Lakeland - Winter Haven Holiday Rentals, Florida: Private House Rentals

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Go beyond your typical stay in Lakeland - Winter Haven

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Our top choices for Lakeland - Winter Haven hotels

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

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

Maria

฿4,387

฿4,913 total

includes taxes & fees

18 Oct - 19 Oct

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 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.

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

Jessica

฿4,408

฿4,936 total

includes taxes & fees

18 Oct - 19 Oct

A gym with treadmills, elliptical machines, and a bench press.

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

Ronald

฿3,975

฿4,452 total

includes taxes & fees

8 Nov - 9 Nov

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

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

Jacqueline

฿4,642

฿5,199 total

includes taxes & fees

11 Oct - 12 Oct

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.

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

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

5. Drury Plaza Hotel Orlando - Disney Springs Area

Lake Buena Vista

Brianne

฿5,433

฿6,113 total

includes taxes & fees

28 Oct - 29 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 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.

6. LEGOLAND Beach Retreat

Winter Haven

soumya

฿5,685

฿7,686 total

includes taxes & fees

12 Oct - 13 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.

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.

7. Home2 Suites By Hilton Winter Haven

Winter Haven

Gustavo

฿4,833

฿5,413 total

includes taxes & fees

18 Oct - 19 Oct

A breakfast bar with various food dispensers, a seating area with a table and chairs, and large windows with a view of greenery.

A hotel room with a large window overlooking a swimming pool and a landscaped area with trees and a building in the background.

A Marriott Fairfield hotel sign with a landscaped garden in front.

A lobby with a central seating area, wooden ceiling, and patterned carpet.

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

Bay Lake

Stephen

฿2,545

฿2,863 total

includes taxes & fees

29 Oct - 30 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 entrance with a covered walkway, columns, and arched windows.

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

9. Comfort Inn & Suites Lakeland North I-4

Lakeland

Maribel

฿2,917

฿3,267 total

includes taxes & fees

8 Nov - 9 Nov

A multi-story hotel with a modern design, featuring a prominent 'Best Western PLUS' sign.

A spacious, modern kitchen area with a coffee station, counter space, and a tiled floor.

A gym with a bench, dumbbells, and a wall with a large TV.

A modern living room with a sectional sofa, a glass coffee table, and a patterned rug.

10. Best Western Plus Lakeland

Lakeland

Jennifer

฿3,403

฿3,811 total

includes taxes & fees

11 Oct - 12 Oct

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

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.

11. SpringHill Suites by Marriott Lakeland

Downtown Lakeland

฿4,208

฿4,713 total

includes taxes & fees

18 Oct - 19 Oct

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

A gym with various exercise equipment, including treadmills, elliptical machines, and a stationary bike.

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.

12. Holiday Inn Express Bartow by IHG

Bartow

฿3,667

฿4,107 total

includes taxes & fees

11 Oct - 12 Oct

A large hotel with multiple floors, a central courtyard, and a reflective water feature.

A covered outdoor seating area with tables and chairs, a ceiling fan, and a view of a pool and buildings in the background.

A modern lobby with a large fireplace, comfortable seating, and a well-lit ceiling.

A hotel room with a sofa, armchair, and a large window with a view of a swimming pool and hotel buildings.

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

Bay Lake

Camille

฿2,888

฿3,249 total

includes taxes & fees

29 Oct - 30 Oct

A hotel with a large pool, palm trees, and colorful signage.

A hotel room with a large bed, a nightstand, a dresser, a flat-screen TV, and a Mickey Mouse themed artwork on the wall.

A hotel with a sign reading "Way Out Poodle" and a large pink sculpture of a person.

A colorful building with a floral theme, featuring a bar area with chairs and a counter.

14. Disney's Pop Century Resort

Bay Lake

฿7,502

฿8,439 total

includes taxes & fees

26 Oct - 27 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.

15. Walt Disney World Dolphin

Bay Lake

Juan

฿5,721

฿8,329 total

includes taxes & fees

4 Nov - 5 Nov

A modern hotel lobby with a central seating area, a reception desk, and a large wall art piece.

