Search for Cheap Deals on
Hotels with Pools in Winter Haven

You choose what matters — star rating, location, amenities.

We pick the perfect hotel, packed with all your must-haves.

Your hotel is revealed right after booking!


Featured Winter Haven Hotels with a Pool

Lake Roy Beach Inn
Lake Roy Beach Inn
2 out of 5
1823 Cypress Gardens Blvd, Winter Haven, FL
Fully refundableReserve now, pay when you stay
Book a stay at this beach hotel in Winter Haven. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff in our reviews. Popular ...
Lake Roy Beach Inn
Howard Johnson by Wyndham Winter Haven FL
Howard Johnson by Wyndham Winter Haven FL
2 out of 5
1300 3rd St Sw, Cypress Gardens & US 17 South, Winter Haven, FL
Fully refundableReserve now, pay when you stay
Stay at this motel in Winter Haven. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Howard Johnson by Wyndham Winter Haven FL
Hampton Inn Winter Haven
Hampton Inn Winter Haven
2.5 out of 5
202 Cypress Gardens Blvd, Winter Haven, FL
Fully refundableReserve now, pay when you stay
Book a stay at this business-friendly hotel in Winter Haven. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Hampton Inn Winter Haven
Winter Haven Gardens Inn
Winter Haven Gardens Inn
2.5 out of 5
1150 3rd Street SW, Winter Haven, FL
Stay at this hotel in Winter Haven. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions LEGOLAND® Florida and Indigo's Family Fun Center ...
Winter Haven Gardens Inn
Rodeway Inn & Suites Winter Haven Chain Of Lakes
Rodeway Inn & Suites Winter Haven Chain Of Lakes
2 out of 5
1911 Cypress Gardens Blvd, Winter Haven, FL
Fully refundableReserve now, pay when you stay
Book a stay at this business-friendly motel in Winter Haven. Enjoy free breakfast, free WiFi, and free parking. Popular attractions LEGOLAND® Florida and Baytree ...
Rodeway Inn & Suites Winter Haven Chain Of Lakes
Travelodge by Wyndham Winter Haven
Travelodge by Wyndham Winter Haven
2.5 out of 5
2275 8th St NW, Winter Haven, FL
Book a stay at this business-friendly motel in Winter Haven. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions LEGOLAND® Florida and ...
Travelodge by Wyndham Winter Haven
Economy Suites
Economy Suites
2 out of 5
1901 Cypress Gardens Blvd, Winter Haven, FL
Fully refundableReserve now, pay when you stay
Stay at this motel in Winter Haven. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff in our reviews. Popular attractions ...
Economy Suites
Holiday Inn Winter Haven, an IHG Hotel
Holiday Inn Winter Haven, an IHG Hotel
3 out of 5
200 Cypress Gardens Boulevard, Winter Haven, FL
Fully refundable
Stay at this 3-star business-friendly hotel in Winter Haven. Enjoy free WiFi, free parking, and room service. Our guests praise the breakfast and the helpful ...
Holiday Inn Winter Haven, an IHG 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.