultimate vacation.brbrPalm Court is ideally situated in the heart of Anna Maria Village. Take a short walk to experience great shops, diverse restaurants, fishing piers and the Community Center. Beautiful white sand beaches are just one short block away and feature a wonderful row of Australian pine trees for shade and cool relaxing. When you’re ready to explore, jump on the free Island trolley that stops at the corner of Magnolia Ave and runs the entire length of Anna Maria Island.brbrThe owners have thought of all conveniences. You will find a modern, fully equipped kitchen, ample linens including beach towels, washer/dryer, and comfortable furnishings. There is a beach gear shed with beach cart, umbrella, chairs, and sand toys. The open tropical courtyard is a wonderful place to enjoy a late afternoon margarita or a relaxed dinner prepared on the charcoal grill.brbrSo, pack your flip flops, and get ready to enjoy charming Palm Court. And if you have a larger group, Villa A can be rented along with Villa B to allow a party of 8 to enjoy all this lovely rental has to offer.brbrbrFlexible check in days for most of the year--with the exception of holidays. Friday arrivals and departures during Peak Season. brbrIf you love this rental but are not getting a quote with the dates you've selected contact us so we can check the availability for you!brbrPlease note that pets are not allowed in this rental.brbr210 B MAGNOLIA ALSO AVAILABLE --RENT BOTH VILLAS TO ACCOMMODATE UP TO 8 GUESTS.brbrVacation rental professionally managed by Fran Maxon Real Estate, Inc

Beautiful Villa, Perfect Small Getaway. Close to beach, beach gear provided!

Anna Maria, Florida, United States

Bed

Bath

Sleeps

$357.94

Welcome to Barefoot Mermaid 3 a relaxed ground floor vacation rental located on the north end of gorgeous Anna Maria Island. The serene location of this property is just amazing. Located steps, less than 50 ft to white powder sand beaches of the Gulf of Mexico and less than a few flip flop steps to the restaurants and shops on Pine Ave and the free island trolley service. Barefoot Mermaid 3 is the Southeast unit of 4 units located within The Gulf Queen Apartments.br Barefoot Mermaid 3 has been newly renovated and decorated to maximize tropical comfort. As you enter you are greeted by an open plan living room and kitchen with gorgeous, polished terrazzo floors. Sit back, relax, and turn on your flat screen tv. We make sure you have the ability to stay connected with our free high-speed internet. br br This 1-bedroom 1 bath accommodates 3 adults. The bedroom features a queen bed and there is a sofa bed in the living room. The bathroom is located just off the bedroom and offers a tub shower combo and single sink. One outdoor parking spot is provided. All 4 units can be rented at the same time to accommodate a large family, reunion, or wedding parties with enough advanced notice. Catch some yoga on the beach starting at 8:30 a. m. on Saturdays at the Pine Ave beach access. br br The Gulf Queen Apartments offers a common laundry area and a golf cart charging station. br br Disclaimers: br br This property features Salty Mermaid Linens which include: br br *White Duvet covers and inserts, white bed linens, multi color beach towels, white bath towels, white washcloths, white bathroom floor towels, black makeup towels, kitchen towels, premium pillows, vacuum sealed throw blankets* br br *A starter kit of paper towels, toilet paper, trash bags, laundry detergent, and coffee & tea. Full sized luxury hand soap, shampoo, conditioner, and body wash are provided at check-in. Also available if requested, while supplies last, is a toothbrush and sewing kit. Any additional items that you may need during your stay can be purchased at one of the local grocery stores.* br br *No Pets Allowed* br br *No smoking or vaping on the premises* br br *1 outdoor parking space provided* br br *Check in time is 4pm on the day of your arrival, Check out time is 10am on the day of your departure. No early access or late departure is allowed unless special arrangements are made with our office, Our cleaning and Inspection team need time to ensure the rental is clean and safe for your stay* br br *Please note, all guests occupying this property who are under the age of 25 must be accompanied by a parent or legal guardian. Thank you!* br br *This home has a 4-night minimum stay requirement* br br *Reservations that are 30 nights or longer will require a mid-stay clean, one of our rental agents will provide more information at the time of booking. br br *Please note this is not a party or large gathering house. Noise complaints may result in eviction* br br *Please note there are security cameras on the exterior of the property*

