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

Hotels with Swimming Pool in Cypress Gardens, Winter Haven

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Check availability on Cypress Gardens Hotels with Swimming Pool

Tonight
Aug 26 - Aug 27
Tomorrow
Aug 27 - Aug 28
This weekend
Aug 28 - Aug 30
Next weekend
Sep 4 - Sep 6

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 building with a large water feature in front, surrounded by palm trees and a fence.
A waterfront property with a dock, lounge chairs, and palm trees.
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.
P5,245
P5,875 total
includes taxes & fees
Aug 27 - Aug 28
Lake Roy Beach Inn
A swimming pool with a white fence, outdoor seating, and a building with balconies in the background.
A hotel room with a bed, two bedside tables, a desk, a chair, and a blue armchair.
A reception area with a wooden floor, seating arrangements, and a reception desk.
A compact hotel room with a kitchenette, a patterned sofa, and a lamp.

2. Rodeway Inn & Suites Winter Haven Chain Of Lakes

Rodeway Inn & Suites Winter Haven Chain Of Lakes
Winter Haven
  • Splash into fun at this lakeside motel with a sun-soaked pool just minutes from LEGOLAND Florida.
P4,985
P5,584 total
includes taxes & fees
Aug 29 - Aug 30
Rodeway Inn & Suites Winter Haven Chain Of Lakes
A rectangular swimming pool with clear blue water, surrounded by a white fence and white lounge chairs.
A bathroom with a toilet, a sink, a towel rack, and a shower curtain.
A spacious room with a large ceiling fan, a marble counter, and a view of the outside through a window.
A hotel room with a floral bedspread, a wooden headboard, two wall-mounted lamps, and a framed picture on the wall.

3. Economy Suites

Economy Suites
Winter Haven
  • Refreshing poolside escape with bar service makes this motel your LEGOLAND® retreat after sunny adventures.
P4,665
P5,225 total
includes taxes & fees
Aug 27 - Aug 28
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 modern hotel with a prominent entrance, multiple floors, and a parking lot.
A reception area with a modern design, featuring a counter, a seating area, and a wall with a unique pattern.

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.
P7,034
P7,878 total
includes taxes & fees
Aug 31 - Sep 1
Best Western Plus Winter Haven Inn & Suites 
A swimming pool with a brick building in the background, outdoor seating, and umbrellas.
A hotel reception area with a curved reception desk, a large chandelier, and a wall-mounted light fixture.
A lobby with a seating area, two elevators, and a large potted plant.

5. 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.
P5,510
P6,171 total
includes taxes & fees
Sep 6 - Sep 7
Holiday Inn Winter Haven by IHG
A swimming pool with lounge chairs and tables, surrounded by a fence and a building with a modern design.
A Hampton Inn hotel with a clear entrance, a covered waiting area, and a sign indicating a clearance of 13'6".
A hotel lobby with a reception desk, seating area, and a bar.
A hotel lobby with a seating area featuring blue patterned chairs, a wooden coffee table, and a sofa.

6. 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.
P7,036
P7,881 total
includes taxes & fees
Sep 6 - Sep 7
Hampton Inn Winter Haven
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 Courtyard by Marriott hotel with a modern design, featuring a covered entrance and a landscaped area with palm trees.

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.
P8,606
P9,638 total
includes taxes & fees
Sep 7 - Sep 8
Courtyard by Marriott Winter Haven
A circular pool with a metal ladder, surrounded by white lounge chairs and palm trees.
A reception area with a reception desk, a potted plant, a fire extinguisher, and a dining area with chairs and tables.
A restaurant with wooden walls, a neon sign, tables, chairs, a kitchen area, and a tiled floor.
A bathtub with a white shower curtain, a grab bar, and a handheld showerhead.

8. 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.
P5,245
P5,875 total
includes taxes & fees
Sep 21 - Sep 22
Howard Johnson by Wyndham Winter Haven FL
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 colorful LEGO-themed beach retreat sign with a beach house and a gas station in the background.
A colorful play structure with a lighthouse in the background.

9. LEGOLAND Beach Retreat

LEGOLAND Beach Retreat
Winter Haven
P10,967
P14,703 total
includes taxes & fees
Aug 28 - Aug 29
LEGOLAND Beach Retreat
View all properties

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

Holiday Inn Winter Haven by IHG

Holiday Inn Winter Haven by IHG

10/10 Excellent
"Clean room"
Yinelis 2-night trip
Posted less than an hour ago
Holiday Inn Winter Haven by IHG
Hyatt Place Lakeland Center

Hyatt Place Lakeland Center

10/10 Excellent
"Great"
Jerald 1-night trip
Posted less than an hour ago
Hyatt Place Lakeland Center
Howard Johnson by Wyndham Winter Haven FL

Howard Johnson by Wyndham Winter Haven FL

8/10 Good
"This was fine for a 1 night stay when taking my kid to college, nothing special but it gets the job done."
Joshua 1-night trip
Posted 18 hours ago
Howard Johnson by Wyndham Winter Haven FL
Holiday Inn Express Lake Wales N-Winter Haven by IHG

Holiday Inn Express Lake Wales N-Winter Haven by IHG

10/10 Excellent
"Had a great time, room was awesome, bed comfortable and when I asked for extra towels and a blanket staff brought it to me. Hotel had a wonderful breakfast every morning and we couldn't ask for a better price either."
Yvonne 3-night trip
Posted 22 hours ago
Holiday Inn Express Lake Wales N-Winter Haven by IHG
Ramada by Wyndham Davenport Orlando South

Ramada by Wyndham Davenport Orlando South

8/10 Good
"Hotel to big not to have a"
tameika 3-night trip
Posted 2 days ago
Ramada by Wyndham Davenport Orlando South
Reunion Resort & Golf Club

Reunion Resort & Golf Club

10/10 Excellent
"We ended up in a bigger room. It was very clean. Loved how close the pool was. Very private and quiet. There were many amenities we didn't try because we were there for a specific purpose but the resort has a lot to offer."
Vicenta 4-night trip
Posted 4 days ago
Reunion Resort & Golf Club

Frequently asked questions

What are some accommodations with pools in Cypress Gardens?
Omni Orlando Resort at ChampionsGate: Hotel located near Reunion Resort Golf Course. Features 5 outdoor pools, a children's pool, and free water-park access. Holiday Inn Winter Haven by IHG: Hotel located near LEGOLAND® Florida. Offers free self parking, an outdoor pool, and complimentary wireless internet 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. Days Inn & Suites by Wyndham Lakeland: Features daily, a pool, and free self parking. Reunion Resort & Golf Club: Aparthotel steps from Reunion Resort Golf Course. Offers 11 outdoor pools, a children's pool, and free water-park access.
What is there to see and do in Cypress Gardens?
Explore places like 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 has an outdoor pool if you plan to visit Cypress Gardens in the driest months of December, November, or February when the average rainfall is 2 inches. Lodging that has a pool indoors 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 9 inches.

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