A baseball player in a white uniform with the number 20, a catcher in an orange uniform, and an umpire standing behind the catcher.

Find Hotels with a Pool in Lakeland - Winter Haven, FL

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check availability on Lakeland - Winter Haven Hotels with a Pool

This weekend
Next weekend

Our top choices for Lakeland - Winter Haven hotels with a pool

1. Home2 Suites by Hilton Orlando at Flamingo Crossings

Home2 Suites by Hilton Orlando at Flamingo Crossings
3.0 star property
Bay Lake
9.4 out of 10, Exceptional, (5,872 reviews)
  • cleanliness
    Splash into vacation mode at this family resort featuring a sun-soaked pool area and thrilling waterslide.
The price is ₩118,526
₩133,341 total
includes taxes & fees
Aug 18 - Aug 19
Home2 Suites by Hilton Orlando at Flamingo Crossings

2. 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, (1,339 reviews)
  • cleanliness
    Sun-soaked pool area creates perfect retreat near LEGOLAND Florida with loungers and umbrellas.
The price is ₩162,877
₩182,421 total
includes taxes & fees
Sep 3 - Sep 4
Best Western Plus Winter Haven Inn & Suites 

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

Holiday Inn Express Lake Wales N-Winter Haven by IHG
2.5 star property
Lake Wales
9.2 out of 10, Wonderful, (1,005 reviews)
  • cleanliness
    Experience the Florida sunshine while floating in the sparkling outdoor pool at this Lake Wales hotel, just minutes from LEGOLAND.
The price is ₩181,483
₩203,261 total
includes taxes & fees
Aug 16 - Aug 17
Holiday Inn Express Lake Wales N-Winter Haven by IHG

4. Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center

Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
3.0 star property
Bay Lake
9.4 out of 10, Exceptional, (5,321 reviews)
  • cleanliness
    Splash into endless fun with an outdoor pool and sunny loungers just steps from Disney magic.
The price is ₩120,250
₩135,281 total
includes taxes & fees
Aug 18 - Aug 19
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center

5. 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, (855 reviews)
  • cleanliness
    Refreshing outdoor pool oasis with loungers and umbrellas provides a sun-soaked relaxation spot near LEGOLAND Florida.
The price is ₩147,187
₩164,849 total
includes taxes & fees
Aug 9 - Aug 10
Staybridge Suites Winter Haven Auburndale by IHG

6. Kompose Boutique Resort at Theme Parks

Kompose Boutique Resort at Theme Parks
3.0 star property
Kissimmee
9.4 out of 10, Exceptional, (5,173 reviews)
  • cleanliness
    Splash down the waterslide or bask poolside at this modern family resort with two hot tubs.
The price is ₩38,454
₩106,884 total
includes taxes & fees
Aug 6 - Aug 7
Kompose Boutique Resort at Theme Parks

7. Homewood Suites by Hilton Orlando at Flamingo Crossings

Homewood Suites by Hilton Orlando at Flamingo Crossings
3.0 star property
Bay Lake
9.4 out of 10, Exceptional, (2,635 reviews)
  • cleanliness
    Dive into poolside bliss with loungers and a thrilling waterslide at this spotless Orlando retreat.
The price is ₩151,160
₩170,056 total
includes taxes & fees
Aug 18 - Aug 19
Homewood Suites by Hilton Orlando at Flamingo Crossings

8. Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance

Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance
3.0 star property
Bay Lake
9.6 out of 10, Exceptional, (2,199 reviews)
  • cleanliness
    Sun-soaked pool sanctuary with poolside bar offers leisurely vacation escape in a serene setting.
The price is ₩133,611
₩150,313 total
includes taxes & fees
Aug 10 - Aug 11
Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance

9. Drury Plaza Hotel Orlando - Disney Springs Area

Drury Plaza Hotel Orlando - Disney Springs Area
4.0 star property
Lake Buena Vista
9.8 out of 10, Exceptional, (6,001 reviews)
  • cleanliness
    Dive into a cool-down oasis with a spacious outdoor pool, hot tub, and poolside bar service.
The price is ₩200,403
₩225,454 total
includes taxes & fees
Aug 31 - Sep 1
Drury Plaza Hotel Orlando - Disney Springs Area

10. LEGOLAND Beach Retreat

LEGOLAND Beach Retreat
3.0 star property
Winter Haven
8.8 out of 10, Excellent, (346 reviews)
The price is ₩253,862
₩340,342 total
includes taxes & fees
Aug 6 - Aug 7
LEGOLAND Beach Retreat
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 Lakeland - Winter Haven

Hotels with pools and free breakfast in Lakeland - Winter Haven

4-star hotels with pools in Lakeland - Winter Haven

5-star hotels with pools in Lakeland - 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 Lakeland - Winter Haven Hotel Reviews