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Find Hotels with a Pool in Lakeland - Winter Haven, FL

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Check availability on Lakeland - Winter Haven Hotels with a Pool

Tonight
Sep 23 - Sep 24
Tomorrow
Sep 24 - Sep 25
This weekend
Sep 25 - Sep 27
Next weekend
Oct 2 - Oct 4

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

1. 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.
₩165,591
₩185,461 total
includes taxes & fees
Sep 28 - Sep 29
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 seating area featuring blue patterned chairs, a wooden coffee table, and a sofa.
A Hampton Inn hotel with a clear entrance, a covered waiting area, and a sign indicating a clearance of 13'6".
A modern bathroom with a bathtub, a large mirror, a vanity with a sink, and neatly arranged towels.

2. 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.
₩148,378
₩166,173 total
includes taxes & fees
Sep 27 - Sep 28
Hampton Inn Winter Haven
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 modern room with a dark blue sofa, a wooden coffee table, and a matching ottoman. A map mural adorns the wall.
A restaurant with tables and chairs, a large painting, and a TV on the wall.

3. Holiday Inn Express Lake Wales N-Winter Haven by IHG

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.
₩168,971
₩189,247 total
includes taxes & fees
Sep 27 - Sep 28
Holiday Inn Express Lake Wales N-Winter Haven by IHG
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 room with two beds, a desk, a television, and a door leading to another room.
A bathroom with a shower, a toilet, a sink, and a mirror.
A hotel lobby with a dining area, bar, and seating arrangements.

4. Holiday Inn Winter Haven by IHG

Holiday Inn Winter Haven by IHG
Winter Haven
  • Dive into crystalline blue waters at this outdoor pool oasis with comfy loungers and sunshine appeal.
₩149,083
₩166,973 total
includes taxes & fees
Oct 4 - Oct 5
Holiday Inn Winter Haven by IHG
A swimming pool area with people playing with building blocks.
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 play structure with a lighthouse in the background.
A brightly colored building with a white picket fence, numbered doors, and a surfboard decoration.

5. LEGOLAND Beach Retreat

LEGOLAND Beach Retreat
Winter Haven
₩217,729
₩296,985 total
includes taxes & fees
Oct 12 - Oct 13
LEGOLAND Beach Retreat
A rectangular swimming pool with a concrete deck, surrounded by a metal fence and lounge chairs.
A modern kitchen with a central island, a dining area with two chairs, and a microwave. There are signs for 'Futfill Grains & Dairy' and 'Build Your Own'.
A modern bathroom with a large mirror, two sinks, a toilet, and a shower area.
A modern living room with a green sectional sofa, two armchairs, a coffee table, and a bookshelf.

6. Best Western Auburndale Inn & Suites

Best Western Auburndale Inn & Suites
Auburndale
  • Splash into Florida sunshine at this inviting hotel where loungers surround a clean, warm outdoor pool for all-day refreshment.
₩137,089
₩153,539 total
includes taxes & fees
Sep 27 - Sep 28
Best Western Auburndale Inn & Suites
A pool area with lounge chairs, a covered seating area, and a building with multiple windows and balconies.
A modern bathroom with a sink, mirror, and shower.
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.

7. Hyatt Place Lakeland Center

Hyatt Place Lakeland Center
Downtown Lakeland
  • Escape to a refreshing lakeside pool retreat where crystal waters shimmer under Florida sunshine, perfect for leisure travelers.
₩151,251
₩169,401 total
includes taxes & fees
Sep 27 - Sep 28
Hyatt Place Lakeland Center
A swimming pool with lounge chairs and a picnic table, surrounded by a white fence and palm trees.
A hotel room with a bed, a sofa, a desk, a TV, 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.
A hotel room with a large bathtub, a bed, a nightstand with a lamp, and a painting of a sunset over the ocean.

8. 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.
₩75,897
₩94,112 total
includes taxes & fees
Oct 14 - Oct 15
Days Inn & Suites by Wyndham Lakeland
A swimming pool with lounge chairs and umbrellas, surrounded by a building with red and beige walls.
An outdoor seating area with sofas, chairs, and a fire pit.
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.

9. 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.
₩187,817
₩210,355 total
includes taxes & fees
Oct 4 - Oct 5
Home2 Suites By Hilton Winter Haven
A modern lobby with a sofa, chairs, a coffee table, and a reception desk.
A hotel room with a bed, a desk, a chair, a small table, a lamp, and a window with curtains.
A hotel room with a bed, a desk, a chair, a lamp, a nightstand, and a window with curtains.
A reception area with a wooden reception desk, a wall-mounted decorative piece, and a vending machine.

