A sunset over a water body with trees silhouetted against the sky.

Hotels with Swimming Pools in Cypress Gardens

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Check availability on Cypress Gardens Hotels with Swimming Pools

This weekend
7 Aug - 9 Aug
Next weekend
14 Aug - 16 Aug

Our top choices for Cypress Gardens hotels with a pool

Outdoor pool, pool umbrellas, pool loungers

1. Best Western Plus Winter Haven Inn & Suites 

Best Western Plus Winter Haven Inn & Suites 
3.5 star property
Winter Haven
9.6 out of 10, Exceptional, (1,342 reviews)
  • cleanliness
    Sun-soaked pool area creates perfect retreat near LEGOLAND Florida with loungers and umbrellas.
The price is S$164
includes taxes & fees
9 Aug - 10 Aug
Best Western Plus Winter Haven Inn & Suites 
Property grounds

2. Lake Roy Beach Inn

Lake Roy Beach Inn
2.0 star property
Winter Haven
7.0 out of 10, Good, (1,002 reviews)
  • cleanliness
    Lakeside pool paradise awaits with serene water views and complimentary loungers for ultimate relaxation.
The price is S$126
includes taxes & fees
9 Aug - 10 Aug
Lake Roy Beach Inn
Outdoor pool

3. Economy Suites

Economy Suites
2.0 star property
Winter Haven
4.8 out of 10, (427 reviews)
  • cleanliness
    Refreshing poolside escape with bar service makes this motel your LEGOLAND® retreat after sunny adventures.
The price is S$102
includes taxes & fees
7 Aug - 8 Aug
Economy Suites
Outdoor pool

4. Rodeway Inn & Suites Winter Haven Chain Of Lakes

Rodeway Inn & Suites Winter Haven Chain Of Lakes
2.0 star property
Winter Haven
5.4 out of 10, (287 reviews)
  • cleanliness
    Splash into fun at this lakeside motel with a sun-soaked pool just minutes from LEGOLAND Florida.
The price is S$116
includes taxes & fees
12 Aug - 13 Aug
Rodeway Inn & Suites Winter Haven Chain Of Lakes
Outdoor pool, open 7:00 AM to 10:00 PM, pool loungers

5. Holiday Inn Winter Haven by IHG

Holiday Inn Winter Haven by IHG
3.0 star property
Winter Haven
9.0 out of 10, Wonderful, (1,008 reviews)
  • cleanliness
    Dive into crystalline blue waters at this outdoor pool oasis with comfy loungers and sunshine appeal.
The price is S$121
includes taxes & fees
6 Sept - 7 Sept
Holiday Inn Winter Haven by IHG
Outdoor pool, pool umbrellas, pool loungers

6. Hampton Inn Winter Haven

Hampton Inn Winter Haven
2.5 star property
Winter Haven
9.0 out of 10, Wonderful, (1,003 reviews)
  • cleanliness
    Shimmering blue waters await at this family-friendly hotel with pool loungers and workout options.
The price is S$128
includes taxes & fees
6 Sept - 7 Sept
Hampton Inn Winter Haven
Outdoor pool, open 9:00 AM to 10:00 PM, pool loungers

7. Courtyard by Marriott Winter Haven

Courtyard by Marriott Winter Haven
3.0 star property
Winter Haven
9.4 out of 10, Exceptional, (775 reviews)
  • cleanliness
    Splash into sunset magic at Winter Haven's outdoor pool featuring loungers and mountain views.
The price is S$200
includes taxes & fees
24 Aug - 25 Aug
Courtyard by Marriott Winter Haven
Outdoor pool, open 9:00 AM to 9:00 PM, pool umbrellas, pool loungers

8. LEGOLAND Beach Retreat

LEGOLAND Beach Retreat
3.0 star property
Winter Haven
8.8 out of 10, Excellent, (348 reviews)
The price is S$256
includes taxes & fees
9 Aug - 10 Aug
LEGOLAND Beach Retreat
Outdoor pool, pool umbrellas, pool loungers

9. Staybridge Suites Winter Haven Auburndale by IHG

Staybridge Suites Winter Haven Auburndale by IHG
3.0 star property
Winter Haven
9.8 out of 10, Exceptional, (857 reviews)
  • cleanliness
    Refreshing outdoor pool oasis with loungers and umbrellas provides a sun-soaked relaxation spot near LEGOLAND Florida.
The price is S$148
includes taxes & fees
16 Aug - 17 Aug
Staybridge Suites Winter Haven Auburndale by IHG
Seasonal outdoor pool

10. Home2 Suites By Hilton Winter Haven

Home2 Suites By Hilton Winter Haven
3.0 star property
Winter Haven
9.4 out of 10, Exceptional, (368 reviews)
  • cleanliness
    Refresh yourself in the seasonal outdoor pool during warm months while staying minutes from LEGOLAND® Florida.
The price is S$199
includes taxes & fees
16 Aug - 17 Aug
Home2 Suites By Hilton Winter Haven
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties

Choose what matters most at hotels with a pool in Cypress Gardens

Breakfast included
4 stars

Top Cypress Gardens Hotel Reviews

Omni Orlando Resort at ChampionsGate

Omni Orlando Resort at ChampionsGate

10/10 Excellent
"We will definitely be going back. Love this place they were amazing with our anniversary. They even gave us champagne and sweets.."
Zachary 2-night trip
Posted 1 day ago
Omni Orlando Resort at ChampionsGate

Frequently asked questions

What are some accommodation options with pools in Cypress Gardens?
Economy Suites: Features free self parking, an outdoor pool and complimentary wireless Internet access. Omni Orlando Resort at ChampionsGate: Hotel located near Reunion Resort Golf Course. Offers 5 outdoor swimming pools, a children's pool and free water park access. Holiday Inn Winter Haven by IHG: Hotel located near LEGOLAND® Florida. Provides free self parking, an outdoor pool and complimentary wireless Internet access. Spectrum Resort Villas Orlando and Waterparks: Hotel located near Reunion Resort Golf Course. Features free water park access, an outdoor pool and spa services. Comfort Inn & Suites Lakeland North I-4: Holiday home located near ChampionsGate Golf Club. Offers complimentary wireless Internet access, a communal pool and kitchens.
What is there to see and do in Cypress Gardens?
Explore places such as LEGOLAND® Florida while you're in Cypress Gardens. Make a point to visit attractions such as Peppa Pig Theme Park Florida and Chain Of Wakes.
When is the best time to book a hotel with a pool in Cypress Gardens?
You may want to think about a place to stay that offers an outdoor swimming pool if you plan to visit Cypress Gardens in the driest months of December, November or February, when the average rainfall is 48 mm. Accommodation that has an indoor pool may be the way to go if you come to town during the rainiest months of August, July and June when the average rainfall is 226 mm.

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