A hotel room with a desk, chair, sofa, TV, and artwork.

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

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.

16. Hyatt Place Lakeland Center

Downtown Lakeland

฿4,071

฿4,560 total

includes taxes & fees

22 Oct - 23 Oct

A modern living room with a green sofa, a round coffee table, and a large painting on the wall.

A rectangular swimming pool with a tiled edge, surrounded by lounge chairs and a small covered seating area.

A hotel room with a bed, a chair, a desk, a TV, a painting, and a window.

17. Best Western Auburndale Inn & Suites

Auburndale

Lorrisa

฿3,403

฿3,811 total

includes taxes & fees

26 Oct - 27 Oct

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 view through a large window of a resort with a pool, palm trees, and a building in the background.

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

18. Wyndham Grand Orlando Resort Bonnet Creek

Orlando

Anthony

฿4,171

฿6,282 total

includes taxes & fees

29 Oct - 30 Oct

An outdoor patio area with a fire pit, yellow and blue seating, and a covered section with a pergola.

A hotel with a prominent "HOME 2" sign, a stone facade, and an arched entrance.

A hotel pool area with multiple lounge chairs and umbrellas, a water slide, and palm trees.

A modern hotel room with a dining area, a living space with a sofa and coffee table, and a kitchenette.

19. Home2 Suites by Hilton Orlando at Flamingo Crossings

Bay Lake

฿3,283

฿3,693 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 modern hotel with a central pool area featuring a red boat and palm trees.

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

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

20. Kompose Boutique Resort at Theme Parks

Kissimmee

Nicolas

฿875

฿2,481 total

includes taxes & fees

12 Oct - 13 Oct

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Holiday Rentals in Lakeland - Winter Haven

Condo

A living room with a sofa, two armchairs, a coffee table, a TV stand, a ceiling fan, and a large window with a view of greenery.

A swimming pool with a lifeguard chair, lounge chairs, and a fence.

A hotel corridor with a concrete walkway, palm trees, and well-maintained lawns.

A golf course with a clear path, sand bunkers, and a variety of trees in the background.

Alhambra Villas by Coolvacay

Solivita

"Great place, clean, and convenient for our trip to Disney and universal."

Aparthotel

A large hotel complex with multiple high-rise buildings, a central swimming pool, and surrounding greenery.

A large, irregularly shaped swimming pool surrounded by lounge chairs and palm trees.

A wooden boardwalk pathway surrounded by lush greenery and trees.

Vacation Village Orlando, Celebration

Kissimmee

"Great friendly staff close to the parks and great food and transportation to local fun spots it was my second visit and ill deffinetly be back again"

Aparthotel

A two-story house with a porch, surrounded by palm trees and greenery.

A swimming pool with lounge chairs and umbrellas, surrounded by a building with multiple balconies.

A room with a framed picture, a television, a wooden cabinet, a chair, and a door leading to a blue hallway.

A pond with a wooden bridge, surrounded by lush greenery and a large yellow building with a flag.

Barefoot'n Resort Kissimmee Orlando

Kissimmee

"Nice rooms pool was great definitely will be back"

Condo

A thatched-roof gazebo with a wooden fence, surrounded by white lounge chairs on a sandy area.

A wooden play structure with a slide and swings, surrounded by trees and sand.

A tennis court with a surrounding fence, a palm tree, and a body of water in the background.

A fitness room with treadmills and an elliptical machine, a sign with exercise room rules, a clock, and a television on the wall.

Lifetime of Vacations Resort

Kissimmee

"We absolutely love coming to lifetime and grand lake resort. This is our favorite place to stay!!"

Condo

A building with a sign reading "High Point World Resort Welcome Center."

A spa area with a hot tub, white chairs, and a sign detailing spa rules.

A swimming pool with a tiled deck, surrounded by a white fence and lounge chairs.

A living room with a green sectional sofa, a yellow ottoman, a flat-screen TV, a plant, and a window with blinds.

High Point World Resort

Kissimmee

"everything was perfect and the bed was sooo soft"

Apartment

A modern kitchen with wooden cabinets, a dining table with chairs, and pendant lights.

