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

Find Hotels with a Pool in Cypress Gardens, FL

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Check availability on Cypress Gardens Hotels with a Pool

Tonight
Oct 20 - Oct 21
Tomorrow
Oct 21 - Oct 22
This weekend
Oct 23 - Oct 25
Next weekend
Oct 30 - Nov 1

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 building with a large water feature in front, surrounded by palm trees and a fence.
A marina with boats docked, surrounded by palm trees and a building with a covered area.

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.
₩117,132
₩131,188 total
includes taxes & fees
Oct 21 - Oct 22
Lake Roy Beach Inn
A rectangular swimming pool with clear blue water, surrounded by a white fence and white lounge chairs.
A pool area with white lounge chairs, a table, and a 3ft no diving sign.
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.

2. Economy Suites

Economy Suites
Winter Haven
  • Refreshing poolside escape with bar service makes this motel your LEGOLAND® retreat after sunny adventures.
₩86,252
₩96,603 total
includes taxes & fees
Oct 21 - Oct 22
Economy Suites
A modern hotel with a swimming pool, outdoor seating, and a well-lit facade.
A reception area with a modern design, featuring a counter, a seating area, and a wall with a unique pattern.
A modern hotel with a prominent entrance, multiple floors, and a parking lot.
A modern hotel lobby with a central reception desk, multiple light fixtures, and a patterned wall.

3. 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.
₩164,611
₩184,364 total
includes taxes & fees
Oct 21 - Oct 22
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 Hampton Inn hotel with a clear entrance, a covered waiting area, and a sign indicating a clearance of 13'6".
A modern bathroom with a bathtub, a large mirror, a vanity with a sink, and neatly arranged towels.
A hotel lobby with a reception desk, seating area, and a bar.

4. 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.
₩157,264
₩176,136 total
includes taxes & fees
Nov 8 - Nov 9
Hampton Inn Winter Haven
A swimming pool with a white fence, lounge chairs, and a building with a balcony.
A hotel room with a sofa, two beds, a desk, a TV, and a carpeted floor.
A restaurant with tables and chairs, a large painting, and a TV on the wall.
A modern room with a dark blue sofa, a wooden coffee table, and a matching ottoman. A map mural adorns the wall.

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

Holiday Inn Express Lake Wales N-Winter Haven by IHG
Lake Wales
  • Experience the Florida sunshine while floating in the sparkling outdoor pool at this Lake Wales hotel, just minutes from LEGOLAND.
₩180,124
₩201,739 total
includes taxes & fees
Oct 25 - Oct 26
Holiday Inn Express Lake Wales N-Winter Haven by IHG
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 room with a desk, chair, sofa, and a painting on the wall.
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.
₩146,416
₩163,986 total
includes taxes & fees
Nov 1 - Nov 2
Holiday Inn Winter Haven by IHG
A pool area with a wooden pergola, lounge chairs, and a view of the water.
A Courtyard by Marriott hotel with a modern design, featuring a covered entrance and a landscaped area with palm trees.
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.
₩202,519
₩226,822 total
includes taxes & fees
Nov 1 - Nov 2
Courtyard by Marriott Winter Haven
A swimming pool with lounge chairs and tables, surrounded by a white building with a brick facade.
A modern living room with a fireplace, a sofa, a coffee table, and a TV mounted on the wall.
A modern kitchen with a dining area, a flat-screen TV, and a large window.
A modern hotel room with a kitchenette, a dining area, and a bed.

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.
₩178,790
₩200,245 total
includes taxes & fees
Nov 8 - Nov 9
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 colorful LEGO-themed beach retreat sign with a beach house and a gas station in the background.
A row of colorful, single-story buildings with a uniform roof design, white picket fences, and a clear pathway leading to the entrance.

9. LEGOLAND Beach Retreat

LEGOLAND Beach Retreat
Winter Haven
₩264,879
₩348,841 total
includes taxes & fees
Nov 13 - Nov 14
LEGOLAND Beach Retreat
A swimming pool with lounge chairs and umbrellas, surrounded by a building with red and beige walls.
A modern kitchen with a central island, bar stools, and a refrigerator.
An outdoor seating area with sofas, chairs, and a fire pit.
A hotel room with a desk, chair, sofa, ottoman, and a large window.

10. Home2 Suites By Hilton Winter Haven

Home2 Suites By Hilton Winter Haven
Winter Haven
  • Refresh yourself in the seasonal outdoor pool during warm months while staying minutes from LEGOLAND® Florida.
₩191,205
₩214,150 total
includes taxes & fees
Nov 1 - Nov 2
Home2 Suites By Hilton Winter Haven
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
"Super limpio todo el hotel en general"
Ashya 2-night trip
Posted 5 hours ago
Holiday Inn Winter Haven by IHG
Holiday Inn Express Lake Wales N-Winter Haven by IHG

Holiday Inn Express Lake Wales N-Winter Haven by IHG

10/10 Excellent
"Clean room with great AC. Good breakfast choices to start the day. Pool was nice for the kids to use after a busy day and a good temperature for a quick swim."
Jerronee 1-night trip
Posted 5 hours ago
Holiday Inn Express Lake Wales N-Winter Haven by IHG
Days Inn & Suites by Wyndham Lakeland

Days Inn & Suites by Wyndham Lakeland

8/10 Good
"Room was perfect. Breakfast however wasn’t that great. Not a lot of options."
Nicholas 1-night trip
Posted 11 hours ago
Days Inn & Suites by Wyndham Lakeland
Howard Johnson by Wyndham Lakeland

Howard Johnson by Wyndham Lakeland

8/10 Good
"The staff was amazing, the were helpful and very nice. The room could have been cleaner but wasn't awful."
Martie 1-night trip
Posted 1 day ago
Howard Johnson by Wyndham Lakeland
Comfort Inn & Suites Lakeland North I-4

Comfort Inn & Suites Lakeland North I-4

8/10 Good
"Fit our budget Free parking, Breakfast included Close to restaurants"
Tommy 2-night trip
Posted 1 day ago
Comfort Inn & Suites Lakeland North I-4
Omni Orlando Resort at ChampionsGate

Omni Orlando Resort at ChampionsGate

10/10 Excellent
"Excelent pool to the kids!"
ELIEZER JOSUE 1-night trip
Posted 2 days ago
Omni Orlando Resort at ChampionsGate
Reunion Resort & Golf Club

Reunion Resort & Golf Club

10/10 Excellent
"Great"
Alexis 3-night trip
Posted 3 days ago
Reunion Resort & Golf Club

Frequently asked questions

What are some accommodations 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 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 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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