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Lakeland - Winter Haven Vacation Rentals

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Check prices for these dates

In two weeks
9 Jan - 11 Jan
In two months
20 Feb - 22 Feb
In three months
20 Mar - 22 Mar
In four months
17 Apr - 19 Apr

Our top choices for Lakeland - Winter Haven holiday rentals

2 outdoor pools, open 8 AM to 10 PM, pool loungers
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, (508)
"Great place"
United States
Bobby
The price is RM506
RM640 total
includes taxes & fees
15 Jan - 16 Jan 2026
Holiday Inn Club Vacations Orlando Breeze Resort by IHG
Desk, laptop workspace, free WiFi
Elita Inn

Aparthotel in Dundee

Elita Inn
3.0 star property
10.0 out of 10, Exceptional, (7)
"Yes this is an awesome place and especially clen we loved it "
United States
Bryson
The price is RM304
RM340 total
includes taxes & fees
29 Dec - 30 Dec
Elita Inn
Exterior
voco Kissimmee Orlando by IHG

Aparthotel in Kissimmee

voco Kissimmee Orlando by IHG
4.0 star property
7.6 out of 10, Good, (1009)
"Place was clean, staff great, cozy very nice area swimming pool"
United States
KRYSTLE
The price is RM251
RM377 total
includes taxes & fees
7 Jan - 8 Jan 2026
voco Kissimmee Orlando by IHG
Interior
Margaritaville Cottages Orlando by Rentyl

Aparthotel in Kissimmee

Margaritaville Cottages Orlando by Rentyl
4.0 star property
8.8 out of 10, Excellent, (1759)
"Great place "
United States
Lauren
The price is RM806
RM1,726 total
includes taxes & fees
4 Jan - 5 Jan 2026
Margaritaville Cottages Orlando by Rentyl
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, (190)
"We lived our stay and can't wait to come back soon"
United States
Ramona
Camp Mack Lodge, Marina & RV Resort
Aerial view
Vacation Village Orlando, Celebration

Condo in Kissimmee

Vacation Village Orlando, Celebration
3.0 star property
8.6 out of 10, Excellent, (3130)
"Great place to stay"
United States
Jose
The price is RM355
RM504 total
includes taxes & fees
12 Jan - 13 Jan 2026
Vacation Village Orlando, Celebration
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)
"Clean and great location"
United States
Anonymous traveller
Disney's Beach Club Villas
Full-sized fridge, microwave, cookware/dishes/utensils, freezer
Jade Manor

Aparthotel in Solterra Resort

Jade Manor
2.5 star property
8.0 out of 10, Very good, (2)
"Amazing "
United States
Nilda
The price is RM243
RM544 total
includes taxes & fees
29 Dec - 30 Dec
Jade Manor
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, (3037)
"Great accommodations, clean and very spacious. Highly recommend to others, especially families. Pool was lovely "
United States
Christopher
The price is RM584
RM1,463 total
includes taxes & fees
4 Jan - 5 Jan 2026
Regal Oaks Resort Vacation Townhomes by IDILIQ
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
Super Cool- Sleeps 17 Newly Built Near Parks
Terrace/patio
Modern Villa

Holiday Home in Haines City

Modern Villa
2.5 star property
The price is RM620
RM897 total
includes taxes & fees
11 Jan - 12 Jan 2026
Modern Villa
Lobby
The Berkley, Orlando

Holiday Home in Kissimmee

The Berkley, Orlando
4.0 star property
9.6 out of 10, Exceptional, (2018)
"The location of the resort is great. The room was perfect for our group. Staff was great, pool, game room. We would stay again. "
United States
Sarha
The price is RM616
RM739 total
includes taxes & fees
5 Jan - 6 Jan 2026
The Berkley, Orlando
Interior
Contemporary 4BR Townhome With Pool & Themed Rooms

Villa in Clermont

Contemporary 4BR Townhome With Pool & Themed Rooms
3.0 star property
The price is RM494
RM1,398 total
includes taxes & fees
11 Jan - 12 Jan 2026
Contemporary 4BR Townhome With Pool & Themed Rooms
Dock
Barefoot Suites

Aparthotel in Kissimmee

Barefoot Suites
3.0 star property
9.0 out of 10, Wonderful, (1801)
"Clean room location "
United States
Bryan
Barefoot Suites
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 RM441
RM975 total
includes taxes & fees
8 Jan - 9 Jan 2026
Davenport Vacation Homes by Shine FM
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

Hilton Vacation Club Mystic Dunes Orlando

Hilton Vacation Club Mystic Dunes Orlando

10/10 Excellent
"The staff was very efficient and kind. everything we request they did it immediately very efficient. Our room very clean and comfortable no complaints at all. I can’t wait to come back."
Terrell 5-night trip
Posted 4 hours ago
Hilton Vacation Club Mystic Dunes Orlando

Find out more about Lakeland - Winter Haven

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