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Search Holiday Rentals in Lakeland - Winter Haven

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Check prices for these dates

In two weeks
30 Jan - 1 Feb
In two months
13 Mar - 15 Mar
In three months
10 Apr - 12 Apr
In four months
8 May - 10 May

Our top choices for Lakeland - Winter Haven holiday rentals

Property amenity
Holiday Inn Club Vacations Orlando Breeze Resort by IHG

Aparthotel in Davenport

Holiday Inn Club Vacations Orlando Breeze Resort by IHG
3.5 star property
9.2 out of 10, Wonderful, (518 reviews)
"Fully stocked kitchen. Wonderful stay"
United States
Jason
The price is 2.791.081 ₫
3.596.751 ₫ total
includes taxes & fees
15 Jan - 16 Jan
Holiday Inn Club Vacations Orlando Breeze Resort by IHG
Exterior
Vacation Village Orlando, Celebration

Condo in Kissimmee

Vacation Village Orlando, Celebration
3.0 star property
8.6 out of 10, Excellent, (3,185 reviews)
"Great staff clean and well maintained facilities and rooms will stay again and highly recommended "
Canada
Ryan
Vacation Village Orlando, Celebration
Lake
Camp Mack Lodge, Marina & RV Resort

Cabin in Lake Wales

Camp Mack Lodge, Marina & RV Resort
3.0 star property
9.0 out of 10, Wonderful, (193 reviews)
"Nice rooms helpful staff would go again for sure"
United States
David
Camp Mack Lodge, Marina & RV Resort
Exterior
voco Kissimmee Orlando by IHG

Aparthotel in Kissimmee

voco Kissimmee Orlando by IHG
4.0 star property
7.6 out of 10, Good, (1,011 reviews)
"Will definitely stay again!!"
United States
Jessica
The price is 1.654.947 ₫
2.474.672 ₫ total
includes taxes & fees
26 Jan - 27 Jan
voco Kissimmee Orlando by IHG
Exterior
Margaritaville Cottages Orlando by Rentyl with H2O Waterpark

Aparthotel in Kissimmee

Margaritaville Cottages Orlando by Rentyl with H2O Waterpark
4.0 star property
8.8 out of 10, Excellent, (1,777 reviews)
"Highly recommended the Margaritaville cottages!"
United States
Christine
The price is 5.226.934 ₫
11.189.901 ₫ total
includes taxes & fees
21 Jan - 22 Jan
Margaritaville Cottages Orlando by Rentyl with H2O Waterpark
Lobby
Regal Oaks Resort Vacation Townhomes by IDILIQ

Condo resort in Kissimmee

Regal Oaks Resort Vacation Townhomes by IDILIQ
4.0 star property
8.4 out of 10, Very good, (3,051 reviews)
"The rooms were very clean and fully stocked. It was very spacious as well. "
United States
Sharlett
Regal Oaks Resort Vacation Townhomes by IDILIQ
Lobby
Elita Inn

Aparthotel in Dundee

Elita Inn
3.0 star property
8.8 out of 10, Excellent, (14 reviews)
"Very nice accommadations..friendly staff"
United States
lance
The price is 1.969.950 ₫
2.206.345 ₫ total
includes taxes & fees
19 Jan - 20 Jan
Elita Inn
Outdoor pool, pool umbrellas, pool loungers
Barefoot Suites

Aparthotel in Kissimmee

Barefoot Suites
3.0 star property
9.0 out of 10, Wonderful, (1,809 reviews)
"Great clean safe and good location "
United States
italo
Barefoot Suites
House (2 Bedrooms) | Interior
2BR Dog-friendly w/ Yard, Screened Porch, & Grill

Cottage in Dixieland

2BR Dog-friendly w/ Yard, Screened Porch, & Grill
2.0 star property
The price is 2.574.068 ₫
7.204.501 ₫ total
includes taxes & fees
15 Jan - 16 Jan
2BR Dog-friendly w/ Yard, Screened Porch, & Grill
3 outdoor pools
Disney's Beach Club Villas

Condo resort in Bay Lake

Disney's Beach Club Villas
5.0 star property
9.2 out of 10, Wonderful, (39 reviews)
"Clean and great location"
United States
Anonymous traveller
Disney's Beach Club Villas
Family House | Private kitchen | Fridge, microwave, oven, stovetop
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 reviews)
"it was a great property to stay in!"
United States
Nancy
The price is 2.862.994 ₫
6.323.014 ₫ total
includes taxes & fees
29 Jan - 30 Jan
Davenport Vacation Homes by Shine FM
Lobby sitting area
The Berkley, Orlando

Holiday Home in Kissimmee

The Berkley, Orlando
4.0 star property
9.6 out of 10, Exceptional, (2,043 reviews)
"Facility and staff were excellent "
United States
Travis
The price is 3.546.315 ₫
4.287.758 ₫ total
includes taxes & fees
14 Jan - 15 Jan
The Berkley, Orlando
Interior
Modern 3 Bed Villa, Newly Renovated, Prime Location

Villa in Kissimmee

Modern 3 Bed Villa, Newly Renovated, Prime Location
3.0 star property
The price is 3.046.856 ₫
7.660.741 ₫ total
includes taxes & fees
14 Jan - 15 Jan
Modern 3 Bed Villa, Newly Renovated, Prime Location
Exterior
Modern Villa

Holiday Home in Haines City

Modern Villa
2.5 star property
The price is 4.019.157 ₫
5.814.906 ₫ total
includes taxes & fees
14 Jan - 15 Jan
Modern Villa
House (3 Bedrooms) | Interior
Hook, Line & Leisure: Lakefront Gem, 2 Mi to Dtwn

Cottage in Winter Haven

Hook, Line & Leisure: Lakefront Gem, 2 Mi to Dtwn
3.0 star property
10.0 out of 10, Exceptional, (3 reviews)
"We stayed here because our soccer team had a tournament in the area. We had a couple families stay and the price was much cheaper than hotels around the area. The house is beautiful and spacious inside. Has alot of upgrades. At first we thought the neighborhood looked a little off, but we had no issues at all with our stay. We have some other tournaments in this area later in the year and we will definitely be booking to stay here again."
United States
John
The price is 4.491.486 ₫
11.511.337 ₫ total
includes taxes & fees
15 Jan - 16 Jan
Hook, Line & Leisure: Lakefront Gem, 2 Mi to Dtwn
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 Express Lake Wales N-Winter Haven by IHG

Holiday Inn Express Lake Wales N-Winter Haven by IHG

10/10 Excellent
"Room looked new, very clean, bed firm but quite comfortable! Breakfast was excellent. I had the biscuit and turkey sausage gravy which was delicious. Better than some breakfast restaurants. Staff was very friendly and helpful!"
Rebecca 1-night trip
Posted 21 hours ago
Holiday Inn Express Lake Wales N-Winter Haven by IHG