Holiday Homes in Lakeland - Winter Haven

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
12 Jun - 14 Jun
In two months
24 Jul - 26 Jul
In three months
21 Aug - 23 Aug
In four months
18 Sept - 20 Sept

Our top choices for Lakeland - Winter Haven holiday homes

Luxury House, 3 Bedrooms, Garden View | Living area

BlockHaven near Legoland & Disney

BlockHaven near Legoland & Disney
3.5 star property
Winter Haven
10.0 out of 10, Exceptional, (3 reviews)
"Great location. Great communication with host. "
United States
Reid
The price is €194
includes taxes & fees
31 May - 1 Jun
BlockHaven near Legoland & Disney
Interior entrance

Family Friendly Davenport Pool Villa

Family Friendly Davenport Pool Villa
4.0 star property
Florida Pines
The price is €448
includes taxes & fees
27 May - 28 May
Family Friendly Davenport Pool Villa
Lobby sitting area

The Berkley, Orlando

The Berkley, Orlando
4.0 star property
Kissimmee
9.6 out of 10, Exceptional, (2,232 reviews)
"Excellent place to stay. Very clean with all the amenities. "
United States
Shari
The price is €123
includes taxes & fees
26 May - 27 May
The Berkley, Orlando
Smart TV

RED DOOR HOUSE!

RED DOOR HOUSE!
South Lake Morton
9.6 out of 10, Exceptional, (59 reviews)
"Excellent property - convenient location- nice place to stay. "
United States
Emily O.
RED DOOR HOUSE!
House

Kissimmee 4BR l Resort Living l Great Location

Kissimmee 4BR l Resort Living l Great Location
2.0 star property
Kissimmee
The price is €409
includes taxes & fees
26 May - 27 May
Kissimmee 4BR l Resort Living l Great Location
1 bedroom, iron/ironing board, travel cot, WiFi

Enjoy in this beautiful and serene south Lakeland area Perfect for 4 traveler

Enjoy in this beautiful and serene south Lakeland area Perfect for 4 traveler
Lakeland Highlands
10.0 out of 10, Exceptional, (22 reviews)
"The place was quiet and very clean"
United States
james
The price is €143
includes taxes & fees
7 Jun - 8 Jun
Enjoy in this beautiful and serene south Lakeland area Perfect for 4 traveler
Fridge, microwave, oven, stovetop

Hidden Emerald-Apartment with Kitchen and Laundry

Hidden Emerald-Apartment with Kitchen and Laundry
Cleveland Heights
10.0 out of 10, Exceptional, (17 reviews)
"The place was clean and easy to find. We appreciated the washer and dryer. "
United States
Bettina D.
The price is €150
includes taxes & fees
1 Jun - 2 Jun
Hidden Emerald-Apartment with Kitchen and Laundry
Living room

Doppio Westside

Doppio Westside
4.0 star property
Davenport
9.4 out of 10, Exceptional, (44 reviews)
"The property exceeded our expectations. There was communication with the host and the instructions provided were detailed and easy to navigate for a seamless stay. It was a quiet location close enough to the major parks. We will definitely look to stay here again when we return to Florida. The decor was clean and modern, felt like home away from home. "
United States
Cecilia
The price is €456
includes taxes & fees
26 May - 27 May
Doppio Westside
Outdoor dining

Minutes to Legoland. Heated Pool and Private Hot Tub. Relaxation Awaits!

Minutes to Legoland. Heated Pool and Private Hot Tub. Relaxation Awaits!
Winter Haven
10.0 out of 10, Exceptional, (55 reviews)
"It was pet friendly. "
United States
Ibia
The price is €337
includes taxes & fees
21 Jun - 22 Jun
Minutes to Legoland. Heated Pool and Private Hot Tub. Relaxation Awaits!
Property grounds

Cozy 1 Bedroom home on Beautiful Lake Alfred

Cozy 1 Bedroom home on Beautiful Lake Alfred
Lake Alfred
8.4 out of 10, Very good, (31 reviews)
"Accommodations were very clean, comfortable and fully equipped for our stay. "
United States
Sharon T.
The price is €159
includes taxes & fees
26 May - 27 May
Cozy 1 Bedroom home on Beautiful Lake Alfred
Fridge, microwave, oven, stovetop

Midway between Disney and the Gulf beaches

Midway between Disney and the Gulf beaches
Polk City
9.8 out of 10, Exceptional, (75 reviews)
"Property was close to everything we wanted tod do, easy access, clean and the host was great. "
United States
Herb
The price is €149
includes taxes & fees
26 May - 27 May
Midway between Disney and the Gulf beaches
Interior

