Cottage vacation rentals in Anna Maria

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Top-rated cottage rentals in Anna Maria

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Guest favorite

The entrance features a bright pink exterior, complemented by white trim and a welcoming white door labeled 'B.' Lush green plants are arranged on either side of the door, enhancing the cheerful appeal. A well-maintained artificial lawn lies in front, with a simple concrete pathway.

Cottage in Indian Rocks Beach

4.89 out of 5 average rating, 285 reviews

Vintage Florida Beach Cottage B

Just a short walk to the beach makes this a great beach getaway for couples or families. On your way you can stop at the Cooky Coconut for lunch, an awesome milkshake or a variety of snacks. With a totally new renovation in 2019, this unit is in updated, very clean and worry free condition. This cottage is located in a quiet residential neighborhood and a great place to relax. Common laundry on shared screened porch. Dogs allowed (extra $45 cleaning). Easy refund policy. Level 2 EV charger

Top guest favorite

Cottage in Dunedin

4.96 out of 5 average rating, 205 reviews

Adorable Dog-Friendly Cottage in Quaint Dunedin

Discover a charming 1920's cottage nestled in the heart of Dunedin, 3 blocks from the water and downtown. This delightful cottage is ideally located 2 blks from the Pinellas Trail, the Fenway Hotel, and the Blue Jay's stadium. Surrounded by lush greenery, the cottage boasts a private outdoor space perfect for you to enjoy your coffee. Inside, you'll find a sunny kitchen, a spacious living and dining area, and comfortable beds to ensure a wonderful stay. Come and enjoy a memorable stay here!

Guest favorite

Cottage in Lutz

4.94 out of 5 average rating, 162 reviews

Little piece of Heaven 2

This 2 bedroom cozy cottage is nestled on a 1.5 acre piece of property on a serene ski sized lake. The cottage is a laid back coastal feel with all of the amenities of home.Tucked away in between the hustle and bustle of Tampa without ever knowing it. Easy access the Veteran's Expressway that will take you to anywhere from Clearwater and our pristine beaches to Downtown St. Pete. I275 will take you to Downtown Tampa, Busch Gardens and Adventure Island. I-4 will take you to Orlando attractions

Guest favorite

A calm waterfront scene is captured at dusk, showcasing a tranquil river reflecting soft hues of blue and purple. Green trees frame the image, leading to a well-lit boardwalk and buildings along the shore, while the horizon is dotted with faint city lights.

Cottage in Bradenton

4.91 out of 5 average rating, 349 reviews

Private King Bed Suite-Near AMI Beach-Walk D’Town.

Your relaxing vacation is here! Private Cottage with a huge deck. Wonderfully furnished with plush linens, beach towels/chairs. A great nights sleep with a king-size bed and pull-out couch which serves as 2nd bed. Private kitchen and bath. TV and fast WIFI. We are located in a historic and quiet neighborhood in DT Bradenton. There are 3 villas on our large corner property. Off street parking. Quiet times are between 10PM until 8:00AM. Please respect others. Walk to many great restaurants!

Top guest favorite

A covered porch area features two wicker chairs with cushions, positioned around a small round table. A lantern is set on the table. Wooden accents frame the entrance and windows, which overlook the peaceful outdoor surroundings.

Cottage in Myakka City

4.99 out of 5 average rating, 135 reviews

NEW! Peaceful Country Cottage near Lakewood Ranch

Enjoy the peace and solitude of the country at this fully renovated cottage. "Country Oaks" Cottage located on seven acres surrounded by nothing but woods and wildlife. We are located approximately 15 miles east of I-75 where you can enjoy privacy away from the bustling city but close enough to enjoy shopping and restaurant options in nearby Lakewood Ranch. Enjoy a trip to historic Arcadia for antique shopping or adventure out to Myakka State Park or TreeUmph! or even local beaches.

Guest favorite

A serene beach scene showcases soft white sand meeting gently lapping waves under a clear blue sky. Dune grass and small green plants are visible in the foreground, adding a natural touch to the tranquil coastal setting.

Cottage in Indian Shores

4.96 out of 5 average rating, 146 reviews

Beautiful Beachfront Cottage on the Water

Renovated, romantic 1937 beach front cottage. Last of its kind in the quiet family setting of Indian Shores Florida, halfway between Clearwater Beach and Treasure Island/John's Pass. Truly an "Old Florida" experience with original pine floors, Florida room and covered porches, as well as updated kitchen and bathroom. This house, uniquely built near ground level, allows it to be waterfront on the beach while shaded by huge pine trees. You won't find a more tranquil setting on the beach.

