
Holiday rentals with a pool in Englewood
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Top-rated rentals with a pool in Englewood
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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

South Florida Paradise with Heated Saltwater Pool!
We were in North Port for the week to visit family. There was plenty of space for my husband and me to work remotely without getting in each other's way. Additionally, the living room and the heated saltwater pool were great places for us to relax during downtime. And the neighborhood was very quiet; we heard absolutely nothing at night. Thanks for a wonderful stay!

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.

3bd 2th Solar Heat Pool Large home W/ big yard
Absolutely gorgeous home. It actually felt like home away from home. My teenage boys were very chill and relaxed. I loved the fact that there were two living room areas.. that way my teens could play their gaming system in one and my toddlers could watch tv in the other. My two toddlers are still asking when are we going back to our new home. lol

Family Friendly Pool Home
House was spacious, clean & clutter free. Neighborhood was quiet and pool was clean and has lights for night swimming. WiFi worked great & living room has smart tv you can log into but downside was be aware no TVs in any of the bedrooms. The ice maker didn’t work in the freezer but we may have missed that in the description. I suggest bringing some on the way because stores are not close by. Overall 100% recommend and would stay there again.

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.

Cheerful 3-bedroom home w/heated pool
The place was very clean and neat. There were lots of towels available for the pool. The manager was very responsive to questions during our stay.

Tropical Pool Vacation Getaway!
Beautiful place to stay. Kitchen was well equipped. Only couple complaints (if you call it that)…my husband and I would have liked to see full beds in the bedroom with twin beds, maybe a few bath and kitchen towels, a dresser in the spare bedrooms sure would have been nice to put clothes in or suitcases on, maybe a tv in each bedroom, the garage door opener didn’t work. Sounds spoiled but just what we are used to. Pool was absolutely amazing!! Gas grill worked just great!
Condo rentals with a pool

Siesta Key Condo, Heated Pool, Newly Renovated
Jessica was very helpful and responsive, answered all our inquiries right away. The apartment is well equipped and has everything you need including plenty of towels, and beach equipment. Convenient to restaurants, close to the beautiful beach.

Best Gulf Coast Condo - rarely available
Our stay was wonderful! This is an old Florida gem! The pool area is so quaint and relaxing. The grassy area and fishing dock is great. The beach access is an easy walk and of course fantastic. It's great that the unit comes with all beaching needs (cart, chairs, towels, games, etc.) for us 'fly in' folks. The unit was very clean and updated. Was sad to see the Hurricane devastation but sure this helped limit the busyness. Maureen is a great host and was always readily available for any questions.

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.

Entire Beachside Condo! Don’t worry Beach Happy!
This place is so much better than pictures! The location is perfect, no streets to cross to get to the beach. The condo was brand new inside and beautifully decorated. The amenities were fantastic. Walking distance to yummy food and live music. The pool across the street is great for the kids as well. I would definitely stay here again!

2 Bed/2 Bath Condo Resort View on Siesta Key Beach
Amazing location, close to everything. Wonderful pool, beach and right next to the trolley spot. Didn’t use the tennis or pickleball courts at all but looked popular too! The place itself had everything we needed, plenty of games provided and newer furniture in the bedrooms, would say the grill below was charcoal, so prepare accordingly.

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!

Peaceful retreat, pool, hot tub, near Siesta Key!
Suzanne was very responsive, the residence was clean, spacious and well equipped. Will definitely stay again.

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!
Quick stats about holiday 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
Wi-Fi availability
480 properties include access to Wi-Fi
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- Crescent Beach
- Cortez Beach
- Bean Point Beach
- Lido Key Beach
- Coquina Beach
- Manasota Key Beach
- Myakka River State Park
- Lakewood National Golf Club
- River Strand Golf and Country Club
- Van Wezel Performing Arts Hall
- Boca Beach
- Tarpon Bay Beach
- Englewood Beach
- Manatee Park
- South Jetty Beach
- Tara Golf & Country Club
- Marie Selby Botanical Gardens
- Del Tura Golf & Country Club
- Middle Beach
- Boca Grande Pass
- Bonita Beach Dog Park
- Lovers Key Beach
- Coral Oaks Golf Course
- Gasparilla Island State Park