Alquileres vacacionales en Osprey

Windsor Lodge Unit #18, studio

Windsor Lodge is a luxurious and beautifully maintained vacation rental located on the golf course within the gated community of The Oaks Golf and Country Club. This elegant unit offers an open and inviting layout with a spacious living area and a comfortable bedroom, complemented by a separate bathroom for added privacy. Guests can enjoy the peaceful surroundings and manicured landscapes that make The Oaks such a desirable community. Access to the community pool provides a refreshing way to rel

Sunshine Cottage

Our Sunshine Cottage is clean, quiet, and all yours! Enjoy the calming views of this beautiful property from your patio. It is located off a main road that takes you to Nokomis Beach in 5 minutes. Ideal for those who enjoy going to the beach, looking for shark teeth and shells. Conveniently located between Sarasota and Venice, it is the perfect place to sightsee, shop and enjoy great local food. Just around the corner from Oscar Scherer State Park and within walking distance of the Legacy Trail.

Charming Florida Cottage - Kayaks Included

Welcome to the Spanish Point Cottage! Our Old Florida style cottage is conveniently located within steps of some of Sarasota's most historic sites making it the ideal place to experience true Florida. Enjoy exploring Historic Spanish Point, kayaking to a secluded beach, walking to Historic Bay Preserve, watching the sunset over the Bay, fishing at Osprey Fishing Pier, walking to dinner all from your well appointed and peaceful oasis. There is no better place to experience true Florida living!

Sand Dollar Retreat

Escape to our relaxing 2-bedroom home in Osprey, Florida, just minutes from the stunning beaches of the Gulf of Mexico, pristine golf courses and MLB spring training. This peaceful retreat sleeps up to 7 adults and offers a perfect blend of comfort & convenience. The master bedroom features a queen bed and the second bedroom has a bunkbed sleep system with a queen mattress on bottom and twin mattress elevated above. There is also an office with a daybed & trundle for additional sleeping space.

Private Coastal Getaway - Your Home Away from Home

Enjoy privacy, luxury, and comfort in this 2-bed, 1-bath coastal guesthouse, perfect for business trips or extended stays. Accommodating up to 4 guests, it features a leather Reclining Sectional, two Queen Beds with storage, and a Private Outdoor Space with seating and a Blackstone grill. Located in Osprey, FL, you're ideally situated between Siesta Key, Nokomis, and Venice beaches—just minutes from sand and sun! Set down your bags and grab complimentary beach chairs, umbrella, and cooler!

Chic & Cozy Getaway • Near Siesta Key Beach

Renovated modern studio in a duplex home with private entrance, full kitchen, bathroom, laundry, and parking. Nestled in a quiet, safe neighborhood just minutes from Lido, Turtle, Nokomis beaches, and Siesta Key—#1 beach in America with soft, white sand. Walk to restaurants, Starbucks, Total Wine, Costco, Target, CVS, Bay Village Assisted Living, Selby Aquatic Center & Vamo Bay Park. Short drive to downtown Sarasota, Venice & scenic bike trails. Ideal for beach getaways or extended stays!

The Lake View

The Lakeview is a cozy independent apartment with a separate entrance and its very own screened in breezeway. The apartment is bright and airy and decorated with fresh coastal Florida colors. Located on a beautiful property overlooking a small lake, It is tucked back from a main road that will bring you to Nokomis beach in five minutes. A short drive to Siesta Beach, Sarasota, and Venice. Around the corner from Oscar Scherer State Park, and walking distance to the Legacy Trail bike path.

Beach Retreat•Renovated Pool Patio•Near Siesta Key

Stay at one of Sarasota’s top-rated Airbnbs, perfectly centered between the ever famous Siesta Key and several other stunning beaches. Lounge by the newly renovated heated pool with upscale chaise lounge chairs, lush garden views, and a stylish patio with ample seating. Inside, enjoy a modern, beach vacation themed design with an open layout, fully stocked kitchen, fast WiFi, and Smart TVs in every bedroom. Your on-site Superhost is nearby but works full time and gives total privacy.

Comfortable + Functional Private Studio Apartment

This comfortable, clean, and private studio apartment is the perfect spot to relax- whether you're here on business or you've spent the whole day on the beach! Recently remodeled with a dining table to take your meals, hot water, a comfortable bed, and well equipped kitchenette, you will be lacking nothing here. This apartment is a guest suite attached to the main living area of the home and is completely private, however there is a resident who lives in the main part of the home.

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. Hot tub is available upon request in off season months, April-October. There will be an additional $30 fee in off season months.

2 BR House 1.6 miles from Siesta Key Beach

Discover the charm of Sarasota in our newly remodeled 2BR/1BA vacation home. Just 1.6 miles from beautiful Siesta Key Beach! Enjoy your morning coffee on a brick patio surrounded by flowers and sunshine. Our comfy beds, blackout curtains, and quiet neighborhood ensure a sweet deep sleep. FIOS wifi and three smart TVs; a fully-equipped kitchen; and a sparkling new bathroom with two sinks, huge mirror, and marble shower offer all the comforts and convenience of home. We welcome you!

Lux Siesta Key Beach Home

March Special DISCOUNT send us a message now! Beach home under 11 minutes to Siesta Key beach & attractions : 20 minutes to the airport 15 minutes to UTC Hammock Fire pit Foosball Backyard patio seating Grill Cozy Decor Comfy beds Fully stocked kitchen Fully stocked bathrooms Minutes to shops & restaurants Quite and safe location Escape to this beautiful home in quiet South Sarasota The perfect blend of comfort, location, and charm for your beach tea