A gym with exercise equipment, a wall-mounted plant, and a window providing natural light.

A hotel with a large swimming pool, a wooden deck with a gazebo, and a reflection pool.

A modern spa room with wooden paneling, a reception desk, and a seating area with cushions.

Landing Apartments Lakeland Near Winston

Lakeland

"Trip was great"

Apartment

An aerial view of a residential area with a large swimming pool, multiple buildings, and a parking lot.

A modern kitchen with a central island, stainless steel appliances, and pendant lighting.

A modern kitchen with a central island, pendant lights, and a dishwasher.

A dining area with a wooden table set for four, surrounded by leather chairs.

Champions Gate condos by UNE

Champions Gate

Aparthotel

A spacious restaurant with marble-topped tables and booths, a central bar area, and a high ceiling with natural light.

A gym with treadmills, elliptical machines, and weight equipment.

A reception area with a counter, computers, and a large window.

A hotel with a central fountain, palm trees, and a paved courtyard.

Villas At Regal Palms

Highlands Reserve

"Love the property great for families"

Aparthotel

A balcony with wicker chairs, a glass table, and a view of trees and a pathway.

A spacious lobby with a central water feature, seating areas, and a view of the outside.

A residential area with multiple houses, a swimming pool, and a lake in the background.

Bahama Bay Resort

Bahama Bay

"Had a wonderful stay at Bahama Bay Resort. The property was clean, comfortable, and had everything we needed for a relaxing stay. The resort itself was beautiful and peaceful, and the location was convenient. Everything went smoothly from check-in to check-out. Would definitely stay here again!"

Aparthotel

A hotel with a swimming pool, palm trees, and outdoor seating areas.

A spacious lobby with a reception desk, seating area, and a staircase.

A stone fire pit with benches, a thatched-roof structure, and a view of a body of water.

A multi-story hotel with balconies, palm trees, and a children's play area with a shark-shaped slide.

Club Wyndham Cypress Palms

Kissimmee

Aparthotel

A resort with multiple swimming pools, a pirate ship-themed water attraction, and lush greenery.

A living room with a blue sofa, patterned armchair, and coffee table.

A person relaxing in a bathtub with a television in the background.

A balcony with a table and chairs, a view of a building, and a railing.

Lake Buena Vista Resort Village & Spa

Orlando

"Great place to stay"

Holiday Home

A covered outdoor dining area with multiple tables and chairs, a kitchen counter, and a ceiling fan.

A modern kitchen with white cabinets, stainless steel appliances, and a central island with bar-style seating.

WonderFull 4Bd with Pool at Champions Gate 1174

Davenport

"This home was exactly as the pictures and more. It was beautiful and perfect size for my family. The pool was also perfect when we didn’t want to be in the crowds anymore at the resorts. Wonder vacation homes were amazing hosts and took great care of all of our questions "

Condo

A garden with a variety of plants and a gravel path.

A modern kitchen with wooden cabinets, stainless steel appliances, and a dining area with a table and chairs.

A hotel room with a large bed, a ceiling fan, a nightstand with a lamp, and a painting on the wall.

A modern apartment with a kitchen, dining area, and living room.

Bryan’s Spanish Cove by Coolvacay

Orlando

"We loved our stay at Bryan’s Spanish cove. The staff was pleasant. Hotel was clean and had all necessities. Pool was awesome!"

Cabin

An outdoor seating area with wooden tables and chairs, a covered pavilion, and a small kiosk.

A compact kitchen with wooden cabinets, a dining area with white chairs, and a sofa with a patterned cushion.

A cozy cabin interior with wooden walls, a ceiling fan, a sofa, a chair, and a rug.

Camp Mack Lodge, Marina & RV Resort

Lake Wales

"Camp Mack is an awesome place for getting away for a few days or longer. The surroundings are beautiful, and the people are so friendly."

Aparthotel

A modern living room with a glass dining table, leather sofas, and a flat-screen TV.

A hotel room with a large bed, a desk with a flat-screen TV, a window with a view of the outdoors, and a painting on the wall.

