Home rentals with a pool near Siesta Beach

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.

4.93 out of 5 average rating, 112 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.

4.92 out of 5 average rating, 120 reviews

Guest house in Sarasota

Super Clean Cozy and Quaint steps from the beach

The best of all worlds, cleanliness and steps from the beach. Avoid the crowds at the public beach in this beautiful private beach with lounge chairs already at the beach for your convenience. Literally yards from the beach, exit the ground floor condo and walk 100 yards to the gate to the private beach. Only 2 miles from the village, with an easy close by trolley stop just outside the complex. Beach cart, umbrella, cooler, beach toys and towels provided for your convenience! Look no further.

Apartment in Longboat Key

4.98 out of 5 average rating, 222 reviews

Oceanfront: Open Tomm $99/nt + Fees!

This sublime oceanfront studio is directly on the pristine white sands and serene blue waters of the Gulf of Mexico in Longboat Key, Florida! On the second floor, overlooking the heated pool and ocean, this dreamy studio condo 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...!

A light-filled living area features a comfortable white sectional sofa with decorative pillows, complemented by a wooden coffee table. Large glass doors lead to an outdoor space, while a television and two lamps enhance the room's functionality and warmth.

4.85 out of 5 average rating, 117 reviews

The Palm Bay Club on Siesta key Beach

Welcome to The Palm Bay Club on Siesta Key Beach Enjoy sunrise to sunset from our great resort that has private bay to beach access . Updated 2 bedroom 2 Bath ground floor with walk out balcony .Each bedroom offers private en-suite, Clean and bright open floor plan, well appointed kitchen ,Central A/C . Resort features 2 heated pools , enjoy the tranquility of the bay from the large hot tub or pool . Fishing pier, tennis & pickle ball courts, gym, laundry area we also offer boat slips

A bright and airy living space features a modern sofa facing a sleek coffee table. The open kitchen is visible in the background, showcasing white cabinetry and bar seating with stylish stools. Light fills the room through large windows, enhancing the spacious feel.

4.96 out of 5 average rating, 131 reviews

Your Modern Beachside Getaway!

Search no more… we have it all! Enjoy this spectacular, newly remodeled beachside home in Siesta Key, equipped with a modern kitchen, hotel luxury pillow-top bed, and high-end finishes throughout! Amenities include private beach access (beachside 3 minute walk), pool access, patio, courtyard, BBQ, parking, and more. And the cherry on top, you’re right across the street for a plethora of restaurants, shops, and conveniences giving you everything you need to enjoy the best of Siesta Key!

4.86 out of 5 average rating, 281 reviews

An open living space features a fully equipped kitchen with wooden cabinetry, a dining table, and seating area. A flat-screen TV is mounted on the wall. Light-colored flooring enhances the spacious feel, while natural light brightens the room through multiple windows.

Cottage in Siesta Key

Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

*Siesta Key elevated villa at Solitude Suites on Siesta Key. *Your own detached private villa, located in a small resort. *Waterfront resort w/ heated pool, kayaks, table tennis & Tiki Hut. * Just a 10-12 min walk to award winning beach. *1 Bedroom w/King bed. *1 full bathroom w/shower. *Large kitchen, open living room, fully furnished inc towels & linens. *Private screened lanai w/ table & chairs. *Beautiful shared pool w/ sun shelf & waterfall. *2 min car ride to beach. *Updated!

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, 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!

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.

4.84 out of 5 average rating, 257 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.

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.

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.

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.

4.93 out of 5 average rating, 122 reviews

Beautiful White Sand Siesta Key Beach

This studio has lots of space and is across from the pool and just a few short steps from the beautiful Siesta beach. Known for it powder sand white beach and tropical breeze. Average Temperature is 70. The two large pools are heated all year. This unit has one king mattress . There are shuffleboard courts an tennis court and is close to everything.

4.77 out of 5 average rating, 533 reviews

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

Beachfront Getaway in Siesta Key

Beachfront complex, this gorgeous home boasts all the luxury you’d expect from a beach house! Beachfront BBQ grills, cabana with lounge chairs,heated swimming pool, Wi-Fi & parking. For your convenience, there are restaurants, grocery store, pharmacy, 24 hours 7-Eleven, bike and Kayak rentals just across the street. A little piece of paradise!

4.84 out of 5 average rating, 222 reviews

An aerial view captures the proximity of the mini resort to the beach. The surrounding landscape features palm trees and a mix of residential buildings, with the inviting shoreline visible in the distance, showcasing the turquoise waters of the ocean.

