
Holiday rentals with a pool in The Villages
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in The Villages
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.
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Popular amenities for The Villages rentals with a pool
House rentals with a pool

The Palms. Luxurious, pool, golf/bird pond view
We rented John’s place for a girls’ weekend and to celebrate with a friend who lives in the area. The home is just we described, very clean, and perfect for our stay. The pool was amazing, extremely peaceful and allowed us to have a much needed relaxing weekend.

Carlton Courtyard Villa - Walk to Sumter Landing
Randy and his wife were always really responsive to any questions we had. They gave advice as to great places to eat and things to do around the area.

The Villages with a View
We came down to The Villages looking for a retirement home. The house was everything we wanted and needed for our stay. They thought of everything… Just bring your bags, everything else is here. GREAT LOCATION, CONVENIENT TO EVERYTHING !!! Jeffrey & Becky K.

New, private pool getaway in The Villages, FL
The pictures didn’t do the house justice. The house was more beautiful than the pictures. The home was absolutely stunning. It’s well stocked with supplies. My biggest fear is going into a home that’s not clean. This house was spotless. Thank you for a wonderful weekend away from home. I loved the pool very clean, I usually don’t get in the pool at Airbnbs because it’s not clean enough for me. Thank you again for everything Trina

The Sunshine Retreat with Golf Car
We had a wonderful stay at this great place in a fantastic location within The Villages. It was very comfortable and offered everything we needed for a relaxing getaway. The value was excellent for our family, and we truly enjoyed the local pools, restaurants, and the wide variety of activities available nearby. Highly recommend for anyone looking for a fun and easy stay in The Villages!

Charming Villages Retreat
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!

The Brownwood Brassie 3BR 2 Bath w/ Golf Cart
The home was beautiful ! The golf cart to travel was a great bonus. John was very helpful throughout the booking process even offering dining recommendations once my wife and I arrived. We cannot wait to come back and visit again !

New beautiful 3x2 listing in The Villages!
Deseree was an awesome host. She provided everything one needs when vacationing away from their own home plus many extras. Very quiet neighborhood with quick access to all activities. Her place was extremely clean which was a huge plus. Her response to any questions that I had were quickly answered and offered help if I didn’t get the answers needed. I will definitely stay here again if I’m in the area. I recommend this rental very highly.
Apartment rentals with a pool

EarlyTimes on the Withlacoochee!
We love the area, we stay in the area every year around the same time and Melissa’s place was not disappointing. The pool was clean, the condo was amazingly comfortable. We had 2 grandkids with us this trip so the pullout sofa bed worked well for them. There were plenty of cooking utensils, pots and pans, and plates and bowls for the days we decided to eat in. Beautiful water front views. Lots of wild life to watch also. Would highly recommend this condo if staying in the area..

Gray Heron Victorian Townhouse
This was the first time I stayed at Geri's place and it was wonderful. Even though I was staying in a condo, the entire complex was very quiet and peaceful. Geri was very responsive and I will definitely consider staying here again when I am back in the area.

Riverside Retreat
Had a great time at the condo. We felt right at home and enjoyed meeting new friends during the unofficial "happy hour". There is no shortage of things to do in the area and this was a great place to stay while visiting our daughter. We will stay here again. The only disappointing thing was that the pool temperature was very cold, but this was not any fault of the hosts themselves, the weather was unusually cold for FL during our stay. We still were able to use the pool during our stay.

Heated Pool: Citrus Hills Condo Near Golfing!
Proactive host who communicated clearly. Quiet peaceful surroundings with easy pool access. Nicely decorated with comfortable furniture. Couldn't ask for anything more.

20 Mi to Disney: Condo w/ Pool Access in Clermont!
This property was clean, spacious, and in a convenient location. The neighborhood was quiet and peaceful. The instructions for check in were very clear and the host was friendly and responsive. We are a family of 5 and it was just right for us. We would stay again. Thank you!

River Retreat
I had a great stay! It was exactly as advertised and I hope to stay here the next time I’m in town. The location was perfect. Within walking distance to many shops and just a short mile to the grocery store and Walmart. Tons of locally owned places for food along with chain places. My favorite thing was being so close to Rainbow Springs State Park. I went hiking a few days and it was amazing. Perfect trip!

The River Studio Condo w/pool, hot tub & boat slip
This little place was perfect for what we were after. We wanted to be right on the water and have the ability to have a slip for our JetSki.

Cypress Cove Waterfront Townhome
Very clean place. easy to find. The host was super easy to work with and communicate with. We will def be back
Home rentals with a private pool

North Timucuan Trail Villa 1208
Fantastic stay, great space , great value . Good communication, everything exactly as advertised in the listing . Would def stay here again .

Spacious Pool Home, Family & Golf Trips-4727
Everything was great - check in was easy, customer service was perfect, prompt response to everything! The house was amazing! More comfortable couches would have been nice - but just a personal preference as I had leather but nice and easy to clean so I can understand that for a rental.

Family Villa Bettina - Recently Remodeled
Very clean, well appointed space. The pool is great.

Four Bedroom Comfort Villa 4668
Very nice place and location was great. Pool was really cold but for this time of year it is to be suspected

Designer Pet-Friendly Retreat with Heated Pool
Quick stats about holiday rentals with a pool in The Villages
Total rentals
300 properties
Nightly prices starting at
₹3,426 before taxes and fees
Total number of reviews
6.7K reviews
Family-friendly rentals
270 properties are a good fit for families
Pet-friendly rentals
100 properties allow pets
Rentals with dedicated workspaces
170 properties have a dedicated workspace
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- Universal Studios Florida
- Orange County Convention Center
- Weeki Wachee Springs
- Universal's Volcano Bay
- Discovery Cove
- Disney's Animal Kingdom Theme Park
- SeaWorld Orlando
- Universal Orlando Resort
- Disney Springs
- ESPN Wide World of Sports
- Amway Center
- Epcot
- Magic Kingdom Park
- Rainbow Springs State Park
- Aquatica
- Disney's Hollywood Studios
- Universal's Islands of Adventure
- Island H2O Water Park
- Walt Disney World Resort Golf
- Blue Spring State Park
- ICON Park
- Universal CityWalk
- Fun Spot America
- Plantation Inn and Golf Resort