House holiday rentals in Lady Lake

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Popular amenities for house rentals in Lady Lake

House rentals with a pool

Top guest favourite
Home in The Villages
4.96 out of 5 average rating, 55 reviews

Beautiful Villages 2/2 Home. Perfect Location

ScottRating, 5 stars2 weeks ago
Thanks we are frequent visitors and stay was amazing! Would recommend!
Top guest favourite
Home in The Villages
5 out of 5 average rating, 22 reviews

The Palms. Luxurious, pool, golf/bird pond view

NikiRating, 5 stars2 weeks ago
We rented John’s place for a girls’ weekend and to celebrate with a friend who lives in the area. The home is just we described, very clean, and perfect for our stay. The pool was amazing, extremely peaceful and allowed us to have a much needed relaxing weekend.
Top guest favourite
Home in The Villages
5 out of 5 average rating, 34 reviews

Pool Home Great Location 3/2 & 2 Golf Carts

TammyRating, 5 stars1 month ago
I’ve stayed at a few Airbnb’s, this was BY FAR the most comfortable one yet!! Honestly, we all felt so at home and settled in~it was perfect! The neighbors were friendly, the golf cart was great!! The town squares were a blast! We would 100% rent this exact home again. Actually, one of my sisters already did for this fall! Dean & Sheila always responded quickly with any questions I had. I can’t say enough good on how perfect this was!!!!!!!!
Top guest favourite
Home in The Villages
5 out of 5 average rating, 9 reviews

On The Links-4bd w/pool in Spanish Springs!

JenniferRating, 5 stars1 month ago
**Perfect Stay!** If you’ve ever checked into an Airbnb and wondered how it got a five-star rating, you won’t have to question that here! This place was spotless, impeccably maintained, and had everything we needed for a comfortable stay. We rented a golf cart, which made getting to the nearby Lake Sumpter bars and restaurants super easy. And let’s talk about the POOL – it was incredibly relaxing! We can’t wait to come back again. Highly recommend!!!
Guest favourite
Home in The Villages
5 out of 5 average rating, 16 reviews

Heated Pool, Dog Friendly, Golf Cart Included

MichelRating, 5 stars2 months ago
Cosy setting, the bar feature is a nice add on. Pool and hot tub setting really nice especially at night with the hung lighting. Hosts very responsive and helpful.
Top guest favourite
Home in The Villages
4.96 out of 5 average rating, 74 reviews

Close to Everything- Live Music, Dining & More!

MatthewRating, 5 starstoday
The place matches the photos. Well kept place. I’ll be returning in feature
Superhost
Home in The Villages
5 out of 5 average rating, 4 reviews

The Villages, Heated Pool Walk to Sawgrass

MistiRating, 5 stars1 week ago
I can’t say enough about this place or the host!! It was way more than I ever expected. We were able to check in sooner than the original check in time. Dave was awesome with communication and periodically checked in to make sure everything was going good throughout our stay. Everything was well stocked in the house from the kitchen (including spices and other little stuff that you would normally have to run out and buy to make a meal) to the bathrooms. There is everything you would need for the pool also. Dave even thought about your furry friends by providing leashes/bowls and treats. The house was immaculate! All you needed to do was literally pack your bags. Thanks for a great stay. We hope to return to the villages in the winter time!
Top guest favourite
Home in Ocala
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!

Weekly house rentals

Guest favourite
Home in The Villages
4.95 out of 5 average rating, 20 reviews

Cheerful King Bed Home in the Villages

BobbyRating, 5 stars1 month ago
Amazing host, amazing location, amazing property and amazing value!
Top guest favourite
Home in Weirsdale
4.96 out of 5 average rating, 70 reviews

Cheerful, two bedroom Animal loving home,

MargaretRating, 5 stars4 weeks ago
Super cute place and great location near the horse park. Adrian was an excellent host and thought of everything. Our folks really enjoyed their stay.
Top guest favourite
Home in Summerfield
4.99 out of 5 average rating, 90 reviews

Getaway on the Waterway: Kayak, SUP, fish, relax!