Townhouse in Siesta Key

Lovebirds’ Retreat | Steps to Siesta Key Beach

Romantic Honeymoon Suite 💕 Steps from Siesta Key Beach, this 1BR/2BA townhouse is perfect for two. Enjoy 2 balconies with sunset views of the beach, pool & gardens, central AC, and a heated lagoon-style pool for dreamy evening swims. Max 4 guests. Complimentary Wi-Fi, beach chairs & parking for 1 car make this the ultimate couples’ escape.

Popular amenities for rentals with a pool near Siesta Beach

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

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.

4.94 out of 5 average rating, 142 reviews

The Sand Castle - Backyard Oasis Mins from Siesta!

A private hot tub is shown within a screened enclosure, featuring clear blue water. Two inflatable rings are floating on the surface. Lush greenery can be seen in the background, providing a natural setting for relaxation.

4.98 out of 5 average rating, 105 reviews

Location! Siesta 1 mile away. Home with HOT SPA.

5 out of 5 average rating, 154 reviews

Home in Siesta Key

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

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.

4.89 out of 5 average rating, 167 reviews

5 minutes to private Siesta Key Beach + 2 pools

4.87 out of 5 average rating, 113 reviews

Trendy & Relaxing: Close to Beach ~ Pool ~ Hot Tub

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.

4.94 out of 5 average rating, 114 reviews

Oasis by Siesta Key Beach and Downtown SRQ w/pool

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.

4.92 out of 5 average rating, 382 reviews

Beach Retreat•Renovated Pool Patio•Near Siesta Key

4.97 out of 5 average rating, 115 reviews

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

Waterfront Pool Home Steps to Beach

Apartment rentals with a pool

A modern living area is visible, showcasing a cozy gray sofa and a glass coffee table atop a patterned rug. The open kitchen features stainless steel appliances and a bright green accent wall. Natural light streams through a nearby window, enhancing the inviting space.

4.93 out of 5 average rating, 208 reviews

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

An aerial view of the Sea Shell condominium displays a four-story building with balconies facing the ocean. The bright blue sky and ocean can be seen beyond the structure, emphasizing the inviting coastal location.

4.92 out of 5 average rating, 146 reviews

Sea Shell Ocean View On Beach Walk Everywhere 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, 141 reviews

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

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.

4.94 out of 5 average rating, 160 reviews

Villa Maria: Minutes to Siesta Key!

A heated swimming pool is surrounded by a spacious deck with lounge chairs. A shaded cabana is visible to one side, enhancing the inviting atmosphere. Palm trees and lush landscaping create a tropical ambiance under a clear blue sky.

4.74 out of 5 average rating, 140 reviews

Best Deals on Siesta Key

Apartment in Longboat Key

4.88 out of 5 average rating, 124 reviews

Sunset and beach view from your balcony Unit 403

Apartment in Longboat Key

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.

4.9 out of 5 average rating, 202 reviews

Beachfront Resort, Ocean View, Pool, Tennis, Gym

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.

4.95 out of 5 average rating, 108 reviews

Seaside on Siesta Key Beach

Other holiday rentals with a pool

4.98 out of 5 average rating, 93 reviews

Your DreamOasisAwaits: SiestaKeyEscape with Pool!

4.99 out of 5 average rating, 82 reviews

A private balcony is showcased with two white lounge chairs and a small table. Lush palm trees provide greenery, while a heated pool can be seen beyond the railing. Sunlight filters through the trees, creating a serene outdoor space.

Flat in Sarasota

Beechwood Suites B

A bright living area features large floor-to-ceiling windows that allow natural light to fill the space. A light-colored sectional sofa and a modern coffee table are present, along with a floor lamp. A balcony is visible in the background, showcasing views of greenery.

4.88 out of 5 average rating, 57 reviews

Beach Haven on Siesta Key Beach

4.93 out of 5 average rating, 84 reviews

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.

Flat in Siesta Key

Siesta Sunsets Suite

4.92 out of 5 average rating, 48 reviews

A bright living area features a sectional sofa and a wicker coffee table, with large windows letting in ample natural light. A flat-screen television is positioned on a wooden console, and decorative artwork adorns the walls, enhancing the space's welcoming demeanor.

Bungalow in Siesta Key

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

4.83 out of 5 average rating, 105 reviews

A spacious sleeping area features a queen-size bed with a light blue patterned bedspread. A cozy armchair is positioned beside the bed, and window treatments allow natural light to brighten the room. Light wood flooring complements the neutral-toned walls.

Flat in Sarasota

Lido Key FL Studio/Efficiency 5

4.81 out of 5 average rating, 90 reviews

A modern living room is presented with light gray walls and a large sliding glass door leading to a screened balcony. A comfortable sectional sofa sits against one wall, complemented by a decorative coffee table and a television displaying a serene beach scene.

Flat in Sarasota

Stylish Gray 2nd-Floor Condo w/ Heated Pool | 1BR

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.