A castle entrance with flags and banners, including a LEGO Kingdoms banner.

Find Hotels with a Pool in Winter Haven, FL

  • Upfront pricing

    Our total price for your stay includes taxes and fees

  • Treat yourself

    Save 10% or more on over 100,000 hotels worldwide with Member Prices
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check availability on Winter Haven Hotels with a Pool

Tonight
Oct 1 - Oct 2
Tomorrow
Oct 2 - Oct 3
This weekend
Oct 2 - Oct 4
Next weekend
Oct 9 - Oct 11

Our top choices for Winter Haven hotels with a pool

A swimming pool with a waterfall feature, lounge chairs, and a gazebo.
Bar (on property)
An aerial view of a resort with multiple swimming pools, palm trees, and lounge areas.
A modern hotel room with a dining area, a sofa, a chair, and a large window with curtains.

1. Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
Orlando
$137 nightly
$154 total
Oct 27 - Oct 28
Total with taxes and fees
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
A resort with a large pool, water slides, palm trees, and beach umbrellas.
A couple walking past a surfboard and a 'Longboard Bar and Grill' sign.
A resort with multiple swimming pools surrounded by lush greenery and a large hotel building.
A modern lobby with a reception desk, seating area, and a bar.

2. The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando
Winter Garden
  • Splash into paradise at this resort with 6 outdoor pools, a lazy river, and a complimentary water park for endless aquatic fun.
$219 nightly
$246 total
Nov 1 - Nov 2
Total with taxes and fees
The Grove Resort & Water Park Orlando
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 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.

3. 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.
$130 nightly
$146 total
Oct 4 - Oct 5
Total with taxes and fees
Staybridge Suites Winter Haven Auburndale 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 bathroom with a shower, a toilet, a sink, and a mirror.
A covered entrance with a brick facade, glass doors, and a bench.
A hotel room with a desk, chair, sofa, and a painting on the wall.

4. 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 nightly
$123 total
Oct 5 - Oct 6
Total with taxes and fees
Holiday Inn Winter Haven by IHG
A modern hotel with a swimming pool, outdoor seating, and a well-lit facade.
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.
A modern hotel lobby with a central reception desk, multiple light fixtures, and a patterned wall.

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.
$130 nightly
$146 total
Oct 18 - Oct 19
Total with taxes and fees
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 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.

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.
$106 nightly
$118 total
Oct 8 - Oct 9
Total with taxes and fees
Hampton Inn Winter Haven
A pool area with a chandelier, a statue, and a view of the outside.
A spa entrance with a wooden facade, a sign indicating a sauna, and a patterned metal partition.
A resort pool area with a winding pool design, lounge chairs, and palm trees.
A modern hotel with a central pool area featuring a red boat and palm trees.

7. Kompose Boutique Resort at Theme Parks

Kompose Boutique Resort at Theme Parks
Kissimmee
  • Splash down the waterslide or bask poolside at this modern family resort with two hot tubs.
$124 nightly
$141 total
Oct 7 - Oct 8
Total with taxes and fees
Kompose Boutique Resort at Theme Parks
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.
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.

8. 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.
$144 nightly
$161 total
Oct 18 - Oct 19
Total with taxes and fees
Home2 Suites By Hilton Winter Haven
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 restaurant with wooden walls, a neon sign, tables, chairs, a kitchen area, and a tiled floor.

9. 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 nightly
$86 total
Oct 4 - Oct 5
Total with taxes and fees
Howard Johnson by Wyndham Winter Haven FL
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.
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.

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.
$156 nightly
$175 total
Oct 18 - Oct 19
Total with taxes and fees
Courtyard by Marriott Winter Haven
View all properties

Choose what matters most at hotels with a pool in Winter Haven

Breakfast included
Hot tub
Water park
4 stars
Spa

Hotels with pools and free breakfast in Winter Haven

A hotel room with two beds, a desk, a microwave, a TV, and a painting on the wall.
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 modern hotel with a swimming pool, outdoor seating, and a well-lit facade.

Best Western Plus Winter Haven Inn & Suites 

Best Western Plus Winter Haven Inn & Suites 
Winter Haven
$130 nightly
$146 total
Oct 18 - Oct 19
Total with taxes and fees
Best Western Plus Winter Haven Inn & Suites 
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.
A swimming pool with lounge chairs and tables, surrounded by a fence and a building with a modern design.

