Cottage vacation rentals in Anna Maria Island

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Popular amenities for Anna Maria Island cottage rentals

Pet-friendly cottage rentals

Guest favorite
A comfortable seating area features two light-colored sofas with throw pillows, arranged around a rustic wooden coffee table. A decorative screen provides partial division from other spaces, and a textured rug is laid beneath the furniture, enhancing the warm ambiance of the room.
Cottage in Tampa
4.76 out of 5 average rating, 156 reviews

Good Vibes Cozy Cottage on Million $ Row

JessicaRating, 5 stars2 weeks ago
Place and location were great! And host was super communicative. It is small but that is expected based on the listing information. Would definitely go back!
Top guest favorite
A spacious backyard is featured, bordered by a wooden fence for privacy and lined with tropical plants and trees. A concrete patio area is included, which features a grill covered for protection. The lawn is open and well-maintained, providing a serene outdoor space.
Cottage in Gulfport
4.96 out of 5 average rating, 152 reviews

The Pelicans Roost / Gulfport

KerryRating, 5 stars3 months ago
Excellent place to stay - had everything promised and was perfect for 3 people. Loved the backyard
Superhost
A wide sandy beach stretches along the shoreline, with gentle waves lapping at the shore. Clear blue skies and a hint of distant buildings mark the horizon. The beach offers ample space for relaxation and recreation.
Cottage in Treasure Island
4.89 out of 5 average rating, 27 reviews

BEACH COTTAGE II

MelissaRating, 5 stars9 months ago
The house was very nice, not huge, but very accurate with what the pictures showed, and it was actually a lot brighter inside than I expected based on the pictures. Everything was clean and with 5 people, there was plenty of space. They provided beach chairs and an umbrella which was wonderful. We also used the grill which we enjoyed having access to. The only thing we would recommend is more pots/pans/serving bowls, etc. for use in the kitchen - that was a little lacking. Otherwise, communication with the host was outstanding. We had a couple of minor issues that were resolved immediately. They let us check in early and stay late based on our schedule and the fact that no one was coming in behind us. Finally, the location is awesome - right across the street from the beach with easy beach access. We had a great time and would definitely recommend this house.
Top guest favorite
A bright living area features a spacious sofa adorned with blue and green decorative pillows, complemented by a matching throw. A wooden coffee table with natural elements sits atop a woven rug. A piece of wall art depicting a serene beach scene adds a calming touch.
Cottage in Indian Rocks Beach
4.99 out of 5 average rating, 169 reviews

Pool | King Bed | Art Mural | Steps to the Beach

Mary AnnRating, 5 stars7 months ago
The cottage was immaculately clean and comfortable. It was stocked with everything you would need such as kitchen necessities, toiletries, extra towels and beach items. The pool was beautiful and even lit up at night. It is a three minute walk to the beach and some of the bars and restaurants. It is a very quiet neighborhood. The host was extremely nice and responsive with everything. We would stay there again. And I loved the free library out front. I left a book in there ☺️If you are thinking about renting this cottage, you definitely should, you won't be disappointed.
Top guest favorite
The charming exterior of the vintage cottage is highlighted by a bright yellow facade. A screened porch welcomes visitors, and decorative plants are arranged along the walkway. A bicycle is parked beside the entrance, enhancing the inviting atmosphere of the outdoor space.
Cottage in Sarasota
5 out of 5 average rating, 36 reviews

Cozy Cottage near Siesta Key Beach

JoyRating, 5 stars3 weeks ago
We thoroughly enjoyed our stay at Canopy Cottage. This was our second year staying and loved it even more. Jami is an excellent host. We loved being close to the Legacy Trail to ride bikes and the sort drive to Siesta Key Beach! Would definitely stay again.
Top guest favorite
An enclosed front porch features two white rocking chairs positioned on a patterned floor. A door with a large letter 'A' offers access, while windows provide natural light. Decorative elements include a small sailboat and hanging plants, complemented by a teal area rug.
Cottage in Gulfport
4.99 out of 5 average rating, 264 reviews

Gulfport Art District - One Block From Beach!

