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Holiday rentals with a pool in Osprey

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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 favourite
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
4.89 out of 5 average rating, 132 reviews

Crystal House on Siesta Key Beach

This is an updated and renovated two bedroom suite on Siesta Key. Complete with marble dining table, stainless appliances and large televisions. There is a computer in the spare bedroom for your convenience along with an Xbox and DVD player. We tried to think of everything so please feel free to make suggestions after your stay. Your satisfaction is our number one concern. The sofa is a Laz-Y-Boy and is not a sleeper but is very comfortable!!! There is a set of twin-twin bunks in the main room!

Top guest favourite
A vibrant sunset lights up the sky in shades of orange and pink, framed by tall trees that line a quiet street. The silhouettes of palm trees add to the tropical ambiance, while homes are visible in the background, nestled among the lush landscaping.
Home in Sarasota
4.92 out of 5 average rating, 102 reviews

Spectacular Sunsets! 15 min Siesta Key!

This villa is spacious and bright with lots of windows. The interior has just been updated. Tropical decor makes you feel like your’e at the beach. Huge flat screen TV. Tile flooring in the living areas and laminate in the bedrooms. Screened lanai overlooks palm tree and mature landscaping. Wireless fast speed internet included. It has everything you need for a short visit or extended stay. Fully equipped kitchen. Washer and Dryer. Beach chairs and towels. One car garage and driveway space.

Top guest favourite
Apartment in Sarasota
5 out of 5 average rating, 101 reviews

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

Whisk your favorite person away to BayDreaming! Escape to this quiet 1BR/1.5BA Siesta Key condo - just an 8-minute walk to Turtle Beach! Perfect for couples, it features a private deck with canal and Gulf views , a heated pool for sunset swims, 2 supyaks and a plush king bed for cozy nights in. Enjoy garage parking, beach gear, and a peaceful, welcoming community. Whether you're here to relax or reconnect, this coastal retreat offers the perfect mix of romance or just plain serenity!

Guest favourite
A bright and airy indoor space features a coastal-themed rug with a starfish design. Light-colored furniture and a wooden table provide a casual dining area, while large windows allow natural light to fill the room and offer views of the backyard.
Home in Pelican Cove
4.92 out of 5 average rating, 382 reviews

Beach Retreat•Renovated Pool Patio•Near Siesta Key

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.

Top guest favourite
A private patio with a round wooden table and two chairs overlooks a manicured lawn leading to the beach. Palm trees sway gently beside the outdoor seating area, offering a serene view of the Gulf waters in the background.
Apartment in Siesta Key
4.97 out of 5 average rating, 355 reviews

On the Beach; Siesta Key SunBum Studio

Welcome back to paradise ! STEPS to your private beach without the tricks or gimmicks found elsewhere on the Siesta Key. This is the only studio in the Palm Bay Club tower on ground level with breathtaking views of the white sand and gulf waters. The Palm Bay Club offers 2 pools, hot tub, gym, boat docks, fishing pier, outdoor grills, tennis/pickle ball courts; not to mention FREE parking+ beach lounge chairs. Enjoy 2 free bikes day rental with booking!

Top guest favourite
A serene community pool is surrounded by a fence and complemented by lounge chairs positioned nearby. The pool's clear blue water reflects the sunlight, while the yellow exterior of the building provides a warm backdrop. Windows with awnings complete the inviting atmosphere of the area.
Apartment in Sarasota
4.94 out of 5 average rating, 160 reviews

Villa Maria: Minutes to Siesta Key!

2 BDRM/2 BTHRM condo very close to Siesta Key (3 min. drive or 20 min. walk). Totally UPDATED! Quality furnishings, super clean, ideal location. Have it all: Spacious condo in a peaceful setting. Just a few minutes drive over the south bridge to Siesta Key. Walking distance to great restaurants and shops on and off the key. Everything is within easy access by walking, car, bike, or free beach shuttle service. Come enjoy everything Sarasota has to offer.

