The Best Hotels with a Pool in Lakeland - Winter Haven, FL from AED 258 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

A modern hotel with a swimming pool, outdoor seating, and a well-lit facade.

A reception area with a modern design, featuring a counter, a seating area, and a wall with a unique pattern.

A hotel room with two beds, a desk, a microwave, a TV, and a painting on the wall.

A modern hotel lobby with a central reception desk, multiple light fixtures, and a patterned wall.

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 479

AED 536 total

includes taxes & fees

12 Oct - 13 Oct

A swimming pool with a clear blue water surface, surrounded by lounge chairs and umbrellas.

A conference room with a large flat-screen TV, wooden chairs, a black table, and a bright yellow chair.

A hotel room with two beds, a desk, a chair, a TV, and a window with a view of trees.

A coffee station with two coffee machines and a display of coffee pods and cups.

2. Holiday Inn Express Bartow by IHG

Bartow

Dive into aquatic bliss at this hotel's refreshing outdoor pool with sun loungers.

AED 400

AED 448 total

includes taxes & fees

11 Oct - 12 Oct

A swimming pool with lounge chairs and tables, surrounded by a fence and a building with a modern design.

A Hampton Inn hotel with a clear entrance, a covered waiting area, and a sign indicating a clearance of 13'6".

A hotel lobby with a seating area featuring blue patterned chairs, a wooden coffee table, and a sofa.

A hotel lobby with a reception desk, seating area, and a bar.

3. Hampton Inn Winter Haven

Winter Haven

Shimmering blue waters await at this family-friendly hotel with pool loungers and workout options.

AED 434

AED 486 total

includes taxes & fees

8 Nov - 9 Nov

A swimming pool with lounge chairs and umbrellas, surrounded by a building with red and beige walls.

A modern lounge area with green upholstered chairs, a herringbone-patterned floor, and a large window providing natural light.

A hotel room with a desk, chair, sofa, ottoman, and a large window.

A modern kitchen with a central island, bar stools, and a refrigerator.

4. 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 528

AED 591 total

includes taxes & fees

18 Oct - 19 Oct

A swimming pool with lounge chairs and tables, surrounded by a white building with a brick facade.

A modern living room with a fireplace, a sofa, a coffee table, and a TV mounted on the wall.

A modern hotel room with a kitchenette, a dining area, and a bed.

A modern kitchen with a dining area, a flat-screen TV, and a large window.

5. 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 492

AED 551 total

includes taxes & fees

18 Oct - 19 Oct

A poolside area with multiple round tables, a pool, and a modern building with large windows in the background.

A modern hotel with a pool area, palm trees, and a parking lot.

An outdoor patio with a fire pit, wicker furniture, and a checkered wall.

A modern hotel lobby with multiple seating areas, a reception desk, and a large digital screen displaying scenic images.

6. SpringHill Suites by Marriott Lakeland

Downtown Lakeland

Dive into sparkling leisure at this downtown Lakeland hotel's outdoor pool and fitness center.

AED 459

AED 515 total

includes taxes & fees

18 Oct - 19 Oct

A pool area with lounge chairs, a covered seating area, and a building with multiple windows and balconies.

A modern bathroom with a sink, mirror, and shower.

A modern hotel lobby with a central seating area, a reception desk, and a large wall art piece.

A modern hotel room with a gray sectional sofa, a small side table, a floor lamp, a large window with a city view, and a bed with a TV.

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 460

AED 515 total

includes taxes & fees

8 Nov - 9 Nov

A hotel pool area with lounge chairs and umbrellas, surrounded by tall buildings and a sunset sky.

An outdoor patio area with wicker furniture, red accents, and palm trees.

A spacious lobby with a reception desk, seating area, and decorative hanging lights.

A modern hotel lobby with seating areas, tables, and decorative wall panels.

8. Drury Plaza Hotel Orlando - Disney Springs Area

Lake Buena Vista

Dive into a cool-down oasis with a spacious outdoor pool, hot tub, and poolside bar service.

AED 593

AED 667 total

includes taxes & fees

28 Oct - 29 Oct

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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 479

AED 536 total

includes taxes & fees

12 Oct - 13 Oct

A modern hotel reception area with a wooden reception desk, a seating area with a table and chairs, and a large wall with geometric patterns.