BrandonRating, 5 stars9 months ago
This is probably our favorite Airbnb to date! The location is fantastic, on a street full of restaurants and bars, about a block from the beach. Yet, it was quiet! The place is very comfortable, with awesome and quirky decor, two bedrooms, and an air-conditioned, screened-in front porch, which was our dog’s favorite part! Great value!
Top guest favorite
A bright and airy living room is presented with a large wall-mounted television. Comfortable seating options are arranged around a central coffee table. Natural light floods the space through large windows, while exposed wooden beams and a textured area rug add character to the room.
Cottage in Bradenton
4.96 out of 5 average rating, 106 reviews

Waterfront*3bd 2ba*Pool* PingPong Table*relaxing

JordanRating, 5 stars1 month ago
Stay was great the space was clean and easy to get in and out of. It is a bit of a drive anywhere you want to go as there is really no close by dinning or shopping areas within a short walking distance, not the hosts fault though. Our children enjoyed the pool and dock as well as the toys and beach items available. The only other thing I would add is if you are a light sleeper or awake easily be prepared for semi-loud commercial vehicles etc early in the morning, there were fans supplied in the main bedroom which may help with this as the windows are single pane and let a-lot of noise through. Over all it was a nice place for our family of 5 to stay and we enjoyed our time in the sunshine state!! Thanks Becca
Top guest favorite
The cottage features a welcoming front porch adorned with vibrant flowers and lush greenery. A stone pathway leads to the entrance, framed by well-maintained landscaping. Large windows allow ample natural light, enhancing the charm of the remodeled exterior.
Cottage in Tampa
4.98 out of 5 average rating, 111 reviews

Wonderful 2-Br, 2 Bath Cottage near the river.

KenRating, 5 stars1 week ago
Doug was a great host! He was very quick to respond to every message. Cottage was very comfortable. Slept great on super comfy beds and quiet neighborhood.

Cottage rentals with a hot tub

Top guest favorite
A light-filled living area features a spacious sectional sofa and a cozy chair, complemented by a decorative area rug. A large television is positioned on a sleek white media console. Soft natural tones enhance the relaxed ambiance, with sunlight filtering through the window blinds.
Cottage in Safety Harbor
4.96 out of 5 average rating, 179 reviews

Harbor Oasis with Hot Tub

JillianRating, 5 stars4 days ago
I’ve found my new favorite staycation spot and where I will enthusiastically recommend to friends and family visiting the area. The space was thoughtfully designed, clean, and comfortable. I will miss my morning coffee on the patio amongst all the plants and birds, my daily work sessions in the small quiet office, and the evening dips in the hot tub. Thanks for your thoughtfulness in creating this space!
Guest favorite
A hot tub is seen on a patio, surrounded by greenery and overlooking a serene river. Two individuals are comfortably seated, enjoying the bubbling water. Trees and shrubs frame the scene, contributing to a peaceful outdoor setting.
Cottage in Tampa
4.95 out of 5 average rating, 119 reviews

Hot tub, 2 floors riverfront, Bush Gardens, kajaks

LyndseyRating, 5 stars6 days ago
Everything was perfect! Absolutely beautiful!
Guest favorite
A coastal-style duplex is framed by lush tropical landscaping, featuring palm trees and colorful flowering plants. The exterior showcases light-hued siding, a spacious front porch with railings, and two garage spaces below. A clear blue sky enhances the inviting atmosphere of the property.
Cottage in Holmes Beach
4.93 out of 5 average rating, 54 reviews

Private Heated Pool and Spa+Close to the Beach!

ErnestRating, 5 stars1 week ago
Craig was an amazing host - extremely accommodating, helpful and proactive! As for Kiwi Cottage, it was everything our family could ask for and more. The kids loved the hot tub and pool, while all of the restaurants and beaches were a short distance away (highly recommend renting the golf cart!). Such an amazing vacation. We can’t wait to return!
Top guest favorite
A bright and airy seating area features a hanging chair and a cozy sofa, adorned with colorful cushions. Natural light floods in through large windows, complemented by light-toned wooden flooring and a textured pink area rug that adds warmth to the space.
Cottage in Largo
4.98 out of 5 average rating, 50 reviews