Top guest favorite

A screened porch area features a combination of comfortable seating and a dining table, surrounded by greenery. A light blue couch and decorative pillows provide a pop of color, while a coffee table sits centrally. The flooring is wooden, and the area is well-lit by natural light.

Cottage in Bradenton

4.97 out of 5 average rating, 116 reviews

Coastal Style 2BR cottage near Anna Maria Island

Relax with the whole family at this peaceful place to stay. Located in a mobile home/RV park 6.5 miles from Anna Maria Island, which offers some of the most beautiful beaches on the gulf coast. Centrally located between St. Petersburg and Siesta Key. This kid friendly community offers many amenities such as Pickle ball, swimming pool, shuffle board, horseshoes and gym on site. Stay a few days or a few months! Snow birds are welcome! Only 3.3 miles to Sarasota Airport.

Superhost

A screened-in patio features a spacious seating area with dark wicker furniture and bright cushions. A wooden sign reading 'SIESTA BEACH' hangs overhead. Lush greenery surrounds the space, enhancing a serene outdoor atmosphere.

Cottage in Sarasota

4.83 out of 5 average rating, 164 reviews

Charming Beach Cottage

** No damage from hurricane, has power *** LOCATION!!! Getaway from the fast paced, high pressure life and slip on some flip flops! Get ready to unwind with the cool sea breeze, sunny adventures on the beach or on the water and explore the meaning of easy island living. Our contemporary designed home is just a few minutes drive from the most picturesque beaches in the nation with LOTS of parking. Feel free to bring your boat:) Restaurants and shopping are plentiful!

Top guest favorite

Cottage in Tampa

4.97 out of 5 average rating, 195 reviews

Bay Lake Cottage

You’ll have the Entire 500sq ft Cottage & private entry, deck/dock, all to yourself. Located on a 37-acre private ski lake.Key-pad entry, private parking. 1 king bed, 1 bath, queen sofa bed, washer/dryer, smart TV’s, blackout curtains,shampoo,conditioner,hairdryer,WiFi. Fully stocked kitchen, smokeless grill, wine fridge upon request, k-cup/drip coffee machine. The lake has bass, we provide fishing poles/tackle box. Rentable Kayaks & Canoe. Pet fee $50.

Guest favorite

Cottage in Anna Maria

4.96 out of 5 average rating, 236 reviews

Turtle Cottage - Anna Maria Island

Great 1 bedroom, 1 bathroom cottage on the quiet north end of the island. The house is conveniently located and within walking distance (two short blocks) to the beach and close to the intersection of Gladiolus Street/Alamanda Road. Spectacular sunrises are just a short walk away at the Rod and Reel Pier, and the sunsets at Bean Point Beach are second to none, just a few blocks away. This great getaway sleeps up to 4.

Guest favorite

A vibrant view of the Little Manatee River is captured, showcasing calm waters reflecting the blue sky. Lush green foliage lines the riverbanks, creating a serene natural backdrop. A wooden railing in the foreground complements the scenic landscape.

Cottage in Ruskin

4.91 out of 5 average rating, 113 reviews

Little Manatee River Cottage

This cottage is located on the Little Manatee River. Sun City Center 10 min Aquatic rentals walking distance. The cottage is updated. Abundant fishing charters, Little Harbor, manatee viewing center and Simmons Park all within minutes. Fully furnished, linens, kitchen utensils; bath towels; blankets pillows comfy furnishings. View sunsets out on the river, on the dock or at Little Harbor sipping your favorite drink.

Guest favorite

The exterior of a remodeled cottage is shown, featuring light blue siding and large windows, framed by lush tropical foliage. A bright white door is centrally positioned, inviting guests into the charming retreat. Decorative stones cover the ground, adding a natural touch to the landscape.

Cottage in Bradenton Beach

4.97 out of 5 average rating, 133 reviews

Darling Old Florida Beach Cottage Steps From Gulf!

Completely Remodeled! Welcome to Cottage By The Sea, a newly remodeled charming retreat just steps from the pristine Gulf of Mexico beaches on Anna Maria Island, nestled in the serene area of Bradenton Beach. This delightful getaway blends the nostalgic charm of "Old Florida" with modern updates, featuring bright and sunny décor. It's time to leave your worries behind and embrace the tranquility of paradise!

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What guests are saying

2 Bedroom Turtle’s Nest Beach Cottage,

4.91 out of 5 average rating, 11 reviews21 months ago

Staying at Shane's place was wonderful! Our family stayed for 8 nights. It was just as described, and the pictures were extremely acurate. The place was very clean and it really was just a short walk (maybe 3 minutes) to the beach. We had everything we needed for our stay. Diane was extremely helpful and responsive and she answered all of our questions in a very timely manner. The neighborhood is beautiful, quiet and very safe. Another family was staying upstairs during our stay, and although you could hear them a little bit, we had no issues with the shared access areas because they were super nice and friendly, too. The beach is absolutely gorgeous and not crowded at all. We had access to beach equipment (chairs, unbrellas, etc, which was a bonus for us). It was a perfect beach vacation for our family of 4 and we can't wait to stay at Shane's place again!

