House holiday rentals in Leesburg

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Popular amenities for house rentals in Leesburg

House rentals with a pool

Top guest favourite
Home in The Villages
4.99 out of 5 average rating, 141 reviews

Whole House 3 Bedroom (sleep 10) Spanish Springs

ChelseaRating, 5 stars1 week ago
Great location in Spanish Springs at the Villages. Close to a lot of options for dining and shopping. Quiet neighborhood & peaceful patio. It’s our third time staying there & we would stay again when in the area.
Guest favourite
Home in The Villages
4.98 out of 5 average rating, 49 reviews

Villages-Waterfrnt, 3 king bds/2.5Ba+golf crt

LynnRating, 5 stars2 months ago
Very nice house. Place was clean. No complaints. Just wish it’s was closer to Brownwood square. Sawgrass is nice but doesn’t have that much there. I think when Eastport opens this house will be a great location
Top guest favourite
Home in Mount Dora
4.99 out of 5 average rating, 128 reviews

Mount Dora, FL Private Corner Home w/pool

StanleyRating, 5 stars4 days ago
We had another great stay at Belkins place. The house was clean, cozy, spacious, and exactly as described in the listing. The location was convenient and quiet, making it easy to get around and relax. Belkins was friendly, helpful, and responsive. She made sure we had everything we needed for a comfortable stay. I would definitely recommend this place to anyone visiting the Mt. Dora area, and we'd be happy to stay again!
Guest favourite
Home in The Villages
4.95 out of 5 average rating, 125 reviews

2/2 custom pool home with 4 person gas golf cart

SarahRating, 5 stars4 weeks ago
Great stay! Close to everything and love the golf cart and pool
Guest favourite
Home in The Villages
4.94 out of 5 average rating, 18 reviews

The Sandpiper Villa

AprilRating, 5 stars1 week ago
Sandpiper is a beautiful home away from home. We visited the Villages to attend my father’s 85th Birthday celebration and party. The Sandpiper is beautifully decorated and the coffee station was so convenient and needed for all the family activities leading up to the party. This two bedroom property was spacious for the 6 of us and very convenient to get to the squares like Saltgrass and Brownwood and grocery stores like Publix. And once Eastport opens you’ll be right there in minutes. The manager owners were extremely helpful and responsive to any questions we had. Would highly recommend Sandpiper to anyone visiting the Villages.
Top guest favourite
Home in Lady Lake
5 out of 5 average rating, 30 reviews

Ranch Retreat~10 beds~New

MarilynRating, 5 stars2 weeks ago
Thank you so much for your warm hospitality. We had an amazing weekend— your beautiful home was incredibly peaceful and made for such a memorable stay. My family was truly happy and felt so welcomed. We deeply appreciate everything!
Guest favourite
Home in The Villages
4.94 out of 5 average rating, 34 reviews

The Sunshine Retreat with Golf Car

BethRating, 5 stars2 weeks ago
We had a wonderful stay at this great place in a fantastic location within The Villages. It was very comfortable and offered everything we needed for a relaxing getaway. The value was excellent for our family, and we truly enjoyed the local pools, restaurants, and the wide variety of activities available nearby. Highly recommend for anyone looking for a fun and easy stay in The Villages!
Top guest favourite
Home in Sumterville
5 out of 5 average rating, 12 reviews

The Golfer's Edge

NevineRating, 5 stars5 days ago
The house was beautiful and clean. We are a family of 5 so we loved that our oldest had her privacy in a separate guest room with a king bed. The young two children were so comfortable sharing the double bed rooms. The mattresses and pillows were very comfortable. The floors, bathrooms, and kitchen were all spotless. When I reached out to Rachel, she immediately responded and took care of our needs. We will definitely be back. My husband and my kids loved riding around in the golf cart. It’s something we never experienced before in any of previous stays elsewhere. Overall we had a great experience.

