House vacation rentals in Leesburg

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Popular amenities for Leesburg house rentals

House rentals with a pool

Superhost
Home in Wildwood
New place to stay

Poolside Palms in The Villages, Florida

CoryRating, 5 stars2 weeks ago
This home was absolutely amazing. It was like being in a brand new place. The out door space was great from the pool, tv, furniture and dining table. The interior of the home was well decorated and comfortable. The kitchen was wonderful to prepare meals in and was lacking nothing. The golf cart was pretty much brand new and worked wonderfully. We would absolutely stay here again.
Top guest favorite
Home in The Villages
4.99 out of 5 average rating, 141 reviews

Whole House-sleeps 10 The Villages Spanish Springs

ChelseaRating, 5 stars2 weeks 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 favorite
Home in The Villages
5 out of 5 average rating, 17 reviews

Heated Pool, Dog Friendly, Golf Cart Included

YolondaRating, 5 stars4 weeks ago
Everything was perfect, beyond expectations! Very nice and responsive hosts, definitely would to love visit again!
Guest favorite
Home in The Villages
4.95 out of 5 average rating, 126 reviews

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

LauraRating, 5 stars5 days ago
The home is beautiful and has everything you need. The pool is amazing. Check in and out was easy and Dena gave me great advice for where to play pickleball. The neighbors were super friendly too!
Top guest favorite
Home in Minneola
4.98 out of 5 average rating, 130 reviews

Pool + Heated spa Family friendly King suite Oasis

VivianRating, 5 stars1 week ago
What an amazing 2 weeks with family!! Don’t hesitate to book this GEM of a home! It’s beautiful, peaceful (on a culdesac) SUPER QUIET at night, great spots to eat at the waterfront and all around Minneola in general. We had an issue with warming the spa and both were very responsive, ordered the part and within 2 days its was perfect. This house had EVERY amenity you would need and then some…games indoor and outdoor, kids books, fire pit, swing, blankets to cozy up on couch, dog bowls, leashes, toys etc. They truly make you feel like it’s home. We can’t rave about it enough!! We were only a short half hour drive away from Disney also. Our 2 small dogs absolutely LOVED chasing lizards and frogs around the pool area! We would LOVE to come back if they would have us! Thank you again for being such great hosts! All you do to make your guests feel comfortable at home does NOT go unnoticed! Until next time beautiful Clermont/Minneola!!! 💕
Top guest favorite
Home in Lady Lake
5 out of 5 average rating, 30 reviews

Ranch Retreat~10 beds~New

MarilynRating, 5 stars3 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!
Top guest favorite
Home in The Villages
4.94 out of 5 average rating, 36 reviews

The Sunshine Retreat with Golf Car

JosephRating, 5 stars1 day ago
We enjoyed Kym's place. Conveniently located to Sawgrass. Enjoyed nightly live music. Enjoyed the front screened in porch in the evenings! Great host, would recommend to book Kym's place!
Guest favorite
Home in Wildwood
5 out of 5 average rating, 17 reviews

The Villages pool property with a 4-person cart!

GwenRating, 5 stars1 week ago
Beautiful house in a really nice area. The house was clean and comfortable. The screened in pool was perfect and clean. The area was nice and the golf cart was fun to use. The only tip I would give to someone staying at the house is to check the consumable items before heading to the store. There was about 2 tbs of watered down dishwashing soap, 1 extra garbage bag and 2 pods of laundry detergent. If you’re staying for a week, that’s not enough. To his credit, the owner said he would drop off some more stuff, but I ended up picking some of it up at the store when I went out. Not a deal breaker by any means, but you just might want to check for that stuff. We enjoyed our stay and would recommend the house to friends.

Weekly house rentals

Top guest favorite
Home in Leesburg
5 out of 5 average rating, 71 reviews

Waterfront cottage Haynes Creek

JeffreyRating, 5 stars2 weeks ago
As depicted in the photos, this is an older single wide trailer. Nothing fancy. But it has everything you need, is comfortable, allows pets, and is extremely well equipped and clean. Spotless actually. We did not use the provided kayaks or paddle boat, as we chose to go to the nearby springs instead. We had an awesome trip.
Top guest favorite
Home in Tavares
4.97 out of 5 average rating, 38 reviews

Entire 3 Bed Home with a Pool, by the Lake

AudraRating, 5 stars2 weeks ago
We stayed at this home with our family of 6. It had all the games, toys, and entertainment a family with four young kids could ask for! We had friends come over and visit us while we were there, and the big backyard with all the entertainment and the pool enclosed from the rain kept our two families happy while they were there with us. Night time, the backyard has lights, as well as the pool, there’s an electric fireplace that could warm us back up quick in the in betweens from our pool time. Just so well thought out how they put seating in every nook of this home, so no matter where our kids wondered, we had a place to relax while they played. We visited a couple springs about 30/40 minutes from our place (that require reservations online now - heads up), and even went to Sea World, and the beach a couple days. All only 1 hr - 1.5hrs from the house. The house felt like home away from home! Thank you for the wonderful home!
Guest favorite
Home in Mount Dora
4.93 out of 5 average rating, 70 reviews

1920's Boho Bungalow | Walk+Bike to Downtown

St Florian Coastal Properties LLCRating, 5 stars1 week ago
This home was clean and a relaxing Delight to hangout at :) the yard out back is beautiful and the bed was comfortable
Top guest favorite
Home in The Villages
4.96 out of 5 average rating, 23 reviews

Perfect Home in The Villages!

