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Cottage vacation rentals in Sarasota County

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Top-rated cottage rentals in Sarasota County

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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, 6 reviews

Cottage & Tree ~ by the Sea

This cute cottage is located on a cul-de-sac, close to downtown Sarasota (5 min), the incredible white sand beaches of the Gulf (10 min), and just a few blocks from The Legacy Trail. Sarasota has award winning restaurants, bars, shopping, and unlimited fun activities. Our home features a large open lot with a gorgeous huge Live Oak tree to relax under. Enjoy fresh cool brand new AC and cozy decor. There is a fully stocked kitchen and grill area for entertaining while in your home away from home.

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!

Welcome to the Key Lime Surf Shack, a bright and stylish 3-bedroom cottage just minutes from world-famous Siesta Key Beach. Perfect for families, couples, or small groups, the home features a king and queen bedroom plus a flex room with a daybed, an open living area with Smart TV, a fully stocked kitchen, and in-unit laundry. Relax in the spacious shared backyard with tropical landscaping, or head out to explore Sarasota’s best dining, shopping, and outdoor activities nearby. Designed with comfo

Guest favorite
The living room features a spacious sectional sofa and a central round coffee table. A ceiling fan is present above, and natural light enters through large windows adorned with patterned curtains. A desk and chairs provide workspace, while art and decor enhance the inviting ambiance.
Cottage in Sarasota
4.93 out of 5 average rating, 41 reviews

Historic Cocoanut Art Cottage

THE COCOANUT ART COTTAGE Located three minutes to downtown! The Cocoanut Art cottage is a restored 1940s two-bedroom, one-bath house with hardwood floors, a fully-equipped kitchen and dining area, living room and outdoor space. Shiplap walls throughout the home are filled with art by Ringling School of Art alumni including Joseph Patrick Arnegger, Tom Stephens, Tim Jaeger and many more. The space is furnished with comfort and style by a local interior architect, a Ringling alumni. VR24-00168

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, 266 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.

Guest favorite
A two-story blue duplex is depicted, featuring large windows and a wooden balcony. A shared heated pool is surrounded by several lounge chairs, with umbrellas positioned nearby. Lush tropical landscaping provides a serene backdrop, and a fenced area creates a private outdoor space.
Cottage in Siesta Key
4.93 out of 5 average rating, 118 reviews

The Marlin: Heated Pool, 4 Houses to Beach

This apartment is a 2nd story unit with vaulted ceilings in the living room and 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 also a washer/dryer in the apartment private for your use. Beach chairs and umbrellas are supplied to you at no charge.

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, 270 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!

Top guest favorite
An enclosed sitting area features a comfortable daybed adorned with colorful throw pillows against light wooden paneling. A small blue table accompanies the seating, with large windows allowing natural light to illuminate the space while offering views of the surrounding greenery.
Cottage in Osprey
4.97 out of 5 average rating, 68 reviews

Mattie’s Cottage by the Bay

Enjoy this 1913 Florida vernacular cottage! Carefully restored, thoughtfully updated house on a quiet, tree-canopied street in historic Osprey, one of Sarasota County’s oldest settlements. Enclosed front porch, screened back porch, and tin roof. Walk to the bayfront, restaurants, shopping, library, parks, and historic sites. A short drive takes you to famous Gulf beaches and all Sarasota and Venice have to offer. Hurricane Milton: Yes, we are cleaned up and have power and internet!

Guest favorite
A comfortable seating area features a dark leather sectional sofa with decorative pillows and a matching recliner. A central ottoman provides additional comfort, while two table lamps illuminate the space. Natural light filters through the blinds, complementing the artwork on the walls.
Cottage in Sarasota
4.92 out of 5 average rating, 59 reviews

Sarasota Home with pool in resort community

Lovely vacation home in gated resort community. Our home is immaculate & in a safe/quiet neighborhood. The large pool is heated/chilled. There’s a playground, tennis/pickle ball, shuffleboard, hair salon, beach supplies and well appointed. It’s NOT an age restricted community, kids are welcome and it’s close to downtown Sarasota, Lido Beach, Siesta Key Beach, Longboat Key, Ringling property, Mall at Town Center, great dining, outstanding nature sites, golfing and fishing activities.

