Hotels With Pool in Winter Haven | Flexible Booking Options

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

Check availability on Winter Haven Hotels with a Pool

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Our top choices for Winter Haven hotels with a pool

6 outdoor pools, free cabanas, pool umbrellas

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

Orlando

$137 nightly

$154 total

Oct 18 - Oct 19

Total with taxes and fees

Outdoor pool, pool umbrellas, sun loungers

Premium bedding, down comforters, pillowtop beds, blackout drapes

Studio Suite, 2 Queen Beds, Kitchen, Lake View | Premium bedding, down comforters, pillowtop beds, blackout drapes

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.

$125 nightly

$140 total

Sep 23 - Sep 24

Total with taxes and fees

3 restaurants; breakfast, lunch, and dinner served

3. 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

Oct 20 - Oct 21

Total with taxes and fees

Standard Room, 2 Queen Beds, Non Smoking, Bathtub (Larger Room) | Desk, laptop workspace, blackout drapes, iron/ironing board

4. Best Western Plus Winter Haven Inn & Suites

Winter Haven

Sun-soaked pool area creates perfect retreat near LEGOLAND Florida with loungers and umbrellas.

$122 nightly

$137 total

Sep 22 - Sep 23

Total with taxes and fees

Outdoor pool, open 8:00 AM to 9:00 PM, sun loungers

Eco-friendly toiletries, hair dryer, towels, soap

Suite | Desk, blackout drapes, iron/ironing board, cribs (free)

5. 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

Sep 27 - Sep 28

Total with taxes and fees

Combined shower/tub, free toiletries, hair dryer, towels

6. Hampton Inn Winter Haven

Winter Haven

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

$114 nightly

$128 total

Sep 27 - Sep 28

Total with taxes and fees

7. Home2 Suites By Hilton Winter Haven

Winter Haven

Refresh yourself in the seasonal outdoor pool during warm months while staying minutes from LEGOLAND® Florida.

$130 nightly

$146 total

Sep 27 - Sep 28

Total with taxes and fees

Outdoor pool, open 8:30 AM to 9:00 PM, pool umbrellas, sun loungers

Blackout drapes, iron/ironing board, cribs (free)

8. 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

Sep 22 - Sep 23

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

Water park

4 stars

Spa

Hotels with pools and free breakfast in Winter Haven

Best Western Plus Winter Haven Inn & Suites

Winter Haven

$122 nightly

$137 total

Sep 22 - Sep 23

Total with taxes and fees

Desk, blackout drapes, iron/ironing board, cribs (free)

Holiday Inn Winter Haven by IHG

Winter Haven

$110 nightly

$123 total

Sep 27 - Sep 28

Total with taxes and fees

Desk, iron/ironing board, cribs (free), WiFi (free)

Hampton Inn Winter Haven

Winter Haven

$114 nightly

$128 total

Sep 27 - Sep 28

Total with taxes and fees

Courtyard by Marriott Winter Haven

Winter Haven

$139 nightly

$156 total

Sep 27 - Sep 28

Total with taxes and fees

Staybridge Suites Winter Haven Auburndale by IHG

Winter Haven

$125 nightly

$140 total

Sep 23 - Sep 24

Total with taxes and fees

Howard Johnson by Wyndham Winter Haven FL

Winter Haven

$77 nightly

$86 total

Sep 22 - Sep 23

Total with taxes and fees

Home2 Suites By Hilton Winter Haven

Winter Haven

$130 nightly

$146 total

Sep 27 - Sep 28

Total with taxes and fees

2 outdoor pools, open 11:00 AM to 9:00 PM, pool umbrellas, sun loungers

Pirate Island Theme | In-room safe, desk, laptop workspace, soundproofing

Kingdom Theme | In-room safe, desk, laptop workspace, soundproofing

Legoland Florida Hotel

Winter Haven

$234 nightly

$262 total

Sep 22 - Sep 23

Total with taxes and fees

Desk, laptop workspace, iron/ironing board (on request), WiFi (free)

Suite, 1 King Bed, Non Smoking | Desk, laptop workspace, iron/ironing board (on request), WiFi (free)

Rodeway Inn & Suites Winter Haven Chain Of Lakes

Winter Haven

$81 nightly

$90 total

Sep 22 - Sep 23

Total with taxes and fees

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.

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Top Winter Haven Hotel Reviews

The Grove Resort & Water Park Orlando

8/10 Good

"We love this resort! Waterpark and close to Disney. Plenty of space to spread out."

Quality Inn & Suites By the Parks

10/10 Excellent

"The staff here were helpful and kind throughout my fiancée and I's stay. Checking in and out was quick and painless. The room was clean and housekeeping came everyday. The air conditioning in the room worked well. The included breakfast lasted 3 hours and included items such as mini omelettes, sausages, biscuits and gravy, a waffle and pancake maker, and much more. The hotel is about 15 minutes from the Disney parks, 25-30 minutes from Universal, and about 40-45 minutes from Orlando International Airport (MCO). Overall, I was very pleased with our stay and have no complaints! :)"

Vacation Village Orlando, Celebration

10/10 Excellent

"First the property is perfectly located! Close enough to walk anywhere. Publix is across the street. The pools are lovely and clean. The rooms are dated but the beds are very comfy. Staff is nice but check in was me going desk to desk then being told to go somewhere else…took forever. Luckily there’s coffee there and it’s good!"

Hilton Vacation Club Mystic Dunes Orlando

10/10 Excellent

"Very quiet and peaceful. The staff was friendly and the grounds were very well kept."

Holiday Inn Club Vacations at Orange Lake Resort by IHG

10/10 Excellent

"The property is beautiful and well maintained. The proximity to Walt Disney World is great! The resort pools are beautiful and drinks were great too. We will definitely be back."

Galleria Palms Hotel

8/10 Good

"Check-in was great! Nice place to stay and close to everything!"

Delta Hotels by Marriott Orlando Celebration

10/10 Excellent

"Love it..everything perfect.loke alway..I had been staying here since 1994"

Omni Orlando Resort at ChampionsGate

10/10 Excellent

"Todo maravilloso"

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 $85 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