A hotel room with a sofa, two beds, a desk, a TV, and a carpeted floor.

A restaurant with tables and chairs, a large painting, and a TV on the wall.

A Holiday Inn Express hotel with a covered entrance, parking lot, and palm trees.

Holiday Inn Express Lake Wales N-Winter Haven by IHG

Lake Wales

AED 481

AED 539 total

includes taxes & fees

18 Oct - 19 Oct

An outdoor patio with a fire pit, wicker furniture, and a view of a lake.

A modern reception area with wooden panel walls and two reception desks.

A spacious indoor area with a bar, seating arrangements, and a large screen displaying content.

A modern hotel lobby with a long reception desk, bar area, and seating arrangement.

Courtyard by Marriott Winter Haven

Winter Haven

AED 528

AED 591 total

includes taxes & fees

18 Oct - 19 Oct

A hotel room with two beds, a large mirror, a wooden floor, and a view of the outdoors.

Hampton Inn Winter Haven

Winter Haven

AED 434

AED 486 total

includes taxes & fees

8 Nov - 9 Nov

A modern kitchen with a wooden counter, coffee machines, and a Coca-Cola refrigerator.

A spacious, modern living area with a herringbone wood floor, a dining area with a wooden table and chairs, and a kitchen in the background.

Staybridge Suites Winter Haven Auburndale by IHG

Winter Haven

AED 492

AED 551 total

includes taxes & fees

18 Oct - 19 Oct

An outdoor seating area with sofas, chairs, and a fire pit.

A reception desk with a sign reading "HOME 2 Suites by Hilton," a minibar, a refrigerator labeled "COLDER," and a snack shelf.

Home2 Suites By Hilton Winter Haven

Winter Haven

AED 528

AED 591 total

includes taxes & fees

18 Oct - 19 Oct

A hotel room with two beds, a desk, a television, and a door leading to another room.

A hotel reception area with a curved reception desk, a large chandelier, and a wall-mounted sign.

A swimming pool with a poolside area, including lounge chairs and umbrellas, adjacent to a building with multiple windows and a brick facade.

A hotel room with a desk, chair, sofa, and a painting on the wall.

Holiday Inn Winter Haven by IHG

Winter Haven

AED 408

AED 457 total

includes taxes & fees

8 Nov - 9 Nov

A compact kitchen with a dining table, chairs, a microwave, and a refrigerator.

A Best Western hotel with a parking lot and a landscaped area with palm trees.

A hotel room with a bed, a nightstand with a lamp, a shelf with artwork, and a green accent wall.

A conference room with a long table, chairs, a large screen, and framed artwork on the walls.

Best Western Auburndale Inn & Suites

Auburndale

AED 372

AED 416 total

includes taxes & fees

21 Oct - 22 Oct

A bar area with wooden cabinets, a counter with bottles, and a sign reading "THE PLACERY".

A modern hotel with a white facade, large windows, and a landscaped entrance.

Hyatt Place Lakeland Center

Downtown Lakeland

AED 460

AED 515 total

includes taxes & fees

8 Nov - 9 Nov

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4-star hotels with pools in Lakeland - Winter Haven

A water play area with wooden structures and a large water fountain.

A multi-level atrium with a glass ceiling, palm trees, and a wooden deck.

A large, multi-story hotel with a central courtyard, palm trees, and illuminated signage.

A spacious indoor atrium with a high glass ceiling, multiple seating areas, and lush greenery.

Gaylord Palms Resort & Convention Center

Kissimmee

AED 955

AED 1,283 total

includes taxes & fees

30 Oct - 31 Oct

A modern hotel with a reflective pool, palm trees, and a clear blue sky.

A modern hotel with a glass facade, multiple floors, and a prominent entrance with a canopy.

A pool area with lounge chairs and a waterfall feature.

A restaurant with tables set for dining, featuring floral centerpieces and candles.

Walt Disney World Swan Reserve

Bay Lake

AED 966

AED 1,293 total

includes taxes & fees

28 Oct - 29 Oct

A modern outdoor lounge area with seating and planters, large windows, and a view of the interior.

A spacious lobby with a curved seating area, a staircase, and a high ceiling.