10. Fairfield by Marriott Inn & Suites Davenport

Fairfield by Marriott Inn & Suites Davenport
Davenport
₩145,017
₩162,419 total
includes taxes & fees
Sep 30 - Oct 1
Fairfield by Marriott Inn & Suites Davenport
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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 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.

Best Western Plus Winter Haven Inn & Suites 

Best Western Plus Winter Haven Inn & Suites 
Winter Haven
₩165,591
₩185,461 total
includes taxes & fees
Sep 28 - Sep 29
Best Western Plus Winter Haven Inn & Suites 
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 hotel room with a sofa, two beds, a desk, a TV, and a carpeted floor.
A Holiday Inn Express hotel with a covered entrance, parking lot, and palm trees.
A modern room with a dark blue sofa, a wooden coffee table, and a matching ottoman. A map mural adorns the wall.

Holiday Inn Express Lake Wales N-Winter Haven by IHG

Holiday Inn Express Lake Wales N-Winter Haven by IHG
Lake Wales
₩168,971
₩189,247 total
includes taxes & fees
Sep 27 - Sep 28
Holiday Inn Express Lake Wales N-Winter Haven by IHG
A Hampton Inn hotel with a clear entrance, a covered waiting area, and a sign indicating a clearance of 13'6".
A hotel room with two beds, a large mirror, a wooden floor, and a view of the outdoors.
A hotel lobby with a reception desk, seating area, and a bar.
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
₩148,378
₩166,173 total
includes taxes & fees
Sep 27 - Sep 28
Hampton Inn Winter Haven
A hotel room with two beds, a desk, a television, and a door leading to another room.
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 room with a desk, chair, sofa, and a painting on the wall.
A Holiday Inn hotel with a clear entrance, multiple flags, and a covered parking area.

Holiday Inn Winter Haven by IHG

Holiday Inn Winter Haven by IHG
Winter Haven
₩149,083
₩166,973 total
includes taxes & fees
Oct 4 - Oct 5
Holiday Inn Winter Haven by IHG
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 Courtyard by Marriott hotel with a modern design, featuring a covered entrance and a landscaped area with palm trees.
A modern reception area with wooden panel walls and two reception desks.

Courtyard by Marriott Winter Haven

Courtyard by Marriott Winter Haven
Winter Haven
₩203,178
₩227,560 total
includes taxes & fees
Sep 29 - Sep 30
Courtyard by Marriott Winter Haven
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 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

LEGOLAND Beach Retreat
Winter Haven
₩217,729
₩296,985 total
includes taxes & fees
Oct 12 - Oct 13
LEGOLAND Beach Retreat
A modern hotel lobby with a central seating area, a reception desk, and a large wall art piece.
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 with a white facade, large windows, and a landscaped entrance.
A bar area with wooden cabinets, a counter with bottles, and a sign reading "THE PLACERY".

Hyatt Place Lakeland Center

Hyatt Place Lakeland Center
Downtown Lakeland
₩151,251
₩169,401 total
includes taxes & fees
Sep 27 - Sep 28
Hyatt Place Lakeland Center
An outdoor seating area with sofas, chairs, and a fire pit.
A modern kitchen with a central island, bar stools, and a refrigerator.
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
₩187,817
₩210,355 total
includes taxes & fees
Oct 4 - Oct 5
Home2 Suites By Hilton Winter Haven
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 lobby with a tiled floor, a reception desk, and a seating area with chairs and a sofa.
A hotel entrance with a glass door, an exit sign above, and a reception desk to the left.
A spacious dining area with multiple tables and chairs, a kitchen in the background, and large windows providing natural light.

Days Inn & Suites by Wyndham Lakeland

Days Inn & Suites by Wyndham Lakeland
Lakeland
₩75,897
₩94,112 total
includes taxes & fees
Oct 14 - Oct 15
Days Inn & Suites by Wyndham Lakeland
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
₩176,189
₩197,332 total
includes taxes & fees
Sep 27 - Sep 28
Staybridge Suites Winter Haven Auburndale by IHG
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4-star hotels with pools in Lakeland - Winter Haven

An aerial view of a resort with multiple swimming pools, a golf course, and lush landscaping.
A spacious lobby with a marble floor, a large potted plant, and a view of a pool and garden.
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.

Omni Orlando Resort at ChampionsGate

Omni Orlando Resort at ChampionsGate
Champions Gate
₩221,185
₩327,743 total
includes taxes & fees
Oct 24 - Oct 25
Omni Orlando Resort at ChampionsGate
A spacious restaurant with high ceilings, hanging pendant lights, and a variety of seating arrangements.
A spacious lobby with a reception desk, seating area, and a decorative flower arrangement.
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.