Family FUN~Pool, GameRoom+Bikes, Near Beach/Trail

KellaRating, 5 stars1 week ago
Great stay for our family! The home is very clean and decorated with a beachy, fun vibe! Great bathroom, comfy beds and lots of places to hang out! The dryer was very helpful with wet towels and beach gear was great. Our favorite part of the home was the backyard. The plunge pool was so fun and we loved the game room and golf. Private yard and we enjoyed the birds over coffee each morning! Recommend for any family!
Guest favorite
A charming coastal cottage is depicted, featuring a welcoming front porch with rocking chairs and vibrant seating. Lush plants in decorative pots frame the entrance. The exterior is painted in soft grey tones, complemented by white shutters and a serene pathway leading to the door.
Cottage in Palm Harbor
4.83 out of 5 average rating, 90 reviews

Happy Camper Cottage | Cozy Oasis with Hot Tub

JasonRating, 5 stars7 months ago
Anna was extremely helpful and accommodating for our last-minute trip with the kids. Her place was super cute and very clean and well kept and we would be happy to recommend it to friends and family or return ourselves. Thank you so much, Anna!
Top guest favorite
A vibrant outdoor area features a sparkling hot tub surrounded by lush greenery. Comfortable seating arrangements and a dining table create an inviting space for relaxation. A charming yellow cottage stands in the background, complemented by various tropical plants and trees.
Cottage in Largo
4.96 out of 5 average rating, 92 reviews

Hidden Oasis #1, hot tub near the beach

MicheleRating, 5 stars3 weeks ago
Ame is a wonderful host! This is the cutest little house, stocked with everything you might need for a stay in sunny Florida! Clean as a whistle, too. Location was perfect, groceries, the beach, pizza and shopping all close by.
Guest favorite
A well-equipped kitchen features white cabinetry and a wooden countertop. Essential appliances include a retro-style refrigerator, a microwave, and a coffee maker. Decorative elements include open shelving with dishware and a vintage-style wall poster, providing a functional yet charming atmosphere.
Cottage in Siesta Key
4.92 out of 5 average rating, 61 reviews

Cozy Cottage 1 block from Beach

ScottRating, 5 stars2 weeks ago
Great private stay a block from the beach and two blocks from the village. The area is very walkable for things to do and eat. If you’re looking for a honeymoon, anniversary or getaway spot this is perfect! And the hot tub is a nice touch.
Top guest favorite
A spacious living area features a light-colored tiled floor and is illuminated by natural light coming through large windows. Comfortable seating options include a colorful sectional sofa, lounge chairs, and a dining table with high-backed chairs. Decorative accents and art pieces add character to the room.
Cottage in Sarasota
4.99 out of 5 average rating, 84 reviews

Quaint Cottage,150 steps away from Crescent Beach!

KimberlyRating, 5 stars2 weeks ago
We loved this rental. My 5 year old daughter spent so much time in the pool - it’s for kids! The beach was just a short walk away and there are many good restaurants nearby. Madeline was a great host! Would definitely stay here again!

Private cottage rentals

Top guest favorite
Cottage in Clearwater
4.99 out of 5 average rating, 71 reviews

Amazing! Coastal Home+ 10 Mins to Dunedin & Beach

RachelRating, 5 stars1 week ago
Peter and Lisa were excellent hosts and their property is beautiful! Gorgeous sun room, lovely and peaceful neighborhood and every room was very clean. We appreciate your hospitality!
Guest favorite
A view of a sandy beach stretches toward calm blue waters under a clear sky. A wooden walkway leads from the beach access point, framed by green grass and beach plants. An umbrella and two figures are visible in the distance on the shore.
Cottage in Redington Shores
4.74 out of 5 average rating, 321 reviews

Below -Deck Studio Gulf Side 40 steps to the beach

MeghanRating, 5 stars2 weeks ago
My daughter and I had a lovely visit. The property is simple, and the location to the beach is perfect!
Top guest favorite
The image showcases a well-maintained pathway leading to a bright green cottage, bordered by shrubs and palm trees. Paved stones create a clear walkway, with seating areas visible in the background, surrounded by a neat gravel landscape.
Cottage in Dunedin
5 out of 5 average rating, 15 reviews

