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Vacation rentals with a pool in Osprey

Find and book unique homes with a pool on Airbnb

Quick stats about vacation rentals with a pool in Osprey

  • Total vacation rentals

    Explore 50 vacation rentals in Osprey

  • Nightly prices starting at

    Osprey vacation rentals start at €52 per night before taxes and fees

  • Verified guest reviews

    Over 400 verified reviews to help you choose

  • Family-friendly vacation rentals

    30 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    50 of Osprey vacation rentals include wi-fi 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.

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Guest favorite
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, 216 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 favorite
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
Top guest favorite
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, 14 reviews
Guest favorite
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, 137 reviews
Top guest favorite
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, 407 reviews
Top guest favorite
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

The Pineapple Escape is the perfect gateway vacation house that has everything you're looking for. With a heated pool for access year round and beautiful kitchen for all your desires. Just a short drive from some of Florida's finest beaches, such as Nokomis Beach on Casey Key,Venice Beach and about 15 minutes drive to #1 beach in US, Siesta Beach in Sarasota,. You'll find this neighborhood to be quite serene and peaceful. Book today to start making memories at The Pineapple Escape.

4.99 out of 5 average rating, 75 reviews
Guest favorite
Apartment in Osprey

Windsor Lodge Unit #18, studio

Experience a luxurious Sarasota vacation rental at Windsor Lodge! Located directly on the golf course within the gated Oaks Golf and Country Club, this elegant retreat is ideal for couples and extended stays. Enjoy a bright, open-concept layout combining the living and sleeping area, plus a separate bathroom for privacy. Relax by the community pool or take in the golf views. You are just minutes from world-class Siesta Key beaches, premium shopping, and Sarasota’s finest dining!

5.0 out of 5 average rating, 7 reviews
Guest favorite
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, 52 reviews
Guest favorite
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

4.95 out of 5 average rating, 110 reviews
Top guest favorite
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
Top guest favorite
Home in Sarasota

Your DreamOasisAwaits: SiestaKeyEscape with Pool!

Welcome to your dream oasis near the world-famous Siesta Key! ✨ This immaculate 2BD/2BA home is a true coastal gem, offering a serene retreat with stylish design and luxurious amenities. Just 1 mile from the sugar-white sands of Siesta Key Beach, this home provides the perfect blend of comfort and convenience—an ideal spot to embrace relaxed Florida living at its finest. 🌴

4.98 out of 5 average rating, 128 reviews

Popular amenities for Osprey rentals with a pool

KitchenWifiPoolFree parking on premisesAir conditioning

House rentals with a pool

Top guest favorite
A Tiki bar with a thatched roof provides a stylish overlook of a heated pool surrounded by lounge chairs. The design features natural wood accents and vibrant decorations, inviting relaxation and leisure. Sunlight reflects off the water, adding to the serene outdoor atmosphere.
Home in South Sarasota

Tiki Bar Paradise! Heated Pool & Gaming Oasis!

4.94 out of 5 average rating, 100 reviews
Top guest favorite
Home in Sarasota Springs

Lake Front House with a Pool

4.94 out of 5 average rating, 179 reviews
Guest favorite
A serene outdoor seating area features several lounge chairs with cushions, positioned on a brick patio overlooking tranquil water. The setting is complemented by a soft sunset in the background, with lush greenery visible across the bay.
Home in Sarasota

Oceanfront home w/sunset views of Sarasota Bay

4.89 out of 5 average rating, 114 reviews
Top guest favorite
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!

4.95 out of 5 average rating, 94 reviews
Guest favorite
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, 9 reviews
Top guest favorite
Home in Nokomis

Cool home w/heated pool near beach

5.0 out of 5 average rating, 17 reviews
Top guest favorite
Home in Sarasota

Florida Oasis Fully Equipped • 12 Min to Beaches

5.0 out of 5 average rating, 17 reviews
Top guest favorite
Home in Sarasota

Resort-Style Vacation Villa

4.98 out of 5 average rating, 42 reviews

Condo rentals with a pool

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.
Condo in Siesta Key

Crystal House on Siesta Key Beach

4.88 out of 5 average rating, 146 reviews
Guest favorite
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.
Condo in Siesta Key

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

4.88 out of 5 average rating, 175 reviews
Guest favorite
Condo in Nokomis

Private Beachside Kitchenette

4.87 out of 5 average rating, 191 reviews
Top guest favorite
Condo in Sarasota

Cottage on Siesta Key Beachside & Stunning sunsets

4.92 out of 5 average rating, 170 reviews
Guest favorite
The living area features a light-colored sofa complemented by an orange accent chair. A coffee table sits on a textured area rug, while wall art adds color to the red accent wall. Glass doors open to a view of outdoors, surrounded by greenery.
Condo in Gulf Gate Estates

Sunny 2nd-Floor Condo w/ Heated Pool | 1BR

4.91 out of 5 average rating, 161 reviews
Guest favorite
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.
Condo in Siesta Key

Comfy Siesta Key Condo

4.85 out of 5 average rating, 110 reviews
Top guest favorite
A dining area is presented with a large wooden table surrounded by blue upholstered chairs. Sunlight pours through expansive windows, revealing views of the turquoise waters and sandy beach beyond. A beach-inspired artwork decorates the wall, adding a touch of coastal charm.
Condo in Siesta Key

Breathtaking Beachfront Views in Siesta Key

5.0 out of 5 average rating, 103 reviews
Top guest favorite
Condo in Siesta Key

Siesta Key Condo. Checkout our great rates!

4.96 out of 5 average rating, 140 reviews

Other vacation rentals with a pool

Top guest favorite
Apartment in Sarasota

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

5.0 out of 5 average rating, 25 reviews
Top guest favorite
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.
Condo in Sarasota

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

4.94 out of 5 average rating, 34 reviews
Guest favorite
Home in Sarasota

Resort style vacation/3772SP

4.89 out of 5 average rating, 9 reviews
Top guest favorite
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.
Guesthouse in Osprey

Storybook Cottage With Pool Near the Bay & Beach

4.9 out of 5 average rating, 90 reviews
Top guest favorite
An outdoor area is showcased featuring a wooden pergola above a dining table with four chairs. A geometric-patterned rug extends under the table, and a pool is visible nearby, surrounded by greenery. Sunlight filters through the trees, illuminating the inviting space.
Home in Venice

Venice Island Home w Heated Pool

4.99 out of 5 average rating, 91 reviews
Top guest favorite
Home in Sarasota

Fresh 5Bedroom w/ Heated Pool Mins to Siesta Beach

5.0 out of 5 average rating, 30 reviews
Superhost
Home in Nokomis

Private Retreat! Indoor HeatedPool/Spa! Near Beach

4.56 out of 5 average rating, 43 reviews
Superhost
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, 23 reviews

When is the best time to visit Osprey?

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