Vacation rentals with a pool in Siesta Key

Find and book unique homes with a pool on Airbnb

Quick stats about vacation rentals with a pool in Siesta Key

  • Total vacation rentals

    Explore 1,820 vacation rentals in Siesta Key

  • Nightly prices starting at

    Siesta Key vacation rentals start at ﺩ.ﺇ 220 per night before taxes and fees

  • Verified guest reviews

    Over 29,460 verified reviews to help you choose

  • Family-friendly vacation rentals

    1,530 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 310 rentals that welcome pets

  • Rentals with dedicated workspaces

    890 properties have a dedicated workspace

  • Wi-Fi availability

    1,790 of Siesta Key vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Siesta Key rentals

  • 4.8 Average rating

    Siesta Key stays are highly rated by guests—averaging 4.8 out of 5!

Top-rated rentals with a pool in Siesta Key

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

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Guest favorite
A spacious bedroom features a modern white bed with plush pillows and a decorative brown pillow. A mirrored closet reflects the elegantly decorated space, which includes a stylish bedside table and soft lighting from a lamp. Natural light filters through the vertical blinds.
Condo in Siesta Key
4.91 out of 5 average rating, 123 reviews

The Honeymoon Suite on Siesta Key Beach

This is a recently renovated honeymoon suite located directly across from the big end of Siesta Key. It is an elegant ground floor pool unit. This unit is equip with marble countertops, tigers eye, lapis lazuli tables, bladeless ceiling fan, alabaster lighting and giant TVs. All of the appliances are stainless/smart and the microwave can cook steaks. There is a gym. The geographic location on the key can not be beat! There is a floating television over the California King luxury memory foam bed.

Guest favorite
Condo in Siesta Key
4.78 out of 5 average rating, 106 reviews

Beachwalk Townhouse with view of Gulf of Mexico

Townhouse with 1550 sq. ft. Private elevator, all new flooring, quartz countertops, sinks, faucets, shower. View of the Beach and Gulf of Mexico from Lanai and Master Bedroom. Only a few steps to Siesta Key Beach Heated Pool, garage, grill, all beach accessories. Relax on the lanai with a view of the beach/gulf or in the downstairs Florida room by the pool. Walking distance to the village of Siesta Key to the many restaurants and amenities. Have a relaxing stay on a wonderful island.

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
4.86 out of 5 average rating, 107 reviews

Comfy Siesta Key Condo

Ground floor 2 bedroom 2 bath condo in the heart of Siesta Key. Master suite with recently remodeled en suite bath. King bed in master. 2nd bedroom has a double bed and easy access to the full bath. Enjoy your morning coffee on the lanai before taking the easy walk Siesta Key private beach. Or just walk out the front door and spend the day at pool. Garage is stocked with beach and pool supplies like chairs, toys and a cooler. We have done some recent freshening up with new furniture.

Top guest favorite
A serene beach scene highlights soft white sand stretching along the coastline. Calm turquoise waters gently lap at the shore under a clear blue sky. Beach loungers and umbrellas are positioned along the sand, with a natural backdrop of greenery in the distance.
Apartment in Longboat Key
5 out of 5 average rating, 107 reviews

Sandy Toes: Open July 26th - 31st!

This sublime oceanfront studio condo is directly on the pristine white sands and serene blue waters of the Gulf of Mexico in Longboat Key, Florida! On the ground floor, overlooking the heated pool and ocean, this dreamy studio is optimal for sunset viewing from a private lanai. Take a 30-second walk to the pool and secluded beach. Enjoy a relaxing vacation at our peaceful condo at The Beach at Longboat Key Resort! To see all four of our listings, click on my Host photo and scroll down...!

Guest favorite
Home in Sarasota
4.93 out of 5 average rating, 398 reviews

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.

Top guest favorite
Home in Siesta Key
4.97 out of 5 average rating, 34 reviews

Luxury Canal-Front Home + Heated Pool Near Beach

This is a thoughtfully renovated canal-front residence near Siesta Beach. A private pool and screened patio offer a refined and tranquil retreat with direct canal views. Bright interiors and carefully curated details create an atmosphere of timeless, understated luxury. Just an 8-minute walk from the world-famous beach, yet surrounded by complete peace and privacy. This home is designed for guests who appreciate discreet luxury and elevated comfort.

Top guest favorite
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.
Condo in Siesta Key
4.97 out of 5 average rating, 384 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.

Top guest favorite
A private heated pool is surrounded by lush palm trees and a well-maintained lawn. An outdoor dining area with a large umbrella is visible, along with two lounge chairs positioned near the pool. The area is brightened by clear blue skies and sunlight.
Home in Siesta Key
5 out of 5 average rating, 161 reviews

Beach, Village, Dock & Private Pool! One-of-a-kind

Rad’s Cozy Cottage – Siesta Key Private Home. Enjoy a heated saltwater pool, canal-front dock, and putting green at this one-of-a-kind tropical getaway. Steps from Siesta Village (shops, restaurants, nightlife) and the powdery-white sands of Siesta Key Beach. Fully updated 2BR/1.5BA cottage with modern kitchen, AC, Wi-Fi, and washer/dryer. Sleeps 6 (king + 2 twins + sofa). Book your island paradise!

Guest favorite
A dining table is set with elegant glassware and neutral tableware. A decorative figurine of a crane stands between two tall candlesticks, with a soft ocean view visible through the screened lanai in the background.
Condo in Siesta Key
4.92 out of 5 average rating, 100 reviews

Siesta Key Oasis with Gulf Views

Located at CRESCENT ROYALE CONDOMINIUMS - one of the finest gated communities on Siesta Key. Large HEATED outdoor pool - this 5th floor unit has an extra large lanai that provides some of the best Gulf views on Siesta Key! 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!

Top guest favorite
Home in Sarasota
4.98 out of 5 average rating, 117 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. 🌴

Top guest favorite
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
4.98 out of 5 average rating, 361 reviews

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!

Top guest favorite
The exterior of the two-story condo building is visible, featuring a series of balconies adorned with umbrellas. Lush greenery surrounds circular seating areas with white chairs and tables, providing a relaxed outdoor atmosphere. Clear blue skies complement the setting.
Condo in Siesta Key
4.93 out of 5 average rating, 237 reviews

Private Siesta Key Escape

BRAND NEW POOL!! Come stay in this stunning and spacious beach unit on PRIVATE CRESCENT BEACH on Siesta Key--our renovation has transformed a vintage beach condo into a unique comfortable coastal space. You will enjoy a quick minute's walk to the crystal sands of the beach. Our second-story unit is on a quiet street with no through traffic to the adjacent beach gate.

Popular amenities for Siesta Key rentals with a pool

When is the best time to visit Siesta Key?

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Avg. priceﺩ.ﺇ 1,036ﺩ.ﺇ 1,355ﺩ.ﺇ 1,509ﺩ.ﺇ 1,149ﺩ.ﺇ 900ﺩ.ﺇ 907ﺩ.ﺇ 907ﺩ.ﺇ 826ﺩ.ﺇ 742ﺩ.ﺇ 764ﺩ.ﺇ 852ﺩ.ﺇ 1,003
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