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Cottage vacation rentals in Sarasota Beach

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Top-rated cottage rentals in Sarasota Beach

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Top guest favorite
A fenced-in outdoor area features a swimming pool surrounded by a red brick patio. Sun loungers are positioned beside the pool, and a pool house is visible in the background, complemented by lush greenery and large trees draped with moss.
Cottage in Palmetto
4.96 out of 5 average rating, 104 reviews

1930s Cottage + Pool 12 miles to Beach

Located in the heart of historic Palmetto FL, you will find this adorable cottage. This home has 2 bedrooms & 1 bath in the main home with a pull out sofa, as well as, a pool house with a full bath & daybed. You will love the southern charm of this home while relaxing by the pool or having morning coffee on the front porch. There are many restaurants & shops w/in walking distance as well as local parks & preserves. If you love the beach, this home is just a short drive to FL's beautiful beaches.

Guest favorite
A vibrant outdoor area features a swimming pool surrounded by lounge chairs and tropical plants. A separate upper level apartment is visible, showcasing a light blue exterior. The enclosed patio area provides shaded seating, enhancing the inviting space for relaxation.
Cottage in Siesta Key
4.93 out of 5 average rating, 121 reviews

The Mermaid: Heated Pool, 4 Houses to Beach

This apartment is a first-floor unit with an open floor plan that sleeps 2 with a maximum of 4 people. The bed makeup in this rental is a king bed in the master and a queen size sofa sleeper. This rental is great for longer stays or guests who like to cook since you have a full kitchen and all the items to cook any meal. There is a washer/dryer in the apartment. Beach chairs and umbrellas are supplied to you at no charge. This is a duplex and has another 1 bedroom 1 bath apartment above you.

Top guest favorite
An aerial view captures the coastline of Manasota Key, showcasing the blue-green waters and sandy beach. The surrounding area features a mix of residential buildings and green spaces, with multiple boats visible in the water and a bridge connecting to nearby islands.
Cottage in Englewood
4.9 out of 5 average rating, 156 reviews

Free kayak/bikes/walk to beach/full cottage #1

Unit #1 Beach cottage very private and quiet, has a full kitchen, King bed in the master and queen sofa bed in the tv room, very comfortable, fast WiFi, AC & heat. All you need to relax and just have fun. Outdoor shower and laundry area, Private parking, Enjoy amazing sunsets/fishing/and restaurants and bars, all walking distance to the beach and bay. Kayaks/snorkel gear/beach toys are included. So start enjoying the beautiful sandy beach on Manasota Key, Lots of sea life and turtles.

Superhost
The cottage features a welcoming exterior with a screened-in lanai, framed by decorative beams and charming window boxes. Lush greenery surrounds the property, and a large tree adds to the tranquil setting. A pathway leads to the front door, enhancing the inviting atmosphere.
Cottage in Sarasota
4.8 out of 5 average rating, 269 reviews

Cozy Cottage by the Bay

Charming and historic decorator cottage near Downtown Sarasota. Located in the highly desirable, quiet, and safe neighborhood of Indian Beach - Sapphire Shores. Just a short drive to some of the nations top rated beaches like Siesta Key Beach. One of the best features of the home is the enclosed lanai at the front of the house. Perfect for enjoying Florida's coveted indoor/outdoor living. It has a private fenced in backyard, with a fire pit. Off street parking for 2 cars in the driveway.

Top guest favorite
A circular pool is surrounded by a landscaped area featuring vibrant plants and red stones. Lounge chairs offer seating nearby, while a shaded umbrella provides relief from the sun. Inflatable rings float in the clear water, and a view of the canal can be seen in the background.
Cottage in Bradenton
4.94 out of 5 average rating, 136 reviews

Waterfront+Pool+Putting Green+Beach Gear! 2BR/2BA

• Perfect for couples, families, or remote work escapes • Unwind by the water • Fish from dock • Well equipped kitchen (no food items) • Starter supplies: coffee, tea, paper goods & toiletries • 2 bd / 2 ba • Selfie Wall • Keyless Entry • Pool • Putting Green *Tap the 🖤 in the corner to save this listing and find it faster later* • 10 miles to beach, *Award Winning Ana Maria Island • 7 miles to IMG Academy • 11 miles to SRQ Airport • 2 miles from Pittsburgh Pirates Training Camp

