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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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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, 101 reviews

Coastal Retreat Villa with pool • near beaches

🌴 Escape to your getaway in sunny Englewood, Florida! Whether you're a couple seeking romance, a solo adventurer, a business traveler, or a family with kids, our home is designed for comfort & relaxation. Nestled in a prime location, it's the ideal home base to anyone looking to unwind and explore. Indulge yourself in this executive cozy, built from the ground in 2018 & featuring 3 bedrooms, 2,5-bath house with a Large (seasonally) heated swimming Pool (heating $ included during colder months)

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, 274 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

The outdoor pool area features a clear blue pool with a shallow entry. Surrounding the pool are various seating options, including lounge chairs and a table with chairs, all under a screened enclosure allowing natural light to filter through.

Home in Englewood

4.84 out of 5 average rating, 208 reviews

Manasota Beach Home w/heated pool walk to beach

Custom built large home only 2 blocks to Manasota Beach. Most guests walk and a beach wagon is provided. Located in a quiet neighborhood with easy access to downtown Venice and Englewood. Very large and private lot with beautiful mature palms! The home has tray and soaring vaulted ceilings. The whole home opens up onto the pool area with sliders in every room. The bedrooms are configured in a split style with the very large master suite being totally private. Rare beach home for rent left!

Top guest favorite

A pool area is enclosed by a screened patio, featuring a curvilinear pool with clear water. Lounge chairs and a vibrant red umbrella are positioned beside the water. The home’s large windows offer views of the surrounding outdoor space.

Home in North Port

4.97 out of 5 average rating, 143 reviews

Cozy & Beautiful Pool Villa in Sarasota County, FL

Welcome to our home! It’s our pleasure to host you! Your family & friends will be close to everything when you stay at this centrally-located place: shopping, dining, beaches, entertainment, Warm Mineral Springs, Aquatic Center, etc. This charming house located in a beautiful & quiet neighborhood, tastefully furnished & decorated, fenced for your privacy & perfect for making memories with family & friends. Plenty of amenities to make your stay as comfortable as possible. Great location.

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, 145 reviews

Gulfstream Haven

Welcome to Gulfstream Haven, a 1700 sf 3 bedroom 2 bath pool home conveniently located 8 minutes from Englewood beach with many shops and restaurants nearby. The home features a king size bed in the master bedroom, 2 singles in 1 bedroom and a king size in another. There is a double sleeper sofa in the family room for 2 extra guests. All bedrooms feature walk in closets. The large screened-in lanai has plenty of seating for all occupants, with direct access to the guest bathroom.

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, 102 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, 111 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, 133 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

4.92 out of 5 average rating, 143 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 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, 198 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 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, 126 reviews

Waterfront Villa Shellflower with private pool

Villa Shellflower is located in Rotonda West on a large and quiet property. Right next to the property is the Rontonda River, a wide freshwater canal. The 1564-square-foot house has been furnished with great attention to detail. The large saltwater pool, the southwest-facing sun deck, as well as the cozy dining area provide the perfect holiday feeling. The next dream beach is only 20 minutes away by car.

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, 332 reviews

NEW 4/NTS AUG 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!

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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 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, 22 reviews

A Perfect Escape Near the Beach (Pet friendly)

Top guest favorite

A spacious lanai features a heated pool with a curved shape, surrounded by a screened enclosure. Comfortable seating areas are arranged nearby, providing an inviting space for relaxation. Natural light filters through the enclosure, accentuating the tranquil atmosphere of the outdoor area.

Home in Englewood

4.97 out of 5 average rating, 60 reviews

3 Bedroom Home | Heated Pool | Close to 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, 17 reviews

Coral Cottage

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

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, 28 reviews

Beautiful Floridian Oasis

A tranquil pool area is enclosed by a black screen, offering privacy and protection. The crystal-clear water of the pool reflects the surroundings, with lush greenery visible through the screens. The shallow ledge provides an inviting space for relaxation.

Home in Englewood

4.97 out of 5 average rating, 34 reviews

Villa Sanddollar Awaits ! 1071HS

Top guest favorite

A comfortable living area features light grey leather seating arranged around a circular coffee table. A framed sea-themed artwork hangs on the wall, while a flat-screen TV is mounted nearby. Natural light filters through sheer curtains, creating an inviting ambiance.

Home in Englewood

5 out of 5 average rating, 41 reviews

The Turtle Nest Pool Home

Top guest favorite

An open living area is presented, featuring a light wood ceiling and modern furnishings. A spacious sectional couch faces a wall-mounted TV and electric fireplace. Pendant lighting hangs above a dining table, which is complemented by natural decor elements and greenery.

4.93 out of 5 average rating, 46 reviews

Bali Bliss Villa • Pool • 6 Min Drive to Beach

Condo rentals with a pool

A covered outdoor patio features a rectangular table surrounded by six black chairs. Palm trees and the tranquil waters of Lemon Bay are visible in the background, providing a scenic view. The spacious area is ideal for relaxation and dining.

Condo in Englewood

4.95 out of 5 average rating, 21 reviews

Bay Breeze @ManasotaKeyCondos

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, 131 reviews

Entire Beachside Condo! Don’t worry Beach Happy!

Top guest favorite

A spacious living area is visible, featuring a comfortable armchair and a decorative wooden table. Large glass doors open to a private balcony with ocean views, where tropical plants are visible. Natural light floods the room, highlighting the textured wall art.

Condo in Englewood

5 out of 5 average rating, 7 reviews

Ocean Oasis on Manasota Key - Ocean View

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

Condo in Englewood

4.92 out of 5 average rating, 49 reviews

Vacay on the Beach !

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

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

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!

Other vacation rentals with a pool

The private solar-heated pool features a clear blue surface and is surrounded by a secure fence. Two lounge chairs are positioned along the edge, offering a relaxing spot to enjoy the outdoors. A beach ball floats gently on the water's surface.

Home in Englewood

5 out of 5 average rating, 13 reviews

Pet Friendly Pool Home with Large Private Yard

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 inviting swimming pool is surrounded by a spacious patio area, featuring several lounge chairs and a dining set. The exterior of the home is visible in the background, with large windows allowing natural light to brighten the interior. Lush greenery lines the property, enhancing the tranquil setting.

Home in Englewood

4.95 out of 5 average rating, 38 reviews

Your Coastal Getaway!

A spacious living area is brightened by natural light from sliding glass doors. Comfortable seating includes a sectional sofa adorned with colorful cushions. A decorative area rug adds warmth, while dining space is visible in the background, accompanied by tasteful coastal decor.

Villa in Englewood

4.96 out of 5 average rating, 82 reviews

$+Best Family Vacay+1.6 miles Englewood Beach+Pool

Top guest favorite

A screened-in patio features a serene saltwater pool, bordered by tan pavers. Lounge chairs and a dining table are positioned nearby, with teal and white area rugs adding a splash of color. The pool is framed by large windows, enhancing the open feel of the space.

Home in Englewood

4.98 out of 5 average rating, 64 reviews

5 O'Clock Somewhere - 2/2 - screened heated pool

Home in Englewood

4.92 out of 5 average rating, 84 reviews

Englewood Cottage with Pool, Hot Tub, and Fire Pit

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

The exterior of a two-story home is depicted, featuring a light blue facade with a large archway entrance. Tall palm trees are positioned beside a neatly landscaped yard, while a driveway leads to the entrance. A pair of bicycles is visible, resting against the side of the house.

Home in Englewood

4.95 out of 5 average rating, 37 reviews

Spacious 4 BR Across From Beach w/ 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

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