Vacation rentals with a pool in Englewood

Find and book unique homes with a pool on Airbnb

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Popular amenities for Englewood rentals with a pool

House rentals with a pool

Top guest favorite
Home in Englewood
5 out of 5 average rating, 34 reviews

Manasota Tree House - steps from the beach & bay

GiselRating, 5 stars2 months ago
We had a fantastic week at the Manasota Tree House. Jennifer was quick to respond and made everything easy from start to finish. The home is beautifully decorated and felt warm and inviting. The location is perfect. Just a short walk to the beach, and the private pool was a great bonus. We’d definitely love to come back.
Guest favorite
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, 119 reviews

Waterfront Villa Shellflower with private pool

JanelisRating, 5 stars1 week ago
Our stay at this Airbnb was absolutely fantastic! The house itself was beautiful, clean, and perfectly located – we truly felt right at home from the moment we arrived. The house has everything you need. The host was super friendly and super communicative. We would happily stay here again in a heartbeat!
Top guest favorite
An inviting outdoor space features a screened lanai with a private pool. A colorful sunset casts reflections on the water. Comfortable seating areas are positioned nearby, along with a dining space and a small basketball hoop at the poolside.
Home in Englewood
5 out of 5 average rating, 28 reviews

Family Fun-Relaxing Home w/heated Pool & Game Room

Brooke Rating, 5 stars1 week ago
This stay was incredible for my family and I! The air bnb had everything we needed and we loved spending time outside by the pool! Additionally, it was close to many beaches and amazing restaurants! I highly recommend this stay and my family and I hope to return soon!
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, 23 reviews

Beautiful Floridian Oasis

DavidRating, 5 stars1 week ago
Tatyana’s place was amazing! Very very comfortable and very spacious. Pool and outdoor area was awesome! Just the overall layout of the house and how nice it was really made us feel comfortable.
Guest favorite
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, 32 reviews

Intracoastal canal front 3 bd 3 ba w/ heated pool

MattRating, 5 stars2 weeks ago
Beautiful home, Amazing kitchen and bathrooms, well set up pool area with a large covered patio. Dock was in good shape and easily accessible for my 23 ft boat. The host was very responsive. The location is excellent because it’s very close to nearby grocery stores and restaurants. Very comfortable beds and furniture.
Top guest favorite
A screened-in outdoor area features a private swimming pool surrounded by lounge chairs and colorful seating. The pool is accented by a gentle curve, and lush greenery is visible in the background, enhancing the space's serene atmosphere.
Home in Englewood
5 out of 5 average rating, 45 reviews

Private Oasis with Heated Pool *Close to beaches*

GabriellaRating, 5 stars1 month ago
It was such a great experience staying here. Alexis went above and beyond to make our stay perfectly. Personally, I think it’s even nicer than what the pictures show. The house is beautiful. The quotes around the house are incredible. The book that is provided with everything to do in town is amazing. It was very clean and had everything we needed to make our stay perfect. The pool was nice and warm. There were so many pool toys/ floats to pick from. Everything you could possibly imagine for the beach! The list goes on. 10/10. Will absolutely book again when we come back! 😍
Top guest favorite
Home in Englewood
5 out of 5 average rating, 58 reviews

Refreshing Pool•Pool Table•2 King Beds-WIFI-PacMan

YuniaRating, 5 stars1 day ago
⭐️⭐️⭐️⭐️⭐️ We had an amazing stay! The property was exactly as described—clean, comfortable, and beautifully maintained. The location was perfect, and we felt right at home from the moment we arrived. Communication with the host was smooth and thoughtful throughout our stay. We truly appreciated all the little touches that made our trip extra special. Thank you for a wonderful experience—we’d love to come back again!
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, 134 reviews

Cozy & Beautiful Pool Villa in Sarasota County, FL

AnthonyRating, 5 stars5 days ago
I stayed at Vera’s house for a week and had an amazing experience from start to finish. The place was exactly as described—clean, spacious, and well-equipped with everything I needed for a comfortable stay. The neighborhood was peaceful and safe, with easy access to shops and local attractions. The host was incredibly responsive and helpful, making check-in and check-out smooth and stress-free. I especially appreciated the thoughtful touches around the home. Highly recommend this host to anyone looking for a relaxing and hassle-free stay. I’d definitely book again!

