Vacation rentals with a pool in Osprey

Pets, Plunges & Peace on the Gulf of Mexico

Yes, you can bring your boat... & your fur bestie! This sunny Nokomis home has a fully equipped kitchen, two cozy bedrooms & a true backyard oasis. The patio, outdoor furniture & a BBQ grill, makes it the perfect spot to host a family gathering or simply unwind with a good book & a glass of wine. Take a plunge in the un-heated pool & bask in the Florida sunshine while enjoying the pleasant coastal breeze. Just a 10 minute drive to the best beaches & close to shops & restaurants. This is the one!

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).

Nokomis Serenity Oasis

Welcome to your private Oasis, with a large private backyard filled with fruit trees and saltwater pool that meets the convenience of a prime location, just minutes from Nokomis Beach, and Legacy Trail. Casperson Beach, shark tooth hunters dream, is a short drive over to Venice Island to enjoy Venice Beach and charming local shops and dining or take a short ride north to Siesta Key Beach, USA's #1 Beach, and Siesta Village offering direct beach access and charming local shops and dining.

Coastal Haven 3BR/2BA Beach Home

Experience the perfect beach getaway at our newly renovated 3-bedroom, 2-bathroom vacation rental. Just minutes from the sandy shores, this charming home offers the ideal blend of relaxation and convenience. Unwind in your private backyard oasis, featuring a sparkling pool—perfect for cooling off on warm days. Located just a short drive from the beach, Coastal Haven combines modern comforts with the charm of coastal living. Book your stay today and make unforgettable memories by the sea!

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.

Heated Pool• Lakeview • 3BR • Nokomis & Siesta Key

Welcome to Lakeview Escape, a peaceful Nokomis townhouse with beautiful lake views, just 7 minutes from Nokomis Beach and with direct access to the Legacy Trail. Enjoy a relaxing stay with fast Wi-Fi, a resort-style community pool, and a comfortable space perfect for families, couples, remote work, and pet-friendly travel. Whether you're here for beach days, biking, or a quiet getaway near Sarasota and Venice, this home offers the perfect balance of location, comfort, and ease.

Beautifully Remodeled Home with Pool Near Siesta

It’s all about Siesta! Newly remodeled, 2 bedrooms, 2 baths, heated pool home is located in the Gulf Gate Estate neighborhood. 2,5 miles from the famous Siesta Key Beach. Great split plan bedrooms and bathrooms. High-speed Wi-FI. Located less than a mile from Publix Grocery, Gulf Gate shopping mall, grocery store, restaurants, cafes, pubs. Walking distance from the nearest convenient/gas station-7Eleven (5min). Parking for up to 3 cars maximum. Must be at least 25 years old.

Sandhill Sarasota

Welcome to your cozy Sarasota escape—designed for quiet moments, shared memories, and effortless comfort. This light-filled home features a warm, open layout with soft tones, inviting furnishings, and a calm, relaxed atmosphere perfect for couples or small families. Thoughtfully designed, family-friendly, and just minutes from beaches, dining, and local favorites—this is a place to slow down, reconnect, and feel at home. Find your quiet at Sandhill Sarasota 😊

The Sand Castle - Backyard Oasis Mins from Siesta!

*UPDATED!* Your family will feel at home in this spacious home that has it all! With a gorgeous backyard, alluring HEATED pool, tropical tiki bar, ping pong and other lawn games, cozy and comfortable rooms, and a kitchen stocked with everything you need to prepare meals for many... you will be more than comfortable here! The location is super convenient- minutes from Siesta Key, downtown Sarasota, and every grocery store and restaurant you could ever want!

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).

New Pool Tropical Waterfront Dock & Optional Boat

Located on a highly desirable street, the house is perched high above Curry Creek offering spectacular water views from every room. The property includes a boat ramp to avoid the public launch. Three kayaks (two tandems and one single). Two miles from Nokomis Beach and only half a mile from The Legacy Bike Trail. You can do so many fun things, or just have a drink on the dock and watch the manatees. Pet Friendly