Vacation 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

Guest favorite
A green golf cart is parked on a stone driveway in front of a light-colored house. The cart features a canopy and seating for four, with two spacious seats in the front. The garage door is seen in the background, providing additional context of the home.
Home in The Villages
4.92 out of 5 average rating, 64 reviews

KingBed w/Cart

KimRating, 5 stars1 month ago
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!
Top guest favorite
A serene saltwater pool is highlighted by soft blue lighting, creating a calming atmosphere. The pool area is enclosed by a screen, with lush greenery visible beyond the protective barrier. Ambient lights illuminate the surroundings, enhancing the tranquil evening setting.
Home in The Villages
5 out of 5 average rating, 12 reviews

TikiTiki walk/ride 2 Lake Sumter *Pool & Hot Tub*

JeniferRating, 5 starstoday
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!
Top guest favorite
The exterior of the home displays a well-manicured front yard with decorative plants and a white picket fence. A paved driveway leads to a two-car garage featuring a symmetrical design, accompanied by a clear blue sky above.
Home in The Villages
4.94 out of 5 average rating, 72 reviews

Golf Cart, King Bed, Small Dogs, and Water System!

AnnRating, 5 stars3 weeks ago
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 !
Top guest favorite
The exterior of the villa is seen, featuring well-maintained landscaping with palm trees and neatly trimmed shrubs. A spacious driveway leads to the entrance, while a two-car garage is visible on the left. The sunlit facade showcases a welcoming atmosphere.
Home in The Villages
4.97 out of 5 average rating, 93 reviews

Fabulous Courtyard Villa close to Sumter Landing

SueRating, 5 stars3 months ago
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.
Top guest favorite
An open-concept living area features a mix of seating options, including a dark leather sofa and stylish accent chairs. A large television is mounted on the wall, and a dining table with seating is visible in the background. The room is illuminated by natural light and recessed lighting.
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!
Top guest favorite
A comfortable living area is featured, with two recliner chairs and a light-colored sofa adorned with decorative pillows. A round coffee table sits at the center, complemented by a patterned area rug. Natural light enters through a window covered with soft drapes.
Home in The Villages
4.94 out of 5 average rating, 17 reviews

The place in The Villages

WynterRating, 5 stars4 weeks ago
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.
Top guest favorite
A two-story frame vernacular style home is surrounded by lush greenery. A wide porch features rocking chairs and is complemented by well-maintained grass. Mature trees provide shade, while a pathway leads to the entrance, creating a welcoming atmosphere for guests.
Home in Ocala Historic District
4.97 out of 5 average rating, 110 reviews

Private historic district apt w/pool-suite A

DawnRating, 5 stars1 week ago
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!
Top guest favorite
The outdoor area features a spacious lanai with comfortable seating and a dining area, connecting to a heated saltwater pool surrounded by a concrete deck. The pool area is enclosed by a screen for comfort, enhancing visibility towards the lush greenery beyond.
Home in The Villages
4.99 out of 5 average rating, 73 reviews

New Luxury Home-Pool-Waterfront View-3 King Suites

LacyRating, 5 stars2 days ago
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

Top guest favorite
A screened patio offers serene views of a calm waterway, bordered by lush greenery. Two comfortable lounge chairs are positioned to enjoy the peaceful surroundings, while the reflections in the water create a sense of tranquility in the natural setting.
Condo in Inverness
5 out of 5 average rating, 40 reviews

Gray Heron Victorian Townhouse

DianaRating, 5 stars1 week ago
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!
A comfortable living area features a spacious sofa adorned with colorful cushions and a glass coffee table. Natural light enters through large windows, illuminating the light wood floors. A ceiling fan and soft lighting create a relaxing ambiance, complemented by a nearby seating area.
Condo in Clermont
4.67 out of 5 average rating, 24 reviews

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

ElizabethRating, 5 stars4 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!
Guest favorite
A modern living area features a light-colored couch adorned with decorative pillows, complemented by two blue armchairs. A geometric area rug adds texture beneath a central coffee table. Light fixtures illuminate the space, enhancing its contemporary design and inviting ambiance.
Condo in Windermere
4.93 out of 5 average rating, 45 reviews

LuXury Apt with Lake View, Cable & fast WiFi

LoisRating, 5 stars3 weeks ago
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!
A spacious lobby welcomes guests with comfortable seating arrangements, including modern sofas and armchairs. Natural light floods the room, highlighting a feature wall with unique texture. Contemporary art pieces adorn the walls, and greenery is incorporated through potted plants.
Condo in Metro West
4.36 out of 5 average rating, 11 reviews

Lovely One Bedroom

NolanRating, 5 stars36 months ago
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.
Guest favorite
The living area features two comfortable sofas adorned with decorative pillows, arranged around a patterned area rug. A dining set with wooden chairs is visible nearby, while a spiral staircase leads to the upper level. Ample natural light enters through multiple windows.
Condo 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
Superhost
A large swimming pool is surrounded by vibrant palm trees and well-maintained landscaping. Poolside lounge chairs are arranged neatly along the perimeter. The deck is finished with a red hue, and the clear blue water reflects the sunny sky.
Condo in Orlando
4.52 out of 5 average rating, 434 reviews

Newly remodeled! Condo in Center of All The Action

MarleneRating, 5 stars2 weeks ago
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.
A serene outdoor pool is surrounded by neatly arranged lounge chairs. Lush palm trees provide shade against a clear blue sky, while a cozy poolside cabana is visible in the background, adding to the inviting atmosphere of the community.
Condo in Apopka
4.83 out of 5 average rating, 23 reviews

Tranquil 2B/2B Stay in Apopka

AmyRating, 5 stars2 weeks ago
Stenard is the best host and really cares about their guests. The home was very comfortable and I loved the blackout curtains.
An outdoor pool is surrounded by lounge chairs, with a terracotta paved deck. The pool's clear blue water reflects the bright sky, while neighboring buildings provide a backdrop. Palm trees add a touch of greenery to the serene environment.
Condo in Kissimmee

1 Bedroom 5-Star Standard Resort Villa Near Disney

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

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Lake County
  5. Lady Lake
  6. Rentals with pools