🏊 Top 10 Lakeland - Winter Haven Hotels with Swimming Pool

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

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check availability on Lakeland - Winter Haven Hotels with Swimming Pools

Tonight

Tomorrow

Next weekend

In two weeks

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

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.

RM532

RM596 total

includes taxes & fees

25 Oct - 26 Oct

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

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

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.

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.

RM551

RM617 total

includes taxes & fees

25 Oct - 26 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 reception desk, seating area, and a bar.

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

3. Hampton Inn Winter Haven

Winter Haven

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

RM482

RM540 total

includes taxes & fees

25 Oct - 26 Oct

A swimming pool area with people playing with building blocks.

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

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

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

4. LEGOLAND Beach Retreat

Winter Haven

RM853

RM1,115 total

includes taxes & fees

30 Oct - 31 Oct

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

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.

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.

RM586

RM657 total

includes taxes & fees

25 Oct - 26 Oct

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

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

6. 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.

RM547

RM613 total

includes taxes & fees

8 Nov - 9 Nov

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

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

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

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 city centre Lakeland hotel's outdoor pool and fitness centre.

RM529

RM592 total

includes taxes & fees

25 Oct - 26 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 hotel lobby with a central seating area, a reception desk, and a large wall art piece.

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 travellers.

RM465

RM521 total

includes taxes & fees

25 Oct - 26 Oct

View all properties

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

RM532

RM596 total

includes taxes & fees

25 Oct - 26 Oct

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

A swimming pool with lounge chairs and a red umbrella.

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

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

Holiday Inn Express Bartow by IHG

Bartow

RM445

RM498 total

includes taxes & fees

31 Oct - 1 Nov

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

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

Courtyard by Marriott Winter Haven

Winter Haven

RM586

RM657 total

includes taxes & fees

25 Oct - 26 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

RM482

RM540 total

includes taxes & fees

25 Oct - 26 Oct

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

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

RM547

RM613 total

includes taxes & fees

8 Nov - 9 Nov

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

LEGOLAND Beach Retreat

Winter Haven

RM853

RM1,115 total

includes taxes & fees

30 Oct - 31 Oct

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

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

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.

Holiday Inn Winter Haven by IHG

Winter Haven

RM449

RM503 total

includes taxes & fees

25 Oct - 26 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

RM586

RM657 total

includes taxes & fees

25 Oct - 26 Oct

A spacious lobby with a grand chandelier, modern seating, and a view of the outdoor area.

A pool area with a chandelier, a statue, and a view of the outside.

A spa entrance with a wooden facade, a sign indicating a sauna, and a patterned metal partition.

A modern hotel with a central pool area featuring a red boat and palm trees.

Kompose Boutique Resort at Theme Parks

Kissimmee

RM123

RM320 total

includes taxes & fees

28 Oct - 29 Oct

A hotel room with two beds, a TV, a microwave, and a desk with a lamp.

A conference room with tables set for an event, featuring pink and white tablecloths and chairs with pink sashes.

A conference room with tables and chairs, pink sashes, and a stage with drapes.

A reception area with a reception desk, a potted plant, a fire extinguisher, and a dining area with chairs and tables.

Howard Johnson by Wyndham Winter Haven FL

Winter Haven

RM312

RM350 total

includes taxes & fees

20 Oct - 21 Oct

View all properties

4-star hotels with pools in Lakeland - Winter Haven

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

Walt Disney World Dolphin

Bay Lake

RM810

RM1,141 total

includes taxes & fees

4 Nov - 5 Nov

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

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

Gaylord Palms Resort & Convention Center

Kissimmee

RM1,003

RM1,358 total

includes taxes & fees

30 Oct - 31 Oct

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

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

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

RM506

RM762 total

includes taxes & fees

29 Oct - 30 Oct

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.

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

A large hotel complex with multiple buildings, a golf course, and a swimming pool area.

Omni Orlando Resort at ChampionsGate

Champions Gate

RM748

RM1,081 total

includes taxes & fees

15 Nov - 16 Nov

A spacious lobby with a high ceiling, wooden beams, and a central fountain.

A spacious lobby with high ceilings, exposed beams, and a tropical theme featuring palm trees and hanging lights.

A water park with multiple slides and a swimming pool surrounded by lounge areas and umbrellas.

An aerial view of a resort with multiple swimming pools, a large central pool, and surrounding greenery.

Margaritaville Resort Orlando with H2O Waterpark

Kissimmee

RM555

RM852 total

includes taxes & fees

25 Oct - 26 Oct

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

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.

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

Embassy Suites by Hilton Orlando Lake Buena Vista South

Kissimmee

RM448

RM508 total

includes taxes & fees

25 Oct - 26 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 spacious lobby with a reception desk, seating area, and decorative hanging lights.

Drury Plaza Hotel Orlando - Disney Springs Area

Lake Buena Vista

RM694

RM781 total

includes taxes & fees

26 Oct - 27 Oct

A pool with a waterfall feature, lounge areas, and a building with a green roof in the background.

A hotel with a swimming pool, lounge chairs, and a fountain.

A golf course with a pond, a hotel with a green roof, and a highway in the background.

A spacious lobby with high ceilings, chandeliers, a reception desk, and seating areas.