Superhost
An open living space features a fully equipped kitchen with wooden cabinetry, a dining table, and seating area. A flat-screen TV is mounted on the wall. Light-colored flooring enhances the spacious feel, while natural light brightens the room through multiple windows.
Cottage in Siesta Key
4.86 out of 5 average rating, 273 reviews

Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

*Siesta Key elevated villa at Solitude Suites on Siesta Key. *Your own detached private villa, located in a small resort. *Waterfront resort w/ FREE pool, kayaks, table tennis & Tiki Hut. * Just a 10-12 min walk to award winning beach. *1 Bedroom w/King bed. *1 full bathroom w/shower. *Large kitchen, open living room, fully furnished inc towels & linens. *Private screened lanai w/ table & chairs. *Beautiful shared pool w/ sun shelf & waterfall. *2 min car ride to beach. *Updated!

Guest favorite
A private pool is surrounded by a paved area, featuring two lounge chairs positioned near the water. Green foliage adds a natural touch, while a white fence encloses the space, creating a secluded atmosphere. The clear blue water reflects the sky, inviting relaxation.
Cottage in Sarasota
4.93 out of 5 average rating, 135 reviews

Private Heated Pool Casita Near Downtown & Beaches

Built in 1925, Our Casaita Verde 2 Bedroom, 1 Bath home still retains its vintage charm but with modern touches. Enjoy watching the 55 inch flat screen TV with HD cable and stay in touch with the world with WI-FI internet. Lounge by the private pool or take in the beautiful evenings on the deck with your favorite beverage. Pet Friendly! Conveniently located near Downtown Sarasota on Bahia Vista with easy drive to Lido Key, our World Famous Siesta Key or I-75 for longer adventures.

Top guest favorite
A mobile home with a welcoming front porch is surrounded by lush greenery and colorful flowering plants. The structure features a light exterior, complemented by a decorative element above the porch. A carport for vehicle parking is visible, alongside a well-maintained pathway.
Cottage in Bradenton
4.97 out of 5 average rating, 121 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.

Guest favorite
Cottage in Bradenton
4.9 out of 5 average rating, 367 reviews

Serene Suite*Walk 2 Dwtn/Riverfront/Dining*AMI*IMG

Our private, old Florida, suite located in historic downtown Bradenton with spacious back deck, king bed, sitting area, kitchen, fast FREE WiFi & parking. Walk to the Riverfront where you will enjoy dining, shopping and some amazing waterfront views. Just minutes to AMI beaches, shops, and endless fun. Walkable to local museums, Planetarium, IMG and other local favorites. Nestled in a quiet neighborhood this suite makes for an enjoyable, peaceful stay.

Top guest favorite
A vibrant yellow cottage is surrounded by a sandy area with palm trees. Colorful adirondack chairs in pink, blue, and green are positioned on the white gravel. A covered outdoor seating area is visible to the side, enhancing the beachside environment.
Cottage in Bradenton Beach
4.99 out of 5 average rating, 210 reviews

Bradenton Beach Sunsets 2, Anna Maria Island, FL

Fully furnished water view beach cottage located on beautiful Anna Maria Island directly across the street from white sand beach and Gulf of Mexico. 1 Bedroom 1 bath unit that sleeps 4 with the queen pull out couch. Beach chairs/umbrellas/Boogie boards/laundry room, etc. provided. Three blocks from historic Bridge Street with lively restaurants and bars. Free island trolley and across the bridge from Cortez fishing village. Free off-street parking.

Top guest favorite
A row of brightly colored Adirondack chairs is positioned on the sandy beach, facing the tranquil ocean. The hues include yellow, orange, green, blue, pink, and purple. A clear blue sky with soft clouds complements the serene shoreline.
Cottage in Nokomis
4.98 out of 5 average rating, 167 reviews

Staycation Sanctuary

Our property is clean and welcoming. You can enjoy a relaxing, warm and peaceful getaway from the rest of the world just steps to the beach. This is the perfect "Old Florida-style" location to experience the comfort and hospitality you so deserve! Grab your bathing suit/flip flops and enjoy tranquillity of beach life, sunsets and lazy days of fishing and bird/dolphin/manatee watching and gathering sea shells-- all only 2 blocks away!