Barefoot Mermaid 3, greatAMI location steps to the beach/fun on Pine Ave

Anna Maria, Florida, United States

Bed

Bath

Sleeps

$325.5

Discover this 2-bedroom condo in Anna Maria. The space features a king bed and twin beds, plus a cozy living room with a sofa bed, balcony, and a dock assigned to the condo for afternoon fishing or just relaxing by the water. With two bathrooms, 1 full bathroom and half bathroom for the 2nd room, the condo is equipped with a refreshing shower and hair dryer, comfort is never far away. Guests can enjoy a serene atmosphere perfect for relaxing after a day of exploring famous Pine Ave, swimming at beautiful turquoise water beach or walking to the famous City Pier, you are also a 2-minute walk to famous Waterfront Restaurant. Whether you’re unwinding indoors or stepping out, this lovely condo offers a fantastic home base. Experience the magic of Anna Maria amazing sunsets at our condo. 2 floor.

Cozy 2-bedroom condo with dock! Best location in Anna Maria. Beach & sunsets

Anna Maria, Florida, United States

Bed

Bath

Sleeps

$486.16

Charming elevated villa in the heart of Anna Maria with private heated pool and fenced yard. Short walk to City Pier and Gulf of Mexico sunsets. Enjoy two covered balconies, one overlooking Pine Avenue, the other your pool. Inside, spacious living areas with vaulted ceilings, designer furnishings, and reclaimed wood floors. Fully equipped kitchen with granite countertops. Relax with HDTV, WiFi, and cable in the comfortable living room. Perfect for a city escape with a traditional, casual feel.brbrTHINGS TO NOTEbr• Streaming services are accessible through your personal account.br• Up to 2 dogs are warmly welcomed in this residence for a fee of $250 plus tax per dog.br• This rental is situated on the second floor.br• Parking information: Complimentary parking is available for 2 vehicles.brbrMaximum Number of Vehicles Allowed: 2 Maximum Number of Day Guests Allowed: 2brbrIMPORTANT INFORMATION:brbrYour booking is with Island Real Estate Vacations. We will send you check-in instructions 30 days prior to your arrival date. Please review the cancellation policy prior to booking. Island Real Estate Vacations will charge your credit card for your deposit payment. You will also see a separate charge by VRBO for their service fee.br brPayment of reservation deposit is considered acceptance of all terms regardless of signature status of contract. Guest is responsible for adhering to the rental terms and dates. Any error on Guest’s part is not the responsibility of the agent. Sub-leasing of your vacation rental is strictly prohibited. A mid-stay clean and charge equal to the standard cleaning fee are required for all stays 21 nights or longer. By providing your phone number, you agree to receive text messages from our company. Message and data rates may apply. Message frequency varies. brbrYour final balance is due 60 days prior to your arrival date. Please note unless alternative arrangements are made, the bank account or credit card on file will be charged your remaining balance automatically at 60 days. If you do not wish to pay with the bank account or credit card on file, please reach out to pay several days in advance of 60 days prior to your arrival. If you initially paid with an eCheck and received the booking incentive, please remember future payments must also be made with an eCheck. Thank you for choosing eCheck to help reduce the cost of business. Please note the eCheck payment option cannot be used within 14 days of arrival. Any refunds on checks and echecks will be delayed at least 14 days after deposit or until funds are verified.brbrAnna Maria Island’s noise ordinance aims to ensure citizens can enjoy a peaceful environment. The ordinance applies to all areas of the city, including public and private property, and places of business. It defines noise as any sound that annoys or disturbs a reasonable person of ordinary sensibilities or causes or tends to cause an adverse physical or psychological effect on such reasonable person. The noise ordinance limits the maximum permissible noise levels to: br7 AM–10 PM: 65 decibels: (Consistently shouting in the pool exceeds 65 decibels)br10 PM–7 AM: 50 decibels: (An audible conversation from 50’ or 15 meters away exceeds 50 decibels)brThe ordinance also prohibits plainly audible noise, which refers to any sound that can be clearly heard by a person using their normal hearing faculties. This means that a person can still be in violation if the noise can be easily heard by responding officers from a distance of 100 feet from the property line. Fines for excessive noise can range from $100 to $1,000.brbrAll our properties provide luxury linens for you to enjoy during your stay.

