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

KingBed w/Cart
Wonderful stay, conveniently located between Spanish Springs and Lake Sumter Town Centers. Loved having the golf cart for easy transportation throughout Villages. Dan was very quick to respond to all questions and concerns - great host!

TikiTiki walk/ride 2 Lake Sumter *Pool & Hot Tub*
By far the most well stocked Airbnb we’ve stayed in! Location was prime to everything, the hosts were very gracious and communicative as well. Adults and kids will have a blast in this house with so many games, activities and fabulous pool and hot tub area. Seriously could not ask for more in a great vacation rental!!

Golf Cart, King Bed, Small Dogs, and Water System!
1000 words isnt enough . so warming and relaxing home. so much to do. book at least 10 days 7 is not enough . u will have memories that will draw you back. . This home exceeds any home i ever rented. around every bend on the golf cart paths you will find anouther bend of fun that goes on and on.... if u are craving a fast food for a quick bite to eat, where else can u go thru drive thru on a golf cart !

Cheerful home , tastefully updated, extra den
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!

Charming Villages Retreat
Matt’s place is beautifully decorated and very comfortable. Any household and basic personal item normally used is there and easily accessible. Matt has thought of everything! There is a lovely screened in lanai, a back porch, side porch and fenced in yard, all with great lighting. Our dog loved the fenced in yard, easy in and out and fun area to play catch with him. The location is close to many stores and restaurants. It was the perfect place for us to relax between house closings!

Private historic district apt w/pool-suite A
This was a beautiful historic home with modern updates. It was comfortable, clean and in a quiet neighborhood. The pool and surrounding area were perfect! Everything was provided that we could have ever needed. We would definitely rent again!

New Luxury Home-Pool-Waterfront View-3 King Suites
Debbie and Joel’s slice of paradise never disappoints. This was our second stay, and it somehow felt even better than the first. From the moment we walked in, we felt at home. The house was spotless, beautifully maintained, and had everything we needed for a relaxing getaway. One of our favorite parts was the peaceful, private lanai. Whether we were floating in the pool after a long day of golf cart rides or listening to one of many summer thunderstorms, it was the perfect spot to unwind. The beds were incredibly comfortable, and every detail, from the cozy decor to the thoughtful touches, made our stay feel extra special. We’re already counting down the days until we can return later this year!

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 !
Apartment rentals with a pool

Gray Heron Victorian Townhouse
We had a blast staying at this wonderful and beautiful house for four days. Gerri made the stay unforgettable! The place was clean, everything what we needed was there. The pictures are exactly how the house looks. I highly recommend this place for everyone who wants to enjoy the beautiful scenery and to have a relaxing time in Inverness. Thank you Geri, we will definitely come back!

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!

LuXury Apt with Lake View, Cable & fast WiFi
The apartment was very nice with a screened in balcony. It had all of the conveniences expected for a comfortable stay. The location was great because it was near plenty of restaurants and shopping, and close to the freeway and the Parks which makes it great for vacationers. The host was very responsive to questions and was pleasant to work with. One thing to note is that the unit is on the second floor and there are no elevators. Otherwise, it was a great choice!

Lovely One Bedroom
Great experience! Easy check-in and check-out. Shaun was very responsive and helpful throughout the entire stay. Place had all basic amenities needed for the stay and it was a very comfortable stay. I would highly recommend if you are staying in the Orlando area.

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

Newly remodeled! Condo in Center of All The Action
It's an excellent option near the parks, especially Orlando. We were 15 minutes away! Super accessible and comfortable. Plus, it's pet-friendly, which makes it a plus beyond anything else in the area. I would definitely come back.

Tranquil 2B/2B Stay in Apopka
Stenard is the best host and really cares about their guests. The home was very comfortable and I loved the blackout curtains.

1 Bedroom 5-Star Standard Resort Villa Near Disney
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 .

Designer Pet-Friendly Retreat with Heated Pool
very clean and roomy! great hosts! big yard. Will be back for sure!

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
Quick stats about holiday rentals with a pool in Lady Lake
Total rentals
90 properties
Nightly prices starting at
₹5,193 before taxes and fees
Total number of reviews
1.1K reviews
Family-friendly rentals
50 properties are a good fit for families
Pet-friendly rentals
50 properties allow pets
Rentals with dedicated workspaces
40 properties have a dedicated workspace
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- Universal Studios Florida
- Orange County Convention Center
- Weeki Wachee Springs
- Universal's Volcano Bay
- Old Town Kissimmee
- Discovery Cove
- Disney's Animal Kingdom Theme Park
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- ICON Park
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