Holiday rentals with a pool in Sumter County

Find and book unique homes with a pool on Airbnb

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Popular amenities for Sumter County rentals with a pool

House rentals with a pool

Top Guest favourite
Home in The Villages
4.96 out of 5 average rating, 55 reviews

Beautiful Villages 2/2 Home. Perfect Location

ScottRating, 5 stars2 weeks ago
Thanks we are frequent visitors and stay was amazing! Would recommend!
Guest favourite
Home in The Villages
4.85 out of 5 average rating, 34 reviews

Beautiful Designer Home in The Villages Fl

AdamRating, 5 stars6 months ago
James was a fantastic host that went above and beyond when communicating. He even let us borrow a set of golf clubs to use. House was clean and conveniently located.
Top Guest favourite
Home in The Villages
4.97 out of 5 average rating, 32 reviews

Haven Escape at the Village of Richmond

LaurenRating, 5 stars5 days ago
Our stay was absolutely amazing. The house is very comfy and close to many shops and restaurants. The location was perfect for where we wanted to be in reference to family. Besides the host being the nicest person ever; the communication regarding any questions I had was super quick and easy. I would recommend this place 1000x over and I will be staying here again next time I am in town!!
Top Guest favourite
Home in The Villages
4.96 out of 5 average rating, 73 reviews

Close to Everything- Live Music, Dining & More!

AndrewRating, 5 stars2 months ago
Very nice and comfortable accommodations. Excellent location near Sumter Landing. The Terra Del Sol pool was fantastic. We enjoyed the lanai in the evenings and had a nice evening cooking on the grill. We would definitely come back.
Top Guest favourite
Home in The Villages
5 out of 5 average rating, 15 reviews

Vacation home in The Villages

RyanRating, 5 stars1 month ago
Marty was very responsive and accommodating! My entire family enjoyed our stay and the house was perfect for everyone's needs! Would definitely recommend for anyone looking to visit The Villages!
Top Guest favourite
Home in Wildwood
4.93 out of 5 average rating, 14 reviews

The Villages - Sunshine and pickleball

CandiRating, 5 stars2 weeks ago
This home was beautiful, pristine, and equipped with anything someone might need during their stay. The area was quiet and peaceful. Lori was very hospitable and friendly. She responded quickly to any questions or requests. Our family enjoyed our stay very much. I would definitely recommend this home to anyone visiting the area!
Top Guest favourite
Home in The Villages
4.98 out of 5 average rating, 42 reviews

Cheerful home , tastefully updated, extra den

KatieRating, 5 stars1 month ago
We had a wonderful 5-night stay! Trina’s home was beautifully furnished + well equipped: solid, quality furniture; soft blankets for cozy comfort; plentiful towels for shower, kitchen and pool; fabulous closet/storage space; bountiful plates, bowls, cups, glasses, cutlery; clean, easily accessible washer and dryer; and a generous stock of toiletries (dishwasher and laundry detergent pods, hand soap, shampoo, conditioner, body wash). Location was fantastic — just steps from a family pool + a short golf cart ride to Lake Sumter for morning coffee, dinner, or ice cream + a stroll on the dock. Extra kudos for connecting us with David’s Villages Golf Cart Rental upon reservation. Our rented golf cart was waiting for us in the garage when we arrived + was picked up the morning of our departure — white glove service that allowed us to focus on our vacation. Trina was very friendly and quick to respond with any questions we had. We highly recommend + would love to return!
Guest favourite
Home in The Villages
4.89 out of 5 average rating, 9 reviews

Charming Villages Retreat

BarbaraRating, 5 stars1 month ago
This Villa is beautifully decorated and you feel right at home. It was absolutely spotless too! The screened Lanai is so comfortable with paddle fans and coverage for any weather. We loved using the golf cart, this was one of the best we have used with extra features most don't have. The location of this Villa is perfect as it is easy to get to Lake Sumter or Spanish Springs. Matt was very responsive to any question I had, check in was flexible and he even left us some delicious homemade cookies! What a thoughtful gesture! Don't hesitate to book this home, you will not be sorry. We can't wait to return!

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