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!
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 stars1 week 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!!
Guest favourite
Home in The Villages
5 out of 5 average rating, 16 reviews

Heated Pool, Dog Friendly, Golf Cart Included

MichelRating, 5 stars2 months ago
Cosy setting, the bar feature is a nice add on. Pool and hot tub setting really nice especially at night with the hung lighting. Hosts very responsive and helpful.
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!
Guest favourite
Home in Lady Lake
4.89 out of 5 average rating, 45 reviews

The Villages, De La Vista West 1762

BradleyRating, 5 stars2 weeks ago
The house was clean and very nice. The location was perfect and the house had all the amenities for my stay. Great communication by Lee!! Would stay again for sure!!!
Guest favourite
Home in The Villages
4.94 out of 5 average rating, 18 reviews

The Sandpiper Villa

AprilRating, 5 stars2 weeks ago
Sandpiper is a beautiful home away from home. We visited the Villages to attend my father’s 85th Birthday celebration and party. The Sandpiper is beautifully decorated and the coffee station was so convenient and needed for all the family activities leading up to the party. This two bedroom property was spacious for the 6 of us and very convenient to get to the squares like Saltgrass and Brownwood and grocery stores like Publix. And once Eastport opens you’ll be right there in minutes. The manager owners were extremely helpful and responsive to any questions we had. Would highly recommend Sandpiper to anyone visiting the Villages.
Superhost
Home in The Villages
4.74 out of 5 average rating, 23 reviews

Renovated! Between Two Squares with Golf Cart !

MariaRating, 5 stars1 month ago
The house was spotless, everything you need is there available for you to used!! Love the beds and the location excellent for everything we went there for. Great restaurants and a lot of entertainment. Love it!!! I recommend this place 100%. You won’t regret it!! We will be back. Thank you Amanda for everything and for being so available at any time. You made us feel welcome!
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!

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