Hampton Inn Winter Haven

Hampton Inn Winter Haven
Winter Haven
$106 nightly
$118 total
Oct 8 - Oct 9
Total with taxes and fees
Hampton Inn Winter Haven
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 reception area with a curved reception desk, a chandelier, and a wall-mounted sign that reads 'Holiday Inn.'
A covered entrance with a brick facade, glass doors, and a bench.

Holiday Inn Winter Haven by IHG

Holiday Inn Winter Haven by IHG
Winter Haven
$110 nightly
$123 total
Oct 5 - Oct 6
Total with taxes and fees
Holiday Inn Winter Haven by IHG
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.
A modern reception area with wooden panel walls and two reception desks.
A modern hotel lobby with a long reception desk, bar area, and seating arrangement.

Courtyard by Marriott Winter Haven

Courtyard by Marriott Winter Haven
Winter Haven
$156 nightly
$175 total
Oct 18 - Oct 19
Total with taxes and fees
Courtyard by Marriott Winter Haven
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 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.

Staybridge Suites Winter Haven Auburndale by IHG

Staybridge Suites Winter Haven Auburndale by IHG
Winter Haven
$130 nightly
$146 total
Oct 4 - Oct 5
Total with taxes and fees
Staybridge Suites Winter Haven Auburndale by IHG
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 restaurant with wooden walls, a neon sign, tables, chairs, a kitchen area, and a tiled floor.
A conference room with tables set for an event, featuring pink and white tablecloths and chairs with pink sashes.

Howard Johnson by Wyndham Winter Haven FL

Howard Johnson by Wyndham Winter Haven FL
Winter Haven
$77 nightly
$86 total
Oct 4 - Oct 5
Total with taxes and fees
Howard Johnson by Wyndham Winter Haven FL
An outdoor seating area with sofas, chairs, and a fire pit.
A hotel room with a desk, chair, sofa, ottoman, and a large window.
A reception desk with a sign reading "HOME 2 Suites by Hilton," a minibar, a refrigerator labeled "COLDER," and a snack shelf.
A modern lounge area with green upholstered chairs, a herringbone-patterned floor, and a large window providing natural light.

Home2 Suites By Hilton Winter Haven

Home2 Suites By Hilton Winter Haven
Winter Haven
$144 nightly
$161 total
Oct 18 - Oct 19
Total with taxes and fees
Home2 Suites By Hilton Winter Haven
A swimming pool area with people playing with building blocks.
A row of colorful, single-story buildings with a uniform roof design, white picket fences, and a clear pathway leading to the entrance.
A children's play area with a slide and climbing structures, a small lighthouse, and a building with a red and white striped roof.
A dining area with tables, chairs, and a colorful mural in the background.

LEGOLAND Beach Retreat

LEGOLAND Beach Retreat
Winter Haven
$196 nightly
$219 total
Oct 12 - Oct 13
Total with taxes and fees
LEGOLAND Beach Retreat
A kitchen area with a stone wall, wooden cabinets, a coffee station, and a staircase with a metal railing.
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 compact hotel room with a kitchenette, a patterned sofa, and a lamp.

Rodeway Inn & Suites Winter Haven Chain Of Lakes

Rodeway Inn & Suites Winter Haven Chain Of Lakes
Winter Haven
$123 nightly
$138 total
Oct 31 - Nov 1
Total with taxes and fees
Rodeway Inn & Suites Winter Haven Chain Of Lakes
A pool with floating building blocks and a colorful building with balconies in the background.
A room with a stone wall, a fireplace, and a sign that reads "YE OLD ADULTS KEEP OUT!".
A dining area with tables and chairs, a central cart with dishes, and large windows with a view of greenery.
A bedroom with a bed, a dresser, a mirror, and a map on the wall.

