Hotels with a Pool in Winter Haven

October 2026
November 2026

Free cancellation options if plans change

Earn rewards on every night you stay

Save more with Member Prices

Check prices for these dates

Next weekend
Sep 25 - Sep 27
In two weeks
Oct 2 - Oct 4

Hotels with a Pool in Winter Haven

1. Best Western Plus Winter Haven Inn & Suites 

Best Western Plus Winter Haven Inn & Suites 
Winter Haven
  • Outdoor pool
  • Pool loungers
$122
$137 total
includes taxes & fees
Sep 22 - Sep 23
Best Western Plus Winter Haven Inn & Suites 

2. Holiday Inn Winter Haven by IHG

Holiday Inn Winter Haven by IHG
Winter Haven
  • Outdoor pool
  • Pool loungers
$110
$123 total
includes taxes & fees
Sep 27 - Sep 28
Holiday Inn Winter Haven by IHG

3. Hampton Inn Winter Haven

Hampton Inn Winter Haven
Winter Haven
  • Outdoor pool
  • Pool loungers
$114
$128 total
includes taxes & fees
Sep 27 - Sep 28
Hampton Inn Winter Haven

4. Courtyard by Marriott Winter Haven

Courtyard by Marriott Winter Haven
Winter Haven
  • Outdoor pool
  • Pool loungers
$139
$156 total
includes taxes & fees
Sep 27 - Sep 28
Courtyard by Marriott Winter Haven

5. Staybridge Suites Winter Haven Auburndale by IHG

Staybridge Suites Winter Haven Auburndale by IHG
Winter Haven
  • Outdoor pool
  • Pool loungers
$125
$140 total
includes taxes & fees
Sep 23 - Sep 24
Staybridge Suites Winter Haven Auburndale by IHG

6. Home2 Suites By Hilton Winter Haven

Home2 Suites By Hilton Winter Haven
Winter Haven
  • Pool
  • Free breakfast
  • Pet friendly
  • Free parking
  • Free WiFi
  • Connecting rooms available
$130
$146 total
includes taxes & fees
Sep 27 - Sep 28
Home2 Suites By Hilton Winter Haven

7. Howard Johnson by Wyndham Winter Haven FL

Howard Johnson by Wyndham Winter Haven FL
Winter Haven
  • Outdoor pool
  • Pool loungers
$77
$86 total
includes taxes & fees
Sep 21 - Sep 22
Howard Johnson by Wyndham Winter Haven FL

8. LEGOLAND Beach Retreat

LEGOLAND Beach Retreat
Winter Haven
  • Outdoor pool
  • Poolside bar
  • Pool loungers
$169
$229 total
includes taxes & fees
Oct 12 - Oct 13
LEGOLAND Beach Retreat

9. Lake Roy Beach Inn

Lake Roy Beach Inn
Winter Haven
  • Outdoor pool
  • Pool loungers
$79
$89 total
includes taxes & fees
Sep 20 - Sep 21
Lake Roy Beach Inn

10. Lake Ida Beach Resort

Lake Ida Beach Resort
Winter Haven
  • Outdoor pool
  • Pool loungers
$71
$80 total
includes taxes & fees
Sep 20 - Sep 21
Lake Ida Beach Resort

11. Rodeway Inn & Suites Winter Haven Chain Of Lakes

Rodeway Inn & Suites Winter Haven Chain Of Lakes
Winter Haven
  • Outdoor pool
$81
$90 total
includes taxes & fees
Sep 21 - Sep 22
Rodeway Inn & Suites Winter Haven Chain Of Lakes

12. Legoland & Lakes Pool Home w/ Private Suite

Legoland & Lakes Pool Home w/ Private Suite
Winter Haven
  • Outdoor pool
$146
$506 total
includes taxes & fees
Sep 25 - Sep 26
Legoland & Lakes Pool Home w/ Private Suite

