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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
1 Sept - 2 Sept
Tomorrow
2 Sept - 3 Sept
This weekend
4 Sept - 6 Sept
Next weekend
11 Sept - 13 Sept

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 hotel room with two beds, a desk, a microwave, a TV, and a painting on the wall.
A reception area with a modern design, featuring a counter, a seating area, and a wall with a unique pattern.
A modern hotel with a prominent entrance, multiple floors, and a parking lot.

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.
€110
includes taxes & fees
3 Sept - 4 Sept
Best Western Plus Winter Haven Inn & Suites 
A swimming pool with a brick building in the background, outdoor seating, and umbrellas.
A hotel room with a bed, a desk with a lamp, a chair, a small table, and a nightstand with a phone.
A modern lobby with a central seating area, a large chandelier, and a television mounted on the wall.

2. 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.
€86
includes taxes & fees
6 Sept - 7 Sept
Holiday Inn Winter Haven by IHG
A hotel room with two beds, a desk, a chair, a TV, and a window with a view of trees.
A swimming pool with a clear blue water surface, surrounded by lounge chairs and umbrellas.
A Holiday Inn Express hotel with a covered entrance, large columns, and a well-lit facade.
A hotel lobby with blue and yellow decor, seating areas, a reception desk, and a TV screen.

3. 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.
€85
includes taxes & fees
20 Sept - 21 Sept
Holiday Inn Express Bartow by IHG
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 entrance with a glass door, an exit sign above, and a reception desk to the left.

4. 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.
€64
includes taxes & fees
27 Sept - 28 Sept
Days Inn & Suites by Wyndham Lakeland
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 wooden counter, coffee machines, and a Coca-Cola refrigerator.
A modern kitchen with a dining area, a flat-screen TV, and a large window.

5. Staybridge Suites Winter Haven Auburndale by IHG

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.
€117
includes taxes & fees
6 Sept - 7 Sept
Staybridge Suites Winter Haven Auburndale by IHG
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.
A modern hotel with a central pool area featuring a red boat and palm trees.
A spacious lobby with a grand chandelier, modern seating, and a view of the outdoor area.

6. 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.
€67
includes taxes & fees
30 Sept - 1 Oct
Kompose Boutique Resort at Theme Parks
A rectangular swimming pool with a clear blue water surface, surrounded by a concrete deck. There are outdoor seating areas with tables and chairs, and a row of palm trees in the background.
A hotel room with a bed, a desk with a chair, a TV mounted on the wall, and a bedside table with a lamp.
A modern bathroom with a white sink, a mirror with LED lighting, a shower curtain, and neatly folded towels on a shelf.

7. Rodeway Inn Lake Wales - Winter Haven

Rodeway Inn Lake Wales - Winter Haven
Lake Wales
  • Sparkling outdoor pool awaits at this cosy retreat where relaxation meets convenience, with poolside terrace views that inspire.
€83
includes taxes & fees
13 Sept - 14 Sept
Rodeway Inn Lake Wales - Winter Haven
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 bar area with wooden cabinets, a counter with bottles, and a sign reading "THE PLACERY".
A modern hotel lobby with a central seating area, a reception desk, and a large wall art piece.

8. 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 travellers.
€108
includes taxes & fees
6 Sept - 7 Sept
Hyatt Place Lakeland Center
A modern lobby with a sofa, chairs, a coffee table, and a reception desk.
A reception area with a wooden reception desk, a wall-mounted decorative piece, and a vending machine.
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.

9. Fairfield by Marriott Inn & Suites Davenport

Fairfield by Marriott Inn & Suites Davenport
Davenport
€103
includes taxes & fees
7 Sept - 8 Sept
Fairfield by Marriott Inn & Suites Davenport
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 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.

10. LEGOLAND Beach Retreat

LEGOLAND Beach Retreat
Winter Haven
€226
includes taxes & fees
11 Sept - 12 Sept
LEGOLAND Beach Retreat
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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 reception area with a modern design, featuring a counter, a seating area, and a wall with a unique pattern.
A modern hotel with a prominent entrance, multiple floors, and a parking lot.