A spacious bar area with a long counter, multiple seating options including round tables and bar stools, and a large window providing a view of the outside.

A modern hotel with multiple floors, a rooftop terrace, and a landscaped courtyard.

JW Marriott Orlando Bonnet Creek Resort & Spa

Orlando

AED 1,028

AED 1,384 total

includes taxes & fees

29 Oct - 30 Oct

Drury Plaza Hotel Orlando - Disney Springs Area

Lake Buena Vista

AED 593

AED 667 total

includes taxes & fees

28 Oct - 29 Oct

A large hotel with a distinctive pyramid-shaped building, a central courtyard with palm trees, and a body of water reflecting the structure.

An aerial view of a resort with multiple swimming pools, a beach area, and a variety of outdoor seating arrangements.

A luxurious lobby with a central fountain, seating areas, and a decorative ceiling.

Walt Disney World Dolphin

Bay Lake

AED 625

AED 909 total

includes taxes & fees

4 Nov - 5 Nov

An aerial view of a resort with a large swimming pool surrounded by palm trees and lounge chairs.

A view through a large window of a resort with a pool, palm trees, and a building in the background.

A pathway leading to a body of water with a fountain, surrounded by palm trees and a building with multiple floors.

A spacious living room with a large window, a sofa set, a coffee table, and a television.

Wyndham Grand Orlando Resort Bonnet Creek

Orlando

AED 455

AED 686 total

includes taxes & fees

29 Oct - 30 Oct

A modern outdoor lounge area with a glass-top table, a fire feature, and seating.

An aerial view of a resort with multiple swimming pools, lounge areas, and palm trees.

A resort with a large pool area, palm trees, and a golf course in the background.

A hotel entrance with a covered outdoor seating area, large windows, and potted plants.

Signia by Hilton Orlando - An Official Walt Disney World® Hotel

Orlando

AED 768

AED 1,071 total

includes taxes & fees

8 Nov - 9 Nov

An aerial view of a resort with multiple swimming pools, a golf course, and lush landscaping.

A spacious lobby with a polished marble floor, a grand chandelier, and a reception desk with wooden paneling.

A spacious lobby with a marble floor, a large potted plant, and a view of a pool and garden.

An outdoor restaurant with wooden pergolas, tables, and chairs, surrounded by greenery.

Omni Orlando Resort at ChampionsGate

Champions Gate

AED 702

AED 1,006 total

includes taxes & fees

1 Nov - 2 Nov

A hotel with a large pool, palm trees, and a waterfall feature.

A spacious dining area with a long table set for a meal, surrounded by chairs.

A hotel lobby with a reception desk, seating area, and a staircase leading to upper floors.

A bar area with a variety of seating options, including patterned chairs and stools, a bar counter with bottles, and a large mirror on the wall.

Caribe Royale Orlando, WorldHotels Elite

Orlando

AED 694

AED 938 total

includes taxes & fees

16 Oct - 17 Oct

A swimming pool with multiple water features, including a waterfall, surrounded by lounge chairs and a wooden bridge.

A hotel room with two beds, a vanity with a mirror, and a large painting on the wall.

A pathway with white columns and a hanging light fixture, leading to a gazebo.

A playground with climbing structures, slides, and benches.

Disney's Port Orleans Resort - Riverside

Golden Oak

AED 1,388

AED 1,562 total

includes taxes & fees

13 Oct - 14 Oct

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5-star hotels with pools in Lakeland - Winter Haven

A large outdoor swimming pool with multiple lounge areas and palm trees.

A swimming pool with palm trees and umbrellas, surrounded by a building with a curved facade and multiple balconies.

A hotel with a swimming pool, lounge chairs, and palm trees.

A modern living room with a Christmas tree, a sofa, a coffee table, and a large window with a view of a green landscape.

Waldorf Astoria Orlando - An Official Walt Disney World® Hotel

Orlando

AED 1,433

AED 1,819 total

includes taxes & fees

29 Oct - 30 Oct

A resort with a large swimming pool, multiple buildings, and a well-lit outdoor area.

A hotel with a blue exterior, white railings, and a well-maintained garden with a central flower bed.

A restaurant with round tables, wooden chairs, and large windows.

