House holiday rentals in Osprey

5 mins to the beach! Come relax!

Relax with the family at this peaceful place to stay. Home located in a unique family friendly neighborhood on the inter-coastal. Enjoy family games, watching the sunset from the lanai and using the enclosed outdoor shower after a day at the white sandy beach! Take out our 2 kayaks on the intercoastal and explore the area. Nokomis beach 5 minutes away and Siesta key 7 miles. So many cute restaurants nearby on the water. Stroll through the neighborhood and see all of the beautiful homes and boats

Secluded 3R Pool Home Retreat Near Sarasota

Welcome to The Osprey Oasis, a private retreat surrounded by lush tropical landscaping and just minutes from Sarasota’s beaches, parks, and downtown. This newly renovated 3-bedroom home features a bright open layout, a gourmet kitchen with stainless steel appliances, and spa-inspired bathrooms. Outside, relax in your own backyard paradise with a heated pool, screened lanai, lounge chairs, outdoor dining bar, grill, and fire pit for cozy evenings. Perfect for families, couples, or small groups, t

4/2.5 Oak Bahay, Heated Pool! 5min to Beach,4Acres

Welcome to Oak Bahay Ranch, our beautiful 4+ acre ranch home with pool! Enjoy the tranquility of this 4 bedroom/2.5 bathrooms with a pool (heated during winter). Bike or drive the quick 2.5 miles to Nokomis and Casey Key Beaches! Oak Bahay Ranch is a nature lover's paradise, close to Legacy Trail, Sarasota County's premier 20+ mile biking/walking trail. Oak Bahay Ranch is an easy drive to world famous Siesta Key Beach (15 mins), downtown Sarasota (20 mins), and downtown Venice (10 mins).

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!

Modern 4BR Home *Heated Pool & Spa*

Discover elegance in this centrally located Sarasota gem, featuring four bedrooms and two bathrooms to accommodate up to eight guests. Enjoy a laid-back vibe while lounging at Sarasota's beaches or immersing yourself in local attractions. Siesta Beach and Lido Beach are within easy reach at 7.6 and 6.4 miles respectively. Rest easy knowing commitment to cleanliness aligns with your travel priorities. Your serene vacation awaits in this beautifully adorned home. *Brand new pool* VR24-00265

Sunny Oasis/Beautiful House/Near Beach/Heated Pool

Beautiful House with 3 bedrooms, heated pool, mini golf and two-car garage. Great location. five-minute drive to the beach. near shopping plazas, restaurants, and the famous Legacy Trail perfect for biking, running, and more. Situated at a dead-end in a peaceful community. Lots of outdoor space around the house with beautiful palm trees and a large patio. bicycles, board games, cornhole, a gas grill, and more at your disposal. Lots of places to visit in the Sarasota and Venice area.

Heated&Renovated Pool•Beach Retreat•15m to Siesta

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.

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!

Cute Little Getaway

Close to the beach and walking distance to 5 restaurants, including one on the water. Our place is less than 2 miles from Nokomis Beach! We have you covered on beach equipment, wagon, chairs, towels and umbrella. The backyard boasts a relaxing, beautiful escape with resort style touches. We have a gas grill to cook your catch, a high powered outdoor fan, and comfy seating in the shade. The house is freshly modernized, open and airy. You will enjoy an outfitted kitchen.

Creekside Paradise I

The 1970 sqft living space hosts 3 bedrooms, 2 bathrooms, an open living room with attached ‘library’, a dining area, as well as a fully equipped kitchen. From the caged pool area you have a view of the North Creek and our Boat Dock. The pool can be electrically heated and measures 32.80ft in length/13.12ft in width. You enter Creekside Paradise I thru the attached 2 car garage, where you can find the beach equipment (chairs, umbrella, cooler).

Charming vacation home, short walk to the beach

Welcome to our charming vacation home! Just a 10-min walk to beautiful Nokomis Beach and a short drive to Siesta Key, Downtown Venice, and all the area’s attractions. Inside, the home is bright, spotless, and fully stocked with essentials. Two spacious bedrooms, each with a walk-in closet and private bath for your comfort and privacy. Enjoy the patio, grill, and peaceful neighborhood. We are looking forward to hosting you!