Airbnb your place

Holiday rentals with a pool in Osprey

Find and book unique homes with a pool on Airbnb

Quick stats about holiday rentals with a pool in Osprey

  • Total holiday rentals

    Explore 50 holiday rentals in Osprey

  • Nightly prices starting at

    Osprey holiday rentals start at ₹5,766 per night before taxes and fees

  • Verified guest reviews

    Over 400 verified reviews to help you choose

  • Family-friendly holiday rentals

    30 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    50 of Osprey holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Osprey rentals

  • 4.9 Average rating

    Osprey stays are highly rated by guests – averaging 4.9 out of 5!

Top-rated rentals with a pool in Osprey

Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

1 of 1 pages1 / 1
Guest favourite
A spacious living area features two large sofas and a patterned accent chair arranged around a central coffee table. Tall windows allow natural light to fill the room, highlighting the neutral color palette. A staircase leads to the upper level, enhancing the open layout.
Home in Nokomis

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).

4.88 out of 5 average rating, 218 reviews
Superhost
Home in Gulf Gate Estates

Beachy Cottage close to Siesta | 3 Bed | Huge Pool

Welcome to The Salty Unicorn, your cheerful Sarasota escape just five miles from Siesta Key Beach. This fully renovated 3-bedroom home is designed for relaxation and fun, with a bright open layout, stylish coastal décor, and plenty of space to gather with family or friends. Start your mornings with coffee by the pool, spend sunny afternoons swimming or lounging in the spacious backyard, and end the day with dinner in the screened lanai. Whether you’re here for beach days, family time, or a peace

4.89 out of 5 average rating, 107 reviews
Top guest favourite
Home in Nokomis

Saltwater Oasis

Welcome to your dream vacation home, where the tranquility of a private saltwater pool meets the convenience of a prime location, just minutes from Nokomis Beach, Legacy Trail and Siesta Key, the USA's #1 Beach. This home offers the perfect blend of comfort, style, and relaxation for your getaway. Our home even features a King sized master bedroom equipped with a sleeper sofa, ensuring young children can stay close to their parents. This is your haven for creating unforgettable memories.

5.0 out of 5 average rating, 14 reviews
Guest favourite
A swing chair hangs from the ceiling in a cozy living space, complemented by a dark sectional sofa and a round coffee table. A decorative rug adds warmth to the wooden floor, while a wall-mounted television and a piece of artwork provide visual interest.
Home in Sarasota

1 House 1400sq. ft. 12 min from Siesta Key!

12 min. from Siesta Key Beach!! Perfect cozy vacation home in quiet, friendly neighborhood. Central to lots of shopping/restaurants. 1-king, 1-queen, bunk beds w/ 1-full & 1-twin. Dog & cat friendly w/ large private fenced yard, & 1-men's & 1-women's bike. Air hockey table w/ board games & pool toys. Fully loaded kitchen & W/D. Spacious living w/ large sectional, swing chair, & all bedrooms come w/ TVs & free Netflix & Hulu. Looking forward to hosting you! Message me anytime w/ questions.

4.8 out of 5 average rating, 189 reviews
Top guest favourite
A spacious pool area is surrounded by a screen enclosure, offering a clear view of the turquoise saltwater pool. The patio features a few lounge chairs and a table, with a grassy backyard visible through the enclosure, enhanced by the natural light streaming in.
Home in Nokomis

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.

5.0 out of 5 average rating, 15 reviews
Top guest favourite
A spacious covered lanai features woven seating and a dining table, providing an inviting space for relaxation and outdoor dining. Three overhead fans enhance airflow. The backdrop reveals a landscaped pool area through large screened windows, with sun loungers positioned beside the heated pebble tech pool.
Home in Nokomis

Tropical Pool Paradise - Minutes from the Beach!

Welcome to your own slice of paradise! This beautifully updated and completely eco-friendly and HEATED pool home in a quiet neighborhood is the perfect setting for your relaxing Florida vacation! You will love the privacy of this home overlooking tropical landscape vistas from the large covered lanai and solar heated pool welcoming you to your PRIVATE OASIS. You will enjoy easy access to our gulf coast beaches just minutes away. Beautiful Nokomis public beach is a 7 minute drive away.

4.94 out of 5 average rating, 97 reviews
Guest favourite
A single-story house is set within a lush green landscape, featuring well-maintained shrubs and palm trees. The façade includes large arched windows and a spacious driveway nearby, with bicycles visible against the side of the house. A clean lawn invites outdoor activities.
Home in Nokomis

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.