Condo rentals with a pool

Superhost
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, 123 reviews

Entire Beachside Condo! Don’t worry Beach Happy!

TaraRating, 5 stars2 weeks ago
We stayed in this lovely place last year and will keep returning! It a perfect location if you love a quiet beach side stay. The renovations are beautiful and Nicholas was very responsive to communication. We couldn't have asked for a more perfect stay!
Guest favorite
The open living area features a light gray sofa with decorative pillows, a coffee table made of white wood, and a television on a console. Natural light floods in, highlighting a cozy atmosphere and the modern kitchen visible in the background.
Condo in Englewood
4.83 out of 5 average rating, 76 reviews

1 bdrm | Steps away to Private Beach w/Dock Access

BrooklynRating, 5 stars6 days ago
Our stay here was great! We had some issues with our AC, and Daniel was quick to send someone out to get it fixed that evening. The location was amazing— we were able to walk across the street to the beach, and on the back side of the building, we were able to fish in the bay. Great stay overall!
Guest favorite
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

MarleneRating, 5 stars9 months ago
This is our second year staying here. It was wonderfully peaceful this last weekend, just like last year. The beach is less than two minutes walk from the door. The kitchen had everything we needed in it. Plenty of beach items for use in the closet. The bathroom had more than enough towels and TP. We also used the pullout couch for our children, and they were very comfortable. we hope to book again soon, thank you!
Superhost
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
4.81 out of 5 average rating, 16 reviews

Spacious 2BR 2BA Beach Condo for Perfect Vacation

MelissaRating, 5 stars1 month ago
Great place looked exactly like the listing, well appointed kitchen! Good location near many amenities. Only thing that would have made it better if there were beach chairs and an umbrella for the beach.
Guest favorite
A heated pool is surrounded by a spacious deck with lounge chairs and a dining area, featuring tropical landscaping. The building's exterior is visible in the background, along with palm trees, creating a relaxing atmosphere.
Condo in Englewood
4.86 out of 5 average rating, 66 reviews

Steps to Water! Beach to Bay, Pool and Dock

JeanaRating, 5 stars1 month ago
We really enjoyed our stay. It was a beautiful area. We found lots of sharp teeth. The condo was amazing. It was clean had so many extras. We couldn't ask for a better place to stay.
Guest favorite
A large heated pool is visible, surrounded by lounge chairs for relaxation. Tall palm trees frame the area, and the building's exterior provides a backdrop. The clear blue water reflects the sunny sky, inviting guests to enjoy a refreshing swim.
Condo in Sarasota
4.86 out of 5 average rating, 149 reviews

Siesta Key Ground Floor Condo 2BR On Trolley Line

AnnRating, 5 stars3 weeks ago
Great stay, the location, the amenities all were wonderful. Melissa and Brandon were super responsive and the place had more essential stocked than most of the other places we have stayed, which was very thoughtful. Melissa also had a regular coffee pot sent out to us right away, since we don’t use Keurig’s which was super nice and very much appreciated. We would definitely come back!
Guest favorite
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, 219 reviews

Near beach. Daily rentals. Pool. king bed

MonicaRating, 5 stars1 week ago
Exactly what we wanted. Great Location, clean and comfortable condo. Super close to the beach.
Top guest favorite
A tranquil community pool is surrounded by palm trees, offering a refreshing space for relaxation. The water reflects the evening sky, while a hammock can be seen nearby, enhancing the inviting atmosphere of the area.
Condo in Englewood
4.95 out of 5 average rating, 44 reviews

Tiki on the Bay

MichaelRating, 5 stars12 months ago
Deedra and her place were great. A relaxing place on the water with a pool, and a host who was responsive and polite. We couldn't have asked for anything more!

Quick stats about vacation rentals with a pool in Englewood

  • Total rentals

    490 properties

  • Total number of reviews

    10K reviews

  • Family-friendly rentals

    410 properties are a good fit for families

  • Pet-friendly rentals

    100 properties allow pets

  • Rentals with dedicated workspaces

    210 properties have a dedicated workspace

  • Wifi availability

    480 properties include access to wifi

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