13. Economy Suites

Economy Suites
Winter Haven
  • Outdoor pool
  • Poolside bar
$76
$85 total
includes taxes & fees
Sep 20 - Sep 21
Economy Suites

14. Legoland Florida Hotel

Legoland Florida Hotel
Winter Haven
  • 2 outdoor pools
  • Pool loungers
$199
$262 total
includes taxes & fees
Sep 22 - Sep 23
Legoland Florida Hotel

15. Best Western Auburndale Inn & Suites

Best Western Auburndale Inn & Suites
Auburndale
  • Outdoor pool
  • Pool loungers
$101
$113 total
includes taxes & fees
Sep 24 - Sep 25
Best Western Auburndale Inn & Suites

16. Holiday Inn Express Lake Wales N-Winter Haven by IHG

Holiday Inn Express Lake Wales N-Winter Haven by IHG
Lake Wales
  • Outdoor pool
  • Pool loungers
$123
$138 total
includes taxes & fees
Sep 27 - Sep 28
Holiday Inn Express Lake Wales N-Winter Haven by IHG

17. Fairfield by Marriott Inn & Suites Davenport

Fairfield by Marriott Inn & Suites Davenport
Davenport
  • Outdoor pool
$103
$115 total
includes taxes & fees
Sep 27 - Sep 28
Fairfield by Marriott Inn & Suites Davenport

18. Days Inn & Suites by Wyndham Lakeland

Days Inn & Suites by Wyndham Lakeland
Lakeland
  • Outdoor pool
$56
$69 total
includes taxes & fees
Oct 11 - Oct 12
Days Inn & Suites by Wyndham Lakeland

19. Home2 Suites By Hilton Lakeland North I-4

Home2 Suites By Hilton Lakeland North I-4
Lakeland
  • Pool
  • Free breakfast
  • Pet friendly
  • Parking available
  • Free WiFi
  • Connecting rooms available
$98
$109 total
includes taxes & fees
Sep 27 - Sep 28
Home2 Suites By Hilton Lakeland North I-4

20. Hampton Inn Orlando-Maingate South

Hampton Inn Orlando-Maingate South
Davenport
  • Outdoor pool
  • Hot tub
$93
$105 total
includes taxes & fees
Sep 27 - Sep 28
Hampton Inn Orlando-Maingate South
See more properties

Discover your perfect hotel with a pool in Winter Haven

Breakfast included
Hot tub
4 stars
5 stars
Water park

Hotels with pools and free breakfast in Winter Haven

Best Western Plus Winter Haven Inn & Suites 

Best Western Plus Winter Haven Inn & Suites 
Winter Haven
$122
$137 total
includes taxes & fees
Sep 22 - Sep 23
Best Western Plus Winter Haven Inn & Suites 

Holiday Inn Winter Haven by IHG

Holiday Inn Winter Haven by IHG
Winter Haven
$110
$123 total
includes taxes & fees
Sep 27 - Sep 28
Holiday Inn Winter Haven by IHG

Hampton Inn Winter Haven

Hampton Inn Winter Haven
Winter Haven
$114
$128 total
includes taxes & fees
Sep 27 - Sep 28
Hampton Inn Winter Haven

Staybridge Suites Winter Haven Auburndale by IHG

Staybridge Suites Winter Haven Auburndale by IHG
Winter Haven
$125
$140 total
includes taxes & fees
Sep 23 - Sep 24
Staybridge Suites Winter Haven Auburndale by IHG

Howard Johnson by Wyndham Winter Haven FL

Howard Johnson by Wyndham Winter Haven FL
Winter Haven
$77
$86 total
includes taxes & fees
Sep 21 - Sep 22
Howard Johnson by Wyndham Winter Haven FL

LEGOLAND Beach Retreat

LEGOLAND Beach Retreat
Winter Haven
$169
$229 total
includes taxes & fees
Oct 12 - Oct 13
LEGOLAND Beach Retreat

