Photo by Visit Central Florida

Search Holiday Rentals in Lakeland - Winter Haven

Start date: Check-in selected.
To Date
End date: Check-out

  • 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
23 Jan - 25 Jan
In two months
6 Mar - 8 Mar
In three months
3 Apr - 5 Apr
In four months
1 May - 3 May

Our top choices for Lakeland - Winter Haven holiday rentals

Property amenity
Holiday Inn Club Vacations Orlando Breeze Resort by IHG

Holiday Inn Club Vacations Orlando Breeze Resort by IHG

Holiday Inn Club Vacations Orlando Breeze Resort by IHG
3.5 star property
Davenport
9.2 out of 10, Wonderful, (517 reviews)
"Fully stocked kitchen. Wonderful stay"
United States
Jason
The price is 3.020.590 ₫
3.853.748 ₫ total
includes taxes & fees
14 Jan - 15 Jan
Holiday Inn Club Vacations Orlando Breeze Resort by IHG
Exterior
Vacation Village Orlando, Celebration

Vacation Village Orlando, Celebration

Vacation Village Orlando, Celebration
3.0 star property
Kissimmee
8.6 out of 10, Excellent, (3,181 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

Camp Mack Lodge, Marina & RV Resort

Camp Mack Lodge, Marina & RV Resort
3.0 star property
Lake Wales
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

voco Kissimmee Orlando by IHG

voco Kissimmee Orlando by IHG
4.0 star property
Kissimmee
7.6 out of 10, Good, (1,003 reviews)
"A great place we had a great time there good service clean and friendly people "
United States
Jose
The price is 1.575.960 ₫
2.384.953 ₫ total
includes taxes & fees
14 Jan - 15 Jan
voco Kissimmee Orlando by IHG
Exterior
Margaritaville Cottages Orlando by Rentyl with H2O Waterpark

Margaritaville Cottages Orlando by Rentyl with H2O Waterpark

Margaritaville Cottages Orlando by Rentyl with H2O Waterpark
4.0 star property
Kissimmee
8.8 out of 10, Excellent, (1,773 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
Fitness facility
Regal Oaks Resort Vacation Townhomes by IDILIQ

Regal Oaks Resort Vacation Townhomes by IDILIQ

Regal Oaks Resort Vacation Townhomes by IDILIQ
4.0 star property
Kissimmee
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

Elita Inn

Elita Inn
3.0 star property
Dundee
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
12 Jan - 13 Jan
Elita Inn
Outdoor pool, pool umbrellas, pool loungers
Barefoot Suites

Barefoot Suites

Barefoot Suites
3.0 star property
Kissimmee
9.0 out of 10, Wonderful, (1,807 reviews)
"Great clean safe and good location "
United States
italo
Barefoot Suites
House (2 Bedrooms) | Interior
2BR Dog-friendly w/ Yard, Screened Porch, & Grill

2BR Dog-friendly w/ Yard, Screened Porch, & Grill

2BR Dog-friendly w/ Yard, Screened Porch, & Grill
2.0 star property
Dixieland
The price is 2.574.068 ₫
7.204.501 ₫ total
includes taxes & fees
12 Jan - 13 Jan
2BR Dog-friendly w/ Yard, Screened Porch, & Grill
3 outdoor pools
Disney's Beach Club Villas

Disney's Beach Club Villas

Disney's Beach Club Villas
5.0 star property
Bay Lake
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

Davenport Vacation Homes by Shine FM

Davenport Vacation Homes by Shine FM
4.0 star property
Tuscan Hills
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 ₫
6.323.015 ₫ total
includes taxes & fees
12 Jan - 13 Jan
Davenport Vacation Homes by Shine FM
Lobby sitting area
The Berkley, Orlando

The Berkley, Orlando

The Berkley, Orlando
4.0 star property
Kissimmee
9.6 out of 10, Exceptional, (2,040 reviews)
"Facility and staff were excellent "
United States
Travis
The price is 3.545.910 ₫
4.287.268 ₫ total
includes taxes & fees
12 Jan - 13 Jan
The Berkley, Orlando
Interior
Modern 3 Bed Villa, Newly Renovated, Prime Location

Modern 3 Bed Villa, Newly Renovated, Prime Location

Modern 3 Bed Villa, Newly Renovated, Prime Location
3.0 star property
Kissimmee
The price is 3.046.856 ₫
7.660.741 ₫ total
includes taxes & fees
12 Jan - 13 Jan
Modern 3 Bed Villa, Newly Renovated, Prime Location
Exterior
Modern Villa

Modern Villa

Modern Villa
2.5 star property
Haines City
The price is 4.018.698 ₫
5.814.243 ₫ total
includes taxes & fees
12 Jan - 13 Jan
Modern Villa
House (3 Bedrooms) | Interior
Hook, Line & Leisure: Lakefront Gem, 2 Mi to Dtwn

Hook, Line & Leisure: Lakefront Gem, 2 Mi to Dtwn

Hook, Line & Leisure: Lakefront Gem, 2 Mi to Dtwn
3.0 star property
Winter Haven
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
12 Jan - 13 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.
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

Holiday Inn Club Vacations at Orange Lake Resort by IHG

Holiday Inn Club Vacations at Orange Lake Resort by IHG

10/10 Excellent
"We havent used the pool yet, but th8s looks like an amazing resort."
Carrie 1-night trip
Posted 1 day ago
Holiday Inn Club Vacations at Orange Lake Resort by IHG