A park with a walking path, benches, and a gazebo.

Grand Lake Resort

Kissimmee

"Place was very clean and staff was a great help very friendly and helpful."

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Stay near popular Lakeland - Winter Haven attractions

The entrance to LEGO Florida with colorful LEGO structures and a large LEGO sign.

LEGOLAND® Florida

9.0/10 (2,150 reviews)

Take the kids to this dynamic theme park for a day full of exciting rides, LEGO® brick creations and the chance to build your own LEGO®robots.

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A lakeside park with a walking path, palm trees, and a dock extending into the water.

Lakeside Village

7.8/10 (443 reviews)

You can find the perfect gifts to bring home at Lakeside Village during your visit to Lakeland. Amble around the area's lakeside or attend a sporting event.

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A wooden boardwalk leading to a sign that reads "Deinonychus Island."

Dinosaur World

8.6/10 (65 reviews)

With more than 200 life-size dinosaur models and many interactive games and activities, this educational theme park is great for families.

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A large aircraft with a red nose and four propellers, mounted on a white structure.

Sun N Fun Air Museum

7.6/10 (272 reviews)

You can spend time exploring the galleries in Sun N Fun Air Museum in Lakeland. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.

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A historic tower with intricate designs, surrounded by lush greenery and a clear blue sky.

Bok Tower Gardens

9.0/10 (158 reviews)

Bok Tower Gardens is just one of the places to see in Lake Wales, so why not enjoy the other things to explore during your travels? Stroll along the lakeside in this family-friendly area or visit its top-notch restaurants.

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RP Funding Center

7.6/10 (545 reviews)

You can enjoy a show at RP Funding Center during your stay in Lakeland. Amble around the area's lakeside or attend a sporting event.

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Publix Field at Joker Marchant Stadium

7.8/10 (448 reviews)

Catch an event at Publix Field at Joker Marchant Stadium during your trip to Lakeland. Stroll along the lakeside or attend a sporting event in this family-friendly area.

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Lakeland Square Mall

7.8/10 (576 reviews)

You can search for that perfect souvenir at Lakeland Square Mall during your visit to Lakeland. Amble around this family-friendly area's lakeside or attend a sporting event.

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Lakeland - Winter Haven and related destinations

Discover the family-friendly area of Lakeland - Winter Haven—lake views, baseball and top sights like LEGOLAND® Florida.

See all hotels in Lakeland - Winter Haven

A child lying on the ground with colorful confetti around, in front of a LEGO sign that reads "LEGO LAND FLORIDA".

Top Lakeland - Winter Haven Hotel Reviews

Embassy Suites By Hilton Orlando Sunset Walk

10/10 Excellent

"Great stay"

The Grove Resort & Water Park Orlando

10/10 Excellent

"The waterpark is super fun. Great for families"

The Berkley, Orlando

10/10 Excellent

"We arrived from Canada at 2 am and a late check in was a smoothly accommodated. Staff were very pleasant and helpful. Rooms were very large and clean. Loved the convenience of the ensuite washer and dryer and the full Kitchen. Large balcony was a great evening retreat.We stayed for 9 nights and will definitely stay here again for our next Orlando stay."

Hilton Vacation Club Mystic Dunes Orlando

10/10 Excellent

"I would like to go back. I love everything of it!"

Margaritaville Cottages Orlando by Rentyl with H2O Waterpark

10/10 Excellent

"I stayed in A cottage, it was clean and huge! Check in was fast and included a margaritas. Parking was right in front of the cottage and it was very quiet with over night security. Lots of entertainment in the area! Only down down side shuttles to Disneyworld and Universal ran one time a day, one time at drop off and one time at pick up. But drop off was one our after the park was open. No free breakfast!"

Holiday Inn Winter Haven by IHG

10/10 Excellent

"Great"

Meliá Orlando Celebration

8/10 Good

"The staff was so helpful and friendly. Thank you!!"

