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

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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 modern hotel with a prominent entrance, multiple floors, and a parking lot.

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

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

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

18 Oct - 19 Oct

A swimming pool with a white fence, lounge chairs, and a building with a balcony.

A modern room with a dark blue sofa, a wooden coffee table, and a matching ottoman. A map mural adorns the wall.

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.

2. 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 481

AED 539 total

includes taxes & fees

18 Oct - 19 Oct

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

A modern bathroom with a bathtub, a large mirror, a vanity with a sink, and neatly arranged towels.

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.

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

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

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

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

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.

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

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

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

A water play area with multiple fountains and colorful play structures.

7. 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

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

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.

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

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

8. 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

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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

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

Best Western Plus Winter Haven Inn & Suites

Winter Haven

AED 479

AED 536 total

includes taxes & fees

18 Oct - 19 Oct

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

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

Holiday Inn Express Lake Wales N-Winter Haven by IHG

Lake Wales

AED 481

AED 539 total

includes taxes & fees

18 Oct - 19 Oct

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

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

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

A Courtyard by Marriott hotel with a modern design, featuring a covered entrance and a landscaped area with palm trees.

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

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

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

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

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

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

A hotel dining area with multiple tables and chairs, ceiling lights, and artwork on the walls.

Holiday Inn Winter Haven by IHG

Winter Haven

AED 408

AED 457 total

includes taxes & fees

8 Nov - 9 Nov

A hotel room with a sofa, a desk, a bed, and a coffee machine.

SpringHill Suites by Marriott Lakeland

Downtown Lakeland

AED 459

AED 515 total

includes taxes & fees

18 Oct - 19 Oct

A hotel lobby with a blue sofa set, a red chair, a patterned carpet, and large windows offering a view of the outdoors.

A hotel breakfast area with a long counter, self-service food stations, and a large flat-screen TV mounted on the wall.

A hotel room with a large bed, a desk with a chair, a TV, and two lamps.

A hotel entrance with a covered walkway, columns, and arched windows.

Comfort Inn & Suites Lakeland North I-4

Lakeland

AED 322

AED 360 total

includes taxes & fees

8 Nov - 9 Nov

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4-star hotels with pools in Lakeland - Winter Haven

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.

A café with tables and chairs, a counter with various items, and a display of bottles.

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

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

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

An indoor venue with a glass ceiling, rows of white chairs, and floral decorations.

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

A bakery display case with various baked goods and a coffee station.

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

A modern reception area with two reception desks, a large decorative wall, and a wooden herringbone floor.

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 a large swimming pool surrounded by palm trees and lounge chairs.

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

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

A hotel with multiple floors, a swimming pool, and palm trees.

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 seating and planters, large windows, and a view of the interior.

A modern hotel with a pool, palm trees, and blue umbrellas.

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

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

A hotel with multiple floors, a swimming pool, and outdoor seating areas.

A rooftop terrace with outdoor seating, a view of fireworks, and a building with a blue awning.

A modern hotel room with a large bed, a desk, a sofa, and a dining area.

A restaurant with a modern interior, large windows, and a view of the cityscape.

Disney's Riviera Resort

Bay Lake

AED 2,384

AED 2,682 total

includes taxes & fees

17 Oct - 18 Oct

A spacious restaurant with high ceilings, hanging pendant lights, and a variety of seating arrangements.

A spacious lobby with a leather sofa, a bar area with stools, and a seating area with tables and chairs.

An outdoor dining area with round tables covered in foliage, surrounded by chairs, and a stone wall with plants.

A spacious outdoor area with multiple white tables and planters, a central digital display, and a modern architectural design.

Embassy Suites by Hilton Orlando Lake Buena Vista South

Kissimmee

AED 403

AED 457 total

includes taxes & fees

18 Oct - 19 Oct

A large, multi-story hotel with a distinctive swan-shaped roof ornament, a waterfront view, and a boat dock.

An outdoor dining area with a long table set for a meal, surrounded by chairs, and decorated with string lights and candles.

A hotel pool area with clear water, palm trees, and lounge chairs.

A modern bar area with a long counter, multiple bar stools, and ambient lighting.

Walt Disney World Swan

Bay Lake

AED 871

AED 1,187 total

includes taxes & fees

28 Oct - 29 Oct

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5-star hotels with pools in Lakeland - Winter Haven

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

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

A modern bar area with a long counter, multiple seating options, and a television screen.

A balcony with a table set for two, overlooking a golf course.

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

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

A waterfront hotel with multiple buildings, a large spherical structure in the background, and reflections on the water.

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

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

A person in a white bathrobe sitting at a breakfast table with plates of food, a teapot, and a cup.

ette hotel Orlando

Kissimmee

AED 1,084

AED 1,230 total

includes taxes & fees

12 Oct - 13 Oct

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

A patio area with wicker furniture, a fire pit, and palm trees.

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 central reception desk, a staircase, and a view of the outside.

A modern kitchen with white cabinets, stainless steel appliances, and a marble island with four bar stools.

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

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

Hilton Vacation Club Mystic Dunes Orlando

10/10 Excellent

"Enjoyed to the full! Clean, great staff A+ all the way for this resort!"

Hilton Vacation Club Aqua Sol Orlando West

10/10 Excellent

"Overall really enjoyed the stay only thing we did not like is there is no door for the bathroom in the master bedroom so no privacy essentially."

The Grove Resort & Water Park Orlando

10/10 Excellent

"Clean rooms"

Omni Orlando Resort at ChampionsGate

10/10 Excellent

"NONE"

Quality Inn & Suites By the Parks

10/10 Excellent

"Fue excelente servicio, volvería de nuevo"

Days Inn & Suites by Wyndham Lakeland

8/10 Good

"Was there for a Family emergency at check in the young lady was very kind and helpful. The room was slightly outdated but very clean and large. Housekeeping was great overall great DEAL for the $"

Holiday Inn Winter Haven by IHG

10/10 Excellent

"Great spot for our volleyball tournament"

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 Lake Wales N-Winter Haven 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. Drury Plaza Hotel Orlando - Disney Springs Area

8. Hyatt Place Lakeland Center

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

Hampton Inn Winter Haven

Courtyard by Marriott Winter Haven

Staybridge Suites Winter Haven Auburndale by IHG

Home2 Suites By Hilton Winter Haven

Holiday Inn Winter Haven by IHG

SpringHill Suites by Marriott Lakeland

Comfort Inn & Suites Lakeland North I-4

4-star hotels with pools in Lakeland - Winter Haven

Drury Plaza Hotel Orlando - Disney Springs Area

Walt Disney World Dolphin

Gaylord Palms Resort & Convention Center

Walt Disney World Swan Reserve

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

Wyndham Grand Orlando Resort Bonnet Creek

JW Marriott Orlando Bonnet Creek Resort & Spa

Disney's Riviera Resort

Embassy Suites by Hilton Orlando Lake Buena Vista South

Walt Disney World Swan

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

Hilton Vacation Club Mystic Dunes Orlando

Hilton Vacation Club Aqua Sol Orlando West

The Grove Resort & Water Park Orlando

Omni Orlando Resort at ChampionsGate

Quality Inn & Suites By the Parks

Days Inn & Suites by Wyndham Lakeland

Holiday Inn Winter Haven by IHG

La Quinta Inn & Suites by Wyndham Lakeland East

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