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Vacation rentals with a pool in Englewood

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Englewood

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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A tranquil pool reflects a colorful sunset with hues of orange and pink in the sky, surrounded by lush greenery. The paved area features decorative stonework, enhancing the serene outdoor setting by the Gulf of Mexico.

Guesthouse in Englewood

4.91 out of 5 average rating, 271 reviews

Gulf front romantic cottage in paradise

Gated and surrounded by lush scenery you will feel like you have suddenly escaped to the caribbean! The pressures of the world melt away as you get your first glimpse of the Gulf of Mexico. Eclectic design with mostly Caribbean influences. Marble floors, tile counter tops and a large shower with a sit down bench. Walk the custom pathways which reveal beautiful orchids and exotic plants. Go kayaking, fish off the beach or look for sharks teeth. Take a swim in the pool or work on your tan.

Top guest favorite

A vibrant outdoor space features a heated pool illuminated with colorful lights. Lounge chairs are arranged near the pool, accompanied by a large umbrella adorned with string lights. Surrounding glass doors offer views into the inviting indoor living areas.

Home in Englewood

5 out of 5 average rating, 16 reviews

Free Heated Pool! Mins from Beach! Private Oasis!

Discover your dream getaway at this stunning 3BR tropical oasis just 5 miles from Englewood Beach! Start your mornings on the screened lanai with coffee, then dive into the heated pool featuring a swim-up bar. Surrounded by lush landscaping, this private escape offers comfort, style, and relaxation. Perfect for families, couples, or friends—close to beaches, golf, dining, and more. Book now and enjoy the ultimate Florida retreat filled with sun, fun, and unforgettable memories!

Top guest favorite

An outdoor pool area is enclosed with a screened lanai, featuring a shaped pool surrounded by neutral-toned flooring. Relaxing lounge chairs are positioned nearby, and colorful pool floats rest on the water's surface, providing a vibrant touch to the tranquil setting.

Home in Englewood

4.99 out of 5 average rating, 99 reviews

Green Bamboo - saltwater pool, great backyard.

Welcome to Green Bamboo, the charming and cozy vacation rental located in the beautiful Englewood, Florida! With its prime location, Green Bamboo is the perfect place to explore all that the area has to offer, from the most amazing beaches in the US to world-class golf courses and spectacular sunsets. Home is situated in a peaceful and gorgeous neighborhood. Just a short drive away (5 miles) you will find beautiful beaches, boat rentals and vibrant shopping and dining options.

Top guest favorite

A private pool area is enclosed with a screen for comfort and protection. Bright blue umbrellas provide shade over several lounge chairs, while rocking chairs are positioned nearby. Sunlight reflects off the water, creating a serene atmosphere amidst green landscaping.

Home in Englewood

5 out of 5 average rating, 109 reviews

*New Listing* ☀️TheAquaOasis🌴Pool-6 miles to beach

Welcome to the Aqua Oasis! This home was built in 2020 and located just 6 miles to multiple beaches in sunny Englewood, FL! The home consists of 3 bedrooms & 2 full baths, an option to heat the outdoor pool, relaxing outdoor chairs around a gas fire pit, fenced in back yard to let your pets roam, and a gas grill to whip up your favorite meals! If your family desires your own, private space and private pool, but you want close proximity to local beaches- THIS IS FOR YOU!

A private saltwater pool is surrounded by a screened lanai, featuring clear water reflecting sunlight. Poolside, a handrail is visible for safety, and tropical landscaping can be seen in the background, enhancing the outdoor recreational space.

Villa in Englewood

4.92 out of 5 average rating, 132 reviews

Unwind at Casa Blu: Sun, fun, pool, close to Beach

Welcome to Casa Blu, your cozy retreat in Florida's sun-kissed paradise. Close to restaurants, parks, and beaches, and Old Englewood. Just 7 miles to Englewood Beach. The stresses of daily life melts away with its single-floor layout, comfy bedrooms with private baths await. Enjoy fast WiFi, Smart TVs, and a fully equipped kitchen. Unwind on the screened lanai or take a dip in the private saltwater pool. Everything's covered, from beach gear to a pack 'n play.

An aerial view captures a spacious outdoor area featuring a heated saltwater pool bordered by lounge chairs and wooden furniture. Lush palm trees and plants surround the patio, while a vibrant yellow house provides a cheerful backdrop.

