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Vacation 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

Superhost
Home in Ocala
4.81 out of 5 average rating, 26 reviews

Family home in quiet neighborhood

StephanieRating, 5 stars6 months ago
We had a wonderful stay as we were visiting during a horse show at WEC. The fully fenced large yard was perfect for our dogs to play & exercise in. The enclosed pool area was very nice! We were able to comfortably spread out in this nicely laid out house with plenty of privacy. My only complaints would be bathrooms lack good water pressure and the beds were hard and would recommend getting either toppers or new mattresses for better comfort.
Guest favorite
A landscaped outdoor area features a pool with a sun shelf and a cascading water feature. Tropical plants are placed around the pool, and a clear blue sky complements the serene atmosphere of the setting.
Home in Floral City
4.86 out of 5 average rating, 29 reviews

Private Resort Pool

JoeyRating, 5 stars1 month ago
Kelly was an awesome host—highly responsive and made everything super easy. The house itself is straight out of a magazine—beautifully designed and spotless. The location is perfect, especially if you're playing at Cabot Citrus. After a long day on the course, coming back to unwind by the picture-perfect backyard and pool was exactly what we needed. Would absolutely stay here again!
Top guest favorite
A spacious private pool is enclosed by a screened structure, featuring a basketball hoop at one end. The crystal-clear water is surrounded by a concrete deck, while colorful flags decorate the fencing, adding a friendly vibe to the outdoor space.
Home in Orlando
5 out of 5 average rating, 127 reviews

Private pool home near Downtown

MonikaRating, 5 stars1 week ago
He was a great host and attended to all my questions and help. My family and I enjoyed it so much! Perfect location! Beautiful home! And the pool is the perfect touch!
Superhost
An aerial view of a spacious backyard reveals a private pool surrounded by lounging chairs. The home is visible to the left, with a driveway leading toward the pool area. Lush greenery borders the property, creating a serene outdoor environment.
Home in Winter Park
4.73 out of 5 average rating, 11 reviews

Prvt 8 Guests /pool/Rollins/Disney/Universal

AngelaRating, 5 stars2 weeks ago
Beautiful, peaceful, and relaxing home with a fantastic pool. Very spacious and modern and conveniently located near restaurants and stores. And not too far from major attractions such as Aquatica water park and airports. I highly recommend this house for a family vacation!
Guest favorite
A large, inviting pool glistens under the sun, surrounded by a spacious patio and palm trees. A stylish, shaded cabana is positioned nearby, offering a retreat for relaxation. The pool area is enclosed and features a clean white fence, enhancing the tranquil outdoor atmosphere.
Home in Orlando
4.88 out of 5 average rating, 200 reviews

Pool-Jacuzzi & Palm Trees/ 8 Universal/ 15 Disney

JamieRating, 5 stars2 weeks ago
This home was clean and conveniently located near a ton of things to do, paces to eat, and a short drive to Disney.
Superhost
The living room features a high, sloped ceiling with skylights, allowing natural light to fill the space. A light-colored sectional sofa is paired with gold-accented side tables. A piano sits in a corner, with a decorative fireplace and a television mounted above it.
Home in Maitland
5 out of 5 average rating, 3 reviews

Casa Feliz

DeborahRating, 5 stars2 weeks ago
Fantastic stay at Casa Feliz!! Quiet peaceful place to chill with great outdoor spaces. Pool was a godsend and heater worked as it should. Lovely walk 5 minutes away Kewanee park. We would recommend this property.
Guest favorite
A clear blue pool is framed by a screened patio, offering a view of the home's outdoor kitchen and seating area. Comfortable lounge chairs surround the pool, with an umbrella positioned for shade. The backdrop features additional residential structures.
Home in Wildwood
5 out of 5 average rating, 16 reviews

The Villages pool property with a 4-person cart!

BarbaraRating, 5 stars1 week ago
Our family enjoyed this home very much. The house was roomy with a modern kitchen and the little outdoor kitchen area was very nice. The pool was a great size and having it heated helped a lot in April weather. The location is a little farther out but we enjoyed the area very much. It was just a short five minute golf cart ride to the Sawgrass Grove area. Dave was very helpful and easy to work with. I highly recommend this home.
Superhost
An inviting pool area features a crystal-clear swimming pool, surrounded by a screened enclosure. Comfortable seating options are visible in the background, along with outdoor tables covered with dark linens. The calm water reflects the sky, enhancing the serene atmosphere.
Home in Inverness
4.78 out of 5 average rating, 110 reviews

3br POOL, Fenced, near Downtown & Trails

DavonRating, 5 stars1 week ago
This was a lovely stay I had NO ISSUES what so ever and the host was very welcoming and friendly I’d definitely recommend this stay for anyone

Condo rentals with a pool

Guest favorite
A sectional sofa is positioned in a cozy seating area, featuring neutral-toned cushions. A small, round coffee table with a gold base complements the space. Light flows through sheer white curtains, while a decorative plant adds a touch of greenery beside a framed wall art piece.
Condo in Florida Center
4.92 out of 5 average rating, 105 reviews

Remodeled 2BD/2BA Condo mins from Universal Studio

JtRating, 5 stars1 week ago
An awesome stay for a week! we recommend this place for anyone wanting to be in a great location near everything on International Drive. Host Maxine is great and helped when we needed it. Thanks Maxine! We will be back.
Top guest favorite
Condo in Orlando
4.92 out of 5 average rating, 108 reviews

P12# Vista Cay/ Walk to OCCC & New EPIC PARK !