Best Western Plus Winter Haven Inn & Suites 

Best Western Plus Winter Haven Inn & Suites 
Winter Haven
€110
includes taxes & fees
3 Sept - 4 Sept
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 Holiday Inn Express hotel with a central entrance, multiple floors, and a parking lot.
A swimming pool with a white fence, lounge chairs, and a building with a balcony.
A bathroom with a white sink, mirror, and shower.

Holiday Inn Express Lake Wales N-Winter Haven by IHG

Holiday Inn Express Lake Wales N-Winter Haven by IHG
Lake Wales
€126
includes taxes & fees
16 Sept - 17 Sept
Holiday Inn Express Lake Wales N-Winter Haven by IHG
An outdoor patio area with a fire pit, yellow and blue seating, and a covered section with a pergola.
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.
A hotel with a prominent "HOME 2" sign, a stone facade, and an arched entrance.

Home2 Suites by Hilton Orlando at Flamingo Crossings

Home2 Suites by Hilton Orlando at Flamingo Crossings
Bay Lake
€91
includes taxes & fees
10 Sept - 11 Sept
Home2 Suites by Hilton Orlando at Flamingo Crossings
A hotel room with a bed, a desk with a lamp, a chair, a small table, and a nightstand with a phone.
A modern lobby with a central seating area, a large chandelier, and a television mounted on the wall.
A gym with various exercise equipment, a clock on the wall, and a door.

Holiday Inn Winter Haven by IHG

Holiday Inn Winter Haven by IHG
Winter Haven
€86
includes taxes & fees
6 Sept - 7 Sept
Holiday Inn Winter Haven by IHG
An outdoor patio with a fire pit, wicker furniture, and a view of a lake.
A spacious indoor area with a bar, seating arrangements, and a large screen displaying content.
A Courtyard by Marriott hotel with a modern design, featuring a covered entrance and a landscaped area with palm trees.
A modern hotel lobby with a long reception desk, bar area, and seating arrangement.

Courtyard by Marriott Winter Haven

Courtyard by Marriott Winter Haven
Winter Haven
€139
includes taxes & fees
7 Sept - 8 Sept
Courtyard by Marriott Winter Haven
A breakfast bar with various food dispensers, a seating area with a table and chairs, and large windows with a view of greenery.
A swimming pool with clear blue water, surrounded by lounge chairs and yellow umbrellas.
A Marriott Fairfield hotel sign with a landscaped garden in front.
A lobby with a central seating area, wooden ceiling, and patterned carpet.

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

Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
Bay Lake
€91
includes taxes & fees
7 Sept - 8 Sept
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
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 hotel lobby with a seating area featuring blue patterned chairs, a wooden coffee table, and a sofa.

Hampton Inn Winter Haven

Hampton Inn Winter Haven
Winter Haven
€110
includes taxes & fees
7 Sept - 8 Sept
Hampton Inn Winter Haven
A modern living room with a fireplace, a sofa, a coffee table, and a TV mounted on the wall.
A modern hotel room with a kitchenette, a dining area, and a bed.
A modern kitchen with a dining area, a flat-screen TV, and a large window.
A spacious, modern living area with a herringbone wood floor, a dining area with a wooden table and chairs, and a kitchen in the background.

Staybridge Suites Winter Haven Auburndale by IHG

Staybridge Suites Winter Haven Auburndale by IHG
Winter Haven
€117
includes taxes & fees
6 Sept - 7 Sept
Staybridge Suites Winter Haven Auburndale by IHG
A large hotel with multiple floors, a central courtyard, and a reflective water feature.
A hotel pool area with lounge chairs, a fire pit, and a large pool.
A hotel room with a sofa, armchair, and a large window with a view of a swimming pool and hotel buildings.
A modern lobby with a large fireplace, comfortable seating, and a well-lit ceiling.

Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance

Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance
Bay Lake
€83
includes taxes & fees
23 Sept - 24 Sept
Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance
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 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".