A spacious lobby with high ceilings, multiple chandeliers, and a polished wooden floor.

Disney's Beach Club Resort

Bay Lake

AED 2,674

AED 3,008 total

includes taxes & fees

13 Oct - 14 Oct

A pool area with lounge chairs and umbrellas, surrounded by tropical plants.

A restaurant interior with wooden tables and chairs, a marble wall, and a seating area with a cushioned bench.

A woman sitting on a white sofa reading a magazine in a modern room with a mannequin in the background.

A man in a white suit standing in a room with a marble countertop and a hanging black lamp.

ette hotel Orlando

Kissimmee

AED 1,084

AED 1,230 total

includes taxes & fees

11 Oct - 12 Oct

A multi-story hotel with a central courtyard, a bell tower, and a covered entrance.

A spacious lobby with a grand chandelier, a piano, and a reception desk.

A spacious lobby with a grand chandelier, a fountain, and a grand piano.

Reunion Resort & Golf Club

Reunion

AED 1,088

AED 1,409 total

includes taxes & fees

12 Oct - 13 Oct

A spacious lobby with a high ceiling, a unique wooden chandelier, a large arched glass door leading outside, and potted plants.

A large, two-story hotel with a prominent clock tower, a covered entrance, and a well-lit facade.

A spacious lobby with a central reception desk, a staircase, and a view of the outside.

Encore Resort and Water Park at Reunion by Rentyl

Kissimmee

AED 1,025

AED 3,122 total

includes taxes & fees

12 Oct - 13 Oct

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

Quality Inn & Suites By the Parks

10/10 Excellent

"Very clean and quiet. The customer service was great as well. 😊"

Holiday Inn Winter Haven by IHG

10/10 Excellent

"Great spot for our volleyball tournament"

Westgate Town Center Resort

10/10 Excellent

"My husband and I always stay here and we always have an amazing time."

La Quinta Inn & Suites by Wyndham Lakeland East

10/10 Excellent

"❤️❤️❤️☕❤️☕"

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

Change your mind

Treat yourself

Be picky

Check availability on Lakeland - Winter Haven Hotels with a Pool

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

1. Best Western Plus Winter Haven Inn & Suites

2. Holiday Inn Express Bartow by IHG

3. Hampton Inn Winter Haven

4. Home2 Suites By Hilton Winter Haven

5. Staybridge Suites Winter Haven Auburndale by IHG

6. SpringHill Suites by Marriott Lakeland

7. Hyatt Place Lakeland Center

8. Drury Plaza Hotel Orlando - Disney Springs Area

9. Best Western Auburndale Inn & Suites

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

Hotels with pools and free breakfast in Lakeland - Winter Haven

Best Western Plus Winter Haven Inn & Suites

Holiday Inn Express Lake Wales N-Winter Haven by IHG

Courtyard by Marriott Winter Haven

Hampton Inn Winter Haven

Staybridge Suites Winter Haven Auburndale by IHG

Home2 Suites By Hilton Winter Haven

Holiday Inn Winter Haven by IHG

Best Western Auburndale Inn & Suites

Hyatt Place Lakeland Center

4-star hotels with pools in Lakeland - Winter Haven

Gaylord Palms Resort & Convention Center

Walt Disney World Swan Reserve

JW Marriott Orlando Bonnet Creek Resort & Spa

Drury Plaza Hotel Orlando - Disney Springs Area

Walt Disney World Dolphin

Wyndham Grand Orlando Resort Bonnet Creek

Signia by Hilton Orlando - An Official Walt Disney World® Hotel

Omni Orlando Resort at ChampionsGate

Caribe Royale Orlando, WorldHotels Elite

Disney's Port Orleans Resort - Riverside

5-star hotels with pools in Lakeland - Winter Haven

Waldorf Astoria Orlando - An Official Walt Disney World® Hotel

Disney's Beach Club Resort

ette hotel Orlando

Reunion Resort & Golf Club

Encore Resort and Water Park at Reunion by Rentyl

Top Lakeland - Winter Haven Hotel Reviews

Quality Inn & Suites By the Parks

Holiday Inn Winter Haven by IHG

Westgate Town Center Resort

La Quinta Inn & Suites by Wyndham Lakeland East

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