Cozy Cottage Near Downtown + Waterfront

TimothyRating, 5 stars1 month ago
Michael’s Citrus Cottage was perfect for our 6 day stay in Dunedin! It had all the amenities we needed. The bed was extremely comfortable, and the shower was one of the best I have seen in all the Airbnbs I have been to. The location is perfect also. Less than a 10 min walk to many restaurants, to 7 microbreweries, and many stores to satisfy your shopping itch. I would stay at Michel’s place again should we travel to Dunedin again.
Superhost
A waterfront area showcases two boats tied to a dock under a canopy. Lush green grass leads to the water's edge, surrounded by dense greenery on both sides. The bright sky adds to the serene atmosphere of this private outdoor setting.
Cottage in Terra Ceia
4.71 out of 5 average rating, 100 reviews

Serene Island Cottage Waterfront Haven

DallasRating, 5 stars1 week ago
This house is an absolute gem! It had everything that we (and our dogs) needed and more! There are so many wonderful spaces to relax in. We enjoyed the main room, screened in back porch, beautiful front courtyard, and sipped coffee in the back yard each morning by the canal. We also had a blast paddling out to the bay in the canoe! The host is super friendly and quick to respond. She has put a lot of nice touches on the property that we really appreciated. We had the best time here and would love to come back! Highly recommend a stay here!
Superhost
A wooden pathway extends towards the waterfront, flanked by lush green grass and small trees. The serene water can be seen in the background under a clear blue sky, creating a calm atmosphere ideal for relaxation.
Cottage in Bradenton
4.85 out of 5 average rating, 53 reviews

Cabin 4 - Old World Waterside Double

AnthonyRating, 5 stars3 weeks ago
Great location, beautiful sunrise, great fishing! My daughter cast out and within five minutes, caught a bass!!
Guest favorite
A serene beach scene is depicted, showcasing a stretch of soft, white sand meeting calm turquoise waters. The clear blue sky features faint wispy clouds, enhancing the tranquil coastal atmosphere. The horizon is marked by a distant boat gently floating on the water.
Cottage in Nokomis
4.83 out of 5 average rating, 48 reviews

The "Sun Cottage" - your relaxing interlude!

KellyRating, 5 stars3 months ago
We love the Sun Cottage. This is our second stay there. A really nice place. Within walking distance or short drive to the beach. Lauren responded to our questions very quickly. We stayed two months so we really appreciated the washer/dryer and the stocked kitchen. We would definitely book again.
Superhost
A patio area is visible featuring two dark wicker chairs with cushions, positioned next to a small potted plant. A sandy pathway leads toward the beach, with a clear view of the sky filled with soft clouds, enhancing the beachside surroundings.
Cottage in Indian Rocks Beach
4.91 out of 5 average rating, 98 reviews

Historic Florida Beach Cottage steps from the sand

JordanRating, 5 stars2 weeks ago
We spent 4 days here with our 3 kids (11, 9 & 3) and absolutely loved it! The cottage is perfect for a family with small kids or a couple of adults. I wouldn’t recommend more than that because of the bathroom. They have really maximized the space & we were pleasantly surprised to see that it was a little different from the photos- in a great way! There is a counter top that wraps around in the kitchen/living area. The beach chairs were a huge bonus as half of us flew in and didn’t have much room for packing. Between the 5 of us, the house had plenty of dishes, towels, trash bags, etc.. much more was provided than your average condo/rental home stay. The neighborhood is amazing and truly a gem, rare to find such peace and quiet on a busy coast. My kids were enamored with Charlie the bird and we really enjoyed having so many walkable options for food (The Grove was our morning routine!) If you are looking in the area, do not hesitate to book this home- you’re in for a treat!
Guest favorite
A spacious screened lanai features comfortable seating options, including wicker chairs and a sofa with striped cushions. Natural light fills the area, creating a bright ambiance, while plants and decorative accents enhance the setting. A wide pocket sliding door connects the lanai to the family room.
Cottage in Bradenton
4.96 out of 5 average rating, 54 reviews

Discover Hidden Cove #2 - Water Views with Privacy

DawnRating, 5 stars1 month ago
Fabulous time at hidden cove - only thing to keep in mind is there are only 2 beach chairs so if you’re with a bunch of beach bound guests that could be a consideration. Loved our stay and would definitely stay again when we want to be in the Bradenton area.

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