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Lakeland - Winter Haven Hotel Guide - Hotels with Pool in Lakeland - Winter Haven, Florida

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Check availability on Lakeland - Winter Haven Hotels with Pool

Tonight
18 Oct - 19 Oct
Tomorrow
19 Oct - 20 Oct
Next weekend
23 Oct - 25 Oct
In two weeks
30 Oct - 1 Nov

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

A pool area with a chandelier, a statue, and a view of the outside.
A spacious lobby with a grand chandelier, modern seating, and a view of the outdoor area.
A modern hotel with a central pool area featuring a red boat and palm trees.
A spa entrance with a wooden facade, a sign indicating a sauna, and a patterned metal partition.

1. Kompose Boutique Resort at Theme Parks

Kompose Boutique Resort at Theme Parks
Kissimmee
  • Splash down the waterslide or bask poolside at this modern family resort with two hot tubs.
€70
includes taxes & fees
28 Oct - 29 Oct
Kompose Boutique Resort at Theme Parks
A swimming pool with a clear blue water surface, surrounded by lounge chairs and umbrellas.
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.
A conference room with a large flat-screen TV, wooden chairs, a black table, and a bright yellow chair.

2. Holiday Inn Express Bartow by IHG

Holiday Inn Express Bartow by IHG
Bartow
  • Dive into aquatic bliss at this hotel's refreshing outdoor pool with sun loungers.
€109
includes taxes & fees
31 Oct - 1 Nov
Holiday Inn Express Bartow by IHG
A modern hotel with a swimming pool, outdoor seating, and a well-lit facade.
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.
A reception area with a modern design, featuring a counter, a seating area, and a wall with a unique pattern.

3. Best Western Plus Winter Haven Inn & Suites 

Best Western Plus Winter Haven Inn & Suites 
Winter Haven
  • Sun-soaked pool area creates perfect retreat near LEGOLAND Florida with loungers and umbrellas.
€130
includes taxes & fees
25 Oct - 26 Oct
Best Western Plus Winter Haven Inn & Suites 
A swimming pool with lounge chairs and tables, surrounded by a fence and a building with a modern design.
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.
A modern bathroom with a bathtub, a large mirror, a vanity with a sink, and neatly arranged towels.

4. Hampton Inn Winter Haven

Hampton Inn Winter Haven
Winter Haven
  • Shimmering blue waters await at this family-friendly hotel with pool loungers and workout options.
€118
includes taxes & fees
25 Oct - 26 Oct
Hampton Inn Winter Haven
A swimming pool with lounge chairs and a picnic table, surrounded by a white fence and palm trees.
A hotel entrance with a glass door, an exit sign above, and a reception desk to the left.
A hotel room with a large bathtub, a bed, a nightstand with a lamp, and a painting of a sunset over the ocean.
A spacious dining area with multiple tables and chairs, a kitchen in the background, and large windows providing natural light.

5. Days Inn & Suites by Wyndham Lakeland

Days Inn & Suites by Wyndham Lakeland
Lakeland
  • Take a refreshing plunge in this hotel's serene outdoor pool, just steps from local attractions.
€66
includes taxes & fees
20 Oct - 21 Oct
Days Inn & Suites by Wyndham Lakeland
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.

6. Wyndham Grand Orlando Resort Bonnet Creek

Wyndham Grand Orlando Resort Bonnet Creek
Orlando
  • Splash into aquatic bliss at this resort with 5 outdoor pools, a lazy river, and poolside cabanas.
€166
includes taxes & fees
29 Oct - 30 Oct
Wyndham Grand Orlando Resort Bonnet Creek
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 colorful play structure with a lighthouse in the background.
A colorful LEGO-themed beach retreat sign with a beach house and a gas station in the background.

7. LEGOLAND Beach Retreat

LEGOLAND Beach Retreat
Winter Haven
€243
includes taxes & fees
30 Oct - 31 Oct
LEGOLAND Beach Retreat
An aerial view of a curved swimming pool with lounge chairs and umbrellas around it.
A rooftop bar with outdoor seating, artificial grass, and colorful umbrellas overhead.
A hotel with a circular brick facade, multiple windows, and a central fountain.
A modern hotel lobby with wooden furniture, pendant lighting, and a visible reception desk.

8. Meliá Orlando Celebration

Meliá Orlando Celebration
Celebration
  • Splash into leisure at a resort-style pool surrounded by cabanas, loungers, and tropical tranquility.
€124
includes taxes & fees
5 Nov - 6 Nov
Meliá Orlando Celebration
A water park with multiple slides and a swimming pool surrounded by lounge areas and umbrellas.
A spacious lobby with high ceilings, exposed beams, and a tropical theme featuring palm trees and hanging lights.
An aerial view of a resort with multiple swimming pools, a large central pool, and surrounding greenery.
A spacious dining area with hexagonal ceiling and large windows offering views of the city.

