
Vacation rentals with a pool in Leesburg
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Leesburg
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.
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Popular amenities for Leesburg rentals with a pool
House rentals with a pool

Villa la Bella
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.

The Silver Lake Estate
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.

Gorgeous Island Estate- 10 BR in 2 Guest Houses
My family vacation at Ever After was wonderful and all 15 of us had a great time. We celebrated the birthdays of 3 of my 7 grandchildren. Each loved getting a chance to decide what we would do on their special day. Of all the activities that were offered, we enjoyed many, but ended up mostly lounging around and in the pool and spa. We all had fun on the pool slide but the kids were obsessed with it, riding it over and over again all day long. The themed bedrooms were impressive and the details that went into decorating them were amazing! Just to clarify for anyone thinking of booking a stay, the main house with the pool is a few minutes walk from the guest houses and the bedrooms are split between the 2 guest houses. We all really enjoyed watching movies in the theater room but would have liked to watch a few on the outdoor screen. The mosquitoes were bad even with the sprays and candles we used to keep them away so we didn't do much outside at night. Thanks, Andrew, for everything.

Mount Dora, FL Private Corner Home w/pool
House was perfect for our girls getaway. Everything was great, clean, comfortable, and nicely decorated. Felt like home away from home.

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

New home in the new part of the villages.
Nice and clean place! Would stay again.

Brownwood Square - Villages Home
Everything about our stay was great. The pool towels were a great touch. The golf cart made experiencing the area much more fun. We felt right at home and would definitely stay here again. Thanks Brandon!!

The Golfer's Edge
We came to visit family again and were thrilled to see that the same Airbnb (Rachel’s) we stayed at before was available. The description is very accurate—truly a five-star home!
Condo rentals with a pool

Studio near Universal Studios with great view
The apartment BNB was really great and exactly as described with all basic amenities provided. Super close, walkable distance, to a variety of restaurants with different cuisines. Universal Studios is a close 10 mins drive/uber ride away. The studio feels super cozy, the view from the balcony is also very nice. Laundry room is right next to the unit which was very convenient. Hosts are quick to respond to any messages/questions you may have. Enjoyed my time at this Airbnb!

Near Disney/Universal Lovely 2bedroom/2bath Condo
The place was great! it was perfect for a quick family trip to Disney. Would highly recommend!

Maria Luz Studio-Huge Terrace/Universal area.
Fantastic and Wonderful! This place has by far been the best!

Mickey's Retreat(K2)
Stayed at Celso’s apartment for 2-weeks. It was a great size for 2 people and an ideal location for those looking to do the Disney and Universal parks. Apartment is just a short drive away from plenty of shops, restaurants and fast food places. It also has a 24h petrol (gas) station just outside of the complex which is really convenient. Overall, really enjoyed our stay the complex is really nice and feels very welcoming. Would highly recommend for two people. Celso was a great host, super responsive to any messages and helpful with any questions we had during our stay. One minor downside, not to the fault of Celso or his apartment, but the complex had a nesting hawk during our stay. This was no issue for 95% of our stay, but did swoop at us once. Would advise being cautious when walking to the car park, especially with young children.

Chic Condo + Star Wars Room | Pool & Near Disney
It was clean, looked like the pictures, responsive host. Would stay again.

2-104 Legacy Dunes, Lake View, Heated Pool, Gym
We loved the condo. It was beautiful and we enjoyed it. The only complaint we had (which was out of Anthony’s control) is the neighbors above us were loud and woke us up a few times with the stomping. Other than that, it was awesome! We would stay with Anthony again.

No BNB fees -Oasis Condo 5 min to Disney
Very beautiful location, calm surroundings and very close to all attractions

Disney & Epic Free Shuttle, Kitchen
Great area to stay and awesome host!
Home rentals with a private pool

Minniehaha Castle Retreat
This house was ideal for our weekend. Everything we needed was provided, and the extras pillows, towels, and toiletries were a nice touch. The pool water heater was a great addition, making the water perfect for the time of year ($10 a day was worth it) . We enjoyed our stay and would recommend it to others.

Designer Pet-Friendly Retreat with Heated Pool
very clean and roomy! great hosts! big yard. Will be back for sure!

Airy, Stylish Home with Pool Heat Included in Davenport
Had a great stay at Phil's place. The home was perfect for mother's day weekend. My daughter loved the pool. The home was clean! 10/10 recommend.

Family Villa Bettina - Recently Remodeled
Very clean, well appointed space. The pool is great.

Visit Disney World from a Sunny Home with a Pool
I can’t say enough good things about this Airbnb – it was absolutely incredible from start to finish. The space was spotless, nicely decorated and had every amenity we could have possibly needed (and then some!). It truly felt like a home away from home, with thoughtful touches throughout that made our stay extra special. The host was communicative welcoming and very helpful!

Family Retreat Near Disney with Pool & Hot Tub!
This home is just at pictured. Has everything you’ll need. Grill and propane being available on site were a very nice bonus. Hot tub and heated pool were fantastic after walking all day. Host was amazing and communication was very quick. Highly recommend this place and location

Sleeps 25! Resort Home near Parks | Coconut Breeze
Excellent space. Looks exactly like the pictures and was very well stocked!

Private Oasis with Pool & Spa- 3400clr
The home was beautiful & exactly as described.
Quick stats about vacation rentals with a pool in Leesburg
Total rentals
50 properties
Nightly prices starting at
G$6,276 GYD before taxes and fees
Total number of reviews
1.4K reviews
Family-friendly rentals
40 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
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- Universal Studios Florida
- Orange County Convention Center
- Weeki Wachee Springs
- Universal's Volcano Bay
- Old Town Kissimmee
- Discovery Cove
- Disney's Animal Kingdom Theme Park
- Universal Orlando Resort
- SeaWorld Orlando
- Disney Springs
- ESPN Wide World of Sports
- Amway Center
- Epcot
- Magic Kingdom Park
- Reunion West
- Aquatica
- Rainbow Springs State Park
- ChampionsGate Golf Club
- Disney's Hollywood Studios
- Kissimmee Lakefront Park
- Walt Disney World Resort Golf
- Island H2O Water Park
- Blue Spring State Park
- ICON Park