AMI Outpost - 3 Bed 2 Bath Elevated Home - by Island Real Estate Vacations

Anna Maria, Florida, United States

Bed

Bath

Sleeps

$331.65

Located at the quiet North end of Anna Maria Island, this charming 2-bedroom, 1-bath villa is a short walk to beautiful white sand beaches at Bean Point where you can watch the dolphins play. Visit a variety of shops and restaurants along Pine Avenue in downtown Anna Maria less than a mile from the villa. Enjoy the Gulf breezes from the screened lanai or patio area. New furnishings throughout. The bedrooms have a King bed and 2 twin beds. Amenities include free wireless internet, Smart TV's, Cable, telephone, washer/dryer, dishwasher, microwave, gas grill, Mr. Coffee, and Keurig. Beach gear includes chairs, towels, beach wagon, umbrellas, and cooler. Occupancy limited to 4 persons, including children. brbrWe offer flexible check-ins and check-outs throughout the year, which makes it easier for you to book flights and get the best prices on your flights. We're close to 3 airports: Tampa International (56 mi./90 min drive), Sarasota International (20 mi/45 min drive), and St. Petersburg/Clearwater International (47 mi/75 min drive).brbrSee our adjoining property Gladiolus Hideaway HomeAway listing #4625973. brbr1. The unit is turn-key furnished. Towels & bed linens are included.brbr2. A beach wagon to haul your gear to the beach is provided. Umbrellas, folding chairs, beach towels, and beach toys too. brbr3. Enjoy outdoor cooking on the gas grill.brbr4. Relax or dine on the screened porch with table and chairs or on the patio under the umbrella.brbr5. Master bedroom has a King size bed & the second bedroom has 2 twins. brbr6. Bathroom has tub and shower. brbr7. There's also an outdoor shower spout for rinsing off after the beach.brbr8. The landline phone provides free local and long distance calling within the US and Canada.brbr9. Free high speed wireless internet.brbr10. Smart TVs located in the living room and master bedroom. Bring your Netflix or Amazon log-in information and stream all your favorite shows! brbr11. Games, books and puzzles for rainy days.brbr12. Sectional sofa and recliner make the living room a comfortable spot for reading or watching TV. brbr13. Ceiling fans in living room and both bedrooms. brbr14. Laundry room is complete with full size washer & dryer. Iron and ironing board provided. brbr15. We provide limited starter supplies including soap, a roll of toilet paper and a roll of paper towels. We keep a variety of cleaning supplies on hand, but we can't guarantee that these supplies will be replaced between guests. We do our best!brbr16. The kitchen is fully equipped with dishes, pots & pans, utensils, microwave, Mr. Coffee 8-cup drip coffee maker, Keurig coffee maker, and dishwasher.brbr17. Park right in front of the cottage. Room for 2 vehicles (no RVs, trailers, or boats). brbr18. This property is a duplex with back-to-back entrances, not side-by-side. You have your own private parking area, patio, and entrance. brbr19. We are located 6 houses from the beach access point at the north end of Gladiolus St. From there it's a short walk down a path between two homes to the beach. In recent years there has been an accretion of sand at Bean Point, so it's another short walk from the end of the path down to the water. All in all, about 5 minutes. A second beach access point at the end of N. Bay Blvd. (one street over) takes you over a wooden walkway right to the beach on the bay side of Bean Point.brbr20. We have a Property Manager on call in case of emergencies or maintenance problems. There is no charge to you for this extra peace of mind!brbr21. We use a cleaning service between guests and they do a great job. If you would like to hire them during your stay, please contact us or the Property Manager.brbrFlexible Check-in and checkout days --with some exceptions for holidays and certain times of the year.brbrIf you love this rental but are not getting a quote with the dates you've selected, contact us so we can check the availability for you!brbrPlease note that pets are not allowed in this rental.brbrVacation rental professionally managed by Fran Maxon Real Estate, Inc

Cute & cozy getaway at north end of Anna Maria Island. 5-min walk to the beach!

