Holiday rentals with a pool in Lady Lake

Find and book unique homes with a pool on Airbnb

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Popular amenities for Lady Lake rentals with a pool

House rentals with a pool

Guest favourite
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 favourite
Home in The Villages
5 out of 5 average rating, 11 reviews

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

MellisaRating, 5 stars1 week ago
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!!
Top guest favourite
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 favourite
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!
Guest favourite
Home in The Villages
4.9 out of 5 average rating, 10 reviews

Charming Villages Retreat

Diane Rating, 5 stars1 month ago
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!
Top guest favourite
Home in Ocala Historic District
4.97 out of 5 average rating, 110 reviews

Private historic district apt w/pool-suite A

DawnRating, 5 stars6 days 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 favourite
Home in The Villages
4.99 out of 5 average rating, 73 reviews

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

LacyRating, 5 stars1 day 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!
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 !

Apartment rentals with a pool

Top guest favourite
Apartment 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!
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!
Guest favourite
Apartment 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!
Apartment 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 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
Superhost
Apartment 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.
Apartment 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.
Apartment in Kissimmee

1 Bedroom 5-Star Standard Resort Villa Near Disney

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

Destinations to explore

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