Guest favourite
A spacious screened lanai features a circular wooden table surrounded by two wooden chairs with patterned cushions. Potted plants and decorative items are placed on the table. Beyond the railing, palm trees and the vibrant blue of the Gulf coast are visible.
Apartment in Siesta Key
4.91 out of 5 average rating, 119 reviews

Siesta Key Beach Front Condo

Located at CRESCENT ROYALE CONDOMINIUMS - one of the finest gated communities on Siesta Key. Large HEATED outdoor pool - this 2 bedroom/2 bath PRIVATELY OWNED vacation condo is steps away from world famous, breathtaking Siesta Beach - consistently VOTED #1 BEST BEACH IN THE USA year after year! This condo is nicely situated on the 2nd floor. The large screened lanai provides spectacular gulf coast views.

Top guest favourite
A stunning pool area is surrounded by lush greenery and tropical plants. A prominent rock feature with multiple waterfalls is visible, providing a serene focal point in the outdoor space. The vibrant blue water complements the natural elements, creating a tranquil retreat.
Island in Sarasota
4.97 out of 5 average rating, 349 reviews

2 DAYS JAN! Sarasota #1 Luxury Villa w/PRIV BEACH!

BOOK 2025 NOW, and stay in Style magazines exclusive beachfront gem! This property OWNS THE BEACH!! UNIQUE PRIVATE POOL & BEACH combo is HEAVEN! Private ELEVATOR! 32,000/gl FREEFORM POOL, with 4 WATERFALLS, HOT GROTTO with HOT falls! NEW BBQ PIT AREA, BIKES, KAYAKS, and PADDLEBOARDS! WRAPAROUND BALCONY, CHEF kitchen. Hosted CELEBS! SHOPPING, FINE DINING, watch our VIDEOS!

Top guest favourite
The living room features a spacious layout with a comfortable gray sofa and rocker recliner. A dining area with a table for six is present, alongside large glass doors that provide ample natural light and a view of the surrounding greenery. A flat screen TV is visible.
Apartment in Siesta Key
4.97 out of 5 average rating, 130 reviews

Siesta Key Condo. Checkout our great rates!

Our beautiful Siesta Key condo is located a short stroll from the famous Siesta Key beach with its beautiful quartz sand and amazing sunsets. The Midnight Cove II condominium complex has private beach access with outstanding amenities and is very family friendly, come and enjoy the natural beauty this complex and all Siesta Key has to offer.

Top guest favourite
A private entrance is framed by a sleek plant and modern features. The entrance door is flanked by a wall light and a smooth concrete pathway, complemented by potted plants that enhance the outdoor space.
Flat in Gillespie Park
4.97 out of 5 average rating, 179 reviews

Gillespie On The Park, Walk to Downtown

Contemporary Studio apartment with balcony above garage. Studio is half block from Gillespie Park with its public walking/jogging/biking paths, tennis courts, basketball court, and retention pond. Within walking distance to downtown and Rosemary District: restaurants, shops, movie theaters, cultural events, Whole Food Market, Starbucks etc.

Guest favourite
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
4.89 out of 5 average rating, 106 reviews

Oceanfront home w/sunset views of Sarasota Bay

Treat your family, friends, and beloved small dogs to an unforgettable oceanfront getaway in sunny Florida! Conveniently located near plenty of Sarasota's shopping and dining areas, your new home away from home is nice and isolated, surrounded by gorgeous views and just a quick walk from the waters of Sarasota Bay.

Top guest favourite
A comfortable living space features a blue sectional sofa and a patterned armchair, complemented by a wooden coffee table. Light streams in through a window with blinds, while a welcoming entry door adds to the serene ambiance.
Villa in Sarasota
4.96 out of 5 average rating, 199 reviews

Newly Renovated- 150 Yards to Beach & Restaurants!

