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

Search Hotels with Pool in Cypress Gardens

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Cypress Gardens Hotels with Pool

Tonight
19 Oct - 20 Oct
Tomorrow
20 Oct - 21 Oct
This weekend
23 Oct - 25 Oct
Next weekend
30 Oct - 1 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.
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 building with a large water feature in front, surrounded by palm trees and a fence.

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.
Rp1.586.376
Rp1.776.741 total
includes taxes & fees
20 Oct - 21 Oct
Lake Roy Beach Inn
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 pool area with white lounge chairs, a table, and a 3ft no diving sign.
A bathroom with a toilet, a sink, a towel rack, and a shower curtain.

2. Economy Suites

Economy Suites
Winter Haven
  • Refreshing poolside escape with bar service makes this motel your LEGOLAND® retreat after sunny adventures.
Rp1.168.150
Rp1.308.400 total
includes taxes & fees
23 Oct - 24 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.

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.
Rp2.350.360
Rp2.632.404 total
includes taxes & fees
25 Oct - 26 Oct
Best Western Plus Winter Haven Inn & Suites 
A swimming pool with a white fence, lounge chairs, and a building with a balcony.
A restaurant with tables and chairs, a large painting, and a TV on the wall.
A hotel room with a sofa, two beds, a desk, a TV, and a carpeted floor.
A modern hotel reception area with a wooden reception desk, a seating area with a table and chairs, and a large wall with geometric patterns.

4. 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.
Rp2.433.645
Rp2.725.682 total
includes taxes & fees
25 Oct - 26 Oct
Holiday Inn Express Lake Wales N-Winter Haven by IHG
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 Hampton Inn hotel with a clear entrance, a covered waiting area, and a sign indicating a clearance of 13'6".

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.
Rp2.129.890
Rp2.385.476 total
includes taxes & fees
11 Nov - 12 Nov
Hampton Inn 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 wooden counter, coffee machines, and a Coca-Cola refrigerator.
A modern kitchen with a dining area, a flat-screen TV, and a large window.

6. 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.
Rp2.415.618
Rp2.705.492 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.
A spacious indoor area with a bar, seating arrangements, and a large screen displaying content.
A modern reception area with wooden panel walls and two reception desks.
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.
Rp2.589.579
Rp2.900.329 total
includes taxes & fees
25 Oct - 26 Oct
Courtyard by Marriott 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 bathroom with a shower, a toilet, a sink, and a mirror.
A hotel room with a desk, chair, sofa, and a painting on the wall.

8. 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.
Rp1.982.970
Rp2.220.925 total
includes taxes & fees
25 Oct - 26 Oct
Holiday Inn Winter Haven by IHG
A swimming pool area with people playing with building blocks.
A colorful play structure with a lighthouse in the background.
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.

9. LEGOLAND Beach Retreat

LEGOLAND Beach Retreat
Winter Haven
Rp3.767.643
Rp4.926.419 total
includes taxes & fees
30 Oct - 31 Oct
LEGOLAND Beach Retreat
A swimming pool with lounge chairs and umbrellas, surrounded by a building with red and beige walls.
A modern lounge area with green upholstered chairs, a herringbone-patterned floor, and a large window providing natural light.
A hotel room with a desk, chair, sofa, ottoman, and a large window.
A modern kitchen with a central island, bar stools, and a refrigerator.

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.
Rp2.589.579
Rp2.900.329 total
includes taxes & fees
1 Nov - 2 Nov
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

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 9 hours ago
Howard Johnson by Wyndham Lakeland
Holiday Inn Express Hotel & Suites Orlando South-Davenport by IHG

Holiday Inn Express Hotel & Suites Orlando South-Davenport by IHG

10/10 Excellent
"Great, modern hotel that is very well maintained. Everything looks clean and in excellent condition."
Juan 1-night trip
Posted 13 hours ago
Holiday Inn Express Hotel & Suites Orlando South-Davenport by IHG
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 14 hours 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 17 hours 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 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.

Explore a world of travel with Expedia