Anna Maria, Florida, United States

2

Bed

Bath

4

Sleeps

$290.61

brThis cute and cozy villa is aptly named Gladiolus Hideaway! Recently remodeled, this stylish yet comfy hideaway is the perfect beach retreat. Tucked away at the quiet North end of Anna Maria Island, you are only a 5-minute walk to the beach access at Bean Point. The villa is very private with its own entrance, parking area and patio. Experience gorgeous sunsets and long walks on beautiful white sand beaches . Explore a variety of shops and restaurants on Pine Avenue less than a mile from the property. You can also pick up the free Island trolley on Pine Avenue.brbrEnjoy Gulf breezes from the screened porch or patio area. Master bedroom has a king bed. A queen bed in the second bedroom makes it possible to accommodate up to four guests. Amenities include free wireless internet, Smart TV in living room and both bedrooms, Roku, Cable channels, land line phone, washer/dryer, dishwasher, microwave, coffee maker (Keurig and Mr. Coffee), gas grill and a variety of beach gear. brbrWe normally do not require Saturday check-ins and check-outs, which makes it easier for you to book flights and get the best prices on your flights. We're close to 3 airports: Tampa International (56 mi./90 min drive), Sarasota International (20 mi/45 min drive), and St. Petersburg/Clearwater International (47 mi/75 min drive).brbr1. The cottage is turn-key furnished. Towels & bed linens are included.brbr2. Enter the property via a private driveway and entrance. brbr3. A beach wagon is provided for hauling your gear to the beach. Umbrellas, folding chairs, cooler, beach towels and beach mats too. brbr4. Enjoy outdoor cooking on the gas grill.brbr5. Relax or dine on the screened porch with table and 2 chairs.brbr6. Lounge on the patio in the sun or under the umbrella. brbr7. Sleep soundly on a comfy King size bed. Second bedroom has a queen size bed. brbr8. Bathroom has a walk-in shower. brbr9. The landline phone provides free local and long distance calling within the US and Canada.brbr10. Free high speed wireless internet.brbr11. Smart TVs with streaming channels located in the living room and master bedroom. Bring your Netflix or Amazon log-in information and stream all your favorite shows! brbr12. Games and puzzles for rainy days. brbr13. Ceiling fans in living room and both bedrooms. brbr14. Full size washer & dryer on the screen porch. Iron and ironing board provided. brbr15. We provide limited starter supplies including soaps, toilet paper and paper towels. We keep a variety of cleaning supplies and detergents on hand, but we can't guarantee that these supplies will be replenished between guests. brbr16. The kitchen is fully equipped with all new stainless appliances, including refrigerator with ice maker, dishwasher, electric range, oven, and microwave. Dishes, pots & pans, utensils, toaster, blender and coffee makers (Mr. Coffee and Keurig) are provided. brbr17. Parking for a maximum of 2 vehicles (no RVs, trailers, or boats). Access to the parking area is by a private driveway off Jacaranda Street. brbr18. Just how close is the beach A beach access point at the end of N. Bay Blvd. (one street over) takes you over a wooden walkway right to the beach on the bay side of Bean Point. About a 5 minute walk. There is another beach access point at the north end of Gladiolus St (one block) that leads to Bean Point. The best swimming beach is on the Gulf side of Bean Point. In recent years there has been an accretion of sand at the point, so it's another short walk from the end of the path down to the water. All in all, about 8 minutes. brbr19. We have a Property Manager who is available to respond to your questions, as well as emergencies or maintenance problems. There is no charge to you for this extra peace of mind!brbr20. We provide a notebook with property information including detailed instructions for how to use the TVs, Roku, etc.brbr21. We use a cleaning service between guests and they do a great job. If you would like to hire the cleaning service during your stay, please contact the Property Manager.brbrIf you love this rental but are not getting a quote with the dates you've selected, contact us so we can check the availability for you!brbrPlease note that pets are not allowed in this rental.brbrVacation rental professionally managed by Fran Maxon Real Estate, Inc

Cozy North end hideaway! 5-min walk to beautiful white sand beach at Bean Point.

Anna Maria, Florida, United States

2

Bed