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Home rentals with a pool near Crescent Beach

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Top-rated rentals with a pool near Crescent Beach

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Top guest favourite
An airy dining area features a glass table supported by a unique wooden base, surrounded by four woven chairs. Natural light floods the open space, highlighting the modern kitchen with white cabinetry and high-end finishes, while a large pendant light adds a stylish touch.
Home in Siesta Key
4.99 out of 5 average rating, 90 reviews

Relax in a Private Tropical Retreat on Siesta Key!

Your dream vacation awaits with a renovated, spacious, and private single-level house. It's a perfect getaway for a relaxing vacation! Enjoy all the comforts of home while being just a short walk away from restaurants, bars, and Siesta Key's beautiful white sand beaches. Nestled on a quiet tree-lined street and tropical gardens, this retreat offers tranquility and serenity. The community boasts a large heated pool and intercoastal waterway pier, ideal for afternoon fishing or sunset beverages!

Top guest favourite
Bungalow in Siesta Key
5 out of 5 average rating, 14 reviews

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

The Siesta Key Bungalows offer a heated pool, courtyard and a dock on Heron Lagoon. This is a resort that has something for everyone. Featuring a bright and airy one bedroom space; experience an open floor plan connecting a welcoming living room and full-kitchen. With a king-size bed and private bathroom you'll feel at home. The Bungalow is fully stocked with linens, care essentials, plus eating and cooking utensils. An additional queen sofa-bed allows accommodations for three guests.

Superhost
Condo in Sarasota
5 out of 5 average rating, 4 reviews

Johnnys Island Palm | Walk to Beach & Dining

Exclusive Amenities Include: • Located in the Heart of South Siesta Key • Olympic-Size Community Heated Pool • Lighted Pickleball & Tennis Courts • Clubhouse, Fitness Center, BBQ & Picnic Areas • Walk to Siesta Key Beach • 2 Bedrooms, 2 Full Baths • 1 King Bed, 2 Queen Beds (Sleeps 6) with Linens Provided • Free WiFi & TVs • Coffee Maker, Kitchen Essentials Provided • Beach Towels, Chairs, & Caddy Provided • In-Home Washer and Dryer • Dedicated Carport Parking Space

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, 340 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, 110 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.

Top guest favourite
A modern, one-story villa is showcased with a light-colored exterior. The front door is flanked by tropical palm trees and vibrant landscaping. A paved driveway leads to an attached garage, enhancing accessibility in this coastal retreat.
Home in Sarasota
5 out of 5 average rating, 27 reviews

Ground floor home 2BD2BA garage Pool Private beach

Enjoy easy access to everything from this centrally located, updated coastal retreat 2 bed 2 bath 1253 sq ft villa w attached garage, washer/dryer Private beach & free loungers 2 pools Sleeps 7- King in master & queen/twin in guest & sofa bed in living No car needed great for families or couples WiFi & lg work space WALK 1/4 m to restaurants, grocery, liquor, coffee & ice cream Siesta Beach #1 in US Superhost- 325+ reviews that average FIVE STAR*

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

Cottage on Siesta Key Special December Pricing

Come experience Siesta Key and relax in our beachside cottage. It is sure to refresh you , whether you prefer an incredible one of a kind sunset or a long leisurely walk on the beach with the cool sugar white sand beneath your toes! This is an escape you deserve. The pool is beautiful and conveniently located on your stroll to the beach. If you enjoy music , we are close to several places you can sit & enjoy under the Tiki Huts with refreshments!

Guest favourite
The outdoor area features several lounge chairs and umbrellas arranged around a clean patio, with well-maintained landscaping in the background. A pathway leads toward the ocean, where turquoise waters can be seen in the distance under clear skies.
Condo in Sarasota
4.97 out of 5 average rating, 110 reviews

203 Luxury Condo With Ocean View, Heated Pool +

Luxurious apartment style condo on Siesta Key Beach, Sarasota Florida overlooking the quartz white sand and turquoise waters of the #1 beach in the USA. Enjoy exquisite ocean views from the balcony or just a few steps to the beach. Our gated community positions you steps away from whatever your heart desires (pool, ocean, grocery store, restaurants, live music and local shops). Your options are limitless on Siesta Key.

