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Vacation rentals with a pool in Siesta Key

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Top-rated rentals with a pool in Siesta Key

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Top guest favourite
A heated pool with a curved shape is surrounded by a screened patio, featuring lounge chairs positioned for relaxation. A spacious covered area showcases seating and dining options, with views of lush greenery and wooden fencing providing privacy.
Home in Sarasota
4.97 out of 5 average rating, 253 reviews

Your private retreat near Siesta Key Beach.

Welcome to your private Retreat! Nestled at the end of a quiet dead-end street. This distinguished property guarantees a relaxing Florida vacation for everyone! Completely remodeled with Coastal-Modern Decor. 3 bedroom, 2 bath, amazing heated pool home and private back yard is located in the Gulf Gate Estate neighborhood. A short drive (less than 2 miles) to the white coastal sands of Siesta Key Beach, Gulf Gate shopping mall, grocery store, restaurants, cafes. Must be at least 25 years old

Top guest favourite
A relaxing outdoor space features a lounge chair adorned with a striped towel and a wide-brimmed hat. A tray holds a refreshing drink beside the crystal-clear pool, surrounded by lush tropical foliage and a colorful float visible in the water.
Villa in Arlington Park
5 out of 5 average rating, 115 reviews

Tropical Luxury Villa: Pool, Game Room, Near Beach

Welcome to your tropical luxury escape! Spacious living flows to the heated pool, game room and sunny patio—perfect for family fun. Bedrooms: 4 private suites, plush linens and blackout shades ensure restful nights. Location: Quiet neighborhood just minutes from the sandy beach, dining and shopping hotspots. Heated pool & sun loungers Arcade-style game room Fast Wi-Fi & 5-star cleanliness Pet friendly with fenced yard Have questions? We reply in under an hour—book your stay today!

Superhost
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.
Condo in Sarasota
4.86 out of 5 average rating, 127 reviews

Anchor house +6 min. from Siesta Beach+heated pool

★ "Ground floor 1 bedroom 1 bathroom apartment" ★ "An incredible apartment and 6 star hospitality!" 🌴 Stylish Retreat Near Siesta Key Heated Pool! Welcome to your perfect Sarasota getaway! This 600 sq. ft. pet-friendly home offers a heated pool access, and a prime location just 6 minutes from Siesta Key Beach. Whether you're here for a beach vacation, a family trip, or a remote work retreat, this home has everything you need for a comfortable and stress-free stay.

Guest favourite
A bright pink flamingo float adorns the clear, inviting waters of the heated pool. Two white umbrellas provide shade for the striped lounge chairs nearby. Flower pots add a touch of greenery to the poolside area, which is enclosed by a white privacy fence.
Home in Sarasota
4.93 out of 5 average rating, 105 reviews

Oasis by Siesta Key Beach and Downtown SRQ w/pool

Enjoy Sarasota in one of the most desirable neighborhoods by Siesta Key! Truly an elite location, take Siesta Dr down to the well-documented #1 beach in the US in around 10 mins. Flourishing Downtown Sarasota is just 5 mins away. The house features a brand new heated pool, fenced in back yard with pavers, open concept living, beautiful kitchen with everything you need, upgraded bathrooms and plenty of space for a big family. We look forward to hosting you and yours!

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.
Condo in Siesta Key
4.96 out of 5 average rating, 341 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!

Guest favourite
A well-appointed kitchen features light-colored cabinetry and countertops, with modern appliances including a microwave and oven. An island provides additional workspace, while a dining area is visible in the background. Soft lighting creates a welcoming ambiance throughout the space.
Condo in Siesta Key
4.96 out of 5 average rating, 111 reviews

Palm Bay Club! Resort Style Living on Siesta Key!

Meticulously Renovated Oversized, 2 Bedroom 2 Bath, Beach to Bay unit! Walk to the Famous Siesta Key beach, voted #1 beach in the US, with the worlds softest sand! This complex spans from the magnificent Bay with yachts and boats to the private beach with free access to Chairs and loungers, Cabanas are available to rent. Nearby Siesta Key Village has great shopping and restaurants. Access to free transportation around the island is right outside your door.

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.
Condo in Siesta Key
4.84 out of 5 average rating, 250 reviews

Cozy 1BR Beach Condo on Siesta Key!

Experience the best of both worlds in this beautiful bayside 2nd floor unit! Sea Club II offers the charm of Old Florida with its shell driveway and old oak and palm trees throughout the property. Relax by the upgraded bayside pool or enjoy Happy Hour by the Tiki Hut or on the open lawn and watch the boats (BIG and small) pass by on the intercoastal. Grills are available for guests to use by the pool area. We also have a new fishing pier and boat dock.

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
4.93 out of 5 average rating, 136 reviews

The Sand Castle - Backyard Oasis Mins from Siesta!

Your family will feel at home in this spacious home that has it all! With a gorgeous backyard, alluring HEATED pool, tropical tiki bar, ping pong and other lawn games, cozy and comfortable rooms, and a kitchen stocked with everything you need to prepare meals for many... you will be more than comfortable here! The location is super convenient- minutes from Siesta Key, downtown Sarasota, and every grocery store and restaurant you could ask for!

