Vacation rentals with a pool in Leesburg

Find and book unique homes with a pool on Airbnb

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Popular amenities for Leesburg rentals with a pool

House rentals with a pool

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 Clermont
4.93 out of 5 average rating, 15 reviews

Gorgeous Island Estate- 10 BR in 2 Guest Houses

Andrea Rating, 5 stars2 weeks ago
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.
Top guest favorite
Home in Mount Dora
4.99 out of 5 average rating, 130 reviews

Mount Dora, FL Private Corner Home w/pool

TerryRating, 5 stars1 day ago
House was perfect for our girls getaway. Everything was great, clean, comfortable, and nicely decorated. Felt like home away from home.
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 stars3 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 Wildwood
4.97 out of 5 average rating, 73 reviews

New home in the new part of the villages.

KasieRating, 5 stars1 month ago
Nice and clean place! Would stay again.
Top guest favorite
Home in Wildwood
5 out of 5 average rating, 17 reviews

Brownwood Square - Villages Home

SherriRating, 5 stars4 weeks ago
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!!
Top guest favorite
Home in Sumterville
5 out of 5 average rating, 13 reviews

The Golfer's Edge

RuthRating, 5 stars1 week ago
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

Guest favorite
Condo in Florida Center
4.9 out of 5 average rating, 111 reviews

Studio near Universal Studios with great view

KinjalRating, 5 stars4 days ago
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!
Guest favorite
Condo in Kissimmee
4.87 out of 5 average rating, 134 reviews

Near Disney/Universal Lovely 2bedroom/2bath Condo

KassidyRating, 5 stars1 week ago
The place was great! it was perfect for a quick family trip to Disney. Would highly recommend!
Guest favorite
Condo in Florida Center
4.88 out of 5 average rating, 225 reviews

Maria Luz Studio-Huge Terrace/Universal area.

LisaRating, 5 stars2 weeks ago
Fantastic and Wonderful! This place has by far been the best!
Guest favorite
Condo in Kissimmee
4.79 out of 5 average rating, 187 reviews

Mickey's Retreat(K2)

JackRating, 5 stars1 month ago
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.
Guest favorite
Condo in Kissimmee
4.93 out of 5 average rating, 136 reviews

Chic Condo + Star Wars Room | Pool & Near Disney

CherylRating, 5 stars1 month ago
It was clean, looked like the pictures, responsive host. Would stay again.
Superhost
Condo in Kissimmee
4.88 out of 5 average rating, 120 reviews

2-104 Legacy Dunes, Lake View, Heated Pool, Gym

Cheryl CarterRating, 5 stars2 days ago
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.
Superhost
Condo in Four Corners
4.72 out of 5 average rating, 120 reviews

No BNB fees -Oasis Condo 5 min to Disney

SoniaRating, 5 stars2 weeks ago
Very beautiful location, calm surroundings and very close to all attractions
Top guest favorite
Condo in Orlando
5 out of 5 average rating, 142 reviews

Disney & Epic Free Shuttle, Kitchen

AlizahRating, 5 stars1 week ago
Great area to stay and awesome host!

Home rentals with a private pool

Superhost
Home in Haines City
4.78 out of 5 average rating, 9 reviews

Minniehaha Castle Retreat

AnetteRating, 5 stars2 months ago
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.
Home in Ocala
New place to stay

Designer Pet-Friendly Retreat with Heated Pool

AngieRating, 5 stars1 week ago
very clean and roomy! great hosts! big yard. Will be back for sure!
Superhost
Home in Davenport
4.95 out of 5 average rating, 115 reviews

Airy, Stylish Home with Pool Heat Included in Davenport

RachelRating, 5 stars1 month ago
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.
Home in Inverness

Family Villa Bettina - Recently Remodeled

ChuckRating, 5 stars60 months ago
Very clean, well appointed space. The pool is great.
Villa in Kissimmee
4.79 out of 5 average rating, 251 reviews

Visit Disney World from a Sunny Home with a Pool

ClaudiaRating, 5 stars1 month ago
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!
Guest favorite
Villa in Kissimmee
4.92 out of 5 average rating, 50 reviews

Family Retreat Near Disney with Pool & Hot Tub!

JenniferRating, 5 stars1 week ago
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
Home in Kissimmee
4.83 out of 5 average rating, 18 reviews

Sleeps 25! Resort Home near Parks | Coconut Breeze

ShanaRating, 5 stars2 weeks ago
Excellent space. Looks exactly like the pictures and was very well stocked!
Home in Kissimmee

Private Oasis with Pool & Spa- 3400clr

TarahRating, 5 stars1 week ago
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

Destinations to explore

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  3. Florida
  4. Lake County
  5. Leesburg
  6. Rentals with pools