
Vacation rentals with a pool in Lady Lake
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Top-rated rentals with a pool in Lady Lake
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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*
This was a fabulous family get away (4 adults/4kids) Kim was amazing from when I first had questions prior to booking to when we left she is very responsive within minutes. For me it’s the small things she has added that no other has. From soaps and lotions to little if you forgot something (it’s provided). Plenty of comfort for sleeping or napping and multiple charging stations even a white noise gadget. The pool and hot tub were amazing! Beautifully decorated home with a kitchen that is stocked to the nines! We had so much fun with games and air hockey! Location was superb close to Lake Sumter landing. We Will definitely book here again! Kim is a super host!

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 !

Fabulous Courtyard Villa close to Sumter Landing
We had a fantastic stay at Gayle’s home. The home more than exceeded our expectations. The home is in a great location. Walkable to the rec centre for pickleball and choice of pools. Close to the market square where great restaurants and live music are available every night. The golf cart was definitely an added bonus and we would highly recommend it as a way to tour the villages. Gayle is a great host, very responsive to our questions and always available to assist. We hope to have the opportunity to stay at this wonderful location again.

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!

The place in The Villages
Ginger’s house was the perfect space for visiting family in the villages. The villa is clean, nicely appointed with comfortable furniture like the double reclining couch, and perfect for a couple or small family. It’s also very convenient to major stores and roads if you need any groceries or want to check out nearby restaurants.

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!
Condo 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 vacation rentals with a pool in Lady Lake
Total rentals
90 properties
Nightly prices starting at
G$12,553 GYD 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
- Universal Orlando Resort
- SeaWorld Orlando
- Disney Springs
- ESPN Wide World of Sports
- Amway Center
- Epcot
- Magic Kingdom Park
- Reunion West
- Aquatica
- Rainbow Springs State Park
- ChampionsGate Golf Club
- Disney's Hollywood Studios
- Walt Disney World Resort Golf
- Island H2O Water Park
- Blue Spring State Park
- ICON Park
- Universal CityWalk