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
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Our top choices for Winter Haven hotels with a pool

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

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
4.0 star property
Orlando
9.2 out of 10, Wonderful, (7,287 reviews)
$111 nightly
The price is $125
Dec 1 - Dec 2
Total with taxes and fees
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

2. Staybridge Suites Winter Haven Auburndale by IHG

Staybridge Suites Winter Haven Auburndale by IHG
3.0 star property
Winter Haven
9.8 out of 10, Exceptional, (936 reviews)
  • cleanliness
    Refreshing outdoor pool oasis with loungers and umbrellas provides a sun-soaked relaxation spot near LEGOLAND Florida.
$134 nightly
The price is $150
Nov 29 - Nov 30
Total with taxes and fees
Staybridge Suites Winter Haven Auburndale by IHG

3. Holiday Inn Winter Haven by IHG

Holiday Inn Winter Haven by IHG
3.0 star property
Winter Haven
9.0 out of 10, Wonderful, (1,012 reviews)
  • cleanliness
    Dive into crystalline blue waters at this outdoor pool oasis with comfy loungers and sunshine appeal.
$118 nightly
The price is $132
Nov 15 - Nov 16
Total with taxes and fees
Holiday Inn Winter Haven by IHG

4. Best Western Plus Winter Haven Inn & Suites 

Best Western Plus Winter Haven Inn & Suites 
3.5 star property
Winter Haven
9.6 out of 10, Exceptional, (1,390 reviews)
  • cleanliness
    Sun-soaked pool area creates perfect retreat near LEGOLAND Florida with loungers and umbrellas.
$122 nightly
The price is $137
Nov 15 - Nov 16
Total with taxes and fees
Best Western Plus Winter Haven Inn & Suites 

5. Marriott's Grande Vista

Marriott's Grande Vista
4.0 star property
Orlando
9.0 out of 10, Wonderful, (5,417 reviews)
$96 nightly
The price is $108
Dec 1 - Dec 2
Total with taxes and fees
Marriott's Grande Vista

6. Hampton Inn Winter Haven

Hampton Inn Winter Haven
2.5 star property
Winter Haven
9.0 out of 10, Wonderful, (1,005 reviews)
  • cleanliness
    Shimmering blue waters await at this family-friendly hotel with pool loungers and workout options.
$118 nightly
The price is $132
Nov 22 - Nov 23
Total with taxes and fees
Hampton Inn Winter Haven

7. The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando
4.0 star property
Winter Garden
8.2 out of 10, Very good, (10,948 reviews)
  • cleanliness
    Splash into paradise at this resort with 6 outdoor pools, a lazy river, and a complimentary water park for endless aquatic fun.
$219 nightly
The price is $246
Dec 10 - Dec 11
Total with taxes and fees
The Grove Resort & Water Park Orlando

8. Home2 Suites By Hilton Winter Haven

Home2 Suites By Hilton Winter Haven
3.0 star property
Winter Haven
9.4 out of 10, Exceptional, (401 reviews)
  • cleanliness
    Refresh yourself in the seasonal outdoor pool during warm months while staying minutes from LEGOLAND® Florida.
$142 nightly
The price is $159
Nov 25 - Nov 26
Total with taxes and fees
Home2 Suites By Hilton Winter Haven

9. Howard Johnson by Wyndham Winter Haven FL

Howard Johnson by Wyndham Winter Haven FL
2.0 star property
Winter Haven
7.4 out of 10, Good, (1,015 reviews)
  • cleanliness
    Splash into fun with sun loungers and umbrellas at this hotel's relaxing outdoor pool.
$85 nightly
The price is $95
Nov 15 - Nov 16
Total with taxes and fees
Howard Johnson by Wyndham Winter Haven FL

10. Kompose Boutique Resort at Theme Parks

Kompose Boutique Resort at Theme Parks
3.0 star property
Kissimmee
9.4 out of 10, Exceptional, (6,449 reviews)
  • cleanliness
    Splash down the waterslide or bask poolside at this modern family resort with two hot tubs.
$58 nightly
The price is $65
Nov 11 - Nov 12
Total with taxes and fees
Kompose Boutique Resort at Theme Parks
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.

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

Hotels with pools and free breakfast in Winter Haven

Hotels with pools and waterparks in Winter Haven

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.

Top Winter Haven Hotel Reviews

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.

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 $65 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