Home in Englewood

4.91 out of 5 average rating, 140 reviews

Island Home & Casita, Pool, Golf Cart, Beach

Complimentary golf cart INCLUDED. With a short stroll to warm sand and crystal waters of Englewood Beach. With all the the modern comforts in place all you have to do is relax on your short stay or extended visit. Updated 2/2 main house and 1/1 Casita with a private entrance. Walk right out the front door to the new expansive pool patio featuring a saltwater heated pool, outdoor kitchen and plenty of furniture for spending time soaking in the warm Florida sun!

A private pool is enclosed within a screened area, illuminated by natural light. The crystal-clear water is accentuated by the surrounding white pool deck. Lush greenery is visible through the screen, providing a serene backdrop against a partly cloudy sky.

Home in Englewood

4.92 out of 5 average rating, 154 reviews

Coastal Home Away From Home with Pool

Come and relax at the perfect vacation getaway for your family in peaceful Englewood Florida. Only 12 minutes from Gulf beaches. Go out and explore the many amazing beaches, bays, lakes and rivers or lay back, relax and enjoy the beautiful private pool and dining on the lanai from your back door. Fully equipped kitchen for all your cooking needs: coffee maker, blender, and more. Clean, new home that will make you feel cozy and comfortable while on vacation.

A serene outdoor seating area features two adirondack chairs in vibrant orange and blue, positioned beside a small green table. The tranquil lake reflects the soft light of a sunset, surrounded by lush tropical vegetation and a peaceful atmosphere.

Home in Englewood

4.87 out of 5 average rating, 39 reviews

Suite Sun

Welcome to your tropical oasis in Englewood, Florida! Step outside and prepare to be amazed by the stunning outdoor space. The inground pool beckons you to take a refreshing dip on warm Florida days. Imagine sipping your favorite beverage as the sky transforms into a canvas of vibrant colors each evening. For the fishing enthusiasts, a private dock awaits your arrival. Cast your line and enjoy the serenity of the lake, all from the comfort of your backyard.

A sparkling swimming pool features clean, blue water surrounded by a spacious pool deck. The area is enclosed by a white fence, providing a safe environment. Sun loungers are positioned nearby, offering a place to relax under the clear sky.

Condo in Englewood

4.88 out of 5 average rating, 197 reviews

Manasota Key

Direct Ocean Front Unit. Imagine having a glass of wine at sunset overlooking world class views of the Gulf of Mexico. Steps to the beach and unsurpassed views. Excellent restaurants and Tiki Bars within walking distance. This unit is a 1 bedroom 1 bath spacious unit that can comfortably sleep 4. It includes a King bed & Full size sleeper sofa. It also has a beautiful kitchen with granite countertops and tile floors throughout. No Pets.

A spacious green house with a contemporary facade is set against a clear blue sky. Surrounding tropical plants and freshly mulched red pathways create a welcoming first impression. A gravel driveway leads to a screened pool area visible in the background, inviting outdoor enjoyment.

Home in Englewood

4.88 out of 5 average rating, 112 reviews

Luxury Lemon Bay 6 BR villa w/ pool & tennis court

This beautiful house is located at the Lemon Bay and close to the Manasota Beach. The beach is just a 0.6 mile walk or 0.8 drive away. The property offers a 1/2 acre lot. This house offers, with a 34x12 feet swimming pool and own tennis court, a completely new rental experience. You will find the barbecue area outside of the pool area. The charging of EV is not allowed and an extra fee will be charged.

Top guest favorite

A view of the serene ocean is displayed from a balcony, featuring a round table accompanied by four white Adirondack chairs. Lush greenery is visible in the foreground, while a clear blue sky and gentle clouds complement the tranquil water.

Condo in Englewood

5 out of 5 average rating, 16 reviews

Beach Bliss Retreat on Manasota Key - Ocean View

Welcome to our ocean view property, perfect for a relaxing getaway! Enjoy stunning views, walk to restaurants, and indulge in activities like jet skis, kayaking, beach yoga, fishing charters, parasailing, sunset boat trips, and local golf courses. After fun filled day, hang out by the pool with your favorite poolside cocktail! Book now for a serene escape filled with adventure and breathtaking beauty.

A freeform pool is framed by lush tropical landscaping, featuring multiple waterfalls that flow into the water. The elevated home overlooks the pool area, complemented by large windows and a wraparound balcony.

