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Search Holiday Homes in Lakeland - Winter Haven

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2 Jan - 4 Jan
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9 Jan - 11 Jan
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23 Jan - 25 Jan
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20 Feb - 22 Feb

Our top choices for Lakeland - Winter Haven holiday homes

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The Berkley, Orlando

Holiday Home in Kissimmee

The Berkley, Orlando
4.0 star property
9.6 out of 10, Exceptional, (2013)
"Really great 2 bedroom, beautiful Room, Nice Pool and Landscape...Will definitely be back."
United States
Thomas
The price is Rp2.550.795
Rp3.059.948 total
includes taxes & fees
4 Jan - 5 Jan 2026
The Berkley, Orlando
Shared kitchen
Charming Room Rentals in Southern Lakeland: Central & Cozy

Holiday Home in Lakeland

Charming Room Rentals in Southern Lakeland: Central & Cozy
2.0 star property
9.4 out of 10, Exceptional, (9)
"Is very clean very quiet and The property was very pretty"
United States
MichaelMustang
Charming Room Rentals in Southern Lakeland: Central & Cozy
Villa, Patio | Terrace/patio
Modern Villa

Holiday Home in Haines City

Modern Villa
2.5 star property
The price is Rp2.568.411
Rp3.715.970 total
includes taxes & fees
1 Jan - 2 Jan 2026
Modern Villa
House | 5 bedrooms
Super Cool- Sleeps 17 Newly Built Near Parks

Holiday Home in Kissimmee

Super Cool- Sleeps 17 Newly Built Near Parks
2.0 star property
The price is Rp1.928.508
Rp6.921.682 total
includes taxes & fees
16 Jan - 17 Jan 2026
Super Cool- Sleeps 17 Newly Built Near Parks
Outdoor pool, open 7:00 AM to 11:00 PM, pool umbrellas, pool loungers
Marriott's Sabal Palms

Holiday Home in Orlando

Marriott's Sabal Palms
4.0 star property
9.6 out of 10, Exceptional, (208)
"Room was great, staff friendly and grounds are clean. "
United States
DENNIS
The price is Rp5.348.035
Rp6.016.539 total
includes taxes & fees
5 Jan - 6 Jan 2026
Marriott's Sabal Palms
Luxury House, 3 Bedrooms, Garden View | Living area | 50-inch Smart TV with digital channels, toys, heated floors
BlockHaven near Legoland & Disney

Holiday Home in Winter Haven

BlockHaven near Legoland & Disney
3.5 star property
The price is Rp1.685.039
Rp4.951.879 total
includes taxes & fees
5 Jan - 6 Jan 2026
BlockHaven near Legoland & Disney
Exterior
Davenport Vacation Homes by Shine FM

Holiday Home in Tuscan Hills

Davenport Vacation Homes by Shine FM
4.0 star property
8.4 out of 10, Very good, (26)
"it was a great property to stay in!"
United States
Nancy
The price is Rp1.829.783
Rp4.041.135 total
includes taxes & fees
8 Jan - 9 Jan 2026
Davenport Vacation Homes by Shine FM
Indoor pool, pool umbrellas, pool loungers
Pool •Spa •Game Rm •10 min Disney-Fun Disney Oasis

Holiday Home in Lindfields

Pool •Spa •Game Rm •10 min Disney-Fun Disney Oasis
5.0 star property
Pool •Spa •Game Rm •10 min Disney-Fun Disney Oasis
Outdoor pool, pool loungers
South Facing W/ Private Pool & Spa

Holiday Home in Crescent Lakes

South Facing W/ Private Pool & Spa
4.0 star property
South Facing W/ Private Pool & Spa
House | 4 bedrooms
Super Liked - 4BD 3 5b 6 Miles To Disney Springs

Holiday Home in Kissimmee

Super Liked - 4BD 3 5b 6 Miles To Disney Springs
2.0 star property
The price is Rp2.396.030
Rp7.246.545 total
includes taxes & fees
16 Jan - 17 Jan 2026
Super Liked - 4BD 3 5b 6 Miles To Disney Springs
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

The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

10/10 Excellent
"Great room. Perfect for our group of 4 adults. Easy access to Disney Parks. Enjoyed the pool and green spaces. Very satisfied. "
Christen 3-night trip
Posted 1 day ago
The Grove Resort & Water Park Orlando

Find out more about Lakeland - Winter Haven

Lakeland - Winter Haven Holiday Homes information

Number of reviews
2,255
Accommodation
71 Holiday Homes
Lowest Price
Rp3.059.948
Highest Price
Rp7.246.545