- Newly Renovated 2 Bed/1 Bath - Private Patio - Beach Gear Provided - New Washer & Dryer Shared Between Both Sides of Duplex - Beachside of Midnight Pass Rd - 3 Minute Walk to Private Beach Access - Neighborhood Heated Saltwater Pool - Short Walk to the Restaurants, Shops, and Bars

Popular amenities for Osprey rentals with a pool

KitchenWifiPoolFree parking on premisesAir conditioning

House rentals with a pool

Guest favourite
A spacious backyard is shown at sunset, featuring a heated pool surrounded by a tiled patio. Tropical palm trees frame the area, and a tiki bar can be seen in the background. Soft outdoor lights create a welcoming ambiance as the sky fills with vibrant orange and purple hues.
Home in Sarasota
4.94 out of 5 average rating, 142 reviews

The Sand Castle - Backyard Oasis Mins from Siesta!

Guest favourite
An inviting beach scene features a sun umbrella providing shade over a wooden lounge chair, set upon soft, sandy shores. The clear blue sky contrasts with the tranquil turquoise waters, creating a peaceful atmosphere near the shoreline.
Home in Siesta Key
4.78 out of 5 average rating, 534 reviews

Beachfront Getaway in Siesta Key

Top guest favourite
A private heated pool features a waterfall, surrounded by lush tropical landscaping and palm trees. Seating options include teal lounge chairs and white sunbeds, while the pool deck is complemented by a well-maintained lawn area. Colorful plants enhance the tranquil outdoor space.
Home in Holmes Beach
4.97 out of 5 average rating, 101 reviews

Salty Harbor AMI pool retreat near the Beach

Guest favourite
Home in Venice
4.92 out of 5 average rating, 130 reviews

Spacious 2 Bedroom Home | Near Beach | Heated Pool

Top guest favourite
The exterior of a well-maintained condominium is displayed, featuring a two-car garage and neatly trimmed hedges. Palm trees and lush landscaping frame the entrance, while a clear blue sky enhances the tropical feel of the setting.
Home in Sarasota
4.89 out of 5 average rating, 169 reviews

5 minutes to private Siesta Key Beach + 2 pools

Superhost
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
4.81 out of 5 average rating, 167 reviews

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

Top guest favourite
A private backyard oasis is highlighted by a heated pool and a hot tub, surrounded by lush tropical landscaping. A shaded area with an umbrella and seating for outdoor dining is visible beside the pool, creating a serene environment for relaxation.
Home in Sarasota
4.97 out of 5 average rating, 115 reviews

Backyard Oasis, Htd Pool/Hot Tub, Beaches, No Fees

Guest favourite
A secluded backyard features a heated pool surrounded by lush greenery and flowering plants. Tropical palm trees and colorful potted plants enhance the tranquil atmosphere, while the tiled pool edge adds a touch of contemporary design.
Home in Sarasota
4.84 out of 5 average rating, 293 reviews

Private Siesta Beach House Oasis with Heated Pool.

Apartment rentals with a pool

Guest favourite
A serene lanai view features a dining table with chairs overlooking the community pool. Lush palm trees frame the scene, while sunlight reflects off the water's surface. A doorway is visible, leading to the interior of the condo.
Apartment in Sarasota
4.96 out of 5 average rating, 214 reviews

Gateway to Siesta Key - 1/2 Mile to the Beach

Guest favourite
A living area features a comfortable green sofa complemented by a lamp casting a warm glow. A white wicker chair adds a coastal touch, positioned beside a small white table. Light wooden floors extend across the space, with soft wall art and a wall-mounted TV enhancing the environment.
Apartment in Siesta Key
4.84 out of 5 average rating, 257 reviews

Cozy 1BR Beach Condo on Siesta Key!

