Hotels With Pool in Winter Haven | Flexible Booking Options

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Our top choices for Winter Haven hotels with a pool

A swimming pool with a waterfall feature, lounge chairs, and a gazebo.

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

Orlando

$111 nightly

Nov 29 - Nov 30

Total with taxes and fees

A swimming pool with lounge chairs and tables, surrounded by a white building with a brick facade.

2. 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.

$134 nightly

Nov 8 - Nov 9

Total with taxes and fees

A swimming pool with a poolside area, including lounge chairs and umbrellas, adjacent to a building with multiple windows and a brick facade.

3. 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

Nov 8 - Nov 9

Total with taxes and fees

A modern hotel with a swimming pool, outdoor seating, and a well-lit facade.

4. 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

Nov 1 - Nov 2

Total with taxes and fees

A resort pool area with palm trees, lounge chairs, and umbrellas.

5. Marriott's Grande Vista

Orlando

$96 nightly

Nov 19 - Nov 20

Total with taxes and fees

A swimming pool with lounge chairs and tables, surrounded by a fence and a building with a modern design.

6. Hampton Inn Winter Haven

Winter Haven

Shimmering blue waters await at this family-friendly hotel with pool loungers and workout options.

$118 nightly

Nov 22 - Nov 23

Total with taxes and fees

A resort with multiple swimming pools, lounge areas, and a view of the sea.

7. 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.

$222 nightly

Oct 30 - Oct 31

Total with taxes and fees

A swimming pool with lounge chairs and umbrellas, surrounded by a building with red and beige walls.

8. 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

Nov 15 - Nov 16

Total with taxes and fees

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

Breakfast included

Hot tub

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.

Best Western Plus Winter Haven Inn & Suites

Winter Haven

$130 nightly

Nov 1 - Nov 2

Total with taxes and fees

A hotel room with two beds, a TV, a microwave, and a desk with a lamp.

Howard Johnson by Wyndham Winter Haven FL

Winter Haven

$77 nightly

Nov 1 - Nov 2

Total with taxes and fees

An outdoor patio with a fire pit, wicker furniture, and a view of a lake.

Courtyard by Marriott Winter Haven

Winter Haven

$152 nightly

Nov 22 - Nov 23

Total with taxes and fees

A modern living room with a fireplace, a sofa, a coffee table, and a TV mounted on the wall.

Staybridge Suites Winter Haven Auburndale by IHG

Winter Haven

$134 nightly

Nov 8 - Nov 9

Total with taxes and fees

An outdoor seating area with sofas, chairs, and a fire pit.

Home2 Suites By Hilton Winter Haven

Winter Haven

$144 nightly

Nov 15 - Nov 16

Total with taxes and fees

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Hotels with pools and waterparks in Winter Haven

A swimming pool with lounge chairs, surrounded by palm trees and a dock extending into a body of water, during sunset.

The Russell Lake House

Winter Haven

$190 nightly

Oct 30 - Oct 31

Total with taxes and fees

An outdoor hot tub area with a pool, surrounded by chairs and a table.

Legoland Splash Escape with pool and hot tub!

Winter Haven

$264 nightly

Nov 1 - Nov 2

Total with taxes and fees

Fully equipped kitchen with stainless steel appliances & huge kitchen island

Family Friendly Lake House W/ Pool Near Legoland

Winter Haven

$458 nightly

Nov 9 - Nov 10

Total with taxes and fees

A covered deck with a view of the water, a seating area with cushions, and a chair.

Lake, Pool, HotTub, Game Room, 8 Beds, Sleeps 17

Winter Haven

$1,007 nightly

Nov 1 - Nov 2

Total with taxes and fees

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Find out more about Winter Haven

Discover top Winter Haven attractions

Winter Haven offers a delightful array of experiences for travelers seeking a memorable getaway. One standout attraction is the stunning lakeside scenery, perfect for leisurely strolls or picnics by the water. The area's crystal-clear lakes provide ample opportunities for kayaking and paddleboarding, allowing you to soak in the beautiful Florida sunshine. For those who appreciate art and culture, the local galleries showcase a vibrant collection of contemporary works, making it a great spot for art enthusiasts to explore. Families will love the interactive exhibits at local museums, where children can engage with hands-on activities that spark their curiosity. Additionally, Winter Haven hosts a variety of seasonal festivals that celebrate local culture, food, and music, providing a lively atmosphere for visitors to enjoy. After a day of exploration, unwind in one of the charming accommodations nearby, where attentive service and comfort await, ensuring a truly relaxing stay.

Top Winter Haven Hotel Reviews

Omni Orlando Resort at ChampionsGate

10/10 Excellent

"Love this resort"

Holiday Inn & Suites Orlando SW - Celebration Area by IHG

10/10 Excellent

"We absolutely love this hotel! The staff is always super friendly and helpful, and the breakfast is really good—especially the make-your-own waffles! The location is perfect because everything is so close by, and having food trucks right next door is definitely a plus! This is one of our favorite hotels to stay at when we visit Orlando. We always enjoy our stay and highly recommend it!"

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.

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Check availability on Winter Haven Hotels with a Pool

Our top choices for Winter Haven hotels with a pool

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