The Best Hotels with a Pool in Lakeland - Winter Haven, FL from AED 255 in 2026

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Check availability on Lakeland - Winter Haven Hotels with a Pool

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

Outdoor pool, pool umbrellas, sun loungers

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

1. Best Western Plus Winter Haven Inn & Suites

Winter Haven

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

AED 434

AED 486 total

includes taxes & fees

7 Sep - 8 Sep

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

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

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

2. Holiday Inn Winter Haven by IHG

Winter Haven

Dive into crystalline blue waters at this outdoor pool oasis with comfy loungers and sunshine appeal.

AED 386

AED 432 total

includes taxes & fees

20 Sep - 21 Sep

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

Lake Wales

Experience the Florida sunshine while floating in the sparkling outdoor pool at this Lake Wales hotel, just minutes from LEGOLAND.

AED 477

AED 535 total

includes taxes & fees

4 Oct - 5 Oct

Premium bedding, down comforters, pillowtop beds, blackout drapes

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

4. 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.

AED 444

AED 498 total

includes taxes & fees

6 Sep - 7 Sep

5. Home2 Suites By Hilton Winter Haven

Winter Haven

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

AED 509

AED 570 total

includes taxes & fees

13 Sep - 14 Sep

Basic Studio Suite, 1 King Bed, Non Smoking | Egyptian cotton sheets, premium bedding, pillowtop beds, desk

6. Days Inn & Suites by Wyndham Lakeland

Lakeland

Take a refreshing plunge in this hotel's serene outdoor pool, just steps from local attractions.

AED 206

AED 255 total

includes taxes & fees

24 Sep - 25 Sep

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

7. Hyatt Place Lakeland Center

Downtown Lakeland

Escape to a refreshing lakeside pool retreat where crystal waters shimmer under Florida sunshine, perfect for leisure travelers.

AED 377

AED 422 total

includes taxes & fees

17 Sep - 18 Sep

8. Kompose Boutique Resort at Theme Parks

Kissimmee

Splash down the waterslide or bask poolside at this modern family resort with two hot tubs.

AED 99

AED 275 total

includes taxes & fees

8 Sep - 9 Sep

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

Breakfast included

4 stars

5 stars

Hot tub

Spa

Hotels with pools and free breakfast in Lakeland - Winter Haven

Best Western Plus Winter Haven Inn & Suites

Winter Haven

AED 434

AED 486 total

includes taxes & fees

7 Sep - 8 Sep

Courtyard by Marriott Winter Haven

Winter Haven

AED 496

AED 556 total

includes taxes & fees

22 Sep - 23 Sep

Holiday Inn Express Bartow by IHG

Bartow

AED 323

AED 362 total

includes taxes & fees

13 Sep - 14 Sep

Kompose Boutique Resort at Theme Parks

Kissimmee

AED 99

AED 275 total

includes taxes & fees

8 Sep - 9 Sep

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

Hampton Inn Winter Haven

Winter Haven

AED 419

AED 469 total

includes taxes & fees

13 Sep - 14 Sep

Holiday Inn Winter Haven by IHG

Winter Haven

AED 386

AED 432 total

includes taxes & fees

20 Sep - 21 Sep

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

LEGOLAND Beach Retreat

Winter Haven

AED 653

AED 875 total

includes taxes & fees

11 Sep - 12 Sep

Superior Studio Suite, 1 King Bed, Non Smoking | Egyptian cotton sheets, premium bedding, pillowtop beds, desk

Days Inn & Suites by Wyndham Lakeland

Lakeland

AED 206

AED 255 total

includes taxes & fees

24 Sep - 25 Sep

Staybridge Suites Winter Haven Auburndale by IHG

Winter Haven

AED 444

AED 498 total

includes taxes & fees

6 Sep - 7 Sep

Premium bedding, pillowtop beds, in-room safe, desk

Room, 1 King Bed (Specialty) | Premium bedding, pillowtop beds, in-room safe, desk