4.93 out of 5 average rating, 138 reviews
Top guest favourite
Home in Sarasota

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.

4.93 out of 5 average rating, 409 reviews
Guest favourite
The property is surrounded by lush greenery, featuring a spacious driveway leading to a single-story home. Tall palm trees and various plants are visible in the yard, creating a tropical ambiance. The structure is situated in a serene neighborhood, showcasing nature's beauty.
Home in Osprey

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).

4.96 out of 5 average rating, 53 reviews
Top guest favourite
A screened-in pool area is presented, featuring a clear blue pool surrounded by stone pavers. Lush greenery and water views are visible through the screen, enhancing the sense of tranquility and connection with nature.
Cottage in Nokomis

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

4.96 out of 5 average rating, 113 reviews
Top guest favourite
A serene outdoor space is highlighted by a heated saltwater pool and a six-person spa. Comfortable lounge chairs line the pool area, and an outdoor grill is situated nearby. The setting is complemented by a vibrant sunset, enhancing the tranquil atmosphere.
Home in Sarasota

Luxury 3/3 with Heated Pool, Spa, & Putting Green!

Experience luxury at this newly remodeled home with a brand-new pool, spa, and putting green. Centrally-located near downtown Sarasota, Siesta Key, Lido Key beaches, and St. Armand’s Circle, it features a full kitchen, 3 king bedrooms, 3 full bathrooms, outdoor dining, high speed internet, a 75” outdoor TV, fire pit, and EV charger. Pet-friendly with a fenced yard, pet crate, bowls & treats. License # VR24-00208

5.0 out of 5 average rating, 110 reviews
Top guest favourite
A covered patio area surrounds a heated pool, visible through large screened openings. Lounge chairs are placed around the pool, offering comfortable seating. The backyard includes a low fence for privacy, and the house's exterior can be seen with large glass doors leading to the interior.
Home in Gulf Gate Estates

Private heated pool, 3Bed, 2Bath, Siesta Key

Family oriented house; Heated pool; Kids scooters, bikes, beach toys, games, etc; 3bed/2bath/laundry; 1 crib; 10 minutes to Siesta Beach; 15 minutes to Siesta Village Restaurants/Shops. 20-25 minutes to Sarasota Airport, Lido Key Beaches & Shops, Venice; BONUS FEATURES: +Fast Wifi, +Cable TVs, +Netflix, +Disney, +Kids activity corner & games, +Kids safety net by pool is optional.

4.98 out of 5 average rating, 106 reviews

Popular amenities for Osprey rentals with a pool

KitchenWifiPoolFree parking on premisesAir conditioning

House rentals with a pool

Guest favourite
A heated pool is enclosed within a screened area, surrounded by lush greenery and outdoor seating. The pool area features a natural stone deck, with lounge chairs positioned for sunbathing. The peaceful environment offers a private retreat for relaxation and enjoyment.
Home in Sarasota

Heated Pool - Just 1 mile to Beach! Updated/Fun!

4.92 out of 5 average rating, 124 reviews
Top guest favourite
Home in Sarasota

Your DreamOasisAwaits: SiestaKeyEscape with Pool!

4.98 out of 5 average rating, 130 reviews
Top guest favourite
A charming house is set within a spacious yard, featuring lush green grass and palm trees. A driveway leads to a light-colored exterior, with the front entrance framed by tropical plants. A clear blue sky adds to the inviting atmosphere of the property.
Home in Nokomis

The Pineapple Escape

4.99 out of 5 average rating, 76 reviews
Top guest favourite
Home in Nokomis

Beautiful Waterfront House, Pool, 7 Min to Beach

4.94 out of 5 average rating, 31 reviews
Guest favourite
A screened-in pool area is showcased, featuring a clear water swimming pool tiled along the edges. Sunlight reflects off the surface, while lounge chairs are visible in the background, surrounded by lush greenery.
Home in Sarasota

Beautiful Home on a prestigious 18 holes golf

5.0 out of 5 average rating, 10 reviews
Top guest favourite
Home in Sarasota

Resort-Style Vacation Villa

4.98 out of 5 average rating, 42 reviews
Guest favourite
The image showcases a screened-in outdoor space featuring a refreshing pool with a jacuzzi area. Sun loungers are arranged nearby, and a bright blue float rests on the water's surface. A flag is displayed, and landscaping accents the serene environment.
Home in Nokomis

