
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.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Englewood rentals with a pool
House rentals with a pool

Manasota Tree House - steps from the beach & bay
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.

Waterfront Villa Shellflower with private pool
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!

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

Beautiful Floridian Oasis
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.

Intracoastal canal front 3 bd 3 ba w/ heated pool
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.

Private Oasis with Heated Pool *Close to beaches*
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! 😍

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

Cozy & Beautiful Pool Villa in Sarasota County, FL
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

Entire Beachside Condo! Don’t worry Beach Happy!
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!

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

Vintage Villa, Thirty-Five
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!

Spacious 2BR 2BA Beach Condo for Perfect Vacation
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.

Steps to Water! Beach to Bay, Pool and Dock
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.

Siesta Key Ground Floor Condo 2BR On Trolley Line
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!

Near beach. Daily rentals. Pool. king bed
Exactly what we wanted. Great Location, clean and comfortable condo. Super close to the beach.

Tiki on the Bay
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
Destinations to explore
- Tampa Bay Vacation rentals
- St Petersburg Vacation rentals
- Seminole Vacation rentals
- Tampa Vacation rentals
- Central Florida Vacation rentals
- Four Corners Vacation rentals
- Kissimmee Vacation rentals
- Orlando Vacation rentals
- Fort Lauderdale Vacation rentals
- Gold Coast Vacation rentals
- Miami Vacation rentals
- Miami Beach Vacation rentals
- Apartment rentals Englewood
- House rentals Englewood
- Rentals with a kayak Englewood
- Beachfront rentals Englewood
- Kid-friendly rentals Englewood
- Rentals with beach access Englewood
- Rentals with a washer and dryer Englewood
- Rentals with lake access Englewood
- Fitness-friendly rentals Englewood
- Rentals with a fireplace Englewood
- Rentals with a patio Englewood
- Rentals with outdoor seating Englewood
- Pet-friendly rentals Englewood
- Bungalow rentals Englewood
- Villa rentals Englewood
- Beach house rentals Englewood
- Family-friendly rentals Englewood
- Cottage rentals Englewood
- Rentals with a fire pit Englewood
- Waterfront rentals Englewood
- Beach condo rentals Englewood
- Condo rentals Englewood
- Rentals with a hot tub Englewood
- Rentals with pools Sarasota County
- Rentals with pools Florida
- Rentals with pools United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Anna Maria Island
- Siesta Beach
- Captiva Island
- Anna Maria Public Beach
- Crescent Beach
- Turtle Beach
- Caspersen Beach
- Bean Point Beach
- Lido Key Beach
- Cortez Beach
- Coquina Beach
- Manasota Key Beach
- Lovers Key Beach
- Myakka River State Park
- River Strand Golf and Country Club
- South Jetty Beach
- North Jetty Beach
- Marie Selby Botanical Gardens
- Englewood Beach
- Lakewood National Golf Club
- Tara Golf & Country Club
- Gasparilla Island State Park
- Stump Pass Beach State Park
- Boca Grande Pass