Lady Lake Holiday Rentals

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Holiday Rentals in Lady Lake

Marilyn’s Romantic Getaway

10.0 out of 10, Exceptional, (54)
"This cottage was fabulous I would stay there forever if available "
Marilyn’s Romantic Getaway

Cozy Villages villa, 2 bed, 2 bath. Great Location

10.0 out of 10, Exceptional, (44)
"A good clean rental property with the added benefit of a four seater golf cart, as we were three adults a four seater was a must. The price was good as well. "
Cozy Villages villa, 2 bed, 2 bath. Great Location

Spacious home and country setting just minutes from The Villages.

8.8 out of 10, Excellent, (3)
"Master bath shower had black mold....self cleaned.....all else AOK"
Spacious home and country setting just minutes from The Villages.

Hot Tub House - Entire 3 Bedroom House in The Villages

10.0 out of 10, Exceptional, (87)
"The house was perfect. Clean and had everything we needed, I would definitely recommend! Ownes communication was also great. "
Hot Tub House - Entire 3 Bedroom House in The Villages

Beautiful view, The Villages- Golf Front Home, Heated Pool, Free Golf Cart, WIFI

10.0 out of 10, Exceptional, (83)
"Enjoyed our stay in the villages"
Beautiful view, The Villages- Golf Front Home, Heated Pool, Free Golf Cart, WIFI

Get Cozy in this newly renovated home by The Villages!

10.0 out of 10, Exceptional, (9)
"Great place, plenty of beds for all of us to stay while visiting family in the nearby Villages. Easy to get to and instructions for accessing the property were straightforward. Host responded quickly to any questions we had. Would gladly stay again!"
Get Cozy in this newly renovated home by The Villages!

Enjoy all that The Villages Florida has to offer in affordable Villages Home

Enjoy all that The Villages Florida has to offer in affordable Villages Home

Fun of The Villages FL. 5 minutes to Spanish Springs. 10 Min to Sumter Landing.

Fun of The Villages FL. 5 minutes to Spanish Springs. 10 Min to Sumter Landing.

Come Enjoy The Golf Course View! This 2 bdrm Home Awaits You

9.4 out of 10, Exceptional, (3)
"Everything we wanted in a clean, comfortable, relaxing setting. Close to everything in the Villages in a quiet and serene neighborhood. Thank you! We will be back again."
Come Enjoy The Golf Course View! This 2 bdrm Home Awaits You

Discover the Ultimate Comfort and Convenience in Country Club Hills!

Discover the Ultimate Comfort and Convenience in Country Club Hills!

Recently Updated & Complete w/Golf Cart, Coffee Bar, & MORE!

9.6 out of 10, Exceptional, (5)
"house was lovely golf,cart did not start.never used it for the week whould rent property again.ron"
Recently Updated & Complete w/Golf Cart, Coffee Bar, & MORE!

2/2 in The Village of Mira Mesa

9.6 out of 10, Exceptional, (5)
"All positive"
2/2 in The Village of Mira Mesa

2/2 in The Village of Orange Blossom Gardens

9.4 out of 10, Exceptional, (3)
"Very clean and spacious. We enjoyed our stay. Thank you."
2/2 in The Village of Orange Blossom Gardens

Private Corner Unit Pool Home w/BBQ & Dog Friendly!

9.0 out of 10, Wonderful, (12)
"The property provided a quiet retreat to work remotely while my son attended a summer program at Beacon college. I enjoyed an after work swim each day. A real unexpected treat was fireworks that could be seen from the livingroom window."
Private Corner Unit Pool Home w/BBQ & Dog Friendly!

Peacefully & Conveniently Located w/BBQ Grill & FREE WiFI! ALL Pets Welcome!

8.8 out of 10, Excellent, (20)
"Wish there was some grass for the dog, good field to run the dog 10 minute walk away. Neighbors very nice. Could use a comfortable chair!!"
Peacefully & Conveniently Located w/BBQ Grill & FREE WiFI! ALL Pets Welcome!

