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

Search Hotels with Pool in Cypress Gardens

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Check availability on Cypress Gardens Hotels with Pool

This weekend
30 Oct - 1 Nov
Next weekend
6 Nov - 8 Nov

Our top choices for Cypress Gardens hotels with a pool

A lakeside view with a dock and a small building, likely a cabin or a house, surrounded by trees.

1. Lake Roy Beach Inn

Lake Roy Beach Inn
2.0 star property
Winter Haven
7.0 out of 10, Good, (1,000 reviews)
  • cleanliness
    Lakeside pool paradise awaits with serene water views and complimentary loungers for ultimate relaxation.
The price is 2.274.712 ₫
2.547.677 ₫ total
includes taxes & fees
30 Oct - 31 Oct
Lake Roy Beach Inn
A sign for Economy Suites with a digital display below it.

2. Economy Suites

Economy Suites
2.0 star property
Winter Haven
4.8 out of 10, (439 reviews)
  • cleanliness
    Refreshing poolside escape with bar service makes this motel your LEGOLAND® retreat after sunny adventures.
The price is 1.674.043 ₫
1.875.032 ₫ total
includes taxes & fees
9 Nov - 10 Nov
Economy Suites
A modern hotel with a swimming pool, outdoor seating, and a well-lit facade.

3. 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, (1,384 reviews)
  • cleanliness
    Sun-soaked pool area creates perfect retreat near LEGOLAND Florida with loungers and umbrellas.
The price is 3.370.193 ₫
3.774.616 ₫ total
includes taxes & fees
1 Nov - 2 Nov
Best Western Plus Winter Haven Inn & Suites 
A swimming pool with lounge chairs and tables, surrounded by a fence and a building with a modern design.

4. Hampton Inn Winter Haven

Hampton Inn Winter Haven
2.5 star property
Winter Haven
9.0 out of 10, Wonderful, (1,000 reviews)
  • cleanliness
    Shimmering blue waters await at this family-friendly hotel with pool loungers and workout options.
The price is 3.054.835 ₫
3.421.416 ₫ total
includes taxes & fees
11 Nov - 12 Nov
Hampton Inn Winter Haven
A swimming pool with a poolside area, including lounge chairs and umbrellas, adjacent to a building with multiple windows and a brick facade.

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, (1,003 reviews)
  • cleanliness
    Dive into crystalline blue waters at this outdoor pool oasis with comfy loungers and sunshine appeal.
The price is 2.834.343 ₫
3.174.465 ₫ total
includes taxes & fees
1 Nov - 2 Nov
Holiday Inn Winter Haven by IHG
A swimming pool area with people playing with building blocks.

6. LEGOLAND Beach Retreat

LEGOLAND Beach Retreat
3.0 star property
Winter Haven
8.6 out of 10, Excellent, (397 reviews)
The price is 5.140.966 ₫
6.770.575 ₫ total
includes taxes & fees
13 Nov - 14 Nov
LEGOLAND Beach Retreat
A swimming pool with a white fence, lounge chairs, and a building with a sign.

7. Holiday Inn Express Lake Wales N-Winter Haven by IHG

Holiday Inn Express Lake Wales N-Winter Haven by IHG
2.5 star property
Lake Wales
9.2 out of 10, Wonderful, (1,001 reviews)
  • cleanliness
    Experience the Florida sunshine while floating in the sparkling outdoor pool at this Lake Wales hotel, just minutes from LEGOLAND.
The price is 3.412.068 ₫
3.821.517 ₫ total
includes taxes & fees
29 Nov - 30 Nov
Holiday Inn Express Lake Wales N-Winter Haven by IHG
A swimming pool with lounge chairs and tables, surrounded by a white building with a brick facade.

8. 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, (931 reviews)
  • cleanliness
    Refreshing outdoor pool oasis with loungers and umbrellas provides a sun-soaked relaxation spot near LEGOLAND Florida.
The price is 3.463.766 ₫
3.879.418 ₫ total
includes taxes & fees
8 Nov - 9 Nov
Staybridge Suites Winter Haven Auburndale by IHG
A pool area with a wooden pergola, lounge chairs, and a view of the water.

9. Courtyard by Marriott Winter Haven

Courtyard by Marriott Winter Haven
3.0 star property
Winter Haven
9.4 out of 10, Exceptional, (792 reviews)
  • cleanliness
    Splash into sunset magic at Winter Haven's outdoor pool featuring loungers and mountain views.
The price is 4.042.784 ₫
4.527.918 ₫ total
includes taxes & fees
29 Nov - 30 Nov
Courtyard by Marriott Winter Haven
A swimming pool with lounge chairs and umbrellas, surrounded by a building with red and beige walls.

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, (393 reviews)
  • cleanliness
    Refresh yourself in the seasonal outdoor pool during warm months while staying minutes from LEGOLAND® Florida.
The price is 3.713.209 ₫
4.158.795 ₫ total
includes taxes & fees
8 Nov - 9 Nov
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.
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Choose what matters most at hotels with a pool in Cypress Gardens

Breakfast included
4 stars

Top Cypress Gardens Hotel Reviews

Holiday Inn Express Lake Wales N-Winter Haven by IHG

Holiday Inn Express Lake Wales N-Winter Haven by IHG

10/10 Excellent
"The breakfast was wonderful"
Brenda 2-night trip
Posted 21 hours ago
Holiday Inn Express Lake Wales N-Winter Haven by IHG

Frequently asked questions

What is there to see and do in Cypress Gardens?
Explore places such as LEGOLAND® Florida while you're in Cypress Gardens. Surround yourself with nature at Lake Eloise.
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.