Embassy Suites by Hilton Orlando Lake Buena Vista South

Embassy Suites by Hilton Orlando Lake Buena Vista South
Kissimmee
₩121,859
₩138,310 total
includes taxes & fees
Oct 18 - Oct 19
Embassy Suites by Hilton Orlando Lake Buena Vista South
A spacious lobby with a high ceiling, wooden beams, and a central fountain.
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.

Margaritaville Resort Orlando with H2O Waterpark

Margaritaville Resort Orlando with H2O Waterpark
Kissimmee
₩174,834
₩272,275 total
includes taxes & fees
Sep 30 - Oct 1
Margaritaville Resort Orlando with H2O Waterpark
An aerial view of a curved swimming pool with lounge chairs and umbrellas around it.
A modern hotel lobby with wooden furniture, pendant lighting, and a visible reception desk.
A hotel with a circular brick facade, multiple windows, and a central fountain.
A modern interior with a wooden counter, hanging pendant lights, and a blue door labeled "The Wilson".

Meliá Orlando Celebration

Meliá Orlando Celebration
Celebration
₩105,714
₩169,209 total
includes taxes & fees
Oct 4 - Oct 5
Meliá Orlando Celebration
A resort with multiple swimming pools, palm trees, and a large hotel building.
A beachside kiosk with a sign reading "PITT-PITT". There are yellow umbrellas, a Coca-Cola cooler, and various snacks and souvenirs displayed.
A hotel room with a bed, a sofa, a dining table with chairs, a lamp, and a ceiling fan.
A hotel with a swimming pool, palm trees, and a well-lit outdoor area.

Holiday Inn Club Vacations at Orange Lake Resort by IHG

Holiday Inn Club Vacations at Orange Lake Resort by IHG
Orange Lake
₩148,296
₩236,386 total
includes taxes & fees
Sep 24 - Sep 25
Holiday Inn Club Vacations at Orange Lake Resort by IHG
A pool with a waterfall feature, lounge areas, and a building with a green roof in the background.
A spacious lobby with high ceilings, chandeliers, a reception desk, and seating areas.
A golf course with a pond, a hotel with a green roof, and a highway in the background.
A hotel with a swimming pool, lounge chairs, and a fountain.

Hilton Vacation Club Mystic Dunes Orlando

Hilton Vacation Club Mystic Dunes Orlando
Kissimmee
₩117,098
₩179,055 total
includes taxes & fees
Sep 30 - Oct 1
Hilton Vacation Club Mystic Dunes Orlando
A hotel pool area with lounge chairs and umbrellas, surrounded by tall buildings and a sunset sky.
A spacious lobby with a reception desk, seating area, and decorative hanging lights.
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

Drury Plaza Hotel Orlando - Disney Springs Area
Lake Buena Vista
₩201,587
₩226,786 total
includes taxes & fees
Sep 30 - Oct 1
Drury Plaza Hotel Orlando - Disney Springs Area
An aerial view of a resort with a large swimming pool surrounded by palm trees and lounge chairs.
A view through a large window of a resort with a pool, palm trees, and a building in the background.
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.

Wyndham Grand Orlando Resort Bonnet Creek

Wyndham Grand Orlando Resort Bonnet Creek
Orlando
₩211,427
₩301,894 total
includes taxes & fees
Oct 3 - Oct 4
Wyndham Grand Orlando Resort Bonnet Creek
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.
A luxurious lobby with a central fountain, seating areas, and a decorative ceiling.

Walt Disney World Dolphin

Walt Disney World Dolphin
Bay Lake
₩296,811
₩410,149 total
includes taxes & fees
Oct 1 - Oct 2
Walt Disney World Dolphin
A resort with multiple swimming pools, a large central pool, and a variety of guest accommodations.
An outdoor dining area with round tables and chairs, a thatched roof structure, and a pool in the background.
A modern kitchen with green cabinets, a white countertop, and a built-in oven.
A modern bar area with seating, a counter, and shelves with glassware and bottles.

Embassy Suites By Hilton Orlando Sunset Walk

Embassy Suites By Hilton Orlando Sunset Walk
Kissimmee
₩176,704
₩268,243 total
includes taxes & fees
Sep 30 - Oct 1
Embassy Suites By Hilton Orlando Sunset Walk
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5-star hotels with pools in Lakeland - Winter Haven

A spacious lobby with a high ceiling, a unique wooden chandelier, a large arched glass door leading outside, and potted plants.
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.