Top guest favorite
A private outdoor space featuring a heated pool and spa, surrounded by palm trees and lounge chairs. The vibrant blue cottage is visible in the background, complemented by carefully arranged landscaping. A pathway of stepping stones leads toward the entrance of the cottage.
Cottage in Anna Maria
4.96 out of 5 average rating, 257 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.

Popular amenities for Sarasota Beach cottage rentals

Kitchen
Wifi
Pool
Free parking on premises
Air conditioning

Cottage rentals with a hot tub

A serene outdoor space showcases a private heated pool and spa, surrounded by lush tropical landscaping. Paved with light-colored stones, the area features several lounge chairs positioned for relaxation under the bright sky. The backdrop includes a white wall and large windows of the house, enhancing natural light.
Cottage in Holmes Beach
5 out of 5 average rating, 3 reviews

Yacht Rock Ranch

Guest favorite
A modern park model home is shown with a red convertible parked in front. Lush palm trees surround the property, providing shade. A spacious patio area with outdoor seating is visible, complementing the vibrant landscaping and inviting exterior.
Cottage in Sarasota
5 out of 5 average rating, 5 reviews

Sarasota Cottage Near Beaches, Downtown & Airport

Top 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
4.94 out of 5 average rating, 65 reviews

Close to the Beach+ Private heated pool and spa!

Cottage in Sarasota County

Modern Lakefront Getaway – Resort Perks Included

Cottage in Siesta Key
New place to stay

Cozy Cottage Near Siesta Key Village!

A charming cottage is seen with a porch featuring a white railing and a blue and white striped umbrella. The exterior showcases light blue siding and a screened-in lanai. Lush green grass frames the entrance, adding to the welcoming appeal of the home.
Cottage in Sarasota
4.67 out of 5 average rating, 3 reviews

Cozy Cottage at Sun Outdoors Sarasota

Top guest favorite
An open living area features tiled flooring and soft lighting, with comfortable seating arrangements including a sofa and armchairs. A dining area is visible, showcasing a wooden table with chairs. Decorative touches such as artwork and a side cabinet enhance the space's charm.
Cottage in Sarasota
4.99 out of 5 average rating, 97 reviews

Quaint Cottage,150 steps away from Crescent Beach!

Superhost
A private backyard space features a hot tub with a bubbling water feature, surrounded by a paved patio. A dining table with chairs is positioned nearby, catering to outdoor meals and relaxation. Lush greenery and landscaping enhance the tranquil environment.
Cottage in Bradenton
4.91 out of 5 average rating, 77 reviews

Sandy Cottage w/ Hot Tub, 20 min to Beach + Garden

Pet-friendly cottage rentals

Superhost
A serene beach scene shows soft, white sand stretching along the shoreline, meeting gentle turquoise waves under a clear blue sky. A few people are visible enjoying the beach, with vibrant green vegetation and distant structures lining the coast.
Cottage in St. Pete Beach
4.8 out of 5 average rating, 290 reviews

Sunny PaG Island rental w/bikes-just steps2beach

Top guest favorite
A bright living area features terracotta tile flooring and large windows allowing natural light to fill the space. A round dining table is set for four, while a comfortable seating area includes a light green sofa and a decorative side table. Tropical decor enhances the ambiance.
Cottage in Holmes Beach
5 out of 5 average rating, 20 reviews

Palm Villa by Beach Boutique Rentals

Superhost
The front view of the bungalow features a welcoming entrance framed by tall palm trees. The light blue exterior contrasts with the lush greenery surrounding the property. A driveway leads to the entrance, inviting visitors to explore the charming cottage just steps away from the beach.
Cottage in Sarasota
5 out of 5 average rating, 3 reviews

Charming 2BD Bungalow Close to Crescent Beach!