Dog-Friendly Yard! Walkable Dixieland District Gem

Dog-Friendly Yard! Walkable Dixieland District Gem
Dixieland
9.6 out of 10, Exceptional, (22 reviews)
"Very clean home & thoughtfully stocked "
United States
Sherhea R.
Dog-Friendly Yard! Walkable Dixieland District Gem
Outdoor pool, a heated pool

Fabulous 3 Bedrooms 3 bath Townhouse in a Resort 15 min to Disney

Fabulous 3 Bedrooms 3 bath Townhouse in a Resort 15 min to Disney
Kissimmee
9.4 out of 10, Exceptional, (14 reviews)
"We came for the AAU National volleyball tournament. Our stay was great."
United States
Rose Y.
Fabulous 3 Bedrooms 3 bath Townhouse in a Resort 15 min to Disney
Fridge, microwave, oven, stovetop

Getaway Clubhouse 5 mil Legoland & .5 mil Downtown

Getaway Clubhouse 5 mil Legoland & .5 mil Downtown
Winter Haven
9.8 out of 10, Exceptional, (12 reviews)
"Very clean, welcoming home, close to the Wedding Venue 650. Close to Legoland as well. Host was very kind and accommodating. Will definitely stay again when going to this area!!"
United States
Cheryl G.
The price is €267
includes taxes & fees
28 May - 29 May
Getaway Clubhouse 5 mil Legoland & .5 mil Downtown
Smart TV, fireplace, offices

EXQUISITE FAMILY HOME

EXQUISITE FAMILY HOME
South Lake Morton
9.6 out of 10, Exceptional, (37 reviews)
"Great host and wonderful house close to a lot of restaurants and other businesses."
United States
Audrey F.
The price is €251
includes taxes & fees
26 May - 27 May
EXQUISITE FAMILY HOME
House

Comfortable Beds - Fully Equipped Kitchen Pool Spa

Comfortable Beds - Fully Equipped Kitchen Pool Spa
2.0 star property
Kissimmee
The price is €512
includes taxes & fees
26 May - 27 May
Comfortable Beds - Fully Equipped Kitchen Pool Spa
Paper towels

Private/Spacious 1BR Central Near LegoLand 2 Miles

Private/Spacious 1BR Central Near LegoLand 2 Miles
Winter Haven
9.0 out of 10, Wonderful, (13 reviews)
"clean room"
United States
sandra
The price is €152
includes taxes & fees
26 May - 27 May
Private/Spacious 1BR Central Near LegoLand 2 Miles
Fridge, microwave, oven, stovetop

Charming 2-bedroom house in Downtown Lake Wales.

Charming 2-bedroom house in Downtown Lake Wales.
Lake Wales
9.8 out of 10, Exceptional, (18 reviews)
"Charming is a great adjective for this property! We felt just like a guest in someone’s home. All the little extras were a nice touch. We would definitely stay again if ever in the area. "
United States
Carol
The price is €132
includes taxes & fees
1 Jun - 2 Jun
Charming 2-bedroom house in Downtown Lake Wales.
Interior

Kissimmee Retreat with Jacuzzi and Games

Kissimmee Retreat with Jacuzzi and Games
Kissimmee
The price is €210
includes taxes & fees
26 May - 27 May
Kissimmee Retreat with Jacuzzi and Games
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Lakeland - Winter Haven Hotel Reviews

The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

2/10 Terrible
"The rooms were not well maintained. The sheets and towels were old and worn. On arrival and being checked in to our 1st room, the washer and dryer did not work. The fridge did not work. After calling about 3 times, we were then moved across the hall to another room. However, this room the dishwasher looked like it was coming out of the slot and there were hardly any pans to use to make breakfast. There was no kettle or hot water in the kitchen. We made do to avoid appearing to be a difficult customer NEVER TO RETURN AND MY FRIENDS WHO WERE PLANNING TO GO WILL NOT BE THERE EITHER….DO BETTER"
KATHYANN 8-night trip
Posted 2 hours ago
The Grove Resort & Water Park Orlando

Find out more about Lakeland - Winter Haven

Lakeland - Winter Haven Holiday Homes information

Number of reviews
2,642
Accommodation
1289 Holiday Homes
Lowest Price
€123
Highest Price
€512

Explore a world of travel with Expedia