Holiday rentals with a pool in South Sarasota

An indoor pool is enclosed within a screened area, offering a clear view of tranquil blue water and surrounding trees. Comfortable outdoor seating is visible, complemented by a sunlit patio space. Large glass doors provide access to the pool area, enhancing the open feel.

4.97 out of 5 average rating, 199 reviews

The Bradford Cottage/Heated Pool /Mins to Siesta

If you are looking for a cozy retreat in a safe and private neighborhood than look no further! From the minute you step inside this immaculate private residence you will feel right at home. With a beautiful open floor plan with plenty of room to spread out, natural light that pours in every room and a spacious back porch overlooking the heated pool this is the perfect place to unwind and relax. Minutes from the #1 rated Siesta Key beach and downtown Sarasota you are in the middle of it all!

The outdoor area features a uniquely shaped heated saltwater pool with clear blue water. Surrounding the pool are loungers placed on a bright, white deck, complemented by tropical plants and palm trees that enhance the tranquil environment.

4.98 out of 5 average rating, 121 reviews

Tropical Oasis Heated Pool Hot Tub Near Siesta Key

Escape to The Funky Fish House! Your private 2BR/3BD/2BA tropical oasis boasts a heated saltwater pool, bubbling hot tub, outdoor shower, and BBQ grill for endless fun, relaxation, and sun-soaked adventures. Just 5 miles from world-famous Siesta Key Beach and steps from Trader Joe’s, this elegantly renovated, fully stocked, stylish retreat invites families or couples to lounge, entertain, soak up the Florida sunshine, and enjoy the ultimate Sarasota vacation in absolute comfort and style!

4.93 out of 5 average rating, 392 reviews

Home in Pelican Cove

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.

A sparkling pool is surrounded by a spacious patio, featuring lounge chairs and a vibrant red umbrella. Lush tropical landscaping creates a serene retreat, providing an inviting space for relaxation and leisure under a clear blue sky dotted with fluffy white clouds.

4.96 out of 5 average rating, 157 reviews

Mid-Century Oasis with Pool in Arlington Park 1

A perfect blend of Sarasota’s architectural heritage and contemporary elegance right in the heart of Arlington Park. This bright, newly renovated 2 bed/2 bath & pull out sofa in a mid-century gem offers a serene escape, providing a refreshing interplay of historical charm and modern luxury. Enjoy the separate sunroom/office for those working from home, or use as an extra sleeping space with comfy pull out sofa. Take a break with a quick dip in the sparkling pool. VR24-00160

5 out of 5 average rating, 107 reviews

The Blessing House- Htd Pool/Spa, Close to Beaches

Welcome to The Blessing House! This home has been beautifully renovated, designed & curated for you to be rejuvenated, relaxed & inspired during your stay. You will love the heated pool & spa, the spacious lanai with plant wall, the fresh and bright design, and the amazing location of this house. The Blessing House is only a 15 min drive to Lido Key Beach & Siesta Key Beach, tons of shops & restaurants and the lovely Arlington Park is only about a 7-10 min walk away.

4.92 out of 5 average rating, 359 reviews

A private caged pool area is surrounded by lush tropical greenery. A turquoise umbrella provides shade over a lounge chair, while a series of blue-tiled steps lead into the pool. Potted roses add a touch of color beside the water.

Guest suite in Sarasota

Beach & Town Posh Location! Jungle Paradise Studio

PRIME! To Town&Beach Locations! *Private Studio* *NO Smoking *NO Children. *Shared Pool. Studio w/private entrance & patio @Designers private Home,Tropical Jungle, like Posh Resort! Quiet, residential area. Sought-after amenities. 10 min/Siesta Beach, shops, dining, & 5mins/Downtown Sarasota. Walk/local markets/ dining/movies & shopping New King bed. New 50" TV. Off street parking. No Smoking/Vaping! No kitchen. No Hotels in my exclusive area! Live like a local!

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, 156 reviews

The Sand Castle - Backyard Oasis Mins from Siesta!

*UPDATED!* 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!

5 out of 5 average rating, 105 reviews

Quiet Gulf & Canal View 1 BR -2 Supyaks-Htd Pool

Whisk your favorite person away to BayDreaming! Retreat to this quiet 1BR/1.5BA condo, just an 8‑minute walk from Turtle Beach. Perfect for couples, it offers a private deck with canal and Gulf views, a heated pool for sunset swims, two supyaks, and a plush king bed for cozy nights. Enjoy garage parking, beach gear, and a peaceful community. Whether you’re here to relax or reconnect, this coastal retreat blends romance with Siesta Key serenity.

4.94 out of 5 average rating, 112 reviews

Sea Esta | Private Saltwater POOL + Putting Green!

BNB Breeze Presents: Sea Esta! Experience this stunning home in the heart of Sarasota, located just 10 minutes away from Siesta Key Beach! From the gorgeous interior, to the INCREDIBLE outdoor oasis, this home has it all! • Heated Saltwater Pool - heated at NO extra cost from Nov 21 - April 1st • Resort-Like Back Yard w/ a Pergola, Turf + Putting Green + Bikes • Pool + Beach Supplies • Fun Outdoor Swinging Dining Table

4.98 out of 5 average rating, 112 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. 🌴

4.97 out of 5 average rating, 359 reviews

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

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!