Quality Inn & Suites By the Parks

8/10 Good

"👍"

Holiday Inn Club Vacations at Orange Lake Resort by IHG

10/10 Excellent

"Clean"

More cheap stays in Lakeland - Winter Haven

Howard Johnson by Wyndham Lakeland

939 W. Robson St. Lakeland FL

฿1,630

฿1,826 total

11 Oct - 12 Oct

includes taxes & fees

Days Inn & Suites by Wyndham Lakeland

4502 N Socrum Loop Rd Lakeland FL

฿1,884

฿2,336 total

4 Nov - 5 Nov

includes taxes & fees

Extended Stay America Premier Suites Lakeland I4

4360 Lakeland Park Drive Lakeland FL

฿2,524

฿2,827 total

18 Oct - 19 Oct

includes taxes & fees

Quality Inn & Suites By the Parks

2945 Entry Point Blvd Kissimmee FL

฿2,525

฿2,866 total

26 Oct - 27 Oct

includes taxes & fees

8.4/10 Very good! (1,816 reviews)

Comfort Inn & Suites Lakeland North I-4

3520 N Hwy 98 Lakeland FL

฿2,917

฿3,267 total

8 Nov - 9 Nov

includes taxes & fees

Hampton Inn by Hilton Plant City

2702 Thonotosassa Rd Plant City FL

฿3,546

฿4,025 total

26 Oct - 27 Oct

includes taxes & fees

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Book Hotels in Lakeland - Winter Haven on Expedia.com

Find hotels in Lakeland - Winter Haven, FL from ฿1,826

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Lakeland - Winter Haven

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Our top choices for Lakeland - Winter Haven hotels

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. Drury Plaza Hotel Orlando - Disney Springs Area

6. LEGOLAND Beach Retreat

7. Home2 Suites By Hilton Winter Haven

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

9. Comfort Inn & Suites Lakeland North I-4

10. Best Western Plus Lakeland

11. SpringHill Suites by Marriott Lakeland

12. Holiday Inn Express Bartow by IHG

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

14. Disney's Pop Century Resort

15. Walt Disney World Dolphin

16. Hyatt Place Lakeland Center

17. Best Western Auburndale Inn & Suites

18. Wyndham Grand Orlando Resort Bonnet Creek

19. Home2 Suites by Hilton Orlando at Flamingo Crossings

20. Kompose Boutique Resort at Theme Parks

Holiday Rentals in Lakeland - Winter Haven

Alhambra Villas by Coolvacay

Vacation Village Orlando, Celebration

Barefoot'n Resort Kissimmee Orlando

Lifetime of Vacations Resort

High Point World Resort

Landing Apartments Lakeland Near Winston

Champions Gate condos by UNE

Villas At Regal Palms

Bahama Bay Resort

Club Wyndham Cypress Palms

Lake Buena Vista Resort Village & Spa

WonderFull 4Bd with Pool at Champions Gate 1174

Bryan’s Spanish Cove by Coolvacay

Camp Mack Lodge, Marina & RV Resort

Grand Lake Resort

Stay near popular Lakeland - Winter Haven attractions

LEGOLAND® Florida

Lakeside Village

Dinosaur World

Sun N Fun Air Museum

Bok Tower Gardens

RP Funding Center

Publix Field at Joker Marchant Stadium

Lakeland Square Mall

Lakeland - Winter Haven and related destinations

Top Lakeland - Winter Haven Hotel Reviews

Embassy Suites By Hilton Orlando Sunset Walk

The Grove Resort & Water Park Orlando

The Berkley, Orlando

Hilton Vacation Club Mystic Dunes Orlando

Margaritaville Cottages Orlando by Rentyl with H2O Waterpark

Holiday Inn Winter Haven by IHG

Meliá Orlando Celebration

Quality Inn & Suites By the Parks

Holiday Inn Club Vacations at Orange Lake Resort by IHG

More cheap stays in Lakeland - Winter Haven

Howard Johnson by Wyndham Lakeland

Days Inn & Suites by Wyndham Lakeland

Extended Stay America Premier Suites Lakeland I4

Quality Inn & Suites By the Parks

Comfort Inn & Suites Lakeland North I-4

Hampton Inn by Hilton Plant City

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