Hyatt Place Lakeland Center

Downtown Lakeland

AED 377

AED 422 total

includes taxes & fees

17 Sep - 18 Sep

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4-star hotels with pools in Lakeland - Winter Haven

Outdoor pool, open 7:00 AM to 11:00 PM, cabanas (surcharge)

Breakfast, lunch, dinner and brunch served

Meliá Orlando Celebration

Celebration

AED 228

AED 392 total

includes taxes & fees

13 Sep - 14 Sep

3 restaurants; breakfast, lunch, dinner, and brunch served

Margaritaville Resort Orlando with H2O Waterpark

Kissimmee

AED 511

AED 780 total

includes taxes & fees

23 Sep - 24 Sep

Drury Plaza Hotel Orlando - Disney Springs Area

Lake Buena Vista

AED 515

AED 579 total

includes taxes & fees

21 Sep - 22 Sep

5 outdoor pools, open 8:00 AM to 10:00 PM, cabanas (surcharge)

10 restaurants; breakfast, lunch, and dinner served

Omni Orlando Resort at ChampionsGate

Champions Gate

AED 614

AED 905 total

includes taxes & fees

12 Sep - 13 Sep

6 outdoor pools, free cabanas, pool umbrellas

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Orlando

AED 453

AED 509 total

includes taxes & fees

29 Sep - 30 Sep

2 outdoor pools, a heated pool, cabanas (surcharge), pool umbrellas

Wyndham Lake Buena Vista – Disney Springs® Area

Lake Buena Vista

AED 328

AED 518 total

includes taxes & fees

7 Sep - 8 Sep

4 outdoor pools, cabanas (surcharge), pool umbrellas

Hilton Vacation Club Mystic Dunes Orlando

Kissimmee

AED 317

AED 485 total

includes taxes & fees

10 Sep - 11 Sep

Embassy Suites by Hilton Orlando Lake Buena Vista South

Kissimmee

AED 330

AED 375 total

includes taxes & fees

4 Oct - 5 Oct

Hilton Orlando Lake Buena Vista - Disney Springs® Area

Lake Buena Vista

AED 434

AED 658 total

includes taxes & fees

14 Sep - 15 Sep

Presidential Suite, 1 King Bed, Balcony, Tower | Living area | 50-inch LCD TV with cable channels, TV, pay movies

Hilton Orlando Buena Vista Palace - Disney Springs® Area

Lake Buena Vista

AED 528

AED 763 total

includes taxes & fees

10 Sep - 11 Sep

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5-star hotels with pools in Lakeland - Winter Haven

Elite House, Private Pool (12 Bedrooms Westside) | Private kitchen | Coffee/tea maker, full-size fridge, microwave, oven

Encore Resort and Water Park at Reunion by Rentyl

Kissimmee

AED 727

AED 2,785 total

includes taxes & fees

14 Sep - 15 Sep

Waldorf Astoria Orlando - An Official Walt Disney World® Hotel

Orlando

AED 1,090

AED 1,432 total

includes taxes & fees

27 Sep - 28 Sep

Outdoor pool, open 9:00 AM to 6:00 PM, free cabanas, pool umbrellas

ette hotel Orlando

Kissimmee

AED 869

AED 986 total

includes taxes & fees

18 Sep - 19 Sep

2 restaurants; breakfast, lunch, and dinner served

Disney's Beach Club Resort

Bay Lake

AED 2,123

AED 2,388 total

includes taxes & fees

7 Sep - 8 Sep

Reunion Resort & Golf Club

Reunion

AED 846

AED 1,134 total

includes taxes & fees

7 Sep - 8 Sep

3 restaurants; breakfast, lunch, and dinner served

Disney's Beach Club Villas

Bay Lake

AED 2,123

AED 2,388 total

includes taxes & fees

9 Sep - 10 Sep

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 Lakeland - Winter Haven Hotel Reviews