Guest favorite
An aerial view captures the expansive Siesta Key coastline, showcasing a stretch of sandy beach meeting calm blue waters. Nearby buildings and lush greenery punctuate the landscape, highlighting the serene environment just minutes away from the cottages.
Cottage in Sarasota
4.78 out of 5 average rating, 143 reviews

Siesta Key Cottages Crescent 1B Beach/Pool/Hot Tub

4 separate BRAND NEW inside (renovated 12/24) 2 bedroom/2 bath (+Queen Sofa Bed+ Chair/Bed) pool homes (Each sleeps 7) ONLY A 4 MINUTE WALK TO SIESTA KEY BEACH #1 in USA (no major streets to cross): First Class! 2 Heated Pools, 2 hot tubs,2 gyms, Smart TV’s in all rooms, fine linens, towels, bikes, beach equipment, private porch, grill, fire pit, outdoor shower, private parking: Great restaurants / nightlife in walking distance. Running/Walking: You have miles of beach to take in!

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
4.92 out of 5 average rating, 133 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.

Guest favorite
A cozy porch area features a hanging swing adorned with colorful cushions, complemented by a small dining table and chairs. The entrance is framed by green lattice work, creating a welcoming space. A sign with the text 'WELCOME' is mounted on the wall.
Cottage in Siesta Key
4.86 out of 5 average rating, 173 reviews

Adorable Cozy Silver Sands Cottage on Siesta Key!!

Adorable one bedroom "Old Florida Cottage" on the intracoastal bay side of Siesta Key. This is a stand alone cottage, ground floor, no elevators or flights of stairs to mess with. New Pool with a tiki hut, fishing dock, boat basin (up to 24'), beach access 4 min. walk across Midnight Pass Rd. to the #1 beach with the whitest, softest sand you'll ever see! Hi Def TV in LR , Wifi, TV in BR, Keurig in the kitchen, stocked with everything but your clothes and toothbrush.

Top guest favorite
A modern cottage is set within a spacious, manicured lawn surrounded by trees. A circular driveway leads to the house, which features a dark metal roof and large windows. Lush greenery frames the property, emphasizing its serene outdoor environment.
Cottage in Sarasota
4.98 out of 5 average rating, 52 reviews

Bee Keepers Cottage

Welcome to Bee Keepers Cottage! Your country in the city. New guest home, private parking (2), designer interior, new stainless kitchen, microwave, dishwasher, stove with oven. Full sized washer and dryer, great high speed internet, screened porch on its own pond. Located on a 16 acre wooded property with many bird feeders, nature wildlife photo ops abound in own your backyard. See deer, wading birds, Bald Eagles, song birds and acres of privacy.

Popular amenities for Sarasota County cottage rentals

Kitchen
Wifi
Pool
Free parking on premises
Air conditioning

Cottage rentals with a hot tub

Top 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

An open-concept living area showcases a spacious sofa, a dinette set, and a modern kitchen featuring light cabinetry and stainless steel appliances. Bar stools are positioned at the kitchen counter, and large windows allow natural light to illuminate the room.
Cottage in Sarasota

Sun Outdoors Sarasota-1 Bedroom Cottage w/Loft

Guest favorite
An aerial view of Siesta Key showcases the pristine coastline and the expansive sandy beach. The turquoise waters meet the shoreline, bordered by lush palm trees and residential areas. The image highlights the tranquil atmosphere and accessibility to the beach, with the vibrant community nestled nearby.
Cottage in Sarasota
4.87 out of 5 average rating, 45 reviews

Siesta Key Cottages Crescent 1A Beach/Pool/Hot Tub

Cottage in Siesta Key
New place to stay

Cozy Cottage Near Siesta Key Village!

The exterior of a charming lakefront retreat is shown, featuring light-colored siding and a welcoming entrance. Palm trees and lush greenery frame the property, creating a relaxing outdoor atmosphere. A set of steps leads to the door, providing accessibility to the home.
Cottage in Sarasota County

Modern Lakefront Getaway – Resort Perks Included

An exterior view of a mobile home is presented, featuring large screened windows and a welcoming door. The home is surrounded by lush greenery and mature trees, providing a peaceful, natural setting. A wooden staircase leads to the entrance, highlighting the inviting outdoor space.
Cottage in Venice
4.4 out of 5 average rating, 10 reviews

Cottage near Venice Beach

Guest favorite
A bright studio space features a spacious king-size bed and a cozy sofa in soft blue tones. Natural light filters through window treatments, highlighting white walls and wooden beams that add warmth. A mirror and wall decor complement the relaxing atmosphere, while a TV is mounted nearby.
Cottage in Siesta Key
4.91 out of 5 average rating, 68 reviews

Cozy Cottage 1 block from Beach

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

Pet-friendly cottage rentals

Guest favorite
A peaceful view of the intracoastal waterway is presented, featuring calm waters that extend to the horizon. A wooden dock extends into the water, with lush greenery lining the foreground. The scene is illuminated by soft sunlight, enhancing the serene ambiance.
Cottage in Englewood
4.95 out of 5 average rating, 166 reviews

Family-Friendly Beach Cottage Manasota Key

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!