Weekly house rentals

Top guest favourite
Home in The Villages
5 out of 5 average rating, 10 reviews

Hideaway in the Villages

AmandaRating, 5 stars1 month ago
Great atmosphere! We rented a golf cart. It’s like 35 a day or something very nice. Make sure you download the villages app so you can get around golf carts have their own road on tunnels that get you across the highway to Publix to restaurants to gas stations like it’s really unique. All with in 3 miles of your stay and all golf cart assessable. Scott was amazing with communication!
Top guest favourite
Home in Weirsdale
4.96 out of 5 average rating, 70 reviews

Cheerful, two bedroom Animal loving home,

MargaretRating, 5 stars3 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.
Guest favourite
Home in The Villages
4.98 out of 5 average rating, 41 reviews

Great location w/ golf cart! Lake Sumter-Brownwood

DavidRating, 5 stars1 month ago
Really well furnished and kitted out. Golf cart worked great. Nice welcome snacks, coffee and cooking supplies. Decor was very well done. Highly recommend this property and will stay again in the future.
Top guest favourite
Home in Tavares
4.97 out of 5 average rating, 35 reviews

Tavares Tropical Hideaway with Canal & Boat Slip

ThomasRating, 5 stars3 weeks ago
We enjoyed our stay very much. the boat slip was handy. The backyard was comfortable and quiet.
Guest favourite
Home in Lake Panasoffkee
4.83 out of 5 average rating, 60 reviews

Brand New! Modern Guesthouse!

AngelaRating, 5 stars2 weeks ago
Everything was nice. A very clean place. The host was great. It was more than what I thought it would be for the price. I would book again.
Superhost
Home in Lady Lake
4.73 out of 5 average rating, 22 reviews

Entire house unique location

DanRating, 5 stars1 week ago
Very clean, peaceful, easy in and out. Located perfectly for me.
Guest favourite
Home in Tavares
4.94 out of 5 average rating, 83 reviews

Retreat Overlooking Lake Dora!

CaitlinRating, 5 stars3 weeks ago
My bridesmaids and I stayed here the night before and night of my wedding, which was at the pavilion on the lake. It was VERY close and easily accessible. Any questions we had were quickly answered. There is security cameras on the premises so we felt safe and comfortable. The location is very spacious and was very clean. Check in/out is super simple and instructions were clear. 100% will recommend in the future
Top guest favourite
Home in The Villages
4.9 out of 5 average rating, 50 reviews

Stunning Villa 2B/2B With Golf Cart

RhondaRating, 5 stars2 weeks ago
We loved staying at Nicole’s house. The house was beautifully decorated and very clean. Nicole was very responsive to any questions. I highly recommend staying here.

Private house rentals

Top guest favourite
Home in The Villages
5 out of 5 average rating, 19 reviews

Patio Villa near Sawgrass Grove!

SteveRating, 5 stars2 months ago
Janine is a lovely host. She goes over and above to make sure her guests are comfortable and have everything they need. Very responsive, kind and flexible. You won’t find a better host on this platform. This area of the Villages has great areas for biking and walking along the preserve away from the busy golf cart paths. The house is lovely; comfortable, spotlessly clean and so light and bright. We loved our winter there and hope we can come back. Thank you for the Christmas touches, the grill, the early check-in and the welcome gift. It was appreciated.
Top guest favourite
Home in Ocklawaha
5 out of 5 average rating, 27 reviews

Live Oak Lake House

JeffreyRating, 5 stars3 weeks ago
Recommend if you want peace and quiet. I would stay again.
Guest favourite
Home in The Villages
4.9 out of 5 average rating, 42 reviews