Guest favourite
An aerial view captures a kidney-shaped pool surrounded by lush greenery and vibrant landscaping. Lounge chairs are positioned nearby, while an umbrella offers shade. The pool design includes a spa area, contributing to a serene outdoor atmosphere.
Home in Bradenton
4.91 out of 5 average rating, 324 reviews

Palm Retreat Gold: Luxury Edition of #1 Rental

High end, luxury 3/2 pool home! 7 4k TVs w/ Netflix and cable (75" in living room), SONOS throughout house/pool, wifi, PS5, private heated salt water pool/Spa, putt putt, foosball, beach gear, Pack & Play, Game room (board games, billiards, shuffle board, arcade), massive kitchen/bar, washer & dryer, garage parking-- all in a quiet and safe neighborhood. Just 5 miles to the best beaches and restaurants. Entire home with no shared amenities!

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.
Condo in Siesta Key
4.92 out of 5 average rating, 116 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, 338 reviews

Oct SALE! Private Sarasota #1 Luxery beach Villa

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!

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.
Condo in Sarasota
4.86 out of 5 average rating, 152 reviews

Siesta Key Ground Floor Condo 2BR On Trolley Line

A cozy Siesta Key ground floor condo unit w 2 bedrooms & 1 bath on the trolley line. Has all the amenities you need for a relaxing beach vacation and your day at the beach. Located conveniently to Crescent beach w access to the south and Siesta Key public beach to the north. Trolley stops right out front. Assigned parking spot directly in front of the unit.

Popular amenities for Siesta Key rentals with a pool

Kitchen
Wifi
Pool
Free parking on premises
Air conditioning

House rentals with a pool

Guest favourite
A heated pool is framed by a screened enclosure, allowing for sunlit swims while providing shade. Comfortable lounge chairs are lined along the poolside, and greenery is visible in the background, creating a serene atmosphere for relaxation.
Home in Sarasota
4.93 out of 5 average rating, 106 reviews

2BR/2BA home w/ heated pool, 5 min to Siesta Key!

Top guest favourite
A charming cottage is depicted with light blue wooden siding and white accents. The front yard is gravelled, surrounded by landscaping featuring mature trees and shrubs. A welcoming porch with a railing leads to the main entrance, enhancing the property's inviting look.
Home in Siesta Key
5 out of 5 average rating, 153 reviews

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

Guest favourite
A three-story coastal home is framed by palm trees, featuring a light-colored exterior. A large balcony is visible on the second floor, and the entrance includes a garage and a fenced area. The setting is serene, highlighting the proximity to the beach.
Home in Holmes Beach
4.94 out of 5 average rating, 116 reviews

The Peachy Beach House, steps to the gulf

Guest favourite
A serene backyard features a heated pool surrounded by lounge chairs and shaded areas. Tropical plants and flowers add color, while the setting sun casts a warm glow. Umbrellas provide shade over the seating, creating a welcoming space for relaxation and outdoor enjoyment.
Home in Bradenton
4.97 out of 5 average rating, 102 reviews

Orange Oasis: Clean, heated pool, near beaches.

Top guest favourite
A private pool area is surrounded by lush greenery, featuring a clear blue water pool and four lounge chairs positioned for relaxation. Umbrellas provide shade, enhancing the serene outdoor space. Tropical plants are situated along the edge, adding to the natural atmosphere.
Home in Sarasota
4.98 out of 5 average rating, 109 reviews

SIESTA BEACH HOUSE HEATED POOL☀️🌴3 MIN TO BEACH!!

Guest favourite
A bright living room features a large, light-colored couch adorned with patterned cushions. A swing chair hangs in the corner, and a coffee table sits in front of the couch. Soft lighting and large windows enhance the cozy atmosphere.
Home in Sarasota
4.97 out of 5 average rating, 102 reviews

Cozy Boho Bungalow Pool/Spa QR Code Walkthrough

Guest favourite
Two bright turquoise adirondack chairs are positioned on a pebbled shoreline, facing a calm canal. Lush palm trees and greenery surround the area, while distant houses line the opposite bank under a clear blue sky.
Home in Bradenton Beach
4.96 out of 5 average rating, 110 reviews

Waterfront Gem/ Pool Spa+ Dock/ Near Bridge Street

Top guest favourite
An expansive backyard features a private heated pool, surrounded by lounge seating and a well-maintained putting green. Softly glowing twilight casts a warm hue over the space, framed by lush greenery and a serene atmosphere.
Home in Bellevue Terrace
5 out of 5 average rating, 116 reviews

Living The Dream: Heated Pool + Mini Golf +Swings

Condo rentals with a pool

Guest favourite
Aerial view showcasing a sandy beach surrounded by vibrant turquoise waters. Lush greenery is visible along the shoreline, with boats floating in the clear water. The scene captures a serene coastline, inviting guests to explore the natural beauty.
Condo in Siesta Key
4.93 out of 5 average rating, 207 reviews

Steps away from beach and village! #1 in Siesta!

