Home rentals with a pool near Turtle Beach

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.

4.97 out of 5 average rating, 60 reviews

Siesta K- Kayak, Boat Dock, Pool, & walk to Beach

This 2 bedroom/ 2 bath condo is right on the waterfront in Siesta Key! It is the upper condo of a two story complex that has a perfect view and feels like your own personal getaway! It comes with a full kitchen, living room w/ a sofa-bed, and two decks. Part of what makes it amazing is the private dock on the Pass. Perfect for kayaking and exploring! Or maybe you'd like to just relax and take a dip in the heated pool? Located in the quiet end, you can enjoy the calm, or head to Siesta Village!

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.

4.94 out of 5 average rating, 32 reviews

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

WATERFRONT PROPERTY - View the Gulf in our waterside rocking chairs and lanai!! Everything you need for a vacation on Siesta Key is INCLUDED. Bikes, paddle boards and Kayaks all included - PADDLE TO A PRIVATE BEACH and Sandbar see pics --Private and quiet relaxing pool setting. This condo is only a half mile WALK to Turtle Beach and minutes to Siesta Key Beach and the village. You are walking access to the free Siesta Key trolley to the beaches, village shopping, restaurants and nightlife.

4.91 out of 5 average rating, 373 reviews

Bungalow in Sarasota

Pool & fenced-in yard in downtown edge bungalow

MESSAGE ME FOR DAYS YOU DONT C. This 2 bed-2 bath house is a homey Florida bungalow with wood floors & natural light in a quiet neighborhood on the downtown core edge. Spacious and private fenced-in backyard with pool, covered grill and eating area. Minutes away from the Legacy Trail, the Bay Park, Payne Park, dining, live music, bars, theatres, comedy, opera house, performance venues, comedy club, antiquing, kayak launches, tennis and basketball courts, farmer's market, shopping and more.

4.97 out of 5 average rating, 265 reviews

Your private retreat near Siesta Key Beach.

Completely Remodeled Private Retreat. COME RELAX, UNWIND, AND MAKE LASTING MEMORIES! From the moment you arrive, you’ll feel the calm, welcoming atmosphere that makes this property stand out. This spacious 3brm 2-bath features an amazing heated pool, a private backyard, and stylish finishes throughout. Whether you’re lounging by the heated pool, enjoying meals in the bright open-concept living space, or exploring the nearby beaches this home is perfect for an unforgettable vacation

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.

4.93 out of 5 average rating, 389 reviews

Beach Retreat•Renovated & Heated Pool•Near 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.

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.

4.97 out of 5 average rating, 368 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. If we are booked check out our additional units under our profile.

5 out of 5 average rating, 8 reviews

Serenity Cottage | Short Walk To Crescent Beach!

🦩Exclusive Amenities Include: • Private Heated Pool & Spa • Multiple Balcony Areas • Just a Short Drive to Siesta Key Village & Siesta Key Beach • 2 Minute Walk to Crescent Beach • 3 Bedrooms, 3.5 Baths • 1 King Bed, 1 Queen Bed, 1 Twin over Full Bunk Bed (Sleeps 7) with linens provided • Outdoor Lounge & Dining Area • Screened in Dining Space • Private 2 Car Garage • Free WiFi & 4 TV’s • Regular & Keurig Coffee Maker, Dishwasher, Washer & Dryer, and Kitchen Essentials

5 out of 5 average rating, 102 reviews

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

Whisk your favorite person away to BayDreaming! Retreat to this quiet 1BR/1.5BA condo, just an 8‑minute walk from Turtle Beach. Perfect for couples, it offers a private deck with canal and Gulf views, a heated pool for sunset swims, two supyaks, and a plush king bed for cozy nights. Enjoy garage parking, beach gear, and a peaceful community. Whether you’re here to relax or reconnect, this coastal retreat blends romance with Siesta Key serenity.

5 out of 5 average rating, 48 reviews

Pool & Spa Oasis • Tiki Hut • 10 Min to Siesta Key

🌴 Heated Pool • Spa • Tiki Hut • 10 Min to Siesta Key Private pool oasis just minutes from Siesta Key — designed for relaxing days and unforgettable nights. Enjoy a heated pool, spa with waterfall, tiki hut lounge, and a fully screened lanai for indoor-outdoor living. Relax poolside, play outdoor games, and unwind under ambient evening lighting. Perfect for families, couples, and groups seeking a memorable Florida getaway.

4.98 out of 5 average rating, 102 reviews

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. 🌴

4.97 out of 5 average rating, 353 reviews

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

JULY AVAIL! 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!

4.89 out of 5 average rating, 38 reviews

Siesta Key private pool house/ beach!

Private pool home, just by the Turtle Beach directly on Siesta Key Island. High ceilings, open floor plan, split bedrooms. 3 bdrm/3 bath. Two Master bdrm suites, 2 washer/dryer. New Master bath and flooring! Beach with deeded beach entrance and 2 great restaurants are only a short stroll away. Under 2 min walk to Turtle Beach! We speak English, Czech, Slovak and Polish.

Popular amenities for rentals with a pool near Turtle Beach

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

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.

5 out of 5 average rating, 86 reviews

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

A private pool area is showcased within a screened enclosure, featuring clear waters and sun loungers. Colorful umbrellas in red and green provide shade, while tall palm plants are arranged around the space. The adjacent home showcases large windows, offering views of the inviting outdoor area.

