Holiday Homes in Lady Lake

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Featured Holiday Homes in Lady Lake and around

Private Pool, Golf Cart, & Pet Friendly. Close to Golf and Town Squares.

10.0 out of 10, Exceptional, (2)
"Great place in a very convenient location "
Private Pool, Golf Cart, & Pet Friendly. Close to Golf and Town Squares.

"Mermaid House" in Downtown Mt. Dora!! Pet Friendly

10.0 out of 10, Exceptional, (57)
"This how was perfect for our weekend anniversary trip. It’s close enough to downtown without being in the middle of downtown. We will stay again! "
"Mermaid House" in Downtown Mt. Dora!! Pet Friendly

Golf Front Home, Solar Heat Pool! FREE golf cart, wifi, awesome view

10.0 out of 10, Exceptional, (209)
"We loved our stay! The house is spacious, well stocked, clean and great location. We enjoyed relaxing on the lanai with the beautiful view of the golf course and pool. David is an excellent host! "
Golf Front Home, Solar Heat Pool! FREE golf cart, wifi, awesome view

Heated Pool house in Lake Panasoffkee

9.6 out of 10, Exceptional, (31)
"I like every room ,the pool, and everything "
The price is €323
includes taxes & fees
2 Jul - 3 Jul
Heated Pool house in Lake Panasoffkee

1 min walk to Downtown! Outdoor Patio! 5 star luxury! Golf Cart Rental!

10.0 out of 10, Exceptional, (32)
"We had a wonderful weekend. Great spot v"
1 min walk to Downtown! Outdoor Patio! 5 star luxury! Golf Cart Rental!

Location! Our Village Gem-5 Star-3 min to Sumter Landing-Restaurants-Town Square

10.0 out of 10, Exceptional, (104)
"Second time we’ve stayed here. Love the location. The owners are responsive; saw us through hurricane Milton. Clean and comfortable. "
Location! Our Village Gem-5 Star-3 min to Sumter Landing-Restaurants-Town Square

Walk to Spanish Springs, free 4 seater golf cart, covered patio! Pools nearby!!

9.6 out of 10, Exceptional, (62)
"Had great time..will definitely stay again"
Walk to Spanish Springs, free 4 seater golf cart, covered patio! Pools nearby!!

Ocala Escape w/ Private Pool, Pets Welcome!

10.0 out of 10, Exceptional, (13)
"This was a great place for us and our dogs. Owners were super responsive with great communication. "
Ocala Escape w/ Private Pool, Pets Welcome!

Better Than A 5 Star Hotel IN THE VILLAGES 2 Bedroom house WiFi, AC, GOLF CART

2.0 star property
9.8 out of 10, Exceptional, (20)
"Very well managed"
The price is €210
includes taxes & fees
13 Jul - 14 Jul
Better Than A 5 Star Hotel IN THE VILLAGES 2 Bedroom house WiFi, AC, GOLF CART

The Downtowner Cottage downtown Mt. Dora Location! Location! Location!

10.0 out of 10, Exceptional, (76)
"Perfect little spot in Mount Dora! Close to everything and very clean. "
The Downtowner Cottage downtown Mt. Dora Location! Location! Location!

Jan 2026 Available! Beautiful 2 BR wGas Golf Cart in Duval. All 5 star reviews!

10.0 out of 10, Exceptional, (103)
"We had a great stay. Property was just as described and close to everything! "
Jan 2026 Available! Beautiful 2 BR wGas Golf Cart in Duval. All 5 star reviews!

Ocala Retreat w/ Pool, Grill & Yard - Pets Welcome

2.0 star property
9.6 out of 10, Exceptional, (14)
"Great Location and comfortable place to stay!!"
Ocala Retreat w/ Pool, Grill & Yard - Pets Welcome

Relax by Lake Eustis in your cozy 2-bedroom retreat

9.8 out of 10, Exceptional, (115)
"The access to the lake is wonderful, fished every day with our boat that was docked at the boat house."
Relax by Lake Eustis in your cozy 2-bedroom retreat

Dora Splash Pad

9.8 out of 10, Exceptional, (110)
"Perfect location to attend my dad's 100th birthday celebration(s). The kids loved the pool and the games."
Dora Splash Pad

Private, Charming apartment in historic District

10.0 out of 10, Exceptional, (53)
"Very well equipped. Nice location, quiet and cozy. Comfortable and convenient. Great price. "
Private, Charming apartment in historic District

4 BR/2 BA, HEATED Pool, Split Floor Plan, King Suite, W/D, Garage & Yard

10.0 out of 10, Exceptional, (16)
"Great stay great neighborhood it’s everything pictured "
4 BR/2 BA, HEATED Pool, Split Floor Plan, King Suite, W/D, Garage & Yard

The Board & Bridle: Luxurious Entire Home near WEC

10.0 out of 10, Exceptional, (11)
"Beautiful property. So much better than a hotel, especially for those traveling with pets. Very clean, beautifully decorated and maintained. "
The Board & Bridle: Luxurious Entire Home near WEC

Retreat Overlooking Lake Dora!

9.6 out of 10, Exceptional, (10)
"We enjoyed it here location is great and we plan to come back soon "
Retreat Overlooking Lake Dora!

Village of Mallory, Close to Sumter Landing Sq. 3BD, 2Bath with Gas Golf Cart.

9.2 out of 10, Wonderful, (47)
"Centrally located to where we needed to be. Owner very quick to respond to our needs"
Village of Mallory, Close to Sumter Landing Sq. 3BD, 2Bath with Gas Golf Cart.

Spacious 4 bedroom 3.5 bath POOL home W/ Gym!!

8.8 out of 10, Excellent, (3)
"I highly recommend this property. The house was located in a very nice community easily accessible from any part of Leesburg. We had an amazing stay and will definitely be going back again."
The price is €558
includes taxes & fees
29 Jun - 30 Jun
Spacious 4 bedroom 3.5 bath POOL home W/ Gym!!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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