4.92 out of 5 average rating, 112 reviews

The outdoor area features a heated pool surrounded by lounge chairs, providing ample space for relaxation. A dining set is positioned nearby, accompanied by an umbrella for shade. Lush greenery and palm trees border the property, complementing the serene atmosphere.

Home in Bellevue Terrace

Rhodes Retreat - Beautiful Pool and Backyard Space

Bright and newly renovated home for a delightful family escape in Sarasota. Central location near beaches, shopping, and downtown, yet nestled in a serene neighborhood. Short walk to charming Amish Village of Pinecraft. Ample parking, garage, and spacious front yard. Option to book separate secondary unit. Siesta Beach 8.7mi, Lido 5.8mi. VR24-00264

Popular amenities for South Sarasota rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.98 out of 5 average rating, 156 reviews

Sunny Paradise w/Pool&HotTub 5 min to Siesta Key!

4.88 out of 5 average rating, 25 reviews

Luxurious Retreat near SiestaKey

A screened outdoor area features a heated pool accompanied by a spacious seating arrangement. A dining table with chairs sits shaded under an umbrella, while lounge chairs are positioned nearby. Lush greenery provides a natural backdrop, enhancing the inviting space.

4.95 out of 5 average rating, 156 reviews

Beautifully Remodeled Home with Pool Near Siesta

Superhost

4.78 out of 5 average rating, 18 reviews

Private Getaway Near Siesta Key!

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.

4.96 out of 5 average rating, 80 reviews

True Island Living House/beach/water views

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.

4.98 out of 5 average rating, 140 reviews

Cozy Boho Bungalow Pool/Spa QR Code Walkthrough

A private heated pool is surrounded by a spacious patio with lounge chairs and an umbrella for shade. The modern two-story home features large glass doors that brighten the living spaces, and vibrant greenery enhances the outdoor area.

4.94 out of 5 average rating, 53 reviews

Private Heated Pool Retreat for Two Families

5 out of 5 average rating, 30 reviews

NEW! Renovated Pool Home Mins 2 Siesta Key Beach

Apartment rentals with a pool

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.

4.91 out of 5 average rating, 120 reviews

The Honeymoon Suite on Siesta Key Beach

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, 377 reviews

On the Beach; Siesta Key SunBum Studio

4.83 out of 5 average rating, 141 reviews

Apartment in Lido Key

LIDO KEY 1 BR/1Bath Heated Pool 16

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.

4.86 out of 5 average rating, 105 reviews

Comfy Siesta Key Condo

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.

4.84 out of 5 average rating, 163 reviews

Siesta Key Ground Floor Condo 2BR On Trolley Line

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.

4.86 out of 5 average rating, 143 reviews

Heated Pool Apartment Near Siesta Key | 1BR

4.92 out of 5 average rating, 161 reviews

Cottage on Siesta Key Beachside & Stunning sunsets

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.

4.97 out of 5 average rating, 120 reviews

Palm Bay Club! Resort Living on Siesta Key!

Other holiday rentals with a pool

5 out of 5 average rating, 28 reviews

A modern living space is showcased, featuring a sectional sofa and a wooden coffee table. A wall-mounted television displays serene ocean imagery. The fully equipped kitchen, visible in the background, includes stainless steel appliances and a casual dining area with two chairs. Natural light enters through large windows.

Guest house in Sarasota

New! Siesta Beach Guest House with pool!

4.94 out of 5 average rating, 93 reviews

A serene outdoor area features a pool with a curved shape, surrounded by a gated enclosure. Lush greenery and tall trees provide shade, while a light-colored building with a metal roof stands nearby. The setting offers a tranquil atmosphere for relaxation.

Guest house in Sarasota

Amazing Location West of the Trail

The exterior of the home features a welcoming entryway with a brown door framed by two dark wooden columns. A neatly landscaped path, lined with smooth stones and small plants, leads to the front entrance, which is flanked by palm trees and greenery.

4.89 out of 5 average rating, 38 reviews

Siesta Getaway- 3.5 miles to beach 3/2 pool home.

4.93 out of 5 average rating, 44 reviews

A single-story home is surrounded by a well-kept lawn, featuring a lush shrub at the forefront. The entrance is framed by a covered porch, with large windows providing natural light. Trees line the property, casting gentle shadows across the yard.

Cottage in Sarasota

Charming Coastal Oasis 2 Bed/2 Bath Cottage

5 out of 5 average rating, 91 reviews

The Dunes-Heated Private Pool Hot Tub-5mi to beach

4.99 out of 5 average rating, 91 reviews

A well-maintained pool area is enclosed by a screened lanai, featuring a refreshing turquoise pool surrounded by a spacious patio and two lounge chairs. Direct access to the house is visible, with additional outdoor seating for relaxing or dining nearby.

Bungalow in Sarasota

*Waterfront house with dock and heated pool

A serene saltwater pool is framed by light-colored stone tiles, reflecting the twilight sky. Lounge chairs in vibrant pink and teal provide seating along the water's edge, while lush greenery surrounds the area, creating an inviting outdoor retreat.

5 out of 5 average rating, 28 reviews

The Pink Palm on Siesta Key