MasonRating, 5 stars5 days ago
Absolutely amazing ⭐️ ⭐️ ⭐️ ⭐️ ⭐️ we stayed for 2 nights as we made our journey driving up to Montreal. My family did not want to leave 🤣 Amazing location and activities! Not only that but Laura’s communication was amazing (way before we arrived, during and after). She has so many little things that most Airbnbs don’t bother with or don’t think of, like beach towels, extras in the bathroom for convenience, batteries and honestly the list goes on and on! I thought this trip was super personalised and was a perfect get away for a family or couple. The neighbour was super friendly as well! Thank you Laura 😊
Guest favourite
Home in Lady Lake
4.9 out of 5 average rating, 67 reviews

STAY IN THE VILLAGES! YOUR HOME AWAY FROM HOME 🌴

BrianRating, 5 stars1 month ago
Communication with Erika was excellent, she reaponded very quickly when I had questions. The house was exactly at shown on the listing. I would stay here again if I'm back in that area.
Top guest favourite
Home in The Villages
5 out of 5 average rating, 10 reviews

Little Paradise in the Villages - with Golf Cart

TimothyRating, 5 stars2 months ago
We enjoyed our two week stay very much. The home had all the necessary basics, was very clean, and comfortable. The hosts were very responsive. We had a minor issue and they had someone there within ten minutes to resolve it! Having the golf cart included is a plus. We navigatigated our travels through The Villages quite comfortably the majority of the two weeks using the cart rather than the car. There is a pool quite close to the home and the home is also located pretty close to Brownwood Square. We would highly recommend this property.
Guest favourite
Home in The Villages
4.91 out of 5 average rating, 43 reviews

Beautiful Designer Home -Golf Cart- Walk to Sumter

JenniferRating, 5 stars1 week ago
Lori’s place is lovely. Spacious, very clean, great location. Lots of basics (!toilet paper , paper towels, spices, aluminum and plastic wrap, garbage bags) so you don’t have to worry about getting it yourself. In the middle of everything. Very quiet and peaceful neighborhood. No problems at check in. Very easy. I would recommend and would definitely stay here again.
Top guest favourite
Home in The Villages
5 out of 5 average rating, 17 reviews

Private Villa by Lake Sumter Square

JonathanRating, 5 stars4 days ago
We really enjoyed our stay! It was the perfect size for our family of 4 (2 littles). Very spacious and clean. It was less than a 2 min drive to Lake Sumter Landing. Laura was great at communicating with us quickly and efficiently. We would highly recommend this home.
Guest favourite
Home in The Villages
4.94 out of 5 average rating, 86 reviews

Walk to Sumter w/cart - Beautiful Courtyard Villa

TinaRating, 5 stars2 weeks ago
Perfect, quiet and just like being at home! Loved getting a paper in the am, Nice touch! Great convenient area!

Private house rentals

Top guest favourite
Home in The Villages
5 out of 5 average rating, 32 reviews

SpringHouse - 3 Bdrm Patio Villa in The Villages

LauraRating, 5 stars1 day ago
Beautiful, spacious, FULL of amenities and lots of room for our own stuff. Walt just made everything so easy and comfortable. We’d love to come back and take advantage of all that The Villages has to offer.
Top guest favourite
Home in The Villages
4.98 out of 5 average rating, 42 reviews

Great location w/ golf cart! Lake Sumter-Brownwood

DianeRating, 5 stars1 month ago
Great location. House was warm & inviting. Rick was a pleasure to deal with. Very responsive to any messages or concerns. We had a great week & hope to stay again.
Top guest favourite
Home in The Villages
4.94 out of 5 average rating, 32 reviews

3/2 Home near Sumter Landing

BarbaraRating, 5 stars3 weeks ago
The house was everything I expected and more. So convenient to everything the pools Sumter Landing, and having the golf cart was a definite, plus.
Top guest favourite
Home in The Villages
4.97 out of 5 average rating, 93 reviews

Fabulous Courtyard Villa close to Sumter Landing

SueRating, 5 stars3 months ago
We had a fantastic stay at Gayle’s home. The home more than exceeded our expectations. The home is in a great location. Walkable to the rec centre for pickleball and choice of pools. Close to the market square where great restaurants and live music are available every night. The golf cart was definitely an added bonus and we would highly recommend it as a way to tour the villages. Gayle is a great host, very responsive to our questions and always available to assist. We hope to have the opportunity to stay at this wonderful location again.
Top guest favourite
Home in The Villages
4.97 out of 5 average rating, 30 reviews

Cozy Patio Villa (Newell)

CharlesRating, 5 stars1 week ago
The house was comfortable, and well stocked and clean. Thanks Anna for sharing such a nice place.
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 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!

Quick stats about house rentals in Lady Lake

  • Total rentals

    130 properties

  • Total number of reviews

    2K reviews

  • Family-friendly rentals

    100 properties are a good fit for families

  • Pet-friendly rentals

    50 properties allow pets

  • Rentals with a pool

    50 properties have a pool

  • Rentals with dedicated workspaces

    70 properties have a dedicated workspace

Destinations to explore

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