Legoland Florida Hotel

Legoland Florida Hotel
Winter Haven
$242 nightly
$271 total
Oct 6 - Oct 7
Total with taxes and fees
Legoland Florida Hotel
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties

Top Winter Haven Hotel Reviews

Vacation Village Orlando, Celebration

Vacation Village Orlando, Celebration

10/10 Excellent
"Great stay! Family friendly, clean rooms, and great staff! Answered questions i had and etc. Definitely would stay again!"
Paula 2-night trip
Posted 6 hours ago
Vacation Village Orlando, Celebration
Galleria Palms Hotel

Galleria Palms Hotel

10/10 Excellent
"Great location so close to the parks"
mario 2-night trip
Posted 8 hours ago
Galleria Palms Hotel
Hilton Vacation Club Aqua Sol Orlando West

Hilton Vacation Club Aqua Sol Orlando West

10/10 Excellent
"Beautiful place"
Rafael 2-night trip
Posted 8 hours ago
Hilton Vacation Club Aqua Sol Orlando West
The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

10/10 Excellent
"Love the resort. Left blankets in the room and called back to return for pickup and the staff “couldn’t find them”"
DAWN 1-night trip
Posted 8 hours ago
The Grove Resort & Water Park Orlando
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 1 day ago
Holiday Inn Winter Haven by IHG
Hilton Vacation Club Mystic Dunes Orlando

Hilton Vacation Club Mystic Dunes Orlando

10/10 Excellent
"Everything was great. The only thing that bothered us was that the housekeeping came into our room at about 8am in the morning when our check out was at 11:00am. She rang the bell but I was in restroom and didn't get to door on time before she let herself inside."
Maribel 2-night trip
Posted 1 day ago
Hilton Vacation Club Mystic Dunes Orlando

Frequently asked questions

How much does a hotel with outdoor pool in Winter Haven cost?
Enjoy staying in a hotel in Winter Haven with an outdoor pool. You can find a great deal from $86 on Expedia. If you're leaning toward a little luxury, prices can rise, and may vary depending on the location, season, and hotel amenities. Be sure to book in advance to enjoy more options and potentially better rates, especially if you're planning a trip during weekends or around public holidays.
Are there hotels with outdoor pools that are close to Chain Of Wakes?
Staybridge Suites Winter Haven Auburndale by IHG is a delightful 3-star option for families seeking an outdoor pool experience near Chain Of Wakes. With an impressive traveller rating of 9.8, this hotel not only features a refreshing outdoor pool but also offers sun loungers for relaxation. Guests rave about the friendly and helpful staff, as well as the spacious and clean rooms. To start your day off right, enjoy their excellent complimentary breakfast, which includes a variety of options.Another fantastic choice is the Best Western Plus Winter Haven Inn & Suites, rated 9.6 by visitors. This 3.5-star hotel boasts an inviting outdoor pool, along with comfortable sun loungers for lounging after a swim. Guests appreciate the clean and comfortable rooms, and the friendly staff is often highlighted in reviews. Additionally, the hotel's complimentary full breakfast and convenient location make it a great option for families looking to explore the area.For those who prefer a more modern atmosphere, Courtyard by Marriott Winter Haven is a solid 3-star choice, receiving a great rating of 9.4. This hotel features an outdoor pool with a lovely lake view, great for a relaxing swim after a day of adventure. Guests enjoy spacious and clean accommodations, along with the convenience of free WiFi and self-parking.Home2 Suites By Hilton Winter Haven, also rated 9.4, is another excellent option, providing free breakfast on weekends and self-parking. Families will appreciate the suite-style rooms that offer extra space, ideal for a comfortable stay.Lastly, the Hampton Inn Winter Haven, with a traveller rating of 9.0, features an outdoor pool and free breakfast options, ensuring a pleasant stay. Guests often praise the friendly staff and the good location, making it a convenient base for exploring nearby attractions.
Is it cheaper to book flights and a Winter Haven hotel with a pool as a package?
Booking a hotel and flight package on Expedia can be cheaper than booking flights and hotels separately. Bundling can lead to significant savings, especially for international travel or when booking well in advance. However, savings vary depending on factors like destination, travel dates and availability, so it's wise to compare options. With access to over 300,000 hotels worldwide, Expedia makes it easy to build the perfect vacation package.
Can I cancel my hotel reservation on Expedia?
Expedia has plenty of refundable hotels. In many cases, you need to cancel your booking 24-48 hours ahead of your arrival date. Remember to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use Expedia's "Fully refundable property" filter during your search to find the right hotel in Winter Haven for you.

Explore a world of travel with Expedia