House vacation 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

Pet-Friendly Modern Retreat Near Siesta Key

Discover your perfect Florida retreat in this stylish, spacious, and pet-friendly home located in a quiet Palmer Ranch neighborhood. Enjoy an open-concept layout with tall ceilings, a fully stocked modern kitchen, luxury linens, and a fenced-in yard ideal for pets and families. Centrally located near beaches, shops, golf, and top attractions, this elegant getaway offers comfort, convenience, and relaxation. Perfect for extended stays, remote work, and unforgettable family memories all year round

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!

The Ibis Cottage

Freshly renovated, The Ibis Cottage is a cozy studio on a beautiful property overlooking a small lake. It is a 5 minute drive to Nokomis Beach, Siesta Beach and Venice Beach are within easy reach, and a block away to the Legacy Trail bike path (Sarasota to Venice). Enjoy seeing a variety of birds on the property including the ibis, heron, and snowy egret. The cottage is conveniently located between Sarasota and Venice. The perfect location for enjoying the Gulf coast and outstanding beaches.

Cozy Beach Cottage

Welcome to your peaceful retreat just 3.3 miles from Casey Key Beach and 5 miles from the Myakka River. Enjoy your private dock on Shackett Creek just a block away, or explore The Legacy Trail less than a mile from your door. Downtown Venice is only 3.5 miles away with great dining and shopping . Spend your days hunting for fossilized shark teeth, kayaking, biking, or relaxing at home by the outdoor fire pit. Whether you’re here to unwind or explore, Nokomis is a nature lover’s paradise!

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.

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. VR24-00265

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.

Great location! Updated & loaded with all you need

Looking for great location for vacation…This coastal 2 BR/2 Bath remodeled home is located in a great neighborhood and close to everything that you would want to explore. Within minutes of Siesta Key, Casey Key, Venice Beach and famous Shark Tooth Caspersen Beach. Only an hour from Tampa, within minutes of all the amenities and shopping you could want. After a day of fun, return to a cozy, clean and comfortable home where you can relax and unwind.