Island in Sarasota

4.97 out of 5 average rating, 330 reviews

NEW 3/NTS JULY OPEN! Sarasota #1 Lux 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!

Vacation rentals for every style

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Popular amenities for Englewood rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

Top guest favorite

A spacious swimming pool is surrounded by a screened-in patio, featuring lounge chairs positioned for relaxation. The area is illuminated with soft lighting, creating a serene atmosphere as twilight descends. Large glass doors connect the pool area to the interior, enhancing the open feel.

5 out of 5 average rating, 10 reviews

Luxury Casa in Venice

Top guest favorite

A refreshing swimming pool is enclosed by a protective screen, allowing for sunlight to illuminate the clear blue water. Two sun loungers are positioned nearby, and lush landscaping is visible in the background, enhancing the serene outdoor space.

Home in Englewood

5 out of 5 average rating, 35 reviews

New house w/pool close to beach & mineral springs

Top guest favorite

A private pool rests within a screened enclosure, surrounded by a paved patio. Colorful lounge chairs are positioned beside the clear blue water, with palm trees and an umbrella visible in the background, creating a serene outdoor space for relaxation.

Home in Englewood

5 out of 5 average rating, 21 reviews

A Perfect Escape Near the Beach (Pet friendly)

Top guest favorite

A screened-in outdoor space features a heated saltwater pool surrounded by lounge chairs. Dining area is visible with a large table set for gatherings. Sunlight reflects off the water, creating a bright atmosphere. A waterway can be seen in the background, enhancing the serene environment.

Home in Rotonda West

5 out of 5 average rating, 7 reviews

Tropical Oasis, pool, pelaton, golf, dog friendly

A private pool area is surrounded by a screened enclosure, featuring a refreshing salt-water pool. Two loungers are positioned for relaxation, with a small table and chairs visible in the background, providing a space for outdoor leisure and enjoyment.

Home in Rotonda West

4.94 out of 5 average rating, 124 reviews

Waterfront Villa Shellflower with private pool

The entryway features a welcoming message on the wall, accompanied by a decorative wreath and a small side table in a vibrant red hue. A patterned area rug lies beneath, adding a touch of comfort to the space, which is illuminated by natural light from the nearby door.

Home in Englewood

4.86 out of 5 average rating, 144 reviews

Gulfstream Haven

Top guest favorite

A modern single-story home is presented with a well-maintained exterior, featuring large windows and a stylish garage door. A sprawling oak tree provides shade, while lush greenery surrounds the entrance. The driveway leads up to the front door, enhancing the welcoming atmosphere.

Home in Englewood

5 out of 5 average rating, 17 reviews

The Windsor @ Englewood Beach

A private pool area is enclosed by a black screen enclosure, providing sunlight while offering a serene view. The pool has a curved shape, with a stone patio surrounding it. Comfortable lounge chairs are positioned nearby, inviting relaxation in a tranquil outdoor space.

Home in Englewood

4.97 out of 5 average rating, 35 reviews

Intracoastal canal front 3 bd 3 ba w/ heated pool

Condo rentals with a pool

An aerial view captures the beachfront property surrounded by palm trees and lush greenery. The ocean is visible in the distance, framed by clear blue skies. A sandy path leads from the building to the beach, emphasizing the proximity to the water.

Condo in Englewood

4.79 out of 5 average rating, 128 reviews

Entire Beachside Condo! Don’t worry Beach Happy!

A spacious community pool is surrounded by a paved deck and overlooks palm tree greenery. The clear blue water reflects a partly cloudy sky, offering a refreshing atmosphere for relaxation. Nearby lounge chairs are arranged along the poolside.

Condo in Venice

4.96 out of 5 average rating, 101 reviews

Vintage Villa, Thirty-Five

An open-concept living area is visible upon entry, showcasing a sleek kitchen and dining space. Neutral tones and modern furnishings complement the atmosphere. A stylish chandelier hangs above the dining table, while a cozy sofa and decorative accents enhance the welcoming environment.

Condo in Englewood

4.82 out of 5 average rating, 17 reviews

Spacious 2BR 2BA Beach Condo for Perfect Vacation

Condo in Englewood

4.92 out of 5 average rating, 48 reviews

Vacay on the Beach !

An inviting pool area features a clear blue swimming pool surrounded by a spacious deck. Light-colored lounge chairs are positioned nearby, with palm trees visible in the background. A building with a vibrant entrance stands to the right, with additional parking and greenery enhancing the setting.