Hilton Vacation Club Mystic Dunes Orlando

Kissimmee

RM353

RM539 total

includes taxes & fees

25 Oct - 26 Oct

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

A couple dining at an outdoor table with candles, surrounded by greenery and a building in the background.

A water slide at a pool with a rocky background and greenery.

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

Caribe Royale Orlando, WorldHotels Elite

Orlando

RM771

RM1,042 total

includes taxes & fees

30 Oct - 31 Oct

A swimming pool with a waterfall feature, lounge chairs, and a gazebo.

A bar area with wicker furniture, ceiling fans, and a bar counter with various bottles.

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

A turtle in a landscaped area with palm trees and a water feature.

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Orlando

RM558

RM628 total

includes taxes & fees

8 Nov - 9 Nov

View all properties

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 golf course with sand bunkers, a pond, and tall trees in the background.

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

Waldorf Astoria Orlando - An Official Walt Disney World® Hotel

Orlando

RM1,447

RM1,857 total

includes taxes & fees

12 Nov - 13 Nov

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

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

Disney's Beach Club Resort

Bay Lake

RM2,971

RM3,343 total

includes taxes & fees

3 Nov - 4 Nov

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

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

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.

ette hotel Orlando

Kissimmee

RM1,204

RM1,367 total

includes taxes & fees

20 Oct - 21 Oct

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.

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

Encore Resort and Water Park at Reunion by Rentyl

Kissimmee

RM1,139

RM3,470 total

includes taxes & fees

19 Oct - 20 Oct

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

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

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

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

Reunion Resort & Golf Club

Reunion

RM1,209

RM1,565 total

includes taxes & fees

19 Oct - 20 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.

View all properties

Top Lakeland - Winter Haven Hotel Reviews

Hilton Vacation Club Mystic Dunes Orlando

8/10 Good

"Clean, large places convenient to pool and golf course. Nice property. Receiving packages is terrible! Our important Amazon arrived. We drove to the gate within 15 minutes of arrival. They would not give it to us. They said it needed to be checked in at their warehouse after first denying that it was there. We had to call all over the place the following day which delayed our trip to the theme park. They couldn’t locate the package. We had a picture of the delivery from Amazon and then they finally said that it was still sitting in the check-in station. It hadn’t gone anywhere. They delivered it, but it took another hour and a half. We also had some rain ponchos that were delivered. Again… They could not find the package. It took three days and we finally got it when we checked out. Terrible terrible service. They need to have another system for receiving parcels. Also… When you are checking in, they want you to commit to a timeshare presentation. We declined and then they called the room at least three times."

The Grove Resort & Water Park Orlando

10/10 Excellent

"Love the place. Great amenities and love the water park."

The Berkley, Orlando

10/10 Excellent

"Excellent rental for a 4 bedroom unit near Disney. Been coming since the property was built, in great shape, great service, good communication and text updates on the room availability."

Quality Inn & Suites By the Parks

10/10 Excellent

"Wonderful stay! The location was very convenient and quiet, breakfast was delicious and the bed was VERY comfy! It certainly looks dated, but it is well maintained with lovey staff"

Westgate Town Center Resort

8/10 Good

"Wonderful resort. Lots to do and convenient to theme parks and offsite restaurants. Downfall, not enough handicap parking for volume of guests."

Explore a world of travel with Expedia

Florida Holiday Rentals

Things to do in Florida

Lakeland - Winter Haven Hotels with Swimming Pool

Change your mind

Treat yourself

Be picky

Check availability on Lakeland - Winter Haven Hotels with Swimming Pools

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. LEGOLAND Beach Retreat

5. Home2 Suites By Hilton Winter Haven

6. Staybridge Suites Winter Haven Auburndale by IHG

7. SpringHill Suites by Marriott Lakeland

8. Hyatt Place Lakeland Center

9. Drury Plaza Hotel Orlando - Disney Springs Area

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

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 Bartow by IHG

Courtyard by Marriott Winter Haven

Hampton Inn Winter Haven

Staybridge Suites Winter Haven Auburndale by IHG

LEGOLAND Beach Retreat

Holiday Inn Winter Haven by IHG

Home2 Suites By Hilton Winter Haven

Kompose Boutique Resort at Theme Parks

Howard Johnson by Wyndham Winter Haven FL

4-star hotels with pools in Lakeland - Winter Haven

Walt Disney World Dolphin

Gaylord Palms Resort & Convention Center

Wyndham Grand Orlando Resort Bonnet Creek

Omni Orlando Resort at ChampionsGate

Margaritaville Resort Orlando with H2O Waterpark

Embassy Suites by Hilton Orlando Lake Buena Vista South

Drury Plaza Hotel Orlando - Disney Springs Area

Hilton Vacation Club Mystic Dunes Orlando

Caribe Royale Orlando, WorldHotels Elite

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

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

Encore Resort and Water Park at Reunion by Rentyl

Reunion Resort & Golf Club

Top Lakeland - Winter Haven Hotel Reviews

Hilton Vacation Club Mystic Dunes Orlando

The Grove Resort & Water Park Orlando

The Berkley, Orlando

Quality Inn & Suites By the Parks

Westgate Town Center Resort

Explore a world of travel with Expedia