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

Find Hotels with a Pool in Cypress Gardens, FL

  • 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 a Pool

Tonight
30 Sep - 1 Oct
Tomorrow
1 Oct - 2 Oct
This weekend
2 Oct - 4 Oct
Next weekend
9 Oct - 11 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 wedding ceremony on a beach with a thatched gazebo and guests seated on chairs.
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.
AED 323
AED 362 total
includes taxes & fees
1 Oct - 2 Oct
Lake Roy Beach Inn
A swimming pool with a white fence, outdoor seating, and a building with balconies in the background.
A kitchen area with a stone wall, wooden cabinets, a coffee station, and a staircase with a metal railing.
A compact hotel room with a kitchenette, a patterned sofa, and a lamp.
A reception area with a wooden floor, seating arrangements, and a reception desk.

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.
AED 453
AED 507 total
includes taxes & fees
30 Oct - 31 Oct
Rodeway Inn & Suites Winter Haven Chain Of Lakes
A residential swimming pool with a covered patio area, a wooden fence, and a house in the background.
A modern living room with two leather sofas, a wooden coffee table, and a floor lamp. A kitchen is visible 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

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

Spacious 4-bedroom house in pleasant Winter Haven with AC
Winter Haven
AED 444
AED 1,481 total
includes taxes & fees
5 Oct - 6 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 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.

4. Economy Suites

Economy Suites
Winter Haven
  • Refreshing poolside escape with bar service makes this motel your LEGOLAND® retreat after sunny adventures.
AED 253
AED 283 total
includes taxes & fees
1 Oct - 2 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 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.

5. 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.
AED 479
AED 536 total
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 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.

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.
AED 389
AED 435 total
includes taxes & fees
8 Oct - 9 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 a desk, chair, sofa, and a painting on the wall.
A bathroom with a shower, a toilet, a sink, and a mirror.
A covered entrance with a brick facade, glass doors, and a bench.

7. 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.
AED 404
AED 453 total
includes taxes & fees
6 Oct - 7 Oct
Holiday Inn Winter Haven by IHG
A circular pool with a metal ladder, surrounded by white lounge chairs and palm trees.
A hotel room with two beds, a TV, a microwave, and a desk with a lamp.
A reception area with a reception desk, a potted plant, a fire extinguisher, and a dining area with chairs and tables.
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.
AED 281
AED 315 total
includes taxes & fees
2 Oct - 3 Oct
Howard Johnson by Wyndham Winter Haven FL
A swimming pool with a white fence, lounge chairs, and a building with a balcony.
A modern room with a dark blue sofa, a wooden coffee table, and a matching ottoman. A map mural adorns the wall.
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.

9. 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.
AED 466
AED 522 total
includes taxes & fees
4 Oct - 5 Oct
Holiday Inn Express Lake Wales N-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.
A spacious indoor area with a bar, seating arrangements, and a large screen displaying content.
An outdoor patio with a fire pit, wicker furniture, and a view of a lake.

10. 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.
AED 602
AED 675 total
includes taxes & fees
4 Oct - 5 Oct
Courtyard by Marriott 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

Comfort Inn & Suites Lakeland North I-4

Comfort Inn & Suites Lakeland North I-4

10/10 Excellent
"Hotel was clean and staff was friendly, overall it was good stay!"
JAMES 2-night trip
Posted less than an hour ago
Comfort Inn & Suites Lakeland North I-4
Ramada by Wyndham Davenport Orlando South

Ramada by Wyndham Davenport Orlando South

10/10 Excellent
"Very good improvements"
Kyle 1-night trip
Posted 7 hours ago
Ramada by Wyndham Davenport Orlando South
Howard Johnson by Wyndham Lakeland

Howard Johnson by Wyndham Lakeland

8/10 Good
"Good"
Gerardo 1-night trip
Posted 15 hours ago
Howard Johnson by Wyndham Lakeland
Holiday Inn Winter Haven by IHG

Holiday Inn Winter Haven by IHG

10/10 Excellent
"Clean room pool area clean. Quick 2 night stay for lacrosse. Plenty of restaurants within a 1/2 mile!"
Michael 2-night trip
Posted 21 hours ago
Holiday Inn Winter Haven by IHG
Holiday Inn Express Hotel & Suites Orlando South-Davenport by IHG

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

10/10 Excellent
"Excelente."
Elizabeth 4-night trip
Posted 2 days ago
Holiday Inn Express Hotel & Suites Orlando South-Davenport by IHG
Hyatt Place Lakeland Center

Hyatt Place Lakeland Center

8/10 Good
"Ac was very noisy and is right by the bed. Worst thing I can say so overall , everything was good."
Catherine 2-night trip
Posted 2 days ago
Hyatt Place Lakeland Center
Reunion Resort & Golf Club

Reunion Resort & Golf Club

8/10 Good
"Beautiful"
Jennine 4-night trip
Posted 6 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.