Vacation rentals with a pool in The Meadows

5 out of 5 average rating, 102 reviews

Condo in Sarasota

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

Whisk your favorite person away to BayDreaming! Escape to this quiet 1BR/1.5BA condo - just an 8-minute walk to Turtle Beach! Perfect for couples, it features a private deck with canal and Gulf views , a heated pool for sunset swims, 2 supyaks and a plush king bed for cozy nights in. Enjoy garage parking, beach gear, and a peaceful, welcoming community. Whether you're here to relax or reconnect, this coastal retreat offers the perfect mix of romance or just plain serenity on sunny Siesta Key!

The outdoor space is enclosed by a screened lanai, showcasing a heated saltwater pool and a dining area with a large table that seats eight. Lounge chairs and a BBQ grill are positioned near the pool, surrounded by tropical landscaping and a clear blue sky.

4.96 out of 5 average rating, 101 reviews

3 bedroom Heated salt water pool close to Siesta

Your family will be close to everything when you stay at this centrally-located place. 15 minutes to Siesta Beach, 10 minutes to UTC mall, 15minutes to downtown, 20 minutes to SRQ airport. This home is fully remodeled, fully furnished, sleeps 8. We have 1 king size bed in the master, second bedroom is queen bed, 3rd bedroom is 1 full and 1 twin beds. This is open plan home with a big family room, 60" TV above electric fireplace, formal dining room seats 6 with the bar seats 4. Master has 55"TV

4.93 out of 5 average rating, 121 reviews

An outdoor area features a heated pool surrounded by a spacious deck. Lounge chairs are positioned nearby for relaxation, and a dining set offers seating for outdoor meals. A screened enclosure provides protection from insects while allowing natural light to filter through.

Home in Glen Oaks

Heated 3BR Pool Home Glen Oaks | Close to Downtown

Family-friendly pool home near Bobby Jones Golf Club, perfectly located in the heart of Sarasota. You’re less than 10 minutes from top attractions, dining, and shopping, Downton Sarasota and just a short drive to the world-famous Siesta Beach or Lido Beach. This private home features its own entrance, a heated pool, and a fully fenced backyard—ideal for families and added privacy. We’re pet-friendly too! Comfortable, central, and close to everything—perfect for your Sarasota getaway VR24-00164

Home in Indian Beach-Sapphire Shores

A private heated pool is enclosed by a screened lanai, surrounded by lush tropical plants. Soft purple lights create a relaxed ambiance. Comfortable seating and dining areas are positioned nearby, inviting leisurely moments by the water.

4.97 out of 5 average rating, 169 reviews

ROYS PLACE private, tropical, romantic paradise.

NAMED #1 BEST AIRBNB WITH POOL IN SARASOTA BY TRIP 101 TRAVEL GUIDE FOR 2022, 2023, 2024. An exceptional vacation is a frame for an exceptional life. Offered for you, a romantic boutique home. Sarasota Chic decor, quality furnishings, lush tropical landscaping. Only property in urban Sarasota with your own private (EXCLUSIVE to you, NOT shared) CLOTHING OPTIONAL heated pool for tropical fun. One block walk to beautiful sunsets over Sarasota Bay. All tropical serenity yet close to everything.

A tranquil view of a small private lake is presented, surrounded by well-maintained homes. The water reflects the clear blue sky and green grass lining the shore, creating a serene setting for relaxation. Lush trees provide shade along the bank.

4.81 out of 5 average rating, 134 reviews

Heated Pool (No Cleaning Fee)

Solar heated plunge pool (14' X 18' small) Not so warm in cold weather with over night in the 40's or 50's. Located 11 miles from Bradenton Beach, 30 minutes (15.5 miles) from Anna Maria Island and 12 minutes from IMG. Our home is on a small private lake.. 3rd bedroom is an office with a queen sleeper sofa. We do not have cable TV; we use streaming services and a local antenna for reception. There is a whole house filtration/water softener installed for great quality water.

A resort-style swimming pool is surrounded by lush tropical landscaping. Palm trees are seen flanking the pool area, which features a spacious deck. A building with large windows and a matching roof is visible in the background, enhancing the relaxed setting.

