Lakeland - Winter Haven Vacation Rentals

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

Tonight
Dec 21 - Dec 22
Tomorrow
Dec 22 - Dec 23
Next weekend
Dec 26 - Dec 28
In two weeks
Jan 2 - Jan 4

Our top choices for Lakeland - Winter Haven vacation 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, (503)
"Great place"
United States
Bobby
The price is P7,340
P9,273 total
includes taxes & fees
Jan 15 - Jan 16, 2026
Holiday Inn Club Vacations Orlando Breeze Resort by IHG
Lobby
Elita Inn

Elita Inn

Elita Inn
3.0 star property
Dundee
10.0 out of 10, Exceptional, (5)
"Yes this is an awesome place and especially clen we loved it "
United States
Bryson
The price is P4,404
P4,933 total
includes taxes & fees
Dec 22 - Dec 23
Elita Inn
Interior entrance
Jade Manor

Jade Manor

Jade Manor
2.5 star property
Solterra Resort
8.0 out of 10, Very Good, (2)
"Amazing "
United States
Nilda
The price is P3,523
P7,892 total
includes taxes & fees
Dec 22 - Dec 23
Jade Manor
Exterior
voco Kissimmee Orlando by IHG

voco Kissimmee Orlando by IHG

voco Kissimmee Orlando by IHG
4.0 star property
Kissimmee
7.4 out of 10, Good, (1000)
"Place was clean, staff great, cozy very nice area swimming pool"
United States
KRYSTLE
The price is P3,817
P5,665 total
includes taxes & fees
Jan 11 - Jan 12, 2026
voco Kissimmee Orlando by IHG
Exterior
Margaritaville Cottages Orlando by Rentyl

Margaritaville Cottages Orlando by Rentyl

Margaritaville Cottages Orlando by Rentyl
4.0 star property
Kissimmee
8.8 out of 10, Excellent, (1751)
"Great place "
United States
Lauren
The price is P11,686
P25,017 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Margaritaville Cottages Orlando by Rentyl
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)
"Clean and great location"
United States
Anonymous traveler
Disney's Beach Club Villas
Outdoor pool
The Irlo

The Irlo

The Irlo
3.0 star property
Kissimmee
4.0 out of 10, (1)
"Room wasn't clean, bed had a wet spot in it and someone's hair that wasn't ours. It felt gross and we left and couldn't even stay."
United States
Cody
The price is P3,817
P12,553 total
includes taxes & fees
Jan 4 - Jan 5, 2026
The Irlo
2 outdoor pools, open 8:00 AM to 10:00 PM, pool umbrellas, sun loungers
The Village Resort Suite and Spa

The Village Resort Suite and Spa

The Village Resort Suite and Spa
2.5 star property
Orlando
The Village Resort Suite and Spa
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, (190)
"We lived our stay and can't wait to come back soon"
United States
Ramona
Camp Mack Lodge, Marina & RV Resort
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 P5,755
P16,107 total
includes taxes & fees
Jan 4 - Jan 5, 2026
2BR Dog-friendly w/ Yard, Screened Porch, & Grill
Exterior
Modern Villa

Modern Villa

Modern Villa
2.5 star property
Haines City
The price is P8,984
P12,999 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Modern Villa
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, (3032)
"Hot tub was nice. Mattresses were the best!!!!"
United States
corey
The price is P8,469
P21,209 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Regal Oaks Resort Vacation Townhomes by IDILIQ
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 P6,401
P16,660 total
includes taxes & fees
Dec 22 - Dec 23
Modern 3 Bed Villa, Newly Renovated, Prime Location
Lobby sitting area
The Berkley, Orlando

The Berkley, Orlando

The Berkley, Orlando
4.0 star property
Kissimmee
9.6 out of 10, Exceptional, (2011)
"Recommended amazing stay."
United States
Elf
The price is P8,935
P10,718 total
includes taxes & fees
Jan 2 - Jan 3, 2026
The Berkley, Orlando
Exterior
Vacation Village Orlando, Celebration

Vacation Village Orlando, Celebration

Vacation Village Orlando, Celebration
3.0 star property
Kissimmee
8.6 out of 10, Excellent, (3110)
"Great place to stay"
United States
Jose
The price is P6,738
P9,116 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Vacation Village Orlando, Celebration
Outdoor pool, open 7:00 AM to 11:00 PM, pool umbrellas, sun loungers
Marriott's Sabal Palms

Marriott's Sabal Palms

Marriott's Sabal Palms
4.0 star property
Orlando
9.6 out of 10, Exceptional, (207)
"Room was great, staff friendly and grounds are clean. "
United States
DENNIS
The price is P15,922
P17,913 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Marriott's Sabal Palms
Terrace/patio
Disney's Animal Kingdom Villas - Kidani Village

Disney's Animal Kingdom Villas - Kidani Village

Disney's Animal Kingdom Villas - Kidani Village
4.0 star property
Bay Lake
9.0 out of 10, Wonderful, (166)
"The animals are amazing and the location for Animal Kingdom was perfect! The room was clean and comfortable."
United States
Kelly
Disney's Animal Kingdom Villas - Kidani Village
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
"HUGE GATED RESORT! Shuttles run around complex from 8AM to 11PM. Pools are heated, lazy river is relaxing! Access to great pools, hot tubs, dining, golf, pickleball & so much more! Marketplace serves Starbucks coffee & has its own grocery & souvenir sections. Family friendly resort, activities for kids & adults. Staff is helpful, friendly & very accommodating. Will be back in the future. "
Justin 5-night trip
Posted 3 days ago
Holiday Inn Club Vacations at Orange Lake Resort by IHG

Find out more about Lakeland - Winter Haven

Search for holiday rentals in Lakeland - Winter Haven on Expedia! You can easily find your home rentals, villas, holiday apartments in Lakeland - