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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

Top guest favourite
Home in Winter Haven
4.99 out of 5 average rating, 126 reviews

Cheerful 4 Bed, 3 Bath Home with Screened Pool

SarahRating, 5 stars2 weeks ago
We had a great stay at Lauras place. We will be back next time we are in Winter Haven. It’s right next door to my mother in laws place which made it convenient. The kitchen was well stocked.
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 stars6 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 stars3 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
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 stars4 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 Winter Haven
4.94 out of 5 average rating, 68 reviews

Paraiso de relax Legoland

DestinyRating, 5 stars2 weeks ago
This is a great place to stay if you are planning a Lego land trip. The pool is a wonderful addition for little ones. If you are planning a long trip, I would bring some extra supplies (extra garbage bags, beach towels, etc). The house has everything you need for a short weekend. We would definitely stay here again’
Guest favourite
Home in Haines City
4.97 out of 5 average rating, 35 reviews

Southern Dunes: pool/spa; air hockey/game room

CindyRating, 5 stars1 month ago
Loved this place so much, the hosts were very responsive. The location was perfect, peaceful and quiet. Lovely people in the neighborhood who were welcoming. The house was exactly how it was pictured. I was even allowed to use the grill with propane included for no extra cost as well as no extra cost for heating of the pool which was amazing. Very beautiful home, felt at home immediately. I would definitely recommend this home and would love to come back for another stay.

Apartment rentals with a pool

Guest favourite
Apartment in Four Corners
4.98 out of 5 average rating, 217 reviews

Luxury 3 Bedroom Home at ChampionsGate Golf Resort

ShaneaRating, 5 stars2 days ago
We had a great stay! The place was nice and spacious perfect for our group of friends. There was plenty of room for everyone to relax comfortably, and everything was clean and well-kept. The check-in process was smooth, and the host was responsive and easy to communicate with. We’d definitely recommend this place to anyone traveling with a group!
Superhost
Apartment in Davenport
4.82 out of 5 average rating, 119 reviews

15 min from Disney On- site Bar, Restaurant & Gym

EvelynRating, 5 stars2 weeks ago
The accommodation is as described and even better. With easy access to the highway directly to Universal and Disney. The check-in instructions were also very clear, making the check-in process easy. It was sparkling when we entered and had everything you needed to cook and feel at home. It is spacious and ideal for 5 people Ellis was very responsive to our questions and always answered immediately. We would definitely choose it again to return! Thank you!!
Superhost
Apartment in Davenport
4.83 out of 5 average rating, 121 reviews

Orlando Spacious 2-Suites & Resort-Style Pool

AnaRating, 5 stars2 weeks ago
I enjoyed my stay here so much. The apartment was so cute and cozy, super clean and spacious. It is in a gated property so itself safe and overall a great location. If and when I am back in town, I will definitely stay here again.
Guest favourite
Apartment in Four Corners
4.87 out of 5 average rating, 142 reviews

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

DiannRating, 5 stars2 weeks 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!
Superhost
Apartment 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
Guest favourite
Apartment 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
Apartment in Davenport
4.84 out of 5 average rating, 171 reviews

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

AngelRating, 5 stars2 weeks ago
Thank you AJ and Nicole had a wonderful time this weekend definitely recommend
Superhost
Apartment in Kissimmee
4.77 out of 5 average rating, 126 reviews

1-101 Legacy Dunes, Gym, Tennis, Close To Disney!

ValentinaRating, 5 stars1 month 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!

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.
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, 252 reviews

Visit Disney World from a Sunny Home with a Pool

AngelaRating, 5 stars1 month ago
Home was beautiful! area was quite and close by of of attractions and restaurants. Only thing I advise is bringing extra wash towels, they are not provided. We went to Walmart which is literally right around the corner.
Guest favourite
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
Superhost
Home in Haines City
4.67 out of 5 average rating, 15 reviews

Beautiful Lakeview Retreat Drivable to Theme Parks

ChrisRating, 5 stars5 days ago
Great stay! Beautiful property on the lake. Would love to stay again sometime. Kayaks were a bonus! Cool to see the alligator cruising the cove!
Home in Davenport
4.83 out of 5 average rating, 48 reviews

Sleeps 16! Pool + Arcade | Orlando Resort Retreat

MindyRating, 5 stars3 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.
Villa in Davenport
4.67 out of 5 average rating, 6 reviews

Amazing Dream Solterra Villa -Disney/club/pool/spa

CraigRating, 5 stars48 months ago
They house is exactly like described and had a lot of room. The cleaning could be a bit better, but they apparently had a very short turn-around. Be prepared to have parties going on around you. They do not enforce the noise ordinance at midnight like they should. We were not their to party, so this did have an affect on some of our guests. Overall, it was a pleasant stay. Edward is a super host for a reason. He always returned my emails and texts. When we needed something he was sure to get it to us. He made us feel comfortable about this purchase from the very beginning.
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

    ₹4,300 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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