Top guest favourite
A landscaped pathway is flanked by vibrant flowering plants and palm trees. Neatly trimmed grass lines the walkway, leading to a serene courtyard. Soft lighting from a garden lantern adds to the peaceful ambiance of this tropical setting.
Condo in Siesta Key
4.93 out of 5 average rating, 157 reviews

Siesta Key Serenity At The Palm Bay Club

Guest favourite
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.
Condo in Siesta Key
4.95 out of 5 average rating, 133 reviews

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

Superhost
A view from above showcases the lush, landscaped grounds of the condo complex, featuring curving pathways and palm trees. In the foreground, a heated pool is visible, with beach access just beyond. The serene beach and expansive ocean create a welcoming atmosphere.
Condo in Siesta Key
4.82 out of 5 average rating, 137 reviews

Sarasota Surf & Racquet Club Siesta Key Condo

Guest favourite
A living room area features large sliding glass doors that open to a private balcony with views of the Gulf of Mexico. Soft gray furniture is arranged around a coffee table, and a flat-screen TV is located on a media console. Natural light fills the space.
Condo in Longboat Key
4.88 out of 5 average rating, 117 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.
Condo in Longboat Key
4.91 out of 5 average rating, 190 reviews

Beachfront Resort, Ocean View, Pool, Tennis, Gym

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.
Condo in Siesta Key
4.95 out of 5 average rating, 101 reviews

Seaside on Siesta Key Beach

Guest favourite
Condo in Sarasota
4.92 out of 5 average rating, 148 reviews

Cottage on Siesta Key Special December Pricing

Other vacation rentals with a pool

Guest favourite
An open-concept living and dining area is highlighted, featuring a white dining table with six chairs, a comfortable seating arrangement, and large glass doors leading to a balcony. A neutral color palette is complemented by a decorative mirror and modern lighting.
Condo in Siesta Key
4.98 out of 5 average rating, 57 reviews

2 BR condo in Siesta Key w/ Private beach access

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
4.77 out of 5 average rating, 527 reviews

Beachfront Getaway in Siesta Key

Guest favourite
A vibrant sunset is captured over the calm ocean waters, with the sun partially dipping below the horizon. A silhouette of a bird is seen flying across the sky, adding movement to the serene scene. The warm orange and yellow tones dominate the visual landscape.
Apartment in Siesta Key
4.93 out of 5 average rating, 76 reviews

Siesta Sunsets Suite

Top guest favourite
A spacious kitchen showcases a large island with seating for four, surrounded by light-colored cabinetry and modern appliances. Natural light illuminates the area through large windows, providing a view of the outdoor pool. Decorative tiles and subtle backsplash add texture to the design.
Home in Siesta Key
5 out of 5 average rating, 27 reviews

Siesta Key Retreat 1mi to Beach!

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.
Condo in Siesta Key
5 out of 5 average rating, 42 reviews

Amazing beach view! Entire unit renovated!

Guest favourite
A curved swimming pool is set against a backdrop of lush tropical foliage and palm trees, with water views extending to a nearby dock. Brightly colored pots with plants are placed around the pool area, enhancing the serene outdoor setting.
Home in Sarasota
4.96 out of 5 average rating, 71 reviews

True Island Living House/beach/water views

Superhost
A bright living room features a large sectional sofa adorned with various cushions. A flat-screen TV is mounted on the wall, presenting a serene beach scene. Natural light enters through sliding glass doors, which lead to a balcony, while decorative wall baskets add visual interest.
Home in Siesta Key
4.79 out of 5 average rating, 14 reviews

2B/2BA Penthouse End-Unit Condo

Guest favourite
The exterior of a modern home is showcased at sunset, featuring a paver driveway leading to a two-car garage. Palm trees and vibrant landscaping are present, while blue-shuttered windows complement the light-colored walls.
Home in Sarasota
4.92 out of 5 average rating, 13 reviews

Luxury Pool Home by Siesta/Lido

When is the best time to visit Siesta Key?

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Avg. price$369 CAD$480 CAD$516 CAD$438 CAD$343 CAD$346 CAD$326 CAD$283 CAD$269 CAD$271 CAD$280 CAD$322 CAD
Avg. temp16 °C18 °C20 °C22 °C25 °C27 °C28 °C28 °C27 °C24 °C20 °C18 °C

Quick stats about vacation rentals with a pool in Siesta Key

  • Total vacation rentals

    Explore 1,620 vacation rentals in Siesta Key

  • Nightly prices starting at

    Siesta Key vacation rentals start at $84 CAD per night before taxes and fees

  • Verified guest reviews

    Over 26,970 verified reviews to help you choose

  • Family-friendly vacation rentals

    1,320 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 270 rentals that welcome pets

  • Rentals with dedicated workspaces

    770 properties have a dedicated workspace

  • Wifi availability

    1,600 of Siesta Key vacation rentals include wifi 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!

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