Hotels with Swimming Pool, Lakeland - Winter Haven Florida

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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.

P8,211

P9,197 total

includes taxes & fees

Oct 25 - Oct 26

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

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.

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

P9,069

P10,157 total

includes taxes & fees

Oct 25 - Oct 26

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 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.

P7,441

P8,334 total

includes taxes & fees

Oct 25 - Oct 26

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 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.

P8,439

P9,452 total

includes taxes & fees

Nov 8 - Nov 9

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

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

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.

P9,047

P10,133 total

includes taxes & fees

Oct 25 - Oct 26

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 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.

6. LEGOLAND Beach Retreat

Winter Haven

P13,163

P17,211 total

includes taxes & fees

Oct 30 - Oct 31

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.

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.

7. SpringHill Suites by Marriott Lakeland

Downtown Lakeland

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

P8,162

P9,142 total

includes taxes & fees

Oct 25 - Oct 26

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

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

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

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.

P10,706

P12,044 total

includes taxes & fees

Oct 26 - Oct 27

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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

P8,211

P9,197 total

includes taxes & fees

Oct 25 - Oct 26

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

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

Holiday Inn Express Bartow by IHG

Bartow

P6,865

P7,689 total

includes taxes & fees

Oct 31 - Nov 1

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

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

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

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

Courtyard by Marriott Winter Haven

Winter Haven

P9,047

P10,133 total

includes taxes & fees

Oct 25 - Oct 26

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

Hampton Inn Winter Haven

Winter Haven

P7,441

P8,334 total

includes taxes & fees

Oct 25 - Oct 26

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 wooden counter, coffee machines, and a Coca-Cola refrigerator.

Staybridge Suites Winter Haven Auburndale by IHG

Winter Haven

P8,439

P9,452 total

includes taxes & fees

Nov 8 - Nov 9

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

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.

LEGOLAND Beach Retreat

Winter Haven

P13,163

P17,211 total

includes taxes & fees

Oct 30 - Oct 31

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

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

Holiday Inn Winter Haven by IHG

Winter Haven

P6,928

P7,759 total

includes taxes & fees

Oct 25 - Oct 26

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

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

Home2 Suites By Hilton Winter Haven

Winter Haven

P9,047

P10,133 total

includes taxes & fees

Oct 25 - Oct 26

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

A resort pool area with a winding pool design, lounge chairs, and palm trees.

Kompose Boutique Resort at Theme Parks

Kissimmee

P1,899

P4,943 total

includes taxes & fees

Oct 28 - Oct 29

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

P4,818

P5,396 total

includes taxes & fees

Oct 20 - Oct 21

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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.

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

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

P12,505

P17,610 total

includes taxes & fees

Nov 4 - Nov 5

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

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

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.

Gaylord Palms Resort & Convention Center

Kissimmee

P15,471

P20,960 total

includes taxes & fees

Oct 30 - Oct 31

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

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.

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

Wyndham Grand Orlando Resort Bonnet Creek

Orlando

P7,810

P11,762 total

includes taxes & fees

Oct 29 - Oct 30

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

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

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

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

Omni Orlando Resort at ChampionsGate

Champions Gate

P11,538

P16,673 total

includes taxes & fees

Nov 15 - Nov 16

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

A spacious dining area with hexagonal ceiling and large windows offering views of the city.

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.

Margaritaville Resort Orlando with H2O Waterpark

Kissimmee

P8,565

P13,153 total

includes taxes & fees

Oct 26 - Oct 27

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

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

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.

Embassy Suites by Hilton Orlando Lake Buena Vista South

Kissimmee

P6,906

P7,838 total

includes taxes & fees

Oct 25 - Oct 26

Drury Plaza Hotel Orlando - Disney Springs Area

Lake Buena Vista

P10,706

P12,044 total

includes taxes & fees

Oct 26 - Oct 27

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

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

A landscaped area with a fountain, a pathway, and a building with balconies.

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

Hilton Vacation Club Mystic Dunes Orlando

Kissimmee

P5,441

P8,321 total

includes taxes & fees

Oct 25 - Oct 26

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 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

Orlando

P11,903

P16,084 total

includes taxes & fees

Oct 30 - Oct 31

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

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

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

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Orlando

P8,616

P9,693 total

includes taxes & fees

Nov 8 - Nov 9

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

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

Waldorf Astoria Orlando - An Official Walt Disney World® Hotel

Orlando

P22,323

P28,656 total

includes taxes & fees

Nov 12 - Nov 13

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

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

Disney's Beach Club Resort

Bay Lake

P45,849

P51,581 total

includes taxes & fees

Nov 9 - Nov 10

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 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.

ette hotel Orlando

Kissimmee

P18,579

P21,088 total

includes taxes & fees

Oct 20 - Oct 21

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

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

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

P17,571

P53,540 total

includes taxes & fees

Oct 19 - Oct 20

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

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

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.

Reunion Resort & Golf Club

Reunion

P18,648

P24,151 total

includes taxes & fees

Oct 19 - Oct 20

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

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."

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Hotels with Swimming Pool in Lakeland - Winter Haven, Florida

Change your mind

Treat yourself

Be picky

Check availability on Lakeland - Winter Haven Hotels with Swimming 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. Drury Plaza Hotel Orlando - Disney Springs Area

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

10. Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town 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 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

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