Cottage in Redington Shores

What guests are saying

Family Friendly Beach Cottage in Madeira Beach, FL

4.84 out of 5 average rating, 128 reviews7 months ago

We had an amazing stay at Mad Beach Cottage! The location is unbeatable—just 60 steps to the sand with no streets to cross. The cottage is cozy and perfect for families, with plenty of space. Everything in the cottage is well thought out for function and convenience. There are plenty thoughtful amenities like a well appointed kitchen, a pack-n-play, and beach toys. The heated pool and BBQ area were fantastic, and we loved being so close to John's Pass for dining and entertainment. The sunsets from the property were amazing! The host was the most responsive host I've ever communicated with on Airbnb. He was able to answer our questions in advance of the stay and provided almost immediate response when we had a question about parking at the property. There was a folder with clear instructions and information about the property, making check in and out a breeze! The host has clearly thought about everything, making this a stress-free, enjoyable stay. I highly recommend this property!

Cottage in Madeira Beach

What guests are saying

Adorable Cozy Silver Sands Cottage on Siesta Key!!

4.85 out of 5 average rating, 161 reviews2 weeks ago

Beautiful sights accompanied with an amazing place to stay! kitchen was stocked with all of the essentials, cutting boards, knives, coffee pot, pots & pans etc... Just a brisk walk from the beach with lots of seating available. Fishing pier on the property kept me busy! My wife and I will be booking again next season!

Cottage in Siesta Key

What guests are saying

Alafia River Cottage

4.93 out of 5 average rating, 84 reviews1 week ago

The Alafia River House did not disappoint. Check in was easy with helpful photos & directions. The neighborhood is pretty quiet but yet close to everything too. The house is tucked in right on the river, the yard is lush & Florida tropical, it is the perfect place to sit & read, eat a meal or take a nap. Watching the chickens and surrounding nature are an added bonus. The home is old with character, but so clean & refreshing. All the things you need and more are carefully stowed in antique furniture. Martha is easy to contact, but you shouldn’t need anything. The kitchen is up to date & has all of the extra things that you probably forgot to bring. My husband and I had a sweet trip & the Alafia River House was a gem. Thank you Martha.

Cottage in Riverview

What guests are saying

Pass-a-Grille Historic Cottage Unit 2

4.97 out of 5 average rating, 144 reviewstoday

We loved our stay at the little cottage. It was extremely clean and very charming! Everything we needed in the kitchen was there, all linens, etc. loved the back patio and the quick walk to the beach on one end of the block and intercostal on the other. We would definitely like to come back to this cottage.

Cottage in Pass-a-Grille Beach

What guests are saying

FayRoy Historic beachfront cottage

4.96 out of 5 average rating, 57 reviews2 weeks ago

Really loved the location of the property. Felt very homey. Really enjoyed our stay here. Was able to cook a couple meals, relax and check out. Wasn’t too quiet where i felt secluded - I like a little beach action during the day, felt like I was with locals, not tourist – but in the evening, when sitting on the porch felt like you had the place to yourself. Can’t wait to come back.

Cottage in Indian Rocks Beach

What guests are saying

Beach Cottage Siesta Key Prime Location & Htd Pool

5 out of 5 average rating, 14 reviews1 week ago

I can highly recommend the Mermaid Mansion! Phyllis provided detailed, tailored recommendations on things to do during our stay and was responsive to any questions I had—so friendly and willing to help. Our stay was AWESOME! The Mermaid Mansion was perfect for my daughter and I. We easily walked a few minutes to the beautiful, pristine beach every day. Phyllis provided everything we needed from beach umbrellas to chairs to a handy wagon to tote everything. The condo is also well equipped. I loved the private courtyard where we could sit outside and eat and enjoy the warm weather. There are also so many restaurants, shops and activities to choose from that are easily walkable. Great location, outstanding hostess, and lovely, comfortable accommodations—go ahead, treat yourself!!!

Cottage in Sarasota

What guests are saying

#5 Beach Front Cottage w view- Indian Rocks Beach

4.77 out of 5 average rating, 102 reviews3 weeks ago

We loved staying at the cottage right on the ocean! You can’t beat the location! A lot of restaurants close and a pickleball court only 2 blocks away! The cottage was stocked with everything we needed for our stay. We already booked again for next year!

Cottage in Indian Rocks Beach

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