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

Cypress Gardens Hotel Guide - Hotels with Pool in Cypress Gardens, Winter Haven

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Check availability on Cypress Gardens Hotels with Pool

Tonight
14 Oct - 15 Oct
Tomorrow
15 Oct - 16 Oct
This weekend
16 Oct - 18 Oct
Next weekend
23 Oct - 25 Oct

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.
A waterfront property with a dock, lounge chairs, and palm trees.
A marina with boats docked, surrounded by palm trees and a building with a covered area.
A wedding ceremony on a beach with a thatched gazebo and guests seated on chairs.

1. Lake Roy Beach Inn

Lake Roy Beach Inn
Winter Haven
  • Lakeside pool paradise awaits with serene water views and complimentary loungers for ultimate relaxation.
€88
includes taxes & fees
15 Oct - 16 Oct
Lake Roy Beach Inn
A residential swimming pool with a covered patio area, a wooden fence, and a house in the background.
A living room with a brick fireplace, a sofa, a coffee table, and a dining area in the background.
A clean, modern kitchen with a built-in oven and microwave, a dining area with a table and chairs, and a massage chair in the corner.
Private kitchen

2. Spacious 4-bedroom house in pleasant Winter Haven with AC

Spacious 4-bedroom house in pleasant Winter Haven with AC
Winter Haven
€350
includes taxes & fees
19 Oct - 20 Oct
Spacious 4-bedroom house in pleasant Winter Haven with AC
A rectangular swimming pool with clear blue water, surrounded by a white fence and white lounge chairs.
A hotel room with a floral bedspread, a wooden headboard, two wall-mounted lamps, and a framed picture on the wall.
A spacious room with a large ceiling fan, a marble counter, and a view of the outside through a window.
A bathroom with a toilet, a sink, a towel rack, and a shower curtain.

3. Economy Suites

Economy Suites
Winter Haven
  • Refreshing poolside escape with bar service makes this motel your LEGOLAND® retreat after sunny adventures.
€65
includes taxes & fees
17 Oct - 18 Oct
Economy Suites
A modern hotel with a swimming pool, outdoor seating, and a well-lit facade.
A modern hotel lobby with a central reception desk, multiple light fixtures, and a patterned wall.
A hotel room with two beds, a desk, a microwave, a TV, and a painting on the wall.
A modern hotel with a prominent entrance, multiple floors, and a parking lot.

4. Best Western Plus Winter Haven Inn & Suites 

Best Western Plus Winter Haven Inn & Suites 
Winter Haven
  • Sun-soaked pool area creates perfect retreat near LEGOLAND Florida with loungers and umbrellas.
€122
includes taxes & fees
18 Oct - 19 Oct
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.
A hotel lobby with a seating area featuring blue patterned chairs, a wooden coffee table, and a sofa.
A hotel lobby with a reception desk, seating area, and a bar.
A modern bathroom with a bathtub, a large mirror, a vanity with a sink, and neatly arranged towels.

5. Hampton Inn Winter Haven

Hampton Inn Winter Haven
Winter Haven
  • Shimmering blue waters await at this family-friendly hotel with pool loungers and workout options.
€118
includes taxes & fees
25 Oct - 26 Oct
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.
A hotel room with two beds, a desk, a television, and a door leading to another room.
A hotel reception area with a curved reception desk, a large chandelier, and a wall-mounted sign.
A bathroom with a shower, a toilet, a sink, and a mirror.

6. Holiday Inn Winter Haven by IHG

Holiday Inn Winter Haven by IHG
Winter Haven
  • Dive into crystalline blue waters at this outdoor pool oasis with comfy loungers and sunshine appeal.
€110
includes taxes & fees
25 Oct - 26 Oct
Holiday Inn Winter Haven by IHG
A pool area with a wooden pergola, lounge chairs, and a view of the water.
A modern reception area with wooden panel walls and two reception desks.
An outdoor patio with a fire pit, wicker furniture, and a view of a lake.
A spacious indoor area with a bar, seating arrangements, and a large screen displaying content.

7. Courtyard by Marriott Winter Haven

Courtyard by Marriott Winter Haven
Winter Haven
  • Splash into sunset magic at Winter Haven's outdoor pool featuring loungers and mountain views.
€169
includes taxes & fees
18 Oct - 19 Oct
Courtyard by Marriott Winter Haven
A swimming pool with lounge chairs and tables, surrounded by a white building with a brick facade.
A modern hotel room with a kitchenette, a dining area, and a bed.
A modern kitchen with a dining area, a flat-screen TV, and a large window.
A modern living room with a fireplace, a sofa, a coffee table, and a TV mounted on the wall.

8. Staybridge Suites Winter Haven Auburndale by IHG

Staybridge Suites Winter Haven Auburndale by IHG
Winter Haven
  • Refreshing outdoor pool oasis with loungers and umbrellas provides a sun-soaked relaxation spot near LEGOLAND Florida.
€135
includes taxes & fees
18 Oct - 19 Oct
Staybridge Suites Winter Haven Auburndale by IHG
A swimming pool area with people playing with building blocks.
A brightly colored building with a white picket fence, numbered doors, and a surfboard decoration.
A row of colorful, single-story buildings with a uniform roof design, white picket fences, and a clear pathway leading to the entrance.
A colorful LEGO-themed beach retreat sign with a beach house and a gas station in the background.

9. LEGOLAND Beach Retreat

LEGOLAND Beach Retreat
Winter Haven
€244
includes taxes & fees
30 Oct - 31 Oct
LEGOLAND Beach Retreat
A circular pool with a metal ladder, surrounded by white lounge chairs and palm trees.
A bathtub with a white shower curtain, a grab bar, and a handheld showerhead.
A reception area with a reception desk, a potted plant, a fire extinguisher, and a dining area with chairs and tables.
A hotel room with two beds, a TV, a microwave, and a desk with a lamp.

10. Howard Johnson by Wyndham Winter Haven FL

Howard Johnson by Wyndham Winter Haven FL
Winter Haven
  • Splash into fun with sun loungers and umbrellas at this hotel's relaxing outdoor pool.
€77
includes taxes & fees
19 Oct - 20 Oct
Howard Johnson by Wyndham Winter Haven FL
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Choose what matters most at hotels with a pool in Cypress Gardens

Breakfast included
4 stars
5 stars
Hot tub
Spa

Top Cypress Gardens Hotel Reviews

Reunion Resort & Golf Club

Reunion Resort & Golf Club

10/10 Excellent
"Huge property - not a golfer but still enjoyed the stay"
Karen G 4-night trip
Posted 7 days ago
Reunion Resort & Golf Club

Frequently asked questions

What are some accommodation options with pools in Cypress Gardens?
Holiday Inn Winter Haven by IHG: Hotel located near LEGOLAND® Florida. Features free self parking, an outdoor pool and complimentary wireless Internet access. Omni Orlando Resort at ChampionsGate: Hotel located near ChampionsGate Golf Club. Offers 5 outdoor swimming pools, a children's pool and free water park access. Spectrum Resort Villas Orlando and Waterparks: Hotel located near Reunion Resort Golf Course. Provides free water park access, an outdoor pool and spa services. Howard Johnson by Wyndham Lakeland: Features daily, a pool and free self parking. Days Inn & Suites by Wyndham Lakeland: Offers daily, a pool and free self parking.
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.