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Cottage holiday rentals in Sarasota County

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Top-rated cottage rentals in Sarasota County

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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!

Experience relaxed coastal living at The Pink Palm, a designer bungalow just steps from the world-famous Siesta Key Beach. Thoughtfully decorated with whimsical coastal touches and curated local art, this two-bedroom retreat blends charm, comfort, and convenience. Spend your mornings with coffee on the covered porch, stroll 15 minutes to Crescent Beach, or enjoy al fresco dinners in the spacious backyard with its dining area and grill. Inside, you’ll find a cozy living room with a plush sofa and

Guest favourite
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, 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

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, 268 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 favourite
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

Ideally located 3 bedroom cottage , 1 block from downtown Siesta Key with 12 restaurants and nightclubs/bars with live entertainment. 3 blocks to beach. Close enough for all the excitement of the village, yet far enough so you have peace, quiet and relaxation. Private heated pool with tanning ledge and bubbler, patio, lanai, gazebo, fire pit, gas grill, bicycles. Beach wagon, Beach chairs, Beach towels, Beach umbrella, washer and dryer, 3 flat screen smart tvs, outdoor security cameras

Guest favourite
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, 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!

Top Guest favourite
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, 70 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 favourite
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 favourite
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, 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!

Guest favourite
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.

Guest favourite
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 favourite
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
Wi-Fi
Pool
Free parking on premises
Air conditioning

Cottage rentals with a hot tub

A charming home exterior is depicted, featuring light yellow siding with white trim. A raised entryway leads to a covered porch with large windows. A golf cart is parked to the side on a paved driveway, surrounded by trees and open space.
Cottage in Sarasota

Family cottage with rare to find private backyard!

Top Guest favourite
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

Cottage in Siesta Key
New place to stay

Cozy Cottage Near Siesta Key Village!

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 favourite
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, 69 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

An expansive outdoor pool is showcased, featuring clear blue water under a bright sky. Surrounding the pool, lounge chairs with shaded umbrellas are arranged for relaxation. A spacious clubhouse with large windows is visible in the background, enhancing the resort's inviting atmosphere.
Cottage in Sarasota

Sunny Landings *Florida*

Pet-friendly cottage rentals

Guest favourite
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

Top Guest favourite
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

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
4.69 out of 5 average rating, 149 reviews

Cozy Florida Cottage

Superhost
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.
Cottage in Sarasota
4.85 out of 5 average rating, 13 reviews

Walkable to Downtown and Parks Brand New Furniture

Superhost
The studio features a spacious bed with light-colored bedding, positioned near a modern seating area. A decorative partition adds privacy, while a glass coffee table rests on a soft area rug. Natural light is welcomed through sliding doors leading to the outdoor space.
Cottage in Bradenton
4.89 out of 5 average rating, 9 reviews

Studio competely remodeled

Guest favourite
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, 174 reviews

Siesta Key Cozy Cottage across from the beach!

Top Guest favourite
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, 26 reviews

Lemon Bay Hideaway near beach and fishing pier

Private cottage rentals

Guest favourite
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, 66 reviews

Walk to Bay light filled private Cottage King bed

Top Guest favourite
Cottage in Sarasota
5 out of 5 average rating, 7 reviews

Cottage & Tree ~ by the Sea

Guest favourite
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 favourite
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 favourite
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

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

Guest favourite
The living area features a spacious sectional sofa with an accent pillow, paired with a sleek coffee table and an armchair. A flat-screen TV is positioned on a white console, surrounded by built-in shelving. Natural light fills the room through two large windows with sheer curtains.
Cottage in Sarasota
4.98 out of 5 average rating, 109 reviews

Chic Sarasota Cottage: Near Beaches & Downtown!

Destinations to explore