Top guest favourite
A tranquil pool area is surrounded by palm trees, reflecting the clear blue sky. Lounge chairs are positioned around the pool's edge, inviting relaxation. The sun casts a warm glow over the scene, enhancing the peaceful ambiance of the resort.
Apartment in Siesta Key
4.98 out of 5 average rating, 125 reviews

Siesta Key For Me @ The Palm Bay Club

Top guest favourite
A screened lanai offers a peaceful retreat with a view of the pond and trees reflecting on the water. Comfortable seating is provided, accompanied by a small table. Natural light flows in, enhancing the serene atmosphere of the space.
Apartment in Bradenton
4.97 out of 5 average rating, 124 reviews

A&A's Paradise near IMG & Anna Maria beaches

Guest favourite
A cozy living area is depicted, featuring a comfortable sofa and two light blue armchairs. A wooden coffee table is centered in the space, while a small TV is positioned on a decorative cabinet. Soft lighting from floor lamps enhances the inviting atmosphere.
Apartment in Sarasota
4.85 out of 5 average rating, 156 reviews

Siesta Key Ground Floor Condo 2BR On Trolley Line

Guest favourite
Apartment in Longboat Key
4.88 out of 5 average rating, 125 reviews

Sunset and beach view from your balcony Unit 403

Guest favourite
A screened lanai offers poolside views, with vibrant orange and blue chairs positioned to enjoy the scenery. Lush greenery borders the area, while palm trees sway in the gentle breeze. Glimpses of the Gulf of Mexico and a heated pool are visible through the railing.
Apartment in Longboat Key
4.9 out of 5 average rating, 202 reviews

Beachfront Resort, Ocean View, Pool, Tennis, Gym

Top guest favourite
A three-story condominium building is shown, featuring a combination of palm trees and lush green landscaping at the forefront. Balconies are visible on each level, with a red-tiled roof adding a distinct character to the architecture.
Apartment in Siesta Key
4.95 out of 5 average rating, 109 reviews

Seaside on Siesta Key Beach

Other holiday rentals with a pool

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
5 out of 5 average rating, 83 reviews

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

Top guest favourite
A cozy deck area features outdoor seating with two bar stools and a small table adorned with flowers. Palm trees provide shade while a serene waterfront view is visible, with a private dock and a pool in the background.
Apartment in Sarasota
4.96 out of 5 average rating, 56 reviews

Bayside - Kayak, Boat Dock, Pool, & walk to Beach

Guest favourite
A spacious patio provides a serene view overlooking Whitaker Bayou, with boats moored along the water. A round dining table, surrounded by white chairs, offers an inviting spot for meals while enjoying the scenery. The area is complemented by a colorful artwork piece on the wall.
Apartment in Indian Beach-Sapphire Shores
5 out of 5 average rating, 12 reviews

Modern 1/1.5 Waterfront at The Strand

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
4.93 out of 5 average rating, 28 reviews

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

Top guest favourite
A modern living space is showcased with a comfortable dark sofa and a round coffee table on a textured area rug. A dining table with four chairs is positioned nearby, while a large window offers a view of the ocean and natural light fills the room.
Apartment in Siesta Key
5 out of 5 average rating, 47 reviews

Amazing beach view! Entire unit renovated!

Top guest favourite
The exterior of the condo is shown, featuring a spacious deck surrounded by palm trees, with an umbrella providing shade. Large windows offer a view into the interior space, and ample outdoor seating is visible. A concrete path leads through the outdoor area.
Flat in Sarasota
5 out of 5 average rating, 11 reviews

Cozy Condo in Siesta key with boat dock

Top guest favourite
A serene pool area is surrounded by lush greenery and palm trees. A vibrant inflatable in the shape of a dog floats in the clear water. Comfortable lounge chairs are positioned nearby, inviting relaxation under the sunny sky.
Home in Venice
5 out of 5 average rating, 21 reviews

Tropical Bliss | Lush Garden Poolside Retreat

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
4.98 out of 5 average rating, 60 reviews

The Pineapple Escape

When is the best time to visit Osprey?

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Avg. price€ 152€ 163€ 202€ 168€ 148€ 141€ 118€ 118€ 118€ 127€ 127€ 127
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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 € 51 per night before taxes and fees

  • Verified guest reviews

    Over 350 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!

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