4.89 out of 5 average rating, 66 reviews

Coastal Retreat 3/2 Near Beaches & Downtown

This beautifully decorated home with resort style amenities is centrally located in Sarasota and is overlooking a gorgeous pond with a fountain. It includes spacious 3 bedrooms and 2.5 bathrooms with the open concept layout and contemporary coastal interior design . Conveniently located near Sarasota's most sought-after destinations! Nestled in close proximity to the pristine, award-winning beaches, vibrant Downtown Sarasota, and the bustling UTC Mall.

A private backyard features a heated saltwater pool surrounded by a spacious patio area. Sun loungers are arranged along the edge of the pool, while trees and shrubbery provide a sense of seclusion. Soft clouds drift in the blue sky above.

4.95 out of 5 average rating, 123 reviews

Coastal Getaway *With Bikes & NEW Saltwater Pool*

Just outside of Downtown near the Legacy Trail, this home is located in a quiet neighborhood only 15 minutes from the Siesta Key Beach. The home stands out with its bright and airy design, brand new saltwater pool in the private backyard, and its breezy living room. The large master bathroom rain shower is perfect to wash off the leftover sand from the beach. You can also spend your evenings grilling out back or playing corn hole in the patio area.

4.99 out of 5 average rating, 145 reviews

A light blue bedroom features a spacious bed with a floral-patterned blanket and a ceiling fan overhead. Double glass doors provide a view of the pool area outside. Storage options include a white dresser and closet, while a small table and chair are positioned nearby.

Guesthouse in Sarasota

Maggie's Hideaway

This adorable little bungalow is hidden away in one of Downtown Sarasota's oldest historical neighborhoods and only a couple miles from Sarasota Bay and surrounding beaches. Beautiful Lido Beach is only five miles west, Siesta Key is seven miles southwest, with Benderson Park being only seven miles east. Fabulous shopping and world class dining is plentiful in this downtown community. There is plenty to see and do in Sarasota - Come see us!

A covered patio area features modern wicker furniture with white cushions, positioned around a glass coffee table. The inviting space overlooks a pristine pool, surrounded by a protective screen. Lush greenery is visible in the background, enhancing the tranquil setting.

4.95 out of 5 average rating, 123 reviews

Luxury Pool Family Oasis-Siesta Key Beach-3BR/2BA

Welcome to your private oasis! This stunning pool home has undergone a meticulous renovation, offering a spacious and luminous retreat. Nestled on a serene street, it provides a peaceful escape while being in close proximity to Sarasota's top destinations. Whether you're seeking the sun-kissed shores of Siesta Key Beach, the vibrant downtown scene, or the flavors of the Fresh Fish Waltz Market, this home offers easy access to it all.

A caged outdoor space features a heated saltwater pool, surrounded by a spacious deck. Sun loungers are positioned nearby, and a covered area for dining is visible in the background. Lush greenery adds a touch of nature to the setting.

4.86 out of 5 average rating, 183 reviews

Beaches, Shopping, Sculling-Sarasota is calling!

Escape to this 3BR, 2BA Sarasota retreat in a quiet neighborhood, just minutes from UTC Mall, Nathan Benderson Park, and a short drive to award-winning beaches. Sleeps 6 comfortably with a bright open layout, fully equipped kitchen, and cozy living spaces. The highlight is the private heated saltwater pool, perfect for relaxing after a day of shopping, dining, or beach adventures. Your Sarasota getaway starts here!

4.97 out of 5 average rating, 351 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, 105 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 The Meadows rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A serene pool area features a rectangular swimming pool surrounded by a spacious deck. Lounge chairs are positioned for relaxation, while lush greenery and a wooden fence provide privacy. A decorative statue adds an elegant touch to the tranquil environment.

4.98 out of 5 average rating, 104 reviews

The Oasis

A heated pool is enclosed within a screened lanai, providing a clear view of the tranquil water. Lush greenery and landscaped plants surround the pool area, while a white privacy fence offers seclusion, enhancing the outdoor space for relaxation and enjoyment.

4.83 out of 5 average rating, 119 reviews

The Coastal Getaway•Private Heated Pool & Patio•

A spacious patio area surrounds a heated pool, sheltered by a screened enclosure. Comfortable seating is arranged by the poolside, with sunlight casting reflections on the water's surface. Lush greenery and a white fence provide a sense of privacy and tranquility.

5 out of 5 average rating, 34 reviews

Beautifully Remodeled Heated Pool Home in Sarasota

5 out of 5 average rating, 44 reviews

An enclosed backyard features a heated saltwater pool with a slightly curved shape, surrounded by greenery. Soft lighting created by string lights enhances the space, while comfortable seating is positioned nearby for relaxation. The pool area is accessible via a set of steps.

