Holiday rentals with a pool in The Villages

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Popular amenities for The Villages rentals with a pool

House rentals with a pool

Top guest favourite
Home in The Villages
5 out of 5 average rating, 21 reviews

The Palms. Luxurious, pool, golf/bird pond view

NikiRating, 5 stars2 days ago
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.
Guest favourite
Home in The Villages
4.78 out of 5 average rating, 87 reviews

Carlton Courtyard Villa - Walk to Sumter Landing

RenelleRating, 5 stars3 weeks ago
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.
Guest favourite
Home in The Villages
4.83 out of 5 average rating, 6 reviews

The Villages with a View

JeffreyRating, 5 stars1 week ago
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.
Guest favourite
Home in Wildwood
4.92 out of 5 average rating, 77 reviews

New, private pool getaway in The Villages, FL

TrinaRating, 5 stars1 month ago
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
Guest favourite
Home in The Villages
4.94 out of 5 average rating, 33 reviews

The Sunshine Retreat with Golf Car

BethRating, 5 stars1 week ago
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!
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!
Superhost
Home in The Villages
4.77 out of 5 average rating, 109 reviews

The Brownwood Brassie 3BR 2 Bath w/ Golf Cart

SamRating, 5 stars1 month ago
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 !
Top guest favourite
Home in The Villages
4.96 out of 5 average rating, 26 reviews

New beautiful 3x2 listing in The Villages!

MonicaRating, 5 stars1 week ago
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

Apartment in Dunnellon

EarlyTimes on the Withlacoochee!

JustinRating, 5 stars23 months ago
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..
Top guest favourite
Apartment in Inverness
5 out of 5 average rating, 39 reviews

Gray Heron Victorian Townhouse

JoanneRating, 5 stars2 weeks ago
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.
Apartment in Dunnellon

Riverside Retreat

RobertRating, 5 stars16 months ago
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.
Apartment in Hernando

Heated Pool: Citrus Hills Condo Near Golfing!

DonRating, 5 stars5 months ago
Proactive host who communicated clearly. Quiet peaceful surroundings with easy pool access. Nicely decorated with comfortable furniture. Couldn't ask for anything more.
Apartment in Clermont
4.67 out of 5 average rating, 24 reviews

20 Mi to Disney: Condo w/ Pool Access in Clermont!

ElizabethRating, 5 stars3 months ago
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!
Apartment in Dunnellon
4.75 out of 5 average rating, 12 reviews

River Retreat

MelissaRating, 5 stars3 months ago
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!
Apartment in Dunnellon
5 out of 5 average rating, 5 reviews

The River Studio Condo w/pool, hot tub & boat slip

LisaRating, 5 stars11 months ago
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.
Guest favourite
Apartment in Inverness
4.87 out of 5 average rating, 60 reviews

Cypress Cove Waterfront Townhome

JasonRating, 5 stars1 month ago
Very clean place. easy to find. The host was super easy to work with and communicate with. We will def be back

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

Destinations to explore