Top guest favorite
A cheerful cottage exterior is highlighted by its pink facade and surrounded by lush green grass. A screened patio extends from the house, while a small, circular heated pool is enclosed with a safety fence. Tall trees and clear blue skies create a serene setting.
Cottage in Nokomis
4.99 out of 5 average rating, 83 reviews

Pink Pineapple Cottage

An open living area features a modern sectional sofa with decorative pillows and a round ottoman. A sleek kitchen with stainless steel appliances and a dining table for four is visible in the background, complemented by neutral-colored walls and light tile flooring.
Cottage in Sarasota
4.78 out of 5 average rating, 72 reviews

Lovely ❤ Cottage - Very Close to Siesta Key & More

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

A newly renovated cottage features a light exterior with pink window shutters. A small patio area is visible in front, complemented by neatly arranged landscaping. A grill is positioned adjacent to the entrance, with a bright blue sky overhead and ample green lawn surrounding the property.
Cottage in Venice
4.7 out of 5 average rating, 147 reviews

Cozy Florida Cottage

Guest favorite
A sunken living room is seen, featuring a gray sectional sofa and a blue sofa. A coffee table sits between them, complemented by a unique side table. A television is positioned on a stand opposite the sofas, with light streaming through the window-covered double doors.
Cottage in Siesta Key
4.9 out of 5 average rating, 173 reviews

Siesta Key Cozy Cottage across from the beach!

Top guest favorite
A bright and airy living area features light-colored walls and wood flooring. Comfortable seating includes a sofa and an armchair, complemented by a coffee table. A ceiling fan is present, and large windows allow natural light to fill the space. A dining area with a small table is visible in the background.
Cottage in Englewood
4.96 out of 5 average rating, 25 reviews

Lemon Bay Hideaway near beach and fishing pier

Private cottage rentals

Guest favorite
A screened lanai is presented with light-colored wicker furniture, featuring green striped cushions. A small coffee table is positioned between the two seating areas, and a bicycle can be seen tucked in the corner, complementing the lush garden views visible through the screens.
Cottage in Sarasota
4.8 out of 5 average rating, 64 reviews

Walk to Bay light filled private Cottage King bed

Top guest favorite
The exterior of a cottage features light-colored siding and a turquoise door, framed by shade from a large oak tree. The entrance is surrounded by white gravel, with lounge chairs and beach equipment visible. Bright sunlight illuminates the scene, enhancing the tropical atmosphere.
Cottage in Siesta Key
4.95 out of 5 average rating, 86 reviews

Surf Shack- Walk to Village/Boat Dock Included

Guest favorite
The charming exterior of the Turtle Cottage showcases cheerful yellow siding, complemented by white railings and a small porch area. A decorative turtle motif is mounted on the wall, adding a coastal touch. The front door is framed by a simple overhang, enhancing the inviting entrance.
Cottage in Nokomis
4.92 out of 5 average rating, 93 reviews

The "Turtle Cottage" - a charming beachy retreat.

Guest favorite
A charming yellow cottage is set against a clear blue sky, featuring a welcoming porch with wooden steps leading up to it. Surrounding palm trees contribute to the relaxed ambiance of the outdoor space.
Cottage in Siesta Key
4.88 out of 5 average rating, 328 reviews

Cottage on Siesta Key Beach

Guest favorite
A spacious bedroom features a large bed adorned with a blue throw and several pillows. Two framed art pieces are displayed above the headboard. Nightstands with lamps are placed on either side, while a door on the left leads to another room.
Cottage in Sarasota
4.94 out of 5 average rating, 36 reviews

The All Hands On Deck Cottage at Casa Limonada

Superhost
The exterior of the guesthouse is shown, featuring a spacious gravel area surrounded by palm trees. The building presents a modern design with large windows. A mix of landscaping is visible, complementing the natural surroundings of Siesta Key.
Cottage in Siesta Key
5 out of 5 average rating, 4 reviews

The Sand Dune

Top guest favorite
A charming cottage exterior is adorned with peach-colored walls and a welcoming blue front door. Lush green landscaping features palm trees and colorful flowering plants, complemented by a gravel driveway and a well-maintained lawn.
Cottage in Englewood
4.98 out of 5 average rating, 60 reviews

Magnolia Cottage

A charming cottage exterior features a light green facade with blue double doors and decorative shutters. Surrounded by tropical plants and a mulch bed, a stone pathway leads to the entrance, inviting guests into a serene atmosphere.
Cottage in Sarasota
4.82 out of 5 average rating, 169 reviews

Charming Beach Cottage

Destinations to explore