Beautiful Designer Home -Golf Cart- Walk to Sumter

StephanieRating, 5 stars1 month ago
The place is walkable from the bus station even at 2am. Very safe and well lit to get there. The golf cart was a plus and allowed us transportation to downtown without walking. Great breakfast places only a ride away. The bedrooms were roomy and clean. The living room was very clean and remotes for tv were self explanatory. The bathrooms had all soaps, shampoos and body soap. I was travels light for the weekend and this place had a hair dryer, magnifying mirror and clean towels. The back porch was cozy and I enjoyed a morning coffee with the chirping of birds and watching squirrels. This place was 6 minutes from my parents place and I would definitely recommend staying here. They even had coffee, coffee pot and creamer! There is a washer and dryer but we didn’t use it those considered it… lol Lori got our guest passes to use the facilities- ie the pool I would say the only thing missing is a map of the cart trails - I didn’t ask so I’m unsure if that is available!
Top guest favourite
Home in The Villages
5 out of 5 average rating, 31 reviews

Moultrie Creek Retreat with Golf Cart!

ElizabethRating, 5 stars5 days ago
Highly recommend. Super clean home, very responsive and provides clear detailed instructions from checking in to check out. The home was perfect place to stay, while visiting family in the villages. Will definitely rent again! 10/10!
Top guest favourite
Home in The Villages
5 out of 5 average rating, 17 reviews

DeLuna Dreamhouse

BarbaraRating, 5 stars1 week ago
We enjoyed our stay at DeLuna Dreamhouse. The host started communication before we checked in and made sure we knew what to expect. The pictures do the house justice as the home is as beautiful as listed. The beds are comfortable, linens are clean, and all of the items you need to access the community and the property are provided (garage openers, keys, and gate cards). The host was very responsive of messages during the stay as well. There were also several nice detailed touches that we appreciated such as toiletries, pantry items, many towels and extra linens, plenty of dishes and hygiene items provided. Would recommend this home and consider it for future stays.
Guest favourite
Home in Leesburg
4.77 out of 5 average rating, 74 reviews

Your home away from home.

NeilRating, 5 stars2 weeks ago
Have stayed here a few times and it's always great.
Top guest favourite
Home in Wildwood
5 out of 5 average rating, 10 reviews

2/2 Villa in St. Catherine

KristiRating, 5 stars1 month ago
We have rented with airbnb before, and from start to finish this property was head and shoulders above the other properties we’ve stayed at. The attention to detail and extra supplies that were stocked in the home made our stay sooo much easier and more comfortable! From laundry soap, to zip lock bags and toilet paper, we didn’t have to worry about any of the “extras”! That was a huge perk and was so impressive to our family. Another great touch was that the couch and beds were extremely comfortable and all of the bedding/sheets were so soft! We felt like they shopped for their home, rather than a “rental”. The hosts were awesome- very responsive and helpful with any questions we had along the way. The house is very well kept and comes with plenty of organization and storage. We would 100% rent from Daniel & Lauren again. Thanks for a smooth and comfortable stay!
Top guest favourite
Home in The Villages
5 out of 5 average rating, 15 reviews

Welcome to the Sawgrass Area in The Villages!

BrianRating, 5 stars3 weeks ago
The house was great from the minute we walked in. Very easy and clear instructions for entry. As soon as you walk in it feels like home and is well maintained. The neighborhood pool is available within a short walk or a quick golf cart ride. Met really friendly people there everyday we stopped in for a swim. We were also a 4/5 minute golf cart drive from Sawgrass. Easy drive up to Brownwood too. The neighborhood was so friendly, and we got “free entertainment” when a band played 1/2 block away at a neighborhood concert / block party. All in all, we had zero issues from check in to check out and would highly recommend this residence to anyone wanting to feel at home for their entire stay.

Quick stats about house rentals in Leesburg

  • Total rentals

    140 properties

  • Total number of reviews

    2.6K reviews

  • Family-friendly rentals

    110 properties are a good fit for families

  • Pet-friendly rentals

    40 properties allow pets

  • Rentals with a pool

    40 properties have a pool

  • Rentals with dedicated workspaces

    70 properties have a dedicated workspace

Destinations to explore

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