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Holiday rentals with a pool in Cypress Gardens

Find and book unique homes with a pool on Airbnb

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Popular amenities for Cypress Gardens rentals with a pool

House rentals with a pool

Guest favourite
Home in Kissimmee
4.92 out of 5 average rating, 116 reviews

10 min Disney | Lakeview Hot Tub, BBQ | Game Room

CarterRating, 5 stars3 days ago
This was definitely a great place to stay, easy to check in and the host was so responsive! I hosted a birthday party and everyone had an amazing time and had everything they needed.
Superhost
Home in Winter Haven
4.92 out of 5 average rating, 36 reviews

Cozy Lakefront Home w/ Pool -7 mins from Legoland

AlejandroRating, 5 stars2 weeks ago
The house in general is fantastic, the beds are very comfortable everything is good but the front yard and the back yard need a little more love to make the house perfect other than that we really enjoyed our stay and recommend the house to anyone who visits Winter Haven
Top Guest favourite
Home in Kissimmee
4.99 out of 5 average rating, 105 reviews

Traveler's Dream - King Bed, Pool, Games, Disney+

LaverneRating, 5 starstoday
We really enjoyed our stay. It was comfortable, clean, and had everything we needed. Thank you for being such a great host—we’d love to come back in the future!
Guest favourite
Home in Four Corners
4.96 out of 5 average rating, 178 reviews

Luxurious Golf Front Oasis: Pool, Spa, View&Cinema

KaylaRating, 5 stars3 weeks ago
We had such a great time staying at Michael’s place! Our five teenagers were never bored with all of the fun amenities! The kids had a great time with the karaoke machine, arcade games and outdoor area! My husband and I love coffee, so we really appreciated the coffee bar and supplies that were provided. The house was beautiful and Michael was extremely responsive. We would stay again!
Guest favourite
Home in Winter Haven
5 out of 5 average rating, 21 reviews

4/2 New Spacious Pool Home

RickkidaRating, 5 stars3 weeks ago
Everything was great. Home was fully stocked with everything you and your family may need. My babies enjoyed the pool and Lego room. If we’re ever in this area again, I would definitely book with Rachel!
Top Guest favourite
Home in Winter Haven
4.96 out of 5 average rating, 23 reviews

Live your best Florida life!

JillRating, 5 stars1 week ago
We had a surprise engagement and also celebrated Father's Day with our local family and home was perfect. Plenty of parking, relaxing environment, beds slept great, and pool was relaxing. The neighborhood was peaceful and private. We plan to stay at Peggy's home again in the near future.
Guest favourite
Home in Haines City
5 out of 5 average rating, 11 reviews

House, backyard on the golf course Park Place

JamesRating, 5 stars1 month ago
Michel's villa in Haines City is amazing. We had been let down by a booking at another AirBnB which didn't match up to the photos and fortunately Michel's place was available for us to book instead. We were so relieved to discover that the pictures of Michel's place were accurate and perhaps didn't do it justice for how beautiful the place actually is. The villa is beautifully presented and equipped, everything is in working order and we had everything we needed. The villa is on a gated community alongside a golf course. The process for gaining access to the neighbourhood at the security barriers was quick and easy. There is a large Walmart nearby which was ideal for buying any supplies we needed during our stay. There are also plenty of restaurants/takeaway options in the area such as Manny's Chophouse and Floridinos. Overall we would rate the stay as 10/10 and we would consider staying here again. Thank you Michel!
Guest favourite
Home in Winter Haven
4.89 out of 5 average rating, 19 reviews

Family Fun: Pool, Arcade Games

CindyRating, 5 stars2 weeks ago
We had the best time during our stay here. My grandbabies loved all the games they had there for them to play with. We also loved having the pool. It was a great place to stay for sure if you’re going to Peppa Pig World or Legoland. Quick drive there and back. Also when we had questions they were prompt to answer. Great Host. Would definitely stay again when we go back if available. Cindy Sirmans

Condo rentals with a pool

Guest favourite
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 favourite
Condo in Four Corners
4.98 out of 5 average rating, 216 reviews

Luxury 3 Bedroom Home at ChampionsGate Golf Resort

JaninaRating, 5 stars2 weeks ago
Excellent service and quality, the host is very concerned about his guests. 100% recommended
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 stars1 week ago
Very beautiful location, calm surroundings and very close to all attractions
Guest favourite
Condo in Four Corners
4.87 out of 5 average rating, 142 reviews

"Ocean's Gate" - 2BD/2BA condo near Disney

DiannRating, 5 stars1 week ago
Great location, comfortable and clean - perfect spot to visit Orlando and all it has to offer!! This condo was clean, modern, comfy beds & furniture, efficiently equipped kitchen, etc. We liked this being in a quiet, private community and really enjoyed the pool & clubhouse! Nothing negative to share! This is a great choice!
Guest favourite
Condo in Kissimmee
4.9 out of 5 average rating, 149 reviews

Cheery 2BR Condo w/zero entry pool near Disney

MindyRating, 5 stars2 weeks ago
very cozy private location with lots of stores within 5 mins. beach accessories available for convenience. will book again.
Superhost
Condo in Davenport
4.84 out of 5 average rating, 170 reviews

Full-Service Gated Resort, Disney, Universal, MCO!

AngelRating, 5 stars1 week ago
Thank you AJ and Nicole had a wonderful time this weekend definitely recommend
Superhost
Condo in Kissimmee
4.77 out of 5 average rating, 126 reviews

1-101 Heated Pool, gym, tennis, Close To Disney!

ValentinaRating, 5 stars4 weeks ago
I had a great stay! The place was clean, comfortable, and just as described. The host was very friendly and responsive, which made everything super easy. I’d definitely stay here again!
Guest favourite
Condo in Kissimmee
4.9 out of 5 average rating, 218 reviews

Perfect place for your Disney escape

AmariRating, 5 stars1 week ago
Nice place to stay!! It’s worth booking with Maria and Andy and they always give you quick responses.

Home rentals with a private pool

Villa in Four Corners
4.33 out of 5 average rating, 3 reviews

Disney's Championsgate: Private Pool & Arcade Fun!

AurianaRating, 5 stars6 months ago
This property was very nice and matched the photos to a T. The house was spotless & very spacious. The renovated design was modern and the themed rooms were perfectly executed. The only downside was the check-in process at the gate, but after a quick phone call, the issue was resolved. I absolutely loved the space. 10/10.
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.
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.
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 favourite
Villa in Kissimmee
4.92 out of 5 average rating, 50 reviews

Family Retreat Near Disney with Pool & Hot Tub!

JenniferRating, 5 stars6 days 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
Superhost
Home in Haines City
4.64 out of 5 average rating, 14 reviews

Beautiful Lakeview Retreat Drivable to Theme Parks

AaronRating, 5 stars3 weeks ago
This place was perfect for our two families (10 people in total) while we visited Legoland. Kitchen and hangout space was great.
Home in Davenport
4.83 out of 5 average rating, 48 reviews

Sleeps 16! Pool + Arcade | Orlando Resort Retreat

MindyRating, 5 stars2 weeks ago
Pictures shown is exactly how the place looks. Felt secure in the neighborhood. Plenty of amenities. Pool and hot tub was a plus. Game room was also a plus for the little ones.
Home in Kissimmee

Private Oasis with Pool & Spa- 3400clr

TarahRating, 5 stars1 week ago
The home was beautiful & exactly as described.

Quick stats about holiday rentals with a pool in Cypress Gardens

  • Total rentals

    70 properties

  • Nightly prices starting at

    $84 NZD before taxes and fees

  • Total number of reviews

    1.8K reviews

  • Family-friendly rentals

    40 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

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