Encore Resort and Water Park at Reunion by Rentyl

Encore Resort and Water Park at Reunion by Rentyl
Kissimmee
₩364,711
₩1,136,947 total
includes taxes & fees
Oct 5 - Oct 6
Encore Resort and Water Park at Reunion by Rentyl
A hotel with a swimming pool, lounge chairs, and palm trees.
A grand lobby with a central clock, a chandelier, and a patterned floor.
A long dining table set with chairs, surrounded by hanging lights and greenery.
A bar area with multiple seating options, a marble countertop, and a decorative ceiling light.

Waldorf Astoria Orlando - An Official Walt Disney World® Hotel

Waldorf Astoria Orlando - An Official Walt Disney World® Hotel
Orlando
₩441,084
₩573,492 total
includes taxes & fees
Sep 27 - Sep 28
Waldorf Astoria Orlando - An Official Walt Disney World® Hotel
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 person in a white bathrobe sitting at a breakfast table with plates of food, a teapot, and a cup.

ette hotel Orlando

ette hotel Orlando
Kissimmee
₩309,807
₩351,632 total
includes taxes & fees
Sep 24 - Sep 25
ette hotel Orlando
A resort with a large swimming pool, multiple buildings, and a well-lit outdoor area.
A spacious lobby with high ceilings, multiple chandeliers, and a polished wooden floor.
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.

Disney's Beach Club Resort

Disney's Beach Club Resort
Bay Lake
₩724,747
₩815,341 total
includes taxes & fees
Sep 27 - Sep 28
Disney's Beach Club Resort
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 spacious lobby with a grand chandelier, a fountain, and a grand piano.
A patio area with wicker furniture, a fire pit, and palm trees.

Reunion Resort & Golf Club

Reunion Resort & Golf Club
Reunion
₩316,375
₩424,201 total
includes taxes & fees
Sep 27 - Sep 28
Reunion Resort & Golf Club
A resort with a large swimming pool, multiple buildings, and a well-lit outdoor area.
A spacious lobby with a central round rug, multiple doors, and potted plants.
A row of white buildings with balconies, connected by a walkway with string lights and street lamps.
A restaurant with round tables, wooden chairs, and large windows.

Disney's Beach Club Villas

Disney's Beach Club Villas
Bay Lake
₩966,329
₩1,087,120 total
includes taxes & fees
Sep 30 - Oct 1
Disney's Beach Club Villas
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 Winter Haven by IHG

Holiday Inn Winter Haven by IHG

10/10 Excellent
"Very close to everything. Front desk lady was really nice. Wasn’t crowded and was very close to everything!"
Andrea 1-night trip
Posted 1 hour ago
Holiday Inn Winter Haven by IHG
The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

10/10 Excellent
"The resort was very clean Friendly staff We loved the water park"
ESMERALDA G 5-night trip
Posted 1 hour ago
The Grove Resort & Water Park Orlando
Holiday Inn Club Vacations at Orange Lake Resort by IHG

Holiday Inn Club Vacations at Orange Lake Resort by IHG

10/10 Excellent
"There really are no complaints at all. It is a gorgeous property. Would highly recommend for family vacation."
Heather 3-night trip
Posted 5 hours ago
Holiday Inn Club Vacations at Orange Lake Resort by IHG
Hilton Vacation Club Aqua Sol Orlando West

Hilton Vacation Club Aqua Sol Orlando West

10/10 Excellent
"Family friendly resort. Lots of activities to do. Affordable for a whole unit with kitchen."
Rachel 2-night trip
Posted 5 hours ago
Hilton Vacation Club Aqua Sol Orlando West
Westgate Vacation Villas Resort

Westgate Vacation Villas Resort

8/10 Good
"All the restaurants closed really early and we were not aware when we booked that the waterpark was not included, and it was going to be an extra fee. Otherwise everything was good, but would still go somewhere else in the future."
Sagan 7-night trip
Posted 9 hours ago
Westgate Vacation Villas Resort
The Berkley, Orlando

The Berkley, Orlando

10/10 Excellent
"It’s a great place with very nice and helpful people willing to help"
Jose 2-night trip
Posted 1 day ago
The Berkley, Orlando
Westgate Town Center Resort

Westgate Town Center Resort

10/10 Excellent
"amazing"
Katte 6-night trip
Posted 1 day ago
Westgate Town Center Resort
Hampton Inn by Hilton Plant City

Hampton Inn by Hilton Plant City

8/10 Good
"Staff was great. Two issues though. Only 2 chairs at the pool for the entire hotel. That does not make sense. Our shower was nice and large. However the fiberglass floor had no type of anti slip texture. My wife slipped before she even got out the soap. Fortunately she did not get hurt. That is a lawsuit waiting to happen. The staff did give us a Matt after we informed them of the issue."
Fred 2-night trip
Posted 2 days ago
Hampton Inn by Hilton Plant City

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