Home in Bellevue Terrace

Heated Pool, Spacious & Open, Midcentury Modern

An inviting exterior view of Sunrise Villa showcases a well-maintained landscape featuring lush greenery and vibrant plants. A spacious driveway leads up to a garage, with decorative stone detailing accentuating the garden area. The home is framed by palm trees, contributing to the tropical ambiance.

5 out of 5 average rating, 111 reviews

Sunrise Villa - Tropical 3 bedroom home with pool

5 out of 5 average rating, 121 reviews

Home in Bellevue Terrace

Living The Dream: Heated Pool + Mini Golf +Swings

4.88 out of 5 average rating, 8 reviews

4 BR Coastal Estate w/ pool near Siesta Key

5 out of 5 average rating, 7 reviews

Seabreeze Pool Retreat.

Condo rentals with a pool

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

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.

4.92 out of 5 average rating, 114 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, 362 reviews

On the Beach; Siesta Key SunBum Studio

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.

4.85 out of 5 average rating, 102 reviews

Comfy Siesta Key Condo

4.97 out of 5 average rating, 126 reviews

A screened lanai offers a peaceful retreat with a view of the pond and trees reflecting on the water. Comfortable seating is provided, accompanied by a small table. Natural light flows in, enhancing the serene atmosphere of the space.

Condo in Bradenton

A&A's Paradise near IMG & Anna Maria beaches

4.88 out of 5 average rating, 126 reviews

Condo in Longboat Key

Sunset and beach view from your balcony Unit 403

4.96 out of 5 average rating, 182 reviews

A light-filled living area showcases a large white sectional sofa adorned with colorful throw pillows. A turquoise coffee table displays decorative shells, and a light-toned area rug is centered beneath. Artwork featuring vibrant coastal scenes is mounted on the walls, enhancing the relaxed ambiance.

Condo in Bradenton

The Seabreeze Cottage with peaceful water views

4.98 out of 5 average rating, 223 reviews

A dining setting on a patio table showcases a plate of breakfast foods, including a toasted bagel, fruit, and a drink. Soft, rolled towels are stacked nearby, with a view of the beach and pool visible in the background.

Condo in Longboat Key

Sun-Kissed Memories!

Other vacation rentals with a pool

4.98 out of 5 average rating, 95 reviews

Your DreamOasisAwaits: SiestaKeyEscape with Pool!

5 out of 5 average rating, 20 reviews

New! Boat Dock + Dolphins + Beaches + Hot tub!

A spacious kitchen with a large marble island offers seating for six. Modern pendant lights hang above, illuminating the sleek cabinetry and stainless steel appliances. A pass-through window enhances connectivity to the outdoor dining area, while a view of landscaped greenery is visible through the window.

5 out of 5 average rating, 24 reviews

Luxury 4/3 Home/Heated Pool/Hot Tub/Arcade Games/

An outdoor space is showcased with a heated pool visible through a screened enclosure. A flat-screen TV is mounted on a wall, overlooking cozy seating and a small table. Potted plants are placed on the white table, complementing the relaxing atmosphere.

5 out of 5 average rating, 15 reviews

House with heated pool, hot tub, golf course

The exterior of a newly renovated home is shown, featuring a light-colored brick facade and a modern garage door. A well-maintained driveway leads to the entrance, which is accentuated by a bright orange door. Landscaping includes gravel beds and low-maintenance plants amidst partial cloud cover.

4.89 out of 5 average rating, 90 reviews

Gorgeous renovation with pool, minutes from beach

Superhost

An inviting outdoor area features a screened patio surrounding a heated pool. Comfortable seating is arranged under the enclosure, with lounge chairs and vibrant accents. Lush greenery is visible in the background, creating a serene atmosphere for relaxation and leisure.

4.9 out of 5 average rating, 10 reviews

Florida Funshine

5 out of 5 average rating, 22 reviews

A spacious living area features large windows that offer views of the outside greenery. Comfortable seating includes a sofa and two chairs, complemented by a dark wood coffee table. A dining area is visible with a round table and four chairs, and a mirror reflects natural light.

Apartment in Sarasota

Beautiful Top Floor Serenata 2Bd/2Ba Apartment