Hyatt Place Lakeland Center

Hyatt Place Lakeland Center
Downtown Lakeland
€108
includes taxes & fees
6 Sept - 7 Sept
Hyatt Place Lakeland Center
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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 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

Omni Orlando Resort at ChampionsGate
Champions Gate
€213
includes taxes & fees
11 Sept - 12 Sept
Omni Orlando Resort at ChampionsGate
A Marriott hotel with a large swimming pool, sun loungers, and palm trees.
A spacious lobby with high ceilings, modern chandeliers, and a large TV screen.
A rooftop lounge with a fire pit, outdoor seating, umbrellas, and a view of a swimming pool and hotel buildings.
A spacious lobby with high ceilings, large windows, and a central atrium.

Orlando World Center Marriott

Orlando World Center Marriott
Orlando
€238
includes taxes & fees
3 Sept - 4 Sept
Orlando World Center Marriott
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.

Drury Plaza Hotel Orlando - Disney Springs Area

Drury Plaza Hotel Orlando - Disney Springs Area
Lake Buena Vista
€144
includes taxes & fees
15 Sept - 16 Sept
Drury Plaza Hotel Orlando - Disney Springs Area
A hotel with a large pool, palm trees, and a waterfall feature.
An outdoor dining area with tables and chairs, a bar, and potted plants.
A hotel lobby with a reception desk, seating area, and a staircase leading to upper floors.
A spacious dining area with a long table set for a meal, surrounded by chairs.

Caribe Royale Orlando, WorldHotels Elite

Caribe Royale Orlando, WorldHotels Elite
Orlando
€205
includes taxes & fees
3 Sept - 4 Sept
Caribe Royale Orlando, WorldHotels Elite
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
€95
includes taxes & fees
9 Sept - 10 Sept
Embassy Suites by Hilton Orlando Lake Buena Vista South
A water play area with wooden structures and a large water fountain.
A large, multi-story hotel with a central courtyard, palm trees, and illuminated signage.
An indoor venue with a glass ceiling, rows of white chairs, and floral decorations.
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
€278
includes taxes & fees
4 Sept - 5 Sept
Gaylord Palms Resort & Convention Center
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

Walt Disney World Dolphin
Bay Lake
€222
includes taxes & fees
2 Sept - 3 Sept
Walt Disney World Dolphin
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 spacious living room with a large window, a sofa set, a coffee table, and a television.
A hotel with multiple floors, a swimming pool, and palm trees.

Wyndham Grand Orlando Resort Bonnet Creek

Wyndham Grand Orlando Resort Bonnet Creek
Orlando
€172
includes taxes & fees
8 Sept - 9 Sept
Wyndham Grand Orlando Resort Bonnet Creek
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.
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.

Margaritaville Resort Orlando with H2O Waterpark

Margaritaville Resort Orlando with H2O Waterpark
Kissimmee
€183
includes taxes & fees
7 Sept - 8 Sept
Margaritaville Resort Orlando with H2O Waterpark
A swimming pool with people in the water, including a person in a green and red inflatable ring.
A modern restaurant with a curved counter, multiple seating areas, and a variety of appliances and decor.
A hotel room with two beds, a desk with a chair, a television, and large abstract paintings on the wall.
A hotel sign with "BUENA VISTA SUITES" and a building with multiple floors and windows.

Buena Vista Suites Orlando

Buena Vista Suites Orlando
Orlando
€133
includes taxes & fees
8 Sept - 9 Sept
Buena Vista Suites Orlando
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5-star hotels with pools in Lakeland - Winter Haven

A hotel with a swimming pool, lounge chairs, and palm trees.
A bar area with multiple seating options, a marble countertop, and a decorative ceiling light.
A spacious hotel corridor with large windows, a blue carpet, and elegant chandeliers.
A long dining table set with chairs, surrounded by hanging lights and greenery.