TerryRating, 5 stars1 month ago
The condo is beautiful with a great view from the Lanai. Katharine and Gilberto were very responsive and very helpful. We asked for a few things to help with cooking and we received them the very next day Likewise, when the blender broke, a new one arrived the following day. The condo is huge and was very quiet. There was nothing better than getting up in the morning and having coffee on the Lanai while overlooking the water! We will be going back!
Top guest favorite
An aerial view showcases a resort pool area surrounded by lush greenery. Two distinct swimming pools are visible, one in a rectangular shape and the other in a flowing design. Sun loungers are arranged around the pools, complemented by umbrellas providing shade.
Condo in Orlando
5 out of 5 average rating, 29 reviews

Cay Lakeview Chic View

GabrielleRating, 5 stars1 week ago
The condo was beautiful and loved that everything was walkable! We had a great stay and definitely recommend to all of our friends!
Top guest favorite
A dining area features a round table set for four, complemented by soft grey chairs. Natural light floods the space through sheer curtains, reflecting off a large mirror. A cozy seating area is visible in the background, highlighting a modern artistic touch on the walls.
Condo in Orlando
5 out of 5 average rating, 8 reviews

Super Cool Penthouse by Main Pool. Nr all Parks

HelenRating, 5 stars2 months ago
Our stay was excellent, the condo is perfectly located by attractions, restraunts, stores and other activities - many in walking distance! clean and well stocked kitchen made making meals a home easy, and the beds were comfortable. Clean, well appointed bathrooms and laundry were convenient and well stocked. Being on the 4th floor got a bit tiring to walk up, but it was very safe and secure with a great veiw of the fountain. Bit of a walk/drive to the open pool (the one right next door is closed for renovations) but it wasn't difficult by car or walking to locate it and enjoy the amenities. Lin was very responsive to questions and offered immediate assistance! I would recommend providing instructions for how to use the remotes for the TV's and the thermostat - though they may have been available and we were so busy we missed them. Would definitely stay here again, it was the perfect place for our trip in every way and the host takes pride in the property and hosting her guests!
Guest favorite
A large swimming pool is framed by palm trees and lounge chairs under a clear sky. The pool area includes a shaded gazebo with seating, and the surrounding paved deck is well-maintained. Sunlight reflects gently on the water's surface, creating a relaxing ambiance.
Condo in Ventura
4.89 out of 5 average rating, 9 reviews

Ventura Country Club Home away from home

HamidRating, 5 stars4 weeks ago
Excellent host, very responsive to our needs. Highly recommend.
Superhost
A serene view of a lush landscape, featuring palm trees along the shoreline of a lake. The image captures the expanse of water reflecting the soft hues of morning light, with a portion of the main pool visible in the foreground.
Condo in Orlando
4.87 out of 5 average rating, 45 reviews

5000-307 - 2 BED, 2 BATH, POOL AND LAKEVIEW

TeresaRating, 5 stars2 weeks ago
Everything was as stated! Condo was clean, comfortable and very convenient for our trip. I would stay there again when in Orlando and recommend to friends and family! Our family had a great time!!
Superhost
Condo in Orlando
4.84 out of 5 average rating, 31 reviews

VC10-205 Luxurious Condo next to Clubhouse

FionaRating, 5 stars1 week ago
Larissa and Rosely's home was clean, modern, and incredibly spacious—plenty of room for my daughter and me to relax. We especially loved the large bathtub in the primary suite—it was a treat after long days out. The unit has all the basic essentials, but if you plan to cook, just double-check what’s stocked and bring anything extra you might need. The pool area is beautiful, and the location couldn’t have been better—super convenient for getting to the Convention Center, just a short drive away. Larissa and Rosely were also very communicative and responded quickly to any questions or changes I needed, which made everything even smoother.
Top guest favorite
An open-concept kitchen features a large island with three stools, surrounded by modern cabinetry and stainless-steel appliances. Natural light fills the space, complementing the neutral wall tones and wooden flooring. A hallway leads to additional areas of the condo, enhancing the spacious feel.
Condo in Orlando
5 out of 5 average rating, 11 reviews

Orlando Convention Center at Vista Cay

JessicaRating, 5 stars1 week ago
The condo was very well maintained and stocked with most everything we needed. We loved that it is located minutes from the Orange County Convention Center since we were in town for a cheer competition. During our stay, we also visited Disney and Universal Studios, which were only 20 minutes away. The condo is within walking distance to a Publix, ABC Liquor, Walgreens, and quite a few restaurants. The condo was perfect, we will definitely stay there again!

Home rentals with a private pool

Quick stats about vacation rentals with a pool in Lady Lake

  • Total rentals

    90 properties

  • Nightly prices starting at

    ﺩ.ﺇ220 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