Condo in Venice

4.93 out of 5 average rating, 54 reviews

Beachfront Venice Villas 1-bed Condo

An aerial view captures the expansive coastline of Manasota Key, showcasing a stretch of sandy beach adjacent to turquoise waters. Green vegetation and residential areas are visible, with boats navigating the nearby waterways, illustrating the serene landscape of this coastal destination.

Condo in Englewood

4.77 out of 5 average rating, 74 reviews

Gulf side condo be on the beach in minutes!

Top guest favorite

A spacious pool area is surrounded by palm trees and tropical plants. Sun loungers are arranged around the pool, inviting relaxation. A shaded gazebo is visible in the background, providing a refreshing retreat. The clear blue sky enhances the bright atmosphere.

Condo in Venice

5 out of 5 average rating, 34 reviews

La Bella Vita!

A heated swimming pool is centrally located, surrounded by colorful lounge chairs in red, yellow, and green. The turquoise water is inviting under clear blue skies, with palm trees bordering the area. Nearby, several outdoor chairs are positioned for relaxation.

Condo in Sarasota

4.91 out of 5 average rating, 225 reviews

Near beach. Daily rentals. Pool. king bed

Other vacation rentals with a pool

Top guest favorite

An enclosed pool area is presented, featuring a sparkling blue pool surrounded by a spacious deck. Two lounge chairs are positioned for relaxation. Large sliding doors allow natural light to fill the adjacent living area, enhancing the open layout.

Home in Englewood

4.98 out of 5 average rating, 47 reviews

Cozy 3BR Gulf Coast house with heated pool

A resort-style backyard features a sparkling pool surrounded by lounge chairs. Each chair is equipped with a towel and a small side table. Lush greenery provides a tropical backdrop, enhancing the inviting outdoor space. The clear blue sky complements the tranquil atmosphere.

Home in Englewood

5 out of 5 average rating, 16 reviews

Luxurious Resort Pool & Spa home

A single-story house with a red tiled roof is shown among lush greenery. Light blue shutters adorn the windows, and a small bench sits on a gravel pathway, with tall trees in the background providing shade.

Bungalow in Englewood

4.9 out of 5 average rating, 10 reviews

1mi to Beach. Jungle Home 1+ acre with Pool

Top guest favorite

A spacious screened lanai features a heated swimming pool with clear blue water. Lounge chairs are positioned around the pool area, providing ample space for relaxation. The surrounding pavers and greenery contribute to a serene outdoor atmosphere.

Villa in Englewood

4.98 out of 5 average rating, 100 reviews

Coastal Retreat Villa with pool • near beaches

Top guest favorite

A private, screened patio houses a heated saltwater pool with clear, inviting water. Surrounding greenery includes lush palms and a spacious lawn. A lounge chair and a blue pool float are visible, creating a relaxing environment for outdoor enjoyment.

Home in Englewood

5 out of 5 average rating, 16 reviews

Coral Cottage

A bright living area features a spacious sofa adorned with colorful cushions, a central coffee table, and a vibrant area rug. Natural light fills the space, highlighting the open floor plan that connects to the dining area and kitchen. Decorative beach-themed artwork enhances the atmosphere.

Villa in Englewood

4.96 out of 5 average rating, 82 reviews

Family Fun+6 mins Manasota Beach+Pool+Game Room

Top guest favorite

The front of the home is framed by several palm trees and succulent plants, providing a tropical ambiance. A well-maintained lawn is visible, leading up to the entrance, which features a modern design with large windows and a covered porch.

Home in Rotonda West

5 out of 5 average rating, 27 reviews

Beautiful Floridian Oasis

Top guest favorite

The entrance of the home is framed by neatly trimmed shrubs and flowering plants, leading to a bright foyer. Visible through the open doorway is a spacious living area and the inviting pool area, creating an appealing connection between indoors and outdoors.

Home in Englewood

4.95 out of 5 average rating, 44 reviews

Amazing! Close to Beaches - Heated Pool

Quick stats about vacation rentals with a pool in Englewood

Total rentals
500 properties
Total number of reviews
11K reviews
Family-friendly rentals
420 properties are a good fit for families
Pet-friendly rentals
120 properties allow pets
Rentals with dedicated workspaces
230 properties have a dedicated workspace
Wifi availability
500 properties include access to wifi

Destinations to explore