
Cottage vacation rentals in Sarasota County
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Top-rated cottage rentals in Sarasota County
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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.

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

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

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.

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.

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!

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!

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.

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!

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.

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.

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
Cottage rentals with a hot tub

Sarasota Cottage Near Beaches, Downtown & Airport

Sun Outdoors Sarasota-1 Bedroom Cottage w/Loft

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

Cozy Cottage Near Siesta Key Village!

Modern Lakefront Getaway – Resort Perks Included

Cottage near Venice Beach

Cozy Cottage 1 block from Beach

Cozy Cottage at Sun Outdoors Sarasota
Pet-friendly cottage rentals

Family-Friendly Beach Cottage Manasota Key

Charming 2BD Bungalow Close to Crescent Beach!

Pink Pineapple Cottage

Lovely ❤ Cottage - Very Close to Siesta Key & More

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

Cozy Florida Cottage

Siesta Key Cozy Cottage across from the beach!

Lemon Bay Hideaway near beach and fishing pier
Private cottage rentals

Walk to Bay light filled private Cottage King bed

Surf Shack- Walk to Village/Boat Dock Included

The "Turtle Cottage" - a charming beachy retreat.

Cottage on Siesta Key Beach

The All Hands On Deck Cottage at Casa Limonada

The Sand Dune

Magnolia Cottage

Charming Beach Cottage
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- Cottage rentals Florida
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- Anna Maria Island
- Siesta Beach
- Crescent Beach
- Captiva Island
- John's Pass
- Turtle Beach
- Caspersen Beach
- Coquina Beach
- Lido Key Beach
- Anna Maria Public Beach
- Cortez Beach
- Vinoy Park
- Bean Point Beach
- Streamsong Resort
- Gulfport Beach Recreation Area
- Jannus Live
- Manasota Key Beach
- North Beach
- River Strand Golf and Country Club
- North Beach At Fort DeSoto Park
- Englewood Beach
- Fort De Soto Park
- Lakewood National Golf Club
- Point Of Rocks
- Things to do Sarasota County
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- Things to do United States
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