5 out of 5 average rating, 15 reviews

Sarasota's Luxury Oasis

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.

4.93 out of 5 average rating, 149 reviews

The Sand Castle - Backyard Oasis Mins from Siesta!

Superhost

5 out of 5 average rating, 4 reviews

Private Pool +Game Room Near Siesta Key | Sleeps 9

4.94 out of 5 average rating, 35 reviews

A screened-in lanai accommodates a private pool, with sunlight reflecting off the clear blue water. Surrounding greenery provides a sense of tranquility. A sitting area is visible, alongside a dining table ready for gatherings, enhancing the outdoor relaxation space.

Home in Venice

RELAX:) Vacation pool home (Shamrock Park&Beaches)

A screened outdoor area features a heated pool accompanied by a spacious seating arrangement. A dining table with chairs sits shaded under an umbrella, while lounge chairs are positioned nearby. Lush greenery provides a natural backdrop, enhancing the inviting space.

4.95 out of 5 average rating, 154 reviews

Beautifully Remodeled Home with Pool Near Siesta

A screened-in pool area features a crystal-clear heated pool with lounge chairs positioned nearby. An umbrella provides shade over a seating area, surrounded by lush greenery and fencing that enhances privacy.

4.95 out of 5 average rating, 233 reviews

Cozy 2BD/2BA with Heated Pool Near Siesta Key

A heated saltwater pool is framed by light blue lounge chairs and a paved patio area. Gentle waves create a soothing effect at the pool's edge. Surrounding greenery and a clear blue sky enhance the outdoor retreat, providing ample space for relaxation and leisure.

4.95 out of 5 average rating, 62 reviews

Retro Beach House w/ Pool Walkable to downtown SRQ

Condo rentals with a pool

An aerial view captures the expansive white sand beach and turquoise waters, lined with beachgoers. The surrounding buildings and amenities are visible, including pools and recreational areas, creating a vibrant coastal atmosphere. Cloud patterns add depth to the bright blue sky above.

4.94 out of 5 average rating, 124 reviews

Beautiful White Sand Siesta Key Beach

The balcony features a cozy seating arrangement comprising two chairs and a coffee table, all set against a stunning ocean view. The turquoise waters and sandy beach are visible beyond the railing, offering a serene backdrop for relaxation.

4.99 out of 5 average rating, 101 reviews

6 Siesta Breakers - Condo, Ocean View, Heated Pool

A heated pool is surrounded by a tiled deck, with lounge chairs available for guests. Palm trees and blue umbrellas create a tropical atmosphere, while the beach and ocean are visible beyond the pool area under a clear blue sky.

4.94 out of 5 average rating, 142 reviews

2 Bed/2 Bath Condo Resort View on Siesta Key Beach

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.

4.89 out of 5 average rating, 138 reviews

Crystal House on Siesta Key Beach

Superhost

A private swimming pool is surrounded by a spacious outdoor area featuring a variety of colorful seating options, including lounge chairs and patio furniture. The pool area is complemented by lush greenery and shaded spots, creating a relaxing atmosphere. A vibrant red umbrella provides additional shade.

4.8 out of 5 average rating, 215 reviews

Near beach. Pool view. King bed. Daily rentals

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.

4.85 out of 5 average rating, 102 reviews

Comfy Siesta Key Condo

4.98 out of 5 average rating, 229 reviews

Condo in Longboat Key

Sun-Kissed Memories!

4.93 out of 5 average rating, 137 reviews

Siesta Key condo, beach access, heated pool

Other holiday rentals with a pool

4.99 out of 5 average rating, 78 reviews

A bright and airy living space features a neutral sofa, an accent table, and a coffee table, all set against light wood flooring. A ceiling fan aids ventilation, while a large window allows natural light to fill the area. The open kitchen displays modern appliances and bar seating.

Apartment in Venice

Venice Island Pool Casita with 2Bedrooms/2 Baths

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.

5 out of 5 average rating, 13 reviews

Modern 1/1.5 Waterfront at The Strand

The exterior of a single-story villa is showcased, surrounded by lush greenery and palm trees. A manicured lawn features various shrubs and plants. The building's neutral-colored walls are complemented by a terracotta roof, creating a harmonious blend with the tropical environment.

5 out of 5 average rating, 20 reviews

Spacious Cozy Tropical Retreat!

5 out of 5 average rating, 29 reviews

Bungalow in Siesta Key

Heated Pool, Dock, Kayaks, 1-mile to Turtle Beach

A tranquil outdoor space features a private heated saltwater pool surrounded by lounge chairs. The patio area is highlighted by soft lighting and palm trees, with additional seating set for dining against the backdrop of a warm sunset sky.

4.9 out of 5 average rating, 88 reviews

Sunshine Manor | Saltwater Pool + Electric Bikes!

4.98 out of 5 average rating, 45 reviews

A spacious single-story house is highlighted, featuring a well-maintained white exterior and a metal roof. Lush green grass surrounds the home, with several palm trees positioned symmetrically along the pathway leading to the entrance. A clear sky and gentle clouds provide a bright backdrop.

Villa in Nokomis

Oasis Getaway -Beautiful House-Infinity Pool-Beach

4.96 out of 5 average rating, 50 reviews

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