
Vacation rentals with a pool in Englewood
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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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Popular amenities for Englewood rentals with a pool
House rentals with a pool

Charming Saltwater Heated Pool House (North Port)
Very beautiful place to stay at with lots of room inside and out.. pool and hot were both excellent very clean and well stocked home with a washer and dryer… host was very easy to text for anything we needed…. Thank you for letting us use your home to stay in.. we had a wonderful time thank you

New 4-bedroom house with saltwater pool and spa!
This is a beautiful, clean, well decorated home in a safe private neighborhood. The kitchen was well stocked and very spacious with lots of storage space. The patio was private with a beautiful pool that was well heated for this time of year. The beds were very comfortable. We felt right at home.

Serene 3BR family retreat | Firepit & POOL
We had a wonderful stay for our family of six. The space was spotless, cozy, and had everything we needed for a relaxing getaway. The washer and dryer (detergent provided!) were super convenient, and the dishwasher made cleanup a breeze. They also thoughtfully provided coffee, sugar, and other essentials. On top of that, the pool was fantastic—perfect for relaxing after a day out. Plus, there were beach chairs and even beach toys available, making our beach trips so much easier and more enjoyable. Everything was just perfect for our needs, and we couldn't have asked for a better experience. Location was indeed serene and safe and not too far from Siesta Beach. We looked forward to coming back to a quiet place after hanging out at Siesta Key Village. Highly recommend, these Guest Favorites have yet to disappoint! Will definitely rebook when in Sarasota in the future.

3bd 2th Solar Heat Pool Large home W/ big yard
We really enjoy the place we have a woderful hoster

Lovely pool house 5 minutes from the beach
Had a lovely stay here. Communication with Carmen was fantastic. Decorating in home was tasteful and lovely and we felt right at home.

Spacious 4BR Getaway – Perfect for Families!
This was such an amazing place! Maksim and Lilia were outstanding hosts and super responsive!!! The house itself was gorgeous and in such a great location. We had access to so many wonderful beaches and attractions. It was truly a home away from home and we were sad to leave. It had everything you could ask for and was very comfortable and relaxing. Probably the best experience we’ve had using Airbnb!

Tropical Pool Vacation Getaway!
Beautiful home, lots of thought out amenities for staying in the area.

Entire Home. 2/bd & 2/bath with Pool.
Very relaxing accommodation. Neat and clean. Especially enjoyed the lanai and pool. Deanna was very responsive to any concerns.
Condo rentals with a pool

Siesta Key Condo, Heated Pool, Newly Renovated
It was a lovely place with so many amenities that made you feel at home! Comfortable beds, nice appliances, great shower pressure, ceiling fans in every room. Lots of towels. The only thing we missed was a lanai but we were A-ok without it!

Condo With Heated Pool, Beaches Only Minutes Away
We were pleasantly surprised by Nicole’s apartment. It was extremely clean, lots of towels, linen, well appointed kitchen and everything else needed to make it like home. We didn’t need to buy or bring anything for the beach because we had beach chairs and an umbrella which were in really great shape. The apartment is within a short driving distance to beaches, stores, restaurants and shop. We had a great time and felt right at home. We highly recommend her place to anyone vacationing in the area.

Lovely 2 bedroom condo with pool & tennis courts
This condo was even cuter in person than it was in the photos. It was super clean, safe, spacious, had a gorgeous screened in balcony that looked out over the pool, and was centrally located really close to groceries, restaurants, multiple beaches, and more. We stayed here as a family of 4 and the kids had their own room and bathroom and we had a master with en suite. I saw another review that said there is a little noise from the busy road outside but you really only notice it if you're trying to sleep with the windows open. We originally booked a hotel that ended up being awful so I found this place last minute and they were able to get us in the very next morning. They let us check in early since we were kind of stranded, and walking in was like a breath of fresh air. Highly recommend this place for 2-4 people!

Siesta Key Oasis with Gulf Views
This was our second time staying here. Love the location. Love the area. Thanks again for a wonderful stay. See you next year!

Siesta Village Short Walk to Beach w heated Pool
This place was fantastic with everything we needed. It was close to everything and a short drive to some of the other local activities. Short walk to multiple beach entrances and a cart, chairs, umbrella, etc. was all available to take to the beach. There’s a local shuttle that takes you all over the island for free and a market around the corner that’s fully stocked with everything you need to cook some meals there. We did the night time LED kayaking and then did the Mangrove Eco Tour with Kayaking SRQ, ask for Kaleb for the mangrove tour, the man knew everything about the area, its history, conservation, and gave some great restaurant and attraction recommendations in the area. Or… just hang out at the beach. We were there during tropical storm Debby and Kathryne communicated with us throughout. Absolute amazing stay… even with a tropical storm! We can’t wait to come back.

Peaceful retreat, pool, hot tub, near Siesta Key!
My husband, daughter , and I rented Suzanne’s place for a 4 night , birthday getaway. The place has self check in and was easy to access with a code. The condo was absolutely spotless and a lot bigger than I imagined. The decor was lovely and definitely had a home feel . Tastefully decorated. The surrounding area is also beautiful and very, very peaceful. We’ve been to Sarasota before, and Suzanne‘s place is just a little bit further away from Siesta Key beach than what we’re used to but close enough that it was not a problem at all. The beds were comfortable. Check out instructions were clear and written down. I would definitely go back. Our stay was great!

Cozy Condo With Heated Pool
Perfect stay for my family! It had everything we needed and more. The beach chairs, mats & cooler made our beach days more enjoyable. Washer and dryer worked great and kitchen had everything we needed. We didn’t have time to use the paddleboard but it’s an awesome bonus. We would definitely stay again!

Top Floor Beautiful View Condo-Shore To Please
This is the perfect vacation rental! The condo is spacious and very well maintained. Has lots of amenities to offer. The location could not be more ideal… walking distance to Siesta Key beach ( right across the street). Has a stop in front of the building for Siesta Key trolley that takes you to Siesta Village. Kathy is a fantastic host. Very accommodating and replies quickly. We could not have asked for a better place to stay and looking forward to going back!
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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- Anna Maria Island
- Siesta Beach
- Captiva Island
- Anna Maria Public Beach
- Crescent Beach
- Turtle Beach
- Caspersen Beach
- Bean Point Beach
- Cortez Beach
- Lido Key Beach
- Coquina Beach
- Manasota Key Beach
- River Strand Golf and Country Club
- Myakka River State Park
- Lovers Key Beach
- Tara Golf & Country Club
- Lakewood National Golf Club
- South Jetty Beach
- Van Wezel Performing Arts Hall
- Englewood Beach
- Tarpon Bay Beach
- Boca Beach
- North Jetty Beach
- Del Tura Golf & Country Club