VictoriaRating, 5 stars6 months ago
Scott’s place was extremely clean and had everything we needed. The only thing I could say was there was not a table to seat 4 people or a coffee table so meals/games called for a little creativity. The advantage of that was the home felt super open. I would definitely book here again. It was a wonderful stay.
Top guest favorite
Home in The Villages
4.9 out of 5 average rating, 50 reviews

Stunning Villa 2B/2B With Golf Cart

RhondaRating, 5 stars3 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.
Top guest favorite
Home in Eustis
5 out of 5 average rating, 57 reviews

Porter's Porch

BarbaraRating, 5 stars3 weeks ago
Deborah was a great host. The little house is very cozy. What was really nice…. Is Deborah give us extra time to check out? It was great because it was much much needed so thank you so much Deborah.☺️ we look forward to staying again.
Guest favorite
Home in Leesburg
4.94 out of 5 average rating, 31 reviews

Royal Oak Lakeview Serenity

MattRating, 5 stars2 weeks ago
My son does fishy bf tournaments all over the state. This is definitely our favorite place we’ve stayed. We will 100% stay again
Top guest favorite
Home in Tavares
4.94 out of 5 average rating, 34 reviews

Quiet Cottage| Boat Parking| Near Downtown & Ramps

JessicaRating, 5 stars1 month ago
I can't BEGIN to say how amazing Lauren's home was! It was perfectly situated! It felt warm and cozy, like a home should! They had such a beautiful setting, secluded, peaceful! She had everything we needed inside & so clean! We highly recommend!

Private house rentals

Top guest favorite
Home in Tavares
5 out of 5 average rating, 25 reviews

Lake Harris Getaway

StephenRating, 5 stars1 month ago
This review has to start with the absolutely beautiful Lake setting and sunset views. You can sit in the backyard and watch Mother Nature at work. From changing cloud formations to the array of birds that land, hunt and just nurture their young. Our check in was great, from the trailer parking and loading our boat at the boat lift dock, to the garage and driveway access to unload. Mike made our stay as if we were at our own home (actually easier). From firewood to a portable screened fire pit, to the grill that allowed for a nice relaxing outside lunch/dinner. The boat dock allowed for quick access to great fishing, lake cruises, and beautiful river and canal trips to multiple restaurants and Tiki Huts throughout the Chain of Lakes. We will definitely book here again and highly recommend this Lake Home for a quiet, relaxing, full Lake experience. Mike made our stay as rewarding as the views we experienced throughout our week. Thank you so much Mike.
Top guest favorite
Home in The Villages
4.91 out of 5 average rating, 70 reviews

Villa la Bella

TerryRating, 5 stars2 weeks ago
We can’t say enough great things about this villa and our host Eric. He was available to answer questions throughout our stay and gave great information before we arrived. Extremely helpful guide❤️ We would very much recommend this villa and the villages as a destination. So much fun. Such great people.
Top guest favorite
Home in Leesburg
5 out of 5 average rating, 13 reviews

The Silver Lake Estate

MarianneRating, 5 stars7 months ago
Anthony’s place was lovely, great place for a family gathering and had all the amenities. We had a very minor issue and not only was Anthony responsive he had the issue resolved ASAP. Thank you for a great weekend. I would love to visit his Maine cabin.
Guest favorite
Home in The Villages
5 out of 5 average rating, 9 reviews

Designer Home in The Villages, FL.

JeannineRating, 5 stars2 months ago
Beautiful, beautiful place. Felt right at home....even better than my home as convenient first floor living. Quite neighborhood, many amenities in the house. Safe and clean environment conveniently located in The Villages.
Top guest favorite
Home in Weirsdale
4.96 out of 5 average rating, 70 reviews

Cheerful, two bedroom Animal loving home,

MargaretRating, 5 stars1 month 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 favorite
Home in Summerfield
4.99 out of 5 average rating, 90 reviews

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

MasonRating, 5 stars1 week 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 😊
Top guest favorite
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 favorite
Home in The Villages
4.95 out of 5 average rating, 20 reviews

19th Hole: Rest,Relax, Unwind 2/2 w/ Cart Villages

CarolineRating, 5 stars2 months ago
Very cute two bedroom that comes with a golf cart! Laurie was super helpful and accommodating. House was easy and lovely and charmingly decorated - highly recommend if you’re visiting The Villages! It was great to have more space than a hotel and we traveled with our six year old so we also really appreciated the separate bedroom and bathtub. The sheets and linens are super soft!

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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