Cottage vacation rentals in Sarasota County

A single-story home is surrounded by a well-kept lawn, featuring a lush shrub at the forefront. The entrance is framed by a covered porch, with large windows providing natural light. Trees line the property, casting gentle shadows across the yard.

4.95 out of 5 average rating, 40 reviews

Charming Coastal Oasis 2 Bed/2 Bath Cottage

Our home is a beautifully remodeled and charming two bed, two bath situated in the perfect area. We just added a brand new heated pool/spa covered with a lanai to keep out the bugs. The home is on a quiet, tree lined street. A quick 10 minute drive to Siesta Key Beach (consistently rated #1 beach in the US) and a 10 minute drive to downtown Sarasota. Great restaurants and shops are all within walking distance. Everything that you need for a comfortable, convenient stay is waiting here for you.

A spacious bedroom features a king-size bed with a colorful striped blanket. A desk with a chair is positioned nearby, along with a small bedside table. Natural light enters through the window, illuminating the area. A bathroom is visible beyond a door, adding convenience.

4.85 out of 5 average rating, 75 reviews

Cozy Cottage close to everything w/ grill on patio

Escape to a serene oasis West of the Trail, The Bromeliads, where salty breezes and tropical gardens welcome you. The 1BR/1BA cottage has modern amenities, ample living space, a king bed with hotel linen, and high-speed Wi-Fi. Relax on the front porch or back patio, surrounded by birdsong and swaying palms. Dine al fresco with the gas grill and lush garden as your backdrop. Stroll to the Bay or explore nearby museums, theaters, fine dining and shopping. You will be minutes from Sarasota’s best!

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.

4.93 out of 5 average rating, 42 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

4.93 out of 5 average rating, 123 reviews

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

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.

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.

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.

4.86 out of 5 average rating, 273 reviews

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

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, 71 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!

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.

4.78 out of 5 average rating, 144 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!

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.

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.

4.86 out of 5 average rating, 174 reviews

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

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.

The exterior of the duplex is showcased with a welcoming pathway lined by lush landscaping. A large tree provides shade, while the combination of modern wood accents and light-colored siding reflects the property's charming design. Natural light filters through the nearby foliage.

4.85 out of 5 average rating, 13 reviews

Walkable to Downtown and Parks Brand New Furniture

Discover Siesta Sunset, a charming two-bedroom, one-bathroom unit just minutes from downtown Sarasota and the stunning Siesta Key Beach. This duplex features a spacious, inviting living area and a large outdoor sitting space with a cornhole game. Enjoy the convenience of being close to vibrant city life, exquisite dining, and shopping, while only a short drive from the beautiful beaches of Siesta Key. Perfect for a relaxing getaway with family or friends!

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.