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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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Cottage in Siesta Key

4.88 out of 5 average rating, 217 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, stand up paddle boards & 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 favourite

Cottage in Myakka City

4.99 out of 5 average rating, 115 reviews

NEW! Peaceful Country Cottage near Lakewood Ranch

Enjoy the peace and solitude of the country at this fully renovated cottage. "Country Oaks" Cottage located on seven acres surrounded by nothing but woods and wildlife. We are located approximately 15 miles east of I-75 where you can enjoy privacy away from the bustling city but close enough to enjoy shopping and restaurant options in nearby Lakewood Ranch. Enjoy a trip to historic Arcadia for antique shopping or adventure out to Myakka State Park or TreeUmph! or even local beaches.

Guest favourite

Cottage in Sarasota

4.94 out of 5 average rating, 142 reviews

Sea-esta Cottage-cheerful 2bd/1ba w/ free parking

Experience ultimate relaxation in this serene and stylish rental. A brand-new home in the heart of Amish Village, Pinecraft. Two cozy bedrooms with plush bedding and soothing coastal decor. Sip your coffee on the front porch, immersed in the tranquility of this idyllic neighborhood. Take a short walk to Yoder's Fresh Market & Restaurant, Coastal 98 Cafe, and the Pinecraft Ice Cream Shop. Just 6 miles to Siesta Key and 7 miles to Lido Beach for endless coastal adventures.

Guest favourite

Cottage in Nokomis

4.98 out of 5 average rating, 124 reviews

Staycation Sanctuary - 100% Smoke-Free Property

Bella Vita! (The Good Life!)…that feeling when you wake up each day in this little slice of Paradise. This is the spot to enjoy a warm peaceful getaway from the rest of the world...just arrive with your bathing suit/flip flops and walk 1.5 blocks to the warm Gulf waters. Tranquillity of beach life, beautiful sunsets and lazy days of fishing and bird watching. Visit the Jetties, where you can see dolphins, manatees and rays, is only 1/2 mile away.

Cottage in Siesta Key

4.84 out of 5 average rating, 133 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, stocked with everything but your clothes and toothbrush.

Cottage in Sarasota

4.83 out of 5 average rating, 151 reviews

Charming Beach Cottage

LOCATION!!! Getaway from the fast paced, high pressure life and slip on some flip flops! Get ready to unwind with the cool sea breeze, sunny adventures on the beach or on the water and explore the meaning of easy island living. Our contemporary designed home is just a few minutes drive from the most picturesque beaches in the nation with LOTS of parking. Feel free to bring your boat:) Restaurants and shopping are plentiful!

Guest favourite

Cottage in Siesta Key

4.89 out of 5 average rating, 145 reviews

Siesta Key Cozy Cottage across from the beach!

Adorable Siesta key cottage one block from the beautiful white sand beach and two blocks from the iconic Siesta Key Village on the north end of the island. Everything is a short walk including all the shops and restaurants of Siesta Village. Very private fenced in yard with barbecue:) Very nice size kitchen with a dining room and a large sunken living room. Both the living room and the bedroom open to the private patio!

Guest favourite

Cottage in Sarasota

4.87 out of 5 average rating, 131 reviews

Charming Lido Cottage

Relax in this quiet free standing 2 bedroom 2 bath cottage one block to the beach. Sleeps up to 6 in three beds. Full kitchen and outdoor Bar-B-Q grill. Two beach bikes included and kayak rentals within a couple of blocks. Lots to do nearby including restaurants, shopping, sight seeing and theaters. Full TV and internet is included. Walk over to the Ritz Tiki Bar at sunset for Lido libations - it's a local hangout too!

Guest favourite

Cottage in Sarasota

4.78 out of 5 average rating, 118 reviews

Charming Guesthouse

Charming Spanish style guest house ....... very private Private courtyard, off street parking Close to downtown Sarasota, restaurants, theater, beaches ( famous Siesta Key Beach ) Quiet neighborhood. Self check in. The “house book” will tell you all the specifics; A/C, TV, dehumidifier, house rules & a section on dining in Sarasota & pamphlets on our area sites!

Guest favourite

Cottage in Englewood

4.96 out of 5 average rating, 141 reviews

Family-Friendly Beach Cottage Manasota Key

Perfect for family / friends who want to escape the stress of the real world into paradise on Manasota Key. This family/group-friendly beach cottage sits across the street from the Gulf of Mexico. The closest public beaches are Manasota Beach and Blind Pass beach ( ea. 4 min drive) The property sits bayside and has private dock access !