Courtyard by Marriott Winter Haven

Courtyard by Marriott Winter Haven
Winter Haven
$139
$156 total
includes taxes & fees
Sep 27 - Sep 28
Courtyard by Marriott Winter Haven

Home2 Suites By Hilton Winter Haven

Home2 Suites By Hilton Winter Haven
Winter Haven
$130
$146 total
includes taxes & fees
Sep 27 - Sep 28
Home2 Suites By Hilton Winter Haven

Rodeway Inn & Suites Winter Haven Chain Of Lakes

Rodeway Inn & Suites Winter Haven Chain Of Lakes
Winter Haven
$81
$90 total
includes taxes & fees
Sep 21 - Sep 22
Rodeway Inn & Suites Winter Haven Chain Of Lakes

Legoland Florida Hotel

Legoland Florida Hotel
Winter Haven
$199
$262 total
includes taxes & fees
Sep 22 - Sep 23
Legoland Florida Hotel
View all properties

Top neighborhoods in Winter Haven

Lucerne Park

Winter Haven's Lucerne Park neighborhood offers attractions including Lake Henry.

Top landmarks in Winter Haven

The entrance to LEGO Florida with colorful LEGO structures and a large LEGO sign.

LEGOLAND® Florida

9.0/10 (2,150 reviews)
Why not give yourself a treat with a trip to LEGOLAND® Florida, one of the most popular family attractions located 3.2 mi (5.2 km) from central Winter Haven. If you have fun at LEGOLAND® Florida, you'll love Peppa Pig Theme Park Florida, just a short walk away.
See properties
A narrow water channel surrounded by lush greenery and tall trees.

Chain of Lakes Park

8.2/10 (185 reviews)
You can catch an event at Chain of Lakes Park, located 1.6 mi (2.5 km) from central Winter Haven. If you think Chain of Lakes Park is cool, you also might like Winter Haven City Tennis Center, located nearby.
See properties

Peppa Pig Theme Park Florida

If thrills are what you're after, head to Peppa Pig Theme Park Florida, located 3.6 mi (5.8 km) from central Winter Haven. If you have fun at Peppa Pig Theme Park Florida, you'll love LEGOLAND® Florida, just a short walk away.
See properties

Theatre Winter Haven

7.4/10 (56 reviews)
Theatre Winter Haven is 1.3 mi (2.2 km) from central Winter Haven, why not stop by during your stay. If you want to experience more of the culture Winter Haven has to offer, head to LEGOLAND® Florida, Chain of Lakes Park, and Indigo's Family Fun Center.
See properties

Inman Park

7.4/10 (14 reviews)
Inman Park is worth a visit, located 1.4 mi (2.3 km) from central Winter Haven.
See properties

Cypresswood Golf and Country Club

6.4/10 (25 reviews)
You might want to practice your swing at Cypresswood Golf and Country Club, a golf course located 5.2 mi (8.4 km) from central Winter Haven. If Cypresswood Golf and Country Club doesn't quite scratch your golfing itch, Lake Region Golf Club, and Winter Pines Golf Course are also nearby.
See properties

Willowbrook Golf Course

6.8/10 (15 reviews)
You might want to play some rounds at Willowbrook Golf Course, located 3.7 mi (6 km) from central Winter Haven. If Willowbrook Golf Course doesn't quite scratch your golfing itch, Lake Henry Golf Club, and Lake Region Golf Club are also nearby.
See properties

Winter Haven City Tennis Center

You can catch an event at Winter Haven City Tennis Center, located 0.5 mi (0.7 km) from central Winter Haven. If you think Winter Haven City Tennis Center is cool, you also might like Chain of Lakes Park and Cindy Hummed Tennis Center, both located nearby.
See properties

About the destination

Winter Haven is a family-friendly place known for its restaurants. Top attractions include LEGOLAND® Florida. There's plenty more to see, including sights like Indigo's Family Fun Center and Theatre Winter Haven.