Vacation rentals with a pool in Siesta Key

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.

4.95 out of 5 average rating, 134 reviews

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

Amazing 2nd floor unit in building C at the Sarasota Surf & Racquet Club. This fully furnished 2 bed/ 2 bath condo offers a resort view and just steps away from the white sands of Siesta Key Beach. This unit is recently updated with an open floor plan, featuring stainless steel appliances, granite counter tops, kitchen bar with stools, living room, and dining room. This unit has flat screen tv's, ceiling fans, and maid service including linens and bath towels. Washer/dryer located down the hall

Apartment in Longboat Key

Tall grasses gently sway in the foreground, framing a serene beach scene. Soft waves lap against the shore, reflecting hues of orange, pink, and purple from the sunset sky. Cloud formations add depth to the view, enhancing the tranquility of the coastal landscape.

4.96 out of 5 average rating, 113 reviews

Longboat Key-OCEAN FRONT- on the beach

My place is located in a small boutique complex located on Longboat Key. Walk to shops, restaurants and park. You’ll love my place because of Gulf front location with full gulf view from living room, kitchen, master bedroom, and screened lanai. Completely updated in 2015 with full kitchen, two full baths and two bedrooms. A perfect place to relax, listen to the surf and watch amazing sunsets over the Gulf of Mexico. My place is good for couples, solo adventurers, and families (with kids).

4.92 out of 5 average rating, 118 reviews

A spacious bedroom features a king size bed with a white bedding set and decorative pillows. Soft blue walls provide a calming backdrop. A ceiling fan is installed overhead, and natural light streams in through the window adorned with light blinds. Complementary artwork adds a touch of coastal charm.

Guesthouse 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.

4.86 out of 5 average rating, 273 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/ FREE 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!

4.9 out of 5 average rating, 193 reviews

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

Beachfront Resort, Ocean View, Pool, Tennis, Gym

Beachfront on beautiful Longboat Key, this condominium offers all the amenities of a resort with the privacy and seclusion that has Silver Sands Beach Resort guests returning each year. Enjoy a coffee on your private patio looking at the Gulf and the beach. Relax on our private beach, walk on our soft white sand, take a dip in our heated beachside pool, or enjoy complimentary chaise lounges and beach umbrellas while breathing in the fresh air. You can't get closer to the beach.

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.

5 out of 5 average rating, 153 reviews

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

FULLY RESTORED POST HURRICANE! HERE IT IS! This “one of a kind” property is uniquely situated between the beach, canal, village with a private heated pool & dock, one of the best spots on Siesta Key! This charming 1,500 sq. ft. cottage beach home is being offered for the 1st time and post hurricane updates! If you want a cute, private original bungalow style beach cottage home all to yourself without the shared wall feel of a condo, then you are in the right spot!

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.

4.93 out of 5 average rating, 106 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!

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, 138 reviews

The Sand Castle - Backyard Oasis Mins from Siesta!

*UPDATE SOON* 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 ever want!

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, 345 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 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.

4.96 out of 5 average rating, 112 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.

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, 251 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.

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.

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.

Popular amenities for Siesta Key rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A serene outdoor space encompasses a private pool, surrounded by paved decking and lush greenery. Lounge seating and a covered dining area offer comfort. An umbrella provides shade, while a playful pink float adds a splash of color, inviting relaxation on sunny days.

5 out of 5 average rating, 3 reviews

Luxury 3BR Pool Near Beach | The Nest Siesta Key

4.98 out of 5 average rating, 146 reviews

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

4.95 out of 5 average rating, 19 reviews

Home in Arlington Park

Coastal Luxe, SaltPool/Spa, 5miles to Siesta

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.

4.93 out of 5 average rating, 106 reviews

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

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.

4.94 out of 5 average rating, 126 reviews

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

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.

5 out of 5 average rating, 28 reviews

Siesta Key Retreat 1mi to Beach!

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.

4.98 out of 5 average rating, 109 reviews

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

A charming yellow home is set against a backdrop of palm trees, with a brick paved driveway leading to a two-car garage. Lush greenery surrounds the property, providing a sense of privacy and tranquility.

4.91 out of 5 average rating, 119 reviews

Siesta Key, FL - Casa Berano

Condo rentals with a pool

The exterior of a pink three-story condo is visible, surrounded by palm trees and tropical plants. A pool area features several lounge chairs and a circular table, with a covered balcony on the second floor. Light clouds decorate the sky, creating a relaxed atmosphere.

4.88 out of 5 average rating, 104 reviews

5213B Calle Menorca - Siesta Key Village Condo

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.

4.93 out of 5 average rating, 207 reviews

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

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, 116 reviews

Beautiful White Sand Siesta Key Beach

A spacious bedroom features a large king-size bed dressed in neutral linens. A flat-screen television is mounted on the wall, while natural light enters through sliding glass doors. A small table and a decorative plant add a touch of elegance to the minimalist decor.

4.82 out of 5 average rating, 330 reviews

[Beach Elements] pool view + private beach & bikes

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.

4.86 out of 5 average rating, 152 reviews

Siesta Key Ground Floor Condo 2BR On Trolley Line

4.88 out of 5 average rating, 118 reviews

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

Sunset and beach view from your balcony Unit 403

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, 103 reviews

Seaside on Siesta Key Beach

4.92 out of 5 average rating, 148 reviews

Cottage on Siesta Key Beachside & Stunning sunsets

Other vacation rentals with a pool

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.

4.98 out of 5 average rating, 58 reviews

2 BR condo in Siesta Key w/ Private beach access

The open-concept kitchen and dining area feature modern furnishings, with a spacious table for six and bar seating along the kitchen island. Floor-to-ceiling windows provide unobstructed views of the beach, allowing natural light to brighten the room.

5 out of 5 average rating, 9 reviews

2BR Penthouse • Stunning Beach Views on Siesta Key

5 out of 5 average rating, 50 reviews

An outdoor lounge area is showcased under a wooden ceiling, featuring a heated pool and elegant patio furnishings. A television is mounted on the wall, and a dining set is positioned nearby, with a barbecue grill just outside the lounging space, surrounded by tropical landscaping.

Home in Holmes Beach

Book Family Tides 7 Nts get 3 FREE~Pool~Beach view

5 out of 5 average rating, 15 reviews

Cottage in Siesta Key

House with pool 1 block to village, 3blks to beach

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.

4.98 out of 5 average rating, 49 reviews

Siesta Dunes 1st Floor Beach Front Retreat + Bikes

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.

5 out of 5 average rating, 43 reviews

Amazing beach view! Entire unit renovated!

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.

4.79 out of 5 average rating, 14 reviews

2B/2BA Penthouse End-Unit Condo