Guest favourite

Cottage in Sarasota

4.9 out of 5 average rating, 178 reviews

"Honeybee Hideaway" Cozy Cottage Near SIESTA KEY

Experience the Honeybee cottage, a classic coastal retreat in historic Sarasota, minutes from Siesta key Beach. Enjoy, cozy vibes, modern amenities, fast, Wi-Fi, and shared laundry facilities. Embrace, tranquility and convenience in this charming oasis, combining rich history, with world-class beaches for a memorable getaway.

Guest favourite

Cottage in Sarasota

4.85 out of 5 average rating, 157 reviews

Heated Pool! Beach! Drift Inn Unit B Siesta Key!

Come and enjoy all that Unit B has to offer! This is a cottage style condo, very comfortable and inviting, fully equipped with your beach vacation in mind. The soft white quartz sands of Crescent Beach on Siesta Key are just a 3 minute walk from the cottage door. So is our lovely, saltwater heated pool.

Holiday rentals for every style

Get the amount of space that is right for you

Villas

Luxurious estates for the ultimate escape

Bungalows

Intimate homes, inviting architecture

Flats

Convenient locations with everyday essentials

Popular amenities for cottage rentals in Sarasota County

Free parking on premises

Air conditioning

Cottage rentals with a hot tub

Cottage in Venice

4.64 out of 5 average rating, 25 reviews

BarefootBeachBungalow@Ramblers Rest Resort!

Guest favourite

Cottage in Sarasota

4.96 out of 5 average rating, 23 reviews

Charming Coastal Oasis 2 Bed/2 Bath Cottage

Cottage in Port Charlotte

5.0 out of 5 average rating, 3 reviews

Cute Port Charlotte Home w/ Resort Amenities!

Cottage in Sarasota

4.67 out of 5 average rating, 3 reviews

Cozy Cottage at Sun Outdoors Sarasota

Cottage in Venice

New place to stay

Cottage near Venice Beach

Cottage in Sarasota

Sun Outdoors Sarasota-1 Bedroom Cottage w/Loft

Cottage in Sarasota

Sunny Landings *Florida*

Cottage in Sarasota

4.82 out of 5 average rating, 34 reviews

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

Pet-friendly cottage rentals

Cottage in Sarasota

4.81 out of 5 average rating, 154 reviews

Dog friendly Cottage

Guest favourite

Cottage in Sarasota

4.96 out of 5 average rating, 69 reviews

Luxury large cottage-studio/wth kitchen & bathroom

Guest favourite

Cottage in Sarasota

5.0 out of 5 average rating, 23 reviews

Cozy Cottage near Siesta Key Beach

Cottage in Sarasota

5.0 out of 5 average rating, 3 reviews

Sunset Shack-steps to beach/walk to St. Armand's

Guest favourite

Cottage in Sarasota

4.96 out of 5 average rating, 26 reviews

Cozy 2 bedroom cottage

Guest favourite

Cottage in Sarasota

5.0 out of 5 average rating, 18 reviews

Lido Key Beach Bungalow with Private Heated Pool!

Guest favourite

Cottage in Nokomis

5.0 out of 5 average rating, 50 reviews

New Pool Tropical Waterfront Dock & Optional Boat

Cottage in Sarasota

4.55 out of 5 average rating, 11 reviews

Charming Bungalow | Close to Beach | 2 Beds

Private cottage rentals

Cottage in Sarasota

4.79 out of 5 average rating, 47 reviews

Bay Shore Craftsman Cottage

Guest favourite

Cottage in Osprey

4.92 out of 5 average rating, 26 reviews

Mattie’s Cottage by the Bay

Guest favourite

Cottage in Sarasota

4.95 out of 5 average rating, 40 reviews

Sarasota Home with pool in resort community

Guest favourite

Cottage in Sarasota

4.97 out of 5 average rating, 36 reviews

Sand dollar cottage of Pinecraft

Guest favourite

Cottage in Sarasota

5.0 out of 5 average rating, 15 reviews

Bamboo Cottage, minutes from the beach.

Guest favourite

Cottage in Sarasota

5.0 out of 5 average rating, 33 reviews

Bee Keepers Cottage

Guest favourite

Cottage in Englewood

4.98 out of 5 average rating, 40 reviews

Magnolia Cottage

Guest favourite

Cottage in Englewood

4.96 out of 5 average rating, 50 reviews

Bamboo Cottage, minutes to beach, no guest fee!

Destinations to explore