9. Margaritaville Resort Orlando with H2O Waterpark

Margaritaville Resort Orlando with H2O Waterpark
Kissimmee
  • Splash into lazy river paradise at this family resort with three outdoor pools and water park thrills.
€186
includes taxes & fees
25 Oct - 26 Oct
Margaritaville Resort Orlando with H2O Waterpark
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.

10. Home2 Suites By Hilton Winter Haven

Home2 Suites By Hilton Winter Haven
Winter Haven
  • Refresh yourself in the seasonal outdoor pool during warm months while staying minutes from LEGOLAND® Florida.
€143
includes taxes & fees
25 Oct - 26 Oct
Home2 Suites By Hilton Winter Haven
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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.
A modern hotel lobby with a central reception desk, multiple light fixtures, and a patterned wall.
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.

Best Western Plus Winter Haven Inn & Suites 

Best Western Plus Winter Haven Inn & Suites 
Winter Haven
€130
includes taxes & fees
25 Oct - 26 Oct
Best Western Plus Winter Haven Inn & Suites 
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.
A conference room with a large flat-screen TV, wooden chairs, a black table, and a bright yellow chair.
A swimming pool with lounge chairs and a red umbrella.

Holiday Inn Express Bartow by IHG

Holiday Inn Express Bartow by IHG
Bartow
€109
includes taxes & fees
31 Oct - 1 Nov
Holiday Inn Express Bartow by IHG
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

Courtyard by Marriott Winter Haven
Winter Haven
€143
includes taxes & fees
25 Oct - 26 Oct
Courtyard by Marriott Winter Haven
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 room with two beds, a large mirror, a wooden floor, and a view of the outdoors.
A swimming pool with lounge chairs and tables, surrounded by a fence and a building with a modern design.

Hampton Inn Winter Haven

Hampton Inn Winter Haven
Winter Haven
€118
includes taxes & fees
25 Oct - 26 Oct
Hampton Inn Winter Haven
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.
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.

Staybridge Suites Winter Haven Auburndale by IHG

Staybridge Suites Winter Haven Auburndale by IHG
Winter Haven
€134
includes taxes & fees
8 Nov - 9 Nov
Staybridge Suites Winter Haven Auburndale by IHG
A swimming pool area with people playing with building blocks.
A dining area with tables, chairs, and a colorful mural in the background.
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 row of colorful, single-story buildings with a uniform roof design, white picket fences, and a clear pathway leading to the entrance.

LEGOLAND Beach Retreat

LEGOLAND Beach Retreat
Winter Haven
€243
includes taxes & fees
30 Oct - 31 Oct
LEGOLAND Beach Retreat
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 dining area with multiple tables and chairs, ceiling lights, and artwork on the walls.

Holiday Inn Winter Haven by IHG

Holiday Inn Winter Haven by IHG
Winter Haven
€110
includes taxes & fees
25 Oct - 26 Oct
Holiday Inn Winter Haven by IHG
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 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

Home2 Suites By Hilton Winter Haven
Winter Haven
€143
includes taxes & fees
25 Oct - 26 Oct
Home2 Suites By Hilton Winter Haven
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 modern hotel with a central pool area featuring a red boat and palm trees.
A spa entrance with a wooden facade, a sign indicating a sauna, and a patterned metal partition.

Kompose Boutique Resort at Theme Parks

Kompose Boutique Resort at Theme Parks
Kissimmee
€70
includes taxes & fees
28 Oct - 29 Oct
Kompose Boutique Resort at Theme Parks
A hotel room with two beds, a TV, a microwave, and a desk with a lamp.
A reception area with a reception desk, a potted plant, a fire extinguisher, and a dining area with chairs and tables.
A conference room with tables set for an event, featuring pink and white tablecloths and chairs with pink sashes.
A restaurant with wooden walls, a neon sign, tables, chairs, a kitchen area, and a tiled floor.

Howard Johnson by Wyndham Winter Haven FL

Howard Johnson by Wyndham Winter Haven FL
Winter Haven
€76
includes taxes & fees
20 Oct - 21 Oct
Howard Johnson by Wyndham Winter Haven FL
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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.
Spa
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

Walt Disney World Dolphin
Bay Lake
€249
includes taxes & fees
4 Nov - 5 Nov
Walt Disney World Dolphin
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

Gaylord Palms Resort & Convention Center
Kissimmee
€296
includes taxes & fees
30 Oct - 31 Oct
Gaylord Palms Resort & Convention Center
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

Wyndham Grand Orlando Resort Bonnet Creek
Orlando
€166
includes taxes & fees
29 Oct - 30 Oct
Wyndham Grand Orlando Resort Bonnet Creek
An aerial view of a resort with multiple swimming pools, a golf course, and lush landscaping.
An outdoor restaurant with wooden pergolas, tables, and chairs, surrounded by greenery.
A spacious lobby with a polished marble floor, a grand chandelier, and a reception desk with wooden paneling.
A large hotel complex with multiple buildings, a golf course, and a swimming pool area.

