Vacation rentals with a pool in Englewood

Find and book unique homes with a pool on Airbnb

When results are available, navigate with up and down arrow keys or explore by touch or swipe gestures.
0 of 0 items showing
1 of 3 pages

Popular amenities for Englewood rentals with a pool

House rentals with a pool

Guest favorite
Home in North Port
5 out of 5 average rating, 14 reviews

3bd 2th Solar Heat Pool Large home W/ big yard

ThomasRating, 5 stars1 week ago
Justin was very responsive to any questions or concerns we had. Setting was private and spacious. Plenty of yard for our dog to roam.
Superhost
Home in Sarasota
4.93 out of 5 average rating, 135 reviews

Centrally located oasis.

JacobRating, 5 stars8 months ago
The place was mostly what it said it would be, the pictures are accurate. Was pretty nice and cozy. Had lots of privacy, which was really nice. House was clean and had all of the amenities that were promised. Bed was really comfortable. The only drawback was that the pool was a little dirty, looked like it hadn’t been cleaned for a few days before we got there but it wasn’t that big of a deal.
Guest favorite
Home in Sarasota
4.97 out of 5 average rating, 77 reviews

Spacious 4BR Getaway – Perfect for Families!

JoelRating, 5 stars3 weeks ago
We stay at a lot of Airbnb's and found this one to be particularly easy and satisfying. The place was exactly as described in the listing. One nice thing is it was better-stocked than many, with things like coffee, basic seasonings and other non-perishable items were there. Lots of extra towels/pillows/blankets, shower soap, dishwasher soap, washing machine soap - stuff like that was all ready to go.
Top guest favorite
Home in Siesta Key
5 out of 5 average rating, 27 reviews

Beautiful House with Heated pool

SarahRating, 5 stars5 months ago
Our girls trip weekend was a huge success!! We all had a wonderful stay here and we didn’t have a single complaint. Check in was super easy and went off without a hitch. The house is exactly as pictured, very open and comfortable. We did not have a single issue while staying! Highly recommend staying here, I promise we will be back!
Superhost
Home in North Port
4.85 out of 5 average rating, 39 reviews

Tropical Pool Vacation Getaway!

BradleyRating, 5 stars1 week ago
We absolutely loved the home. It was super clean and just as advertised. Our little boy loved the heated pool. It was perfect. The neighborhood is quiet and convenient to lots of restaurants. Beds are comfortable. I would not hesitate to stay here again.
Top guest favorite
Home in Cape Coral
4.93 out of 5 average rating, 45 reviews

Spacious Canal Oasis With Private Pool & BBQ Area

BrookeRating, 5 stars3 weeks ago
We had a great mini vacation with our dogs enjoying the water and pool/spa. The place was very spacious and close to everything we wanted to do. Phong was very responsive and helpful throughout our stay. We would definitely come back.
Top guest favorite
Home in Fort Myers
4.98 out of 5 average rating, 116 reviews

The Parsonage-Private Villa-Heated Pool & Spa.

CarneshaRating, 5 stars6 months ago
Michelle's place was a great place to stay while our team was in town for work. Michelle was always responsive and accommodating. If available, we will most certainly stay again in the weeks to come.
Guest favorite
Home in Sarasota
4.92 out of 5 average rating, 26 reviews

Beautiful, Spacious Heated Pool Home

JayRating, 5 stars4 days ago
The photos didn't do the place justice. Very beautiful, well kept and quiet. Pool had lots of inflatables etc., very clean and great for the whole family. Great furnishings, lots of towels/linens and fully functional appliances. Flexible with check-in, very responsive and helpful. Thank you Alice for all you do!

Condo rentals with a pool

Superhost
Condo in Englewood
4.87 out of 5 average rating, 45 reviews

Condo With Heated Pool, Beaches Only Minutes Away

KarenRating, 5 stars8 months ago
I thoroughly enjoyed the ARBNB . It was very clean and I felt like I was right at home . The kitchen was well stocked and the appliances worked perfectly . I loved the washer and dryer! It was close to restaurants and beaches . The location was quiet and close to beaches . Would highly recommend property to anyone traveling. Plus the pool was clean and close to unit !
Superhost
Condo in Osprey
4.89 out of 5 average rating, 9 reviews

Lovely 2 bedroom condo with pool & tennis courts

MarlynRating, 5 stars12 months ago
This is our second year staying in this complex. There are many walking trails that are a short drive, close to several beaches, restaurants and grocery stores.
Superhost
Condo in Siesta Key
5 out of 5 average rating, 3 reviews

Our House at the Beach Luxury Condo

DenieseRating, 5 stars10 months ago
This is the perfect location- balcony overlooks over Siesta Beach, trolley pick up right in front of building and walkable to the village. The simplicity of check in to check out! This was our first trip to Siesta Keys. Every location is easy to get to and close to all the other Gulf Beaches. We didn’t need to contact the host for anything because it was all there and exactly as described. Another perfect vacation in the books and we will be back!
Guest favorite
Condo in Siesta Key
4.87 out of 5 average rating, 101 reviews

Siesta Village Short Walk to Beach w heated Pool

CoryRating, 5 stars7 months ago
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.
Superhost
Condo in Siesta Key
4.87 out of 5 average rating, 87 reviews

Lovely Top Floor Condo with Sunset Views

TishaRating, 5 stars8 months ago
We had a wonderful time during our vacation here as we were also visiting with family.. The rental was cozy and had all accommodations we needed. Beautiful area and grounds. Only issue was the elevator on the unit’s side acted up while there mid week. Another elevator was accessible on the other side to use. Would definitely return.
Guest favorite
Condo in Sarasota
4.97 out of 5 average rating, 61 reviews

Peaceful retreat, pool, hot tub, near Siesta Key!

JulieRating, 5 stars2 months ago
Great place to stay! It was a very safe community with nice extras and was pretty close to the beaches. So nice to have the extra beach supplies to go shark tooth hunting at Caspersen Beach. The condo was clean and spacious.
Guest favorite
Condo in Siesta Key
4.94 out of 5 average rating, 100 reviews

Siesta Key Beach Front Condo

AnneRating, 5 stars3 weeks ago
We loved our stay! Ideal location across from siesta key beach and one mile walk or free trolley ride into town with lots of restaurants, shops and a gourmet supermarket. The condo was clean, comfortable and well stocked and Evan was very responsive to any questions we had.
Superhost
Condo in Englewood
4.8 out of 5 average rating, 44 reviews

Cozy Condo With Heated Pool

JamesRating, 5 stars7 months ago
We loved our stay. Less than 10 minutes from the beach. The kids found all kinds of shells and sharks teeth. Lots of restaurants close to the property. Kids loved the pool on property. We have 6 in our family and and had plant of room for everybody. We would definitely stay at the property again.

Quick stats about vacation rentals with a pool in Englewood

  • Total rentals

    390 properties

  • Nightly prices starting at

    $70 before taxes and fees

  • Total number of reviews

    8.8K reviews

  • Family-friendly rentals

    320 properties are a good fit for families

  • Pet-friendly rentals

    70 properties allow pets

  • Rentals with dedicated workspaces

    150 properties have a dedicated workspace

Destinations to explore