The Best Hotels with a Pool in Lakeland - Winter Haven, FL from NT$2,217 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 modern hotel with a prominent entrance, multiple floors, and a parking lot.

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

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.

NT$4,163

NT$4,662 total

includes taxes & fees

Oct 18 - Oct 19

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

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.

NT$4,182

NT$4,684 total

includes taxes & fees

Oct 18 - Oct 19

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

3. Hampton Inn Winter Haven

Winter Haven

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

NT$3,772

NT$4,225 total

includes taxes & fees

Nov 8 - Nov 9

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

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.

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

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.

NT$4,278

NT$4,791 total

includes taxes & fees

Oct 18 - Oct 19

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

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

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.

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.

NT$4,586

NT$5,137 total

includes taxes & fees

Oct 18 - Oct 19

A swimming pool area with people playing with building blocks.

A colorful LEGO-themed beach retreat sign with a beach house and a gas station in the background.

A colorful play structure with a lighthouse in the background.

A brightly colored building with a white picket fence, numbered doors, and a surfboard decoration.

6. LEGOLAND Beach Retreat

Winter Haven

NT$5,395

NT$7,294 total

includes taxes & fees

Oct 12 - Oct 13

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

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

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.

7. SpringHill Suites by Marriott Lakeland

Downtown Lakeland

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

NT$3,994

NT$4,473 total

includes taxes & fees

Oct 18 - Oct 19

A swimming pool with lounge chairs and a table, surrounded by a building with large windows and a fenced area.

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.

8. Comfort Inn & Suites Lakeland North I-4

Lakeland

Splash into a sun-drenched outdoor pool oasis with fitness options at this shopper-friendly lakeland retreat.

NT$2,795

NT$3,131 total

includes taxes & fees

Nov 8 - Nov 9

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

Best Western Plus Winter Haven Inn & Suites

Winter Haven

NT$4,163

NT$4,662 total

includes taxes & fees

Oct 18 - Oct 19

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

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

Holiday Inn Express Lake Wales N-Winter Haven by IHG

Lake Wales

NT$4,182

NT$4,684 total

includes taxes & fees

Oct 18 - Oct 19

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

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

Hampton Inn Winter Haven

Winter Haven

NT$3,772

NT$4,225 total

includes taxes & fees

Nov 8 - Nov 9

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 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.

Courtyard by Marriott Winter Haven

Winter Haven

NT$4,586

NT$5,137 total

includes taxes & fees

Oct 18 - Oct 19

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

NT$4,278

NT$4,791 total

includes taxes & fees

Oct 18 - Oct 19

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

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

NT$4,586

NT$5,137 total

includes taxes & fees

Oct 18 - Oct 19

A row of colorful, single-story buildings with a uniform roof design, white picket fences, and a clear pathway leading to the entrance.

A children's play area with a slide and climbing structures, a small lighthouse, and a building with a red and white striped roof.

A dining area with tables, chairs, and a colorful mural in the background.

LEGOLAND Beach Retreat

Winter Haven

NT$5,395

NT$7,294 total

includes taxes & fees

Oct 12 - Oct 13

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

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

Holiday Inn Winter Haven by IHG

Winter Haven

NT$3,544

NT$3,969 total

includes taxes & fees

Nov 8 - Nov 9

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

SpringHill Suites by Marriott Lakeland

Downtown Lakeland

NT$3,994

NT$4,473 total

includes taxes & fees

Oct 18 - Oct 19

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

A hotel with a central entrance, multiple floors, and a sign reading 'Comfort Inn & Suites.'

Comfort Inn & Suites Lakeland North I-4

Lakeland

NT$2,795

NT$3,131 total

includes taxes & fees

Nov 8 - Nov 9

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4-star hotels with pools in Lakeland - Winter Haven

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

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

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

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

Drury Plaza Hotel Orlando - Disney Springs Area

Lake Buena Vista

NT$5,156

NT$5,800 total

includes taxes & fees

Oct 28 - Oct 29

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.

Walt Disney World Dolphin

Bay Lake

NT$5,429

NT$7,903 total

includes taxes & fees

Nov 4 - Nov 5

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.

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

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

Gaylord Palms Resort & Convention Center

Kissimmee

NT$8,304

NT$11,153 total

includes taxes & fees

Oct 30 - Oct 31

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

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

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

Walt Disney World Swan Reserve

Bay Lake

NT$8,397

NT$11,242 total

includes taxes & fees

Oct 28 - Oct 29

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.

A hotel room with a large window, a bed, a chair, a desk, a lamp, and a television.

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

Orlando

NT$6,757

NT$9,398 total

includes taxes & fees

Oct 29 - Oct 30

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

NT$3,959

NT$5,962 total

includes taxes & fees

Oct 29 - Oct 30

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

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.

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

JW Marriott Orlando Bonnet Creek Resort & Spa

Orlando

NT$8,939

NT$12,032 total

includes taxes & fees

Oct 29 - Oct 30

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

A resort with a large pool, multiple buildings, and a fireworks display in the background.

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.

Disney's Riviera Resort

Bay Lake

NT$20,720

NT$23,310 total

includes taxes & fees

Oct 17 - Oct 18

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

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

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

A spacious lobby with a reception desk, seating area, and a decorative flower arrangement.

Embassy Suites by Hilton Orlando Lake Buena Vista South

Kissimmee

NT$3,501

NT$3,973 total

includes taxes & fees

Oct 18 - Oct 19

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.

Walt Disney World Swan

Bay Lake

NT$10,433

NT$13,533 total

includes taxes & fees

Nov 10 - Nov 11

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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

NT$11,913

NT$15,198 total

includes taxes & fees

Oct 30 - Oct 31

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

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

Disney's Beach Club Resort

Bay Lake

NT$23,242

NT$26,147 total

includes taxes & fees

Oct 13 - Oct 14

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

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

ette hotel Orlando

Kissimmee

NT$9,418

NT$10,690 total

includes taxes & fees

Oct 12 - Oct 13

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

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

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

Reunion Resort & Golf Club

Reunion

NT$9,453

NT$12,243 total

includes taxes & fees

Oct 12 - Oct 13

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

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

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

NT$8,907

NT$27,141 total

includes taxes & fees

Oct 12 - Oct 13

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

Holiday Inn Club Vacations at Orange Lake Resort by IHG

10/10 Excellent

"Es la tercera vez que me quedo en el resort y me encanta por su limpieza, buen servicio al cliente. Como familia disfrutamos las piscinas.Me gusta la comodidad de las guaguas que te llevan a las diferentes piscinas y parquecitos. Excelente resort."

Quality Inn & Suites By the Parks

10/10 Excellent

"Clean room, delicious breakfast, friendly staff"

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"

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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Book Hotels with a Pool in Lakeland - Winter Haven on Expedia.com

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. Staybridge Suites Winter Haven Auburndale by IHG

5. Home2 Suites By Hilton Winter Haven

6. LEGOLAND Beach Retreat

7. SpringHill Suites by Marriott Lakeland

8. Comfort Inn & Suites Lakeland North I-4

9. Drury Plaza Hotel Orlando - Disney Springs Area

10. Hyatt Place Lakeland Center

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

LEGOLAND Beach Retreat

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

Holiday Inn Club Vacations at Orange Lake Resort by IHG

Quality Inn & Suites By the Parks

Days Inn & Suites by Wyndham Lakeland

Holiday Inn Winter Haven by IHG

Westgate Town Center Resort

La Quinta Inn & Suites by Wyndham Lakeland East

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