Omni Orlando Resort at ChampionsGate

Omni Orlando Resort at ChampionsGate
Champions Gate
€236
includes taxes & fees
15 Nov - 16 Nov
Omni Orlando Resort at ChampionsGate
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.
A spacious dining area with hexagonal ceiling and large windows offering views of the city.

Margaritaville Resort Orlando with H2O Waterpark

Margaritaville Resort Orlando with H2O Waterpark
Kissimmee
€186
includes taxes & fees
25 Oct - 26 Oct
Margaritaville Resort Orlando with H2O Waterpark
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.
An outdoor dining area with round tables covered in foliage, surrounded by chairs, and a stone wall with plants.

Embassy Suites by Hilton Orlando Lake Buena Vista South

Embassy Suites by Hilton Orlando Lake Buena Vista South
Kissimmee
€111
includes taxes & fees
25 Oct - 26 Oct
Embassy Suites by Hilton Orlando Lake Buena Vista South
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.
A water play area with multiple fountains and colorful play structures.
A spacious lobby with a reception desk, seating area, and decorative hanging lights.

Drury Plaza Hotel Orlando - Disney Springs Area

Drury Plaza Hotel Orlando - Disney Springs Area
Lake Buena Vista
€170
includes taxes & fees
26 Oct - 27 Oct
Drury Plaza Hotel Orlando - Disney Springs Area
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 spacious lobby with high ceilings, chandeliers, a reception desk, and seating areas.
A landscaped area with a fountain, a pathway, and a building with balconies.

Hilton Vacation Club Mystic Dunes Orlando

Hilton Vacation Club Mystic Dunes Orlando
Kissimmee
€118
includes taxes & fees
25 Oct - 26 Oct
Hilton Vacation Club Mystic Dunes Orlando
A hotel with a swimming pool, palm trees, and a large building with multiple 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.
A hotel lobby with a reception desk, seating area, and a staircase leading to upper floors.
A water slide at a pool with a rocky background and greenery.

Caribe Royale Orlando, WorldHotels Elite

Caribe Royale Orlando, WorldHotels Elite
Orlando
€227
includes taxes & fees
30 Oct - 31 Oct
Caribe Royale Orlando, WorldHotels Elite
A swimming pool with a waterfall feature, lounge chairs, and a gazebo.
A turtle in a landscaped area with palm trees and a water feature.
An aerial view of a resort with multiple swimming pools, palm trees, and lounge areas.
Bar (on property)

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
Orlando
€137
includes taxes & fees
8 Nov - 9 Nov
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
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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 balcony with a table set for two, overlooking a golf course.
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.

Waldorf Astoria Orlando - An Official Walt Disney World® Hotel

Waldorf Astoria Orlando - An Official Walt Disney World® Hotel
Orlando
€405
includes taxes & fees
12 Nov - 13 Nov
Waldorf Astoria Orlando - An Official Walt Disney World® Hotel
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

Disney's Beach Club Resort
Bay Lake
€719
includes taxes & fees
19 Oct - 20 Oct
Disney's Beach Club Resort
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 person in a white bathrobe sitting at a breakfast table with plates of food, a teapot, and a cup.
A woman sitting on a white sofa reading a magazine in a modern room with a mannequin in the background.

ette hotel Orlando

ette hotel Orlando
Kissimmee
€298
includes taxes & fees
20 Oct - 21 Oct
ette hotel Orlando
Water park
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

Encore Resort and Water Park at Reunion by Rentyl
Kissimmee
€756
includes taxes & fees
20 Oct - 21 Oct
Encore Resort and Water Park at Reunion by Rentyl
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 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 Resort & Golf Club
Reunion
€341
includes taxes & fees
19 Oct - 20 Oct
Reunion Resort & Golf Club
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

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."
Shelley Dawn 7-night trip
Posted 6 hours ago
Hilton Vacation Club Mystic Dunes Orlando
The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

10/10 Excellent
"Love the place. Great amenities and love the water park."
Saed 3-night trip
Posted 6 hours ago
The Grove Resort & Water Park Orlando
The Berkley, Orlando

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."
Gordon 3-night trip
Posted 12 hours ago
The Berkley, Orlando
Quality Inn & Suites By the Parks

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"
John 2-night trip
Posted 2 days ago
Quality Inn & Suites By the Parks
Westgate Town Center Resort

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."
Karen 3-night trip
Posted 5 days ago
Westgate Town Center Resort

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