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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

Guest favorite
Home in Ocala
5 out of 5 average rating, 8 reviews

Vacation Pool House Ocala

KimRating, 5 stars4 months ago
We thoroughly enjoyed Tracy's home. We traveled to the World Equestrian Center from Wisconsin. The home was spotless and in a great location. The pool area was great and it truly made our 2 weeks in Ocala fantastic. It was so comfortable coming back to her home each night to relax. Thank you!
Guest favorite
A screened-in pool area features a rectangular pool surrounded by a spacious deck. Lounge chairs are positioned nearby, offering a relaxing space. Lush greenery is visible through the screened walls, allowing for an unobstructed view of the outdoor environment.
Home in Ocala
4.93 out of 5 average rating, 15 reviews

Pool House 1 Mile From World Equestrian Center

ChristopherRating, 5 stars4 months ago
Great location, great home! Very comfortable, would stay here again!
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!
Guest favorite
A circular fire pit area is surrounded by six blue adirondack chairs, set on a stone patio. Lush greenery and colorful plants frame the space, with a view of the house and pool area in the background. Sunlight brightens the inviting outdoor gathering spot.
Home in Clermont
4.92 out of 5 average rating, 108 reviews

Spacious Bungalow with Private Pool and Courtyard

RobinRating, 5 stars1 week ago
We had the best time. We loved the sun room. we stayed in there the most. Would definitely rent 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 stars6 days 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 enclosed swimming pool area features a clear blue pool surrounded by a spacious deck. Multiple lounge chairs are positioned along the perimeter, providing seating options. The area is covered by a mesh screen, allowing natural light while ensuring an insect-free environment.
Home in Orlando
4.66 out of 5 average rating, 111 reviews

Orlando Home with pool

SamanthaRating, 5 stars3 months ago
Lovely spot for a family with a baby in a very convenient and safe location! The home itself was very clean with great amenities. The weather was not the greatest, so we didn’t get to take advantage of the pool, but I’m looking forward to returning in the future for another Disney trip.
Top guest favorite
A inviting pool area showcases tranquil blue water, bordered by lush greenery and decorative potted plants. Sunlight reflects off the surface, while a well-maintained lawn complements the serene atmosphere.
Home in Longwood
5 out of 5 average rating, 108 reviews

Private 4-Bedroom home with pool!

MichaelRating, 5 stars3 weeks ago
Nicholas was a super responsive communicative and friendly host. He was able to accommodate an early arrival with no problem and met us upon arrival to review the workings of the house. He lives next door and was able to respond immediately to any questions. The interior of the house is beautiful and looks to have been very recently completely remodeled and renovated and furnished. The pool was a great amenity and very refreshing after a day in the heat and humidity. Appliances and televisions were new and furnishings stylish and up to date. We hope to stay at his home again next year. Nicholas is a super friendly guy and was a pleasure to encounter.
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, 15 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.

Condo rentals with a pool

Guest favorite
A community pool is surrounded by paved decking and palm trees, providing a serene outdoor space. Loungers are positioned around the pool, and a few umbrellas offer shade. The area is enclosed by a fence, ensuring privacy and security.
Condo in Lake Mary
5 out of 5 average rating, 23 reviews

3/2 near beaches and theme parks

SridherRating, 5 stars5 months ago
Nice spot, will book again if in the area. Very responsive hosts.
Top guest favorite
A warm bedroom setting features a spacious bed with a neutral-toned duvet. Beside the bed, a wooden dresser holds a small potted plant and a decorative item. A lamp provides soft light, and a full-length mirror reflects the room's ambiance.
Condo in Orlando Central Business District
5 out of 5 average rating, 42 reviews

Perfect Downtown Stay – Business & Leisure

ShalondaRating, 5 starstoday
Urbano was extremely helpful with getting settled in his place! He offered helpful advice on nearby places to eat and made everything easy for us! Highly recommend!!!
The rooftop pool area features a large, illuminated swimming pool surrounded by lounge chairs. City skyline views are visible in the background as sunset colors reflect off the water, and a shaded lounge area is situated at one end of the pool deck.
Condo in Orlando Central Business District
4.79 out of 5 average rating, 24 reviews

New Penthouse Loft 25th Top Floor

JordanRating, 5 stars102 months ago
This was a great location with a great view! A friend and I came down to Orlando for the ACC Championship game and the location was exactly where we wanted to be at an affordable price! Walking distance to restaurants around the lake and walking distance to downtown bars/Wall St! Gene was very hospitable, had a welcome gift waiting for us and he was easy to contact with any questions! Would definitely consider staying here again on my next visit to Orlando!
Superhost
The image captures the serene lake at sunset, reflecting warm hues of orange and pink across the water's surface. A small boat is anchored near a wooden dock, which is lined with personal touches. Trees line the shore in the distance, enhancing the tranquil scene.
Condo in Winter Park
5 out of 5 average rating, 3 reviews

Renovated Winter Park Lakeside Condo

NancyRating, 5 stars12 months ago
The place was totally renovated, Spotless, everything was furnished. We loved the washer and dryer in the unit, beautiful kitchen, new bathrooms, beautiful living room, leather couch, neighbors were quiet and very friendly. We could walk to grocery stores. , restaurants, shopping, park Avenue . We sat by the lake, just a few doors down everyday . Price was very affordable. This was our favorite place to stay, we stayed 6 weeks .
A living area features a light-colored sofa with decorative pillows, paired with a comfortable armchair. Natural light floods in through multiple windows, illuminating the hardwood floor. A dining area with chairs is visible in the background, creating an inviting space for relaxation and meals.
Condo in Altamonte Springs
4.78 out of 5 average rating, 9 reviews

Ultimate relaxation at Forestway

AaronRating, 5 stars2 weeks ago
Stayed at Dee's place with my wife and kids while visiting friends nearby in Orlando. It was a great place for us to come back to at the end of the day and get some much needed rest. The beds were very comfortable and the AC and fans in each room kept us very cool. I would definitely recommend Dee's place for anyone looking for a quiet place to stay in the area!
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, 34 reviews

Gray Heron Victorian Townhouse

DakotahRating, 5 stars2 weeks ago
I absolutely love this Air BnB! I love the host! I’ve stayed here twice! I always check to see if this place is available when I book a trip to Crystal River! And I get super bummed if its booked! I really love it!! Clean, responsive, away from the hustle and bustle but definitely close enough to enjoy the springs!
Superhost
A spacious living area is featured, furnished with a light gray sectional sofa and matching ottoman. Natural light floods in through large windows, illuminating the room. A dining area with a wooden table and chairs is visible, complemented by decorative plants throughout.
Condo in Lake Mary
4.7 out of 5 average rating, 23 reviews

Entire Condo in Lake Mary 3/2 w/dedicated office

ValerieRating, 5 stars1 week ago
Brent is very friendly, and responsive. He is a great host, and the unit was great for what we needed. We would definitely stay again. However, like previous reviewers have noted, there are personal items in the unit. But we had a two week reservation, and there was enough empty drawer space to unpack everything. The pool is nice and very convenient to use, shopping and I-4 is very convenient to get to.
Top guest favorite
A night view from the balcony captures the bright lights of downtown Orlando, showcasing modern buildings and bustling streets below. The calm waters in the distance reflect the city lights, creating a serene atmosphere against the lively urban backdrop.
Condo in Orlando Central Business District
5 out of 5 average rating, 19 reviews

Condo downtown Orlando

SamuelRating, 5 stars1 week ago
This is exactly what my wife and I wanted. Condo was conveniently close to everything and we enjoyed our privacy while we were there. Will definitely stay again. Thank you!!

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