Coastal 3BR Getaway|5 Min to Beach|Pool+Peloton

4.96 out of 5 average rating, 24 reviews
Guest favourite
Home in Nokomis

Modern Pool Home in Nokomis

4.9 out of 5 average rating, 10 reviews

Apartment rentals with a pool

Top guest favourite
Apartment in Sarasota

Cottage on Siesta Key Beachside & Stunning sunsets

4.92 out of 5 average rating, 172 reviews
Guest favourite
Apartment in Nokomis

Private Beachside Kitchenette

4.87 out of 5 average rating, 193 reviews
Top guest favourite
Apartment in Sarasota

Quiet Gulf & Canal View 1 BR -2 Supyaks-Htd Pool

5.0 out of 5 average rating, 109 reviews
Guest favourite
The exterior of the condo displays a modern design with a light color palette. Palm trees are positioned around the landscaped area, and two garages are visible, along with a walkway leading to the entrance. The sunny sky enhances the welcoming appearance of the property.
Apartment in Siesta Key

Comfy Siesta Key Condo

4.85 out of 5 average rating, 110 reviews
Guest favourite
A modern living area showcases a comfortable sectional sofa and armchair, complemented by a wooden coffee table. A large flat-screen TV is positioned on a media console. Natural light floods the space through sliding glass doors that lead to a balcony, enhancing the open feel.
Apartment in Siesta Key

Spacious 2-Floor, 2BR, 2.5BA Condo Near Everything

4.88 out of 5 average rating, 179 reviews
Guest favourite
A modern living area features a blue sofa with decorative pillows and a low coffee table. A dining set with white chairs is visible in the background. Bright natural light filters through sheer curtains, enhancing the neutral grey walls and stylish artwork.
Apartment in Gulf Gate Estates

Heated Pool Apartment Near Siesta Key | 1BR

4.87 out of 5 average rating, 157 reviews
Top guest favourite
Apartment in Siesta Key

Siesta Key Condo. Checkout our great rates!

4.96 out of 5 average rating, 141 reviews
Superhost
A modern dining area is highlighted by a marble table with an elegant vase and tableware arranged for a meal. Stainless steel appliances and a large television are visible in the background, with natural light flowing in from sliding glass doors leading to an outdoor space.
Apartment in Siesta Key

Crystal House on Siesta Key Beach

4.88 out of 5 average rating, 146 reviews

Other holiday rentals with a pool

Guest favourite
Flat in Osprey

Windsor Lodge Unit #18, studio

5.0 out of 5 average rating, 7 reviews
Top guest favourite
Flat in Sarasota

Near Siesta Key | Beach Kit + Cooler | Pool & Gym

5.0 out of 5 average rating, 30 reviews
Top guest favourite
An aerial view showcases the waterfront property, highlighting the building's proximity to the canal. Nearby greenery and water feature prominently, while the surrounding area includes various residential and commercial structures, indicating a vibrant community. The pool is visible, situated on the property.
Apartment in Sarasota

Waterfront w/ Pool, mins to SK Beaches, bikes/sups

4.94 out of 5 average rating, 34 reviews
Top guest favourite
The cottage exterior features a welcoming entrance with red accents and a porch area. Lush greenery surrounds the building, enhancing the natural setting. A paved pathway leads to the front door, while a screened structure in the background adds a touch of outdoor living space.
Guest house in Osprey

Storybook Cottage With Pool Near the Bay & Beach

4.9 out of 5 average rating, 92 reviews
Top guest favourite
A spacious living room is presented with neutral-toned sofas adorned with colorful cushions. A coffee table with decorative items is centered between the seating, while light enters through large windows framed by soft blue curtains. A decorative plant adds a touch of greenery.
Home in Sarasota

Great Rates! Sunny Sarasota Villa! W/ 2 bicycles!

4.98 out of 5 average rating, 43 reviews
Superhost
Home in Sarasota

Pine Village, near Siesta Key

4.85 out of 5 average rating, 13 reviews
Guest favourite
Home in Sarasota

Beautiful 2/2 villas on Palmer Ranch

4.96 out of 5 average rating, 28 reviews
Superhost
Home in Nokomis

Private Retreat! Indoor HeatedPool/Spa! Near Beach

4.56 out of 5 average rating, 43 reviews

When is the best time to visit Osprey?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price₹20,471₹19,606₹20,278₹20,471₹14,416₹14,320₹13,455₹13,455₹13,455₹12,205₹13,455₹14,704
Avg. temp16°C18°C20°C22°C25°C27°C28°C28°C27°C24°C20°C18°C

Destinations to explore