Guest favorite
A quaint cottage is nestled among lush greenery, featuring a light-colored exterior and a sloped roof. Two chairs are positioned near the entrance, inviting outdoor relaxation. The setting emphasizes privacy with natural landscaping, creating a serene atmosphere close to the lush garden.
Cottage in Englewood
4.93 out of 5 average rating, 86 reviews

Private garden cottage

Guest favorite
A serene sunset over the Little Manatee River is captured, with vibrant hues of orange and pink reflecting on the water surface. The dark outline of trees defines the horizon, creating a peaceful natural backdrop.
Cottage in Ruskin
4.91 out of 5 average rating, 125 reviews

Little Manatee River Cottage

Top guest favorite
A charming cottage exterior features a light blue facade complemented by a carport and a paver-styled driveway. Two teal Adirondack chairs are positioned in a gravel area, surrounded by palm trees, creating a relaxed atmosphere. The welcoming entrance is highlighted by a large window.
Cottage in Siesta Key
5 out of 5 average rating, 15 reviews

Cottage w/pool 1 block to village, 3blks to beach

Guest favorite
An aerial view highlights the river house set amid lush greenery, featuring a large wooden deck and fenced yard. The property is bordered by the Braden River, with its tranquil waters reflecting the surrounding trees and homes.
Cottage in Bradenton
4.96 out of 5 average rating, 45 reviews

2/2 Charming Riverfront Cottage w Deck & Kayaks

Superhost
A charming beachfront bungalow features a mint green exterior with a vibrant door, surrounded by well-maintained landscaping. The front yard is enclosed by a white picket fence, with tropical plants and decorative stones enhancing the inviting atmosphere.
Cottage in Sarasota
4.58 out of 5 average rating, 12 reviews

Chic Peaceful 3BD Cottage - Walk to Siesta!

Private cottage rentals

Top guest favorite
The cottage exterior features a light blue facade with a centered front door, flanked by two large windows. A small porch with a bench is present, along with potted plants. A single-car garage is visible, and a manicured lawn surrounds the home.
Cottage in Sarasota
5 out of 5 average rating, 7 reviews

Cottage & Tree ~ by the Sea

Top guest favorite
A comfortable living space features a light grey sofa with two blue cushions and a yellow accent pillow. A round mirror hangs on the wall, reflecting natural light. The white coffee table displays a decorative bowl, with a woven rug beneath providing texture to the floor.
Cottage in Englewood
4.96 out of 5 average rating, 26 reviews

Oystercatcher 3min walk to sunset, bikes, kayaks

Guest favorite
The exterior of a modular home is showcased, featuring a covered porch with two chairs under a sloped roof. Lush plants and palm trees surround the entrance, and a paved driveway leads to the home. Clear blue skies provide a bright backdrop.
Cottage in Bradenton
4.95 out of 5 average rating, 75 reviews

Cheerful 2 bedroom , plus bunk room vacation home.

Top guest favorite
The entrance features a charming porch with a white front door framed by tall windows on either side. A simple welcome mat lies in front of the door, and colorful landscaping with plants and red foliage completes the inviting exterior.
Cottage in Palmetto
4.98 out of 5 average rating, 83 reviews

Central Quiet Bright Cottage, near Skyway Bridge.

Guest favorite
A charming cottage exterior is framed by lush greenery and white gravel, featuring a light-colored front door adorned with decorative wreaths. Two wicker chairs are positioned on the front porch, inviting relaxation and tranquility.
Cottage in Bradenton
4.96 out of 5 average rating, 26 reviews

Charming 1930s Cottage in Village of the Arts

Guest favorite
The exterior of a brightly colored cottage features a pale blue facade with navy blue shutters and a welcoming front porch. A U.S. flag is displayed on the porch, while lush greenery surrounds the home. A driveway provides access to an open carport.
Cottage in Palmetto
4.91 out of 5 average rating, 45 reviews

Aqua Breeze Cottage - Winter retreat 2 bd, 2 ba

Guest favorite
A comfortably furnished living area features a neutral sofa adorned with patterned pillows. Two geometric wooden tables are positioned in front, with a single armchair nearby. Light wood ceilings enhance the bright atmosphere, while decorative artwork is displayed on the wall.
Cottage in Holmes Beach
4.97 out of 5 average rating, 38 reviews

Sailfish Gulf Suites #4, Garden Views, Steps from

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
4.95 out of 5 average rating, 57 reviews

Discover Hidden Cove #2 - Water Views with Privacy

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Sarasota County
  5. Siesta Key
  6. Sarasota Beach
  7. Cottage rentals