Waldorf Astoria Orlando - An Official Walt Disney World® Hotel

Waldorf Astoria Orlando - An Official Walt Disney World® Hotel
Orlando
€330
includes taxes & fees
7 Sept - 8 Sept
Waldorf Astoria Orlando - An Official Walt Disney World® Hotel
A large, multi-story hotel with a central entrance, multiple wings, and a clock tower.
A spacious lobby with a central reception desk, a staircase, and a view of the outside.
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

Encore Resort and Water Park at Reunion by Rentyl
Kissimmee
€653
includes taxes & fees
14 Sept - 15 Sept
Encore Resort and Water Park at Reunion by Rentyl
A pool area with lounge chairs and umbrellas, surrounded by tropical plants.
A woman sitting on a white sofa reading a magazine in a modern room with a mannequin in the background.
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.

ette hotel

ette hotel
Kissimmee
€223
includes taxes & fees
6 Sept - 7 Sept
ette hotel
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 multi-story hotel with a central courtyard, a bell tower, and a covered entrance.

Reunion Resort & Golf Club

Reunion Resort & Golf Club
Reunion
€266
includes taxes & fees
2 Sept - 3 Sept
Reunion Resort & Golf Club
A resort with a large swimming pool, multiple buildings, and a well-lit outdoor area.
A waterfront hotel with multiple buildings, a large spherical structure in the background, and reflections on the water.
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.

Disney's Beach Club Resort

Disney's Beach Club Resort
Bay Lake
€664
includes taxes & fees
14 Sept - 15 Sept
Disney's Beach Club Resort
A resort with a large swimming pool, multiple buildings, and a well-lit outdoor area.
A row of white buildings with balconies, connected by a walkway with string lights and street lamps.
A spacious lobby with a central round rug, multiple doors, and potted plants.
A restaurant with round tables, wooden chairs, and large windows.

Disney's Beach Club Villas

Disney's Beach Club Villas
Bay Lake
€554
includes taxes & fees
2 Sept - 3 Sept
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

Westgate Vacation Villas Resort

Westgate Vacation Villas Resort

10/10 Excellent
"This was a very gorgeous resort so many things to do. Some activities require payment others are included in your stay. Great for traveling with kids."
Tiombe 4-night trip
Posted 12 hours ago
Westgate Vacation Villas Resort
Holiday Inn Club Vacations at Orange Lake Resort by IHG

Holiday Inn Club Vacations at Orange Lake Resort by IHG

10/10 Excellent
"Awesome place"
Jordan 1-night trip
Posted 13 hours ago
Holiday Inn Club Vacations at Orange Lake Resort by IHG
The Berkley, Orlando

The Berkley, Orlando

10/10 Excellent
"What went well: Large suite w/ nice kitchen, nice in-unit laundry, nice pools, way better than average workout room, nice staff, free parking. Suggestion: Extend pool hours to an hour earlier and later. Good for others to know: If you grew up like I did staying in standard motels/hotels on trips, this 4-star-style hotel offers a very nice alternate experience. // Though I can imagine some people I know who came up on the other side of 4-star finding this one nice but more 4-star-lite or quaint. // For me, the location was not convenient to certain Orlando-area places, like Disney Springs, but the price was right at around $120/night all in."
Todd 1-night trip
Posted 16 hours ago
The Berkley, Orlando
Comfort Inn & Suites Lakeland North I-4

Comfort Inn & Suites Lakeland North I-4

10/10 Excellent
"Very nice hotel. Good area, easy parking, restaurants nearby."
ROBIN 1-night trip
Posted 17 hours ago
Comfort Inn & Suites Lakeland North I-4
Hilton Vacation Club Aqua Sol Orlando West

Hilton Vacation Club Aqua Sol Orlando West

8/10 Good
"Muy accesible"
lillian 3-night trip
Posted 21 hours ago
Hilton Vacation Club Aqua Sol Orlando West
Hilton Vacation Club Mystic Dunes Orlando

Hilton Vacation Club Mystic Dunes Orlando

10/10 Excellent
"My stay was amazing. Will return again."
Rahsaan 5-night trip
Posted 2 days ago
Hilton Vacation Club Mystic Dunes Orlando
Quality Inn & Suites By the Parks

Quality Inn & Suites By the Parks

10/10 Excellent
"Todo estuvo excelente"
Mariano 2-night trip
Posted 2 days ago
Quality Inn & Suites By the Parks

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