Holiday rentals in Osprey

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Top-rated holiday rentals in Osprey

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Guest favourite

Villa in Nokomis

4.92 out of 5 average rating, 147 reviews

*Sale JUNE 8 $98! New Reno BEACH Villa 2KING/2BTH!

EXCLUSVE CASEY KEY beach just .5 mi. away!! Sarasota 10 mins away! Miles of uncrowded beach! Two KING bedrooms, two bath villa! The Villa is a short 1 minute drive from Casey Key Beach! Two new 55" 4K T.V's. New appliances and furnishings throughout! Kayaking, biking, boating... all right here! Lush tropical backyard and fire pit. There are many wonderful restaurants and shops within a five minute drive. Restoring this Villa has been a labor of love for us, read our reviews!! Come stay...:)

Guest favourite

Home in Sarasota

4.95 out of 5 average rating, 132 reviews

Sarasota Florida -Wild Orchid Creek Cottage Home

Come enjoy old Florida living at this completely renovated cottage style home on nearly seven acres. Relax and unwind in this 1000 square foot private home with king bed and queen sleeper to accommodate up to four people. Open concept living, dining room and full kitchen. Laundry facilities available. Equipped with WiFi and direct tv. While enjoying the private backyard space, it is common to spot abundant wildlife and wildflowers. Wild orchids in many of the oak trees bloom in early summer.

Guest favourite

Guest house in Sarasota

4.96 out of 5 average rating, 251 reviews

Sarasota guest house only 8 miles to Siesta Key

Our Florida-themed guest house has everything you need to enjoy your vacation in beautiful Sarasota, Florida. It is a very comfortable, clean and private one bedroom and one bathroom guest house. It is a completely separate space and has it's own private entrance. It is conveniently located in a quiet, safe neighborhood near Interstate I-75, Shopping, Dining, Twin Lakes Park, Serenoa Golf Course, Myakka River State Park and just 8 miles from the #1 beach in the U.S. - Siesta Key Beach.

Guest favourite

Home in Sarasota

4.99 out of 5 average rating, 207 reviews

The Key Lime Cottage 2 miles from Siesta Key Beach

Great location. 2 miles from the # 1 rated Beach in America , Siesta Key . The cottage is near several other beaches as well. Close to restaurants and shopping. 1 hour from Tampa and 2 hours from Orlando. The Key Lime Cottage is totally updated with new stainless steel & granite in the kitchen . There are two new beds ..... one is a queen size and the other is a full size. (URL HIDDEN) Linens & towels are all new. New tile and wood floors throughout. Quite neighborhood for walking .

Guest favourite

Guest house in Sarasota

4.93 out of 5 average rating, 379 reviews

Clean and Modern Sarasota Studio w/ Beach Gear!

Our studio is private, comfortable, stylish, & efficient. Whether you are coming for business or leisure, we are sure you will have everything you need. Our home is newer (built in 2020) and we designed this space specifically with Airbnb guests in mind. Our neighborhood is central to almost all of Sarasota! We were born and raised here, and in our opinion this area is central to everything! Whether you are headed to Siesta, Myakka State Park, or UTC mall, you won't be driving for long!

Guest favourite

Cottage in Nokomis

4.97 out of 5 average rating, 127 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.

Guest favourite

Cottage in Osprey

4.93 out of 5 average rating, 28 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.

Guest favourite

Home in Osprey

4.93 out of 5 average rating, 40 reviews

Private house with loft

Have fun with the whole family at this brand new, modern private free standing guest house. Full bedroom with king size bed, with a finished loft including a queen bed. There’s also a queen pull out sofa in the living area. Enjoy your privately fenced backyard with a hot tub and putting green. Centrally located between Siesta Key beach and Nokomis beach.

Guest favourite

Guest suite in Sarasota

4.9 out of 5 average rating, 241 reviews

Quiet, private suite short walk to SK Beach

This newly remodeled guest suite is tastefully decorated. The neighborhood is ideally located walking distance to one of the best beaches in the world, Siesta Key Beach. Guests have their own parking space and entry to a private back yard with grill and outdoor furniture. This is a nice private space that is very quiet and well appointed.

Guest favourite

Cottage in Nokomis

4.92 out of 5 average rating, 86 reviews

The "Turtle Cottage" - a charming beachy retreat.

The Cottages of Nokomis would like to introduce you to the "Turtle Cottage", a rustic, quaint cottage brimming with Old Florida charm - .5 miles to the beach (10 minute walk, 3 minute bike ride) or if you'd rather stay home it's comfy! - put your feet up and close your eyes - you've found your little piece of paradise!

Guest favourite

Flat in Venice

4.99 out of 5 average rating, 393 reviews

Hales Corner, Cozy & Private Beach Town Getaway

Our cozy corner is close to parks, art and culture, restaurants and dining beaches, movie theatre, play house theatre, and local attractions and just 2 hours from Disney!!. You’ll love our place because of the people, the ambiance, the neighborhood, the outdoors space, and of course, the beautiful beaches.

Guest favourite

Flat in Nokomis

4.96 out of 5 average rating, 127 reviews

Casa del Sol II (Non-Smoking Property)

Spacious 3 bedroom 2 bath with 800 sq ft covered porch overlooking neighborhood. Carport under building for up to 4 cars. Private stairway entrance. Lots of sliding glass doors gives you a treehouse effect. All electric home powered by 120 solar panels. 4 minute walk to beautiful Nokomis Beach.