Sparkling! Walking distance to Sumter Landing,pools & more,or take our golf cart

10.0 out of 10, Exceptional, (10)
"House was immaculate and well stocked with everything we needed. Host was very responsive to questions both before and during stay. It was the perfect location for us to hop in the golf cart and head to Lake Sumter Landing. Would definitely stay here again. "
Sparkling! Walking distance to Sumter Landing,pools & more,or take our golf cart

Fully Furnished Brand New Villa in Village of St. Catherine's with Cart

10.0 out of 10, Exceptional, (80)
"Eve"
Fully Furnished Brand New Villa in Village of St. Catherine's with Cart

Cutest Cottage in Ocala you tube it !

6.6 out of 10, (14)
"As brand new Husband and Wife; this was a perfect experience for us! Everything was as pictured. We enjoyed our visit and have a wonderful memory to treasure. Thank you!"
The price is AU$266
includes taxes & fees
25 Nov - 26 Nov
Cutest Cottage in Ocala you tube it !

Available with no weather damage. SUMMER BREEZE Lakeside Home Chain of Lakes Fl

9.8 out of 10, Exceptional, (108)
"I rented this house for my parents during hurricane milton. Jackie was amazing to work with beings I live out of town. My parents thought the place was beautiful & would love to go back."
Available with no weather damage. SUMMER BREEZE Lakeside Home Chain of Lakes Fl

WOW...ELEGANT... Courtyard VILLA + Golf CART, Steps to POOL, 3 Min to Sumter SQ

9.4 out of 10, Exceptional, (74)
"This worked out great for us and would stay again next time we visit The Villages "
WOW...ELEGANT... Courtyard VILLA + Golf CART, Steps to POOL, 3 Min to Sumter SQ
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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Other types of properties in Lady Lake you may be interested in

Microtel Inn & Suites by Wyndham Lady Lake/The Villages

3.0 star property
8.0 out of 10, Very good, (1005)
"Sheila, at the desk, gave some tips on things to do in town. Very friendly and check-in was easy. "
The price is AU$138
includes taxes & fees
26 Nov - 27 Nov
Microtel Inn & Suites by Wyndham Lady Lake/The Villages

SureStay Plus Hotel by Best Western The Villages

2.5 star property
8.4 out of 10, Very good, (355)
"Clean"
The price is AU$152
includes taxes & fees
25 Nov - 26 Nov
SureStay Plus Hotel by Best Western The Villages

Comfort Suites The Villages

2.5 star property
9.0 out of 10, Wonderful, (1006)
"Comfort Inn might be the best hotel ever"
The price is AU$149
includes taxes & fees
8 Dec - 9 Dec
Comfort Suites The Villages
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

Frequently asked questions

Are there holiday rentals in Lady Lake?

Yes, there are holiday rentals close to the most popular sights in Lady Lake, or you can select a more secluded option if you're looking for a relaxing stay. Discover why Lady Lake is known for its shops and lakeside. While you're here, grab a bite or have a drink at the restaurants.

What are some of the best holiday rentals that Lady Lake has to offer?

Marilyn’s Romantic Getaway: This highly rated holiday home rental in Lady Lake offers a fireplace, 1 hot tub and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Some other top choices in Lady Lake are Cozy Villages villa, 2 bed, 2 bath. Great Location and Get Cozy in this newly renovated home by The Villages!.

How many holiday rentals are there in Lady Lake?

With 174 Expedia holiday rentals, you're guaranteed to find just the right place for your Lady Lake stay.

What can I see and do in Lady Lake?

Bird Island and Little Pine Island are a couple of lovely local spots to get outside and enjoy nature. Other places in town to visit include Spanish Springs Town Square and Lakes Of Lady Lake Golf Club.

What are holiday rentals like in Lady Lake?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Lady Lake. Holiday rentals provide amenities such as hot tubs, fire pits and patios so you'll have all the conveniences of home. If you're concerned about a sanitised environment, a holiday rental can offer a sense of privacy away from public hotel lifts and busy lobbies while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular choice for small groups.