Top guest favourite
Home in Sarasota
4.98 out of 5 average rating, 146 reviews

Family Retreat w/Pool&HotTub 5 min to Siesta Key!

Family-Friendly 3BR Home w/ Private Heated Pool, Hot Tub & Backyard– Near Siesta Key! Located just minutes from world-famous beaches, and a wide variety of dining, shopping, and entertainment options, this home is the perfect base for your Sarasota vacation. Whether you’re planning a family trip, a couples’ retreat, or a friends’ getaway, you’ll love the blend of comfort, convenience, and fun!

Top guest favourite
Aerial view captures the pristine beach alongside the expansive manicured grounds of a gated community. The layout features several buildings with red roofs, centered around a heated salt water pool. The shoreline and beach-goers are visible in the distance.
Condo in Siesta Key
4.98 out of 5 average rating, 48 reviews

Siesta Dunes 1st Floor Beach Front Retreat + Bikes

Steps from the beach, this spacious 2 bedroom condo has everything you will need for your Siesta Key vacation. Located in the beautiful gated community of Siesta Dunes, with heated salt water pool, and its own private beach access, complete with beach chairs, umbrellas and towels. Stroll though the well-manicured grounds on your way to the pool, the sundeck and the beach.

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, 337 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 rentals with a pool near Crescent Beach

Kitchen
Wifi
Pool
Free parking on premises
Air conditioning

House rentals with a pool

Top guest favourite
A serene outdoor space features a sparkling pool surrounded by lush greenery. Comfortable seating is provided under a large umbrella, while decorative light fixtures enhance the ambiance. Tropical plants and well-maintained landscaping create a refreshing atmosphere for relaxation and enjoyment.
Home in Sarasota
4.98 out of 5 average rating, 82 reviews

Your DreamOasisAwaits: SiestaKeyEscape with Pool!

Guest favourite
A private heated pool is surrounded by a spacious stone patio, featuring comfortable lounge chairs. Lush greenery provides a tropical backdrop, while a charming cottage with turquoise siding is visible nearby. Soft sunlight reflects on the tranquil water, enhancing the peaceful ambiance of this outdoor area.
Home in Siesta Key
5 out of 5 average rating, 15 reviews

Toes In The Sand | Private Pool, Walk to Beach!

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!

Guest favourite
A well-lit bedroom features a spacious bed with a light-colored bedspread. Two large windows offer views of the outdoors, framed by sheer curtains. A ceiling fan hangs above, providing airflow. A comfortable chair and a dresser add practical elements to the inviting space.
Home in Sarasota
5 out of 5 average rating, 10 reviews

The Palms Away

Superhost
Home in Venice
4.91 out of 5 average rating, 122 reviews

Spacious 2 Bedroom Home | Near Beach | Heated Pool

Top guest favourite
A private courtyard featuring a heated pool is surrounded by lush tropical landscaping. Comfortable lounge chairs are positioned beside the pool, and a small fountain adds a soothing element. A cozy seating area is visible near the entrance to the adjoining building.
Home in Sarasota
4.94 out of 5 average rating, 126 reviews

Pool Courtyard, patio w/ fire pit, 2 mls downtown

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, 277 reviews

Private Siesta Beach House Oasis with Heated Pool.

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

Condo 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
A panoramic view showcases a sandy beach stretching along the coastline, framed by swaying palm trees. The tranquil azure waters of the Gulf are visible, and a few sun loungers are scattered across the beach, enhancing the serene coastal atmosphere.
Condo in Siesta Key
4.94 out of 5 average rating, 77 reviews

Beach & Pool Open! Beachfront View All Rooms. Chai

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
4.89 out of 5 average rating, 126 reviews

Crystal House on Siesta Key Beach

Guest favourite
A serene beach scene captures calm waves gently lapping at the shore under a sky filled with scattered clouds. Soft hues of orange and blue reflect in the water, suggesting an approaching sunset over the tranquil coastline.
Condo in Sarasota
4.85 out of 5 average rating, 80 reviews

Private Beach Access. Pool. Grill. Siesta Key

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 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, 188 reviews

Beachfront Resort, Ocean View, Pool, Tennis, Gym

Superhost
An aerial view captures a landscaped area featuring a spacious pool surrounded by palm trees. The expanse of Crescent Beach is visible beyond the manicured gardens, with the ocean stretching towards the horizon under a bright blue sky.
Condo in Siesta Key
4.89 out of 5 average rating, 101 reviews

Sarasota Surf & Racquet Club Siesta Key Condo

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

Other vacation rentals with a pool

Superhost
Aerial view of the Siesta Key beachfront, highlighting the Crescent Arms condominium complex set against the powdery white sands and turquoise waters of the Gulf of Mexico. The surrounding area features other buildings and beachgoers enjoying the sun and surf.
Condo in Sarasota
4.75 out of 5 average rating, 24 reviews

Beachfront Condo - 2BR Luxury - Crescent Beach

Top guest favourite
The living area features two brown leather sofas flanking a wooden coffee table, with a decorative plant beside an illuminated lamp. Natural light enters through a large window, while a light blue wall and patterned rug enhance the comfortable surroundings.
Condo in Siesta Key
4.94 out of 5 average rating, 49 reviews

Spectacular Siesta Key Beachfront Condo

Guest favourite
A spacious living area features comfortable wicker furniture and a neutral color palette. Large glass doors provide views of the greenery outside, while a subtle area rug adds texture to the tiled floor. A decorative painting is mounted on the wall, enhancing the coastal theme.
Condo in Siesta Key
4.95 out of 5 average rating, 19 reviews

Siesta Key - Intracoastal, Pool & the Beach!

Guest favourite
A spacious dining area is presented with a round glass table surrounded by dark wooden chairs. A modern light fixture hangs above, illuminating the area. The kitchen features white cabinetry, stainless steel appliances, and a large island with bar stools, creating a welcoming and functional space.
Condo in Sarasota
4.96 out of 5 average rating, 67 reviews

Siesta Key Spacious, Modern 2 bed, 2 bath condo

Guest favourite
A villa with a light-colored exterior features a spacious driveway made of pavers. Lush tropical landscaping adds color, while a large parking garage is visible on the right side. In the background, a multi-story building is partly shown under a partly cloudy sky.
Villa in Sarasota
5 out of 5 average rating, 9 reviews

Newly Remodeled Luxury Beach Villa on Siesta Key!

Top guest favourite
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 Sarasota
5 out of 5 average rating, 61 reviews

Breathtaking Beachfront Views in Siesta Key

Guest favourite
A view of the beach is captured from a balcony, showcasing the expanse of the Gulf of Mexico and the white sandy shore. Lush green landscaping lines the pathway leading to the beach, framed by palm trees. Sunlight illuminates the scene, accentuating the tranquil atmosphere.
Condo in Sarasota
4.95 out of 5 average rating, 43 reviews

Siesta Key Beachfront Condo - Private beach access

Superhost
A spacious living area includes a comfortable sofa and a dining table set for four. Natural light brightens the room through large windows, reflecting off a mirrored wall. The decor features soft tones and a patterned area rug beneath a coffee table.
Condo in Siesta Key
5 out of 5 average rating, 3 reviews

Midnight Cove II 533F: Pristine Condo Near Beach

Quick stats about rentals with a pool near Crescent Beach

  • Total rentals

    1.2K properties

  • Nightly prices starting at

    $98 CAD before taxes and fees

  • Total number of reviews

    28K reviews

  • Family-friendly rentals

    1K properties are a good fit for families

  • Pet-friendly rentals

    80 properties allow pets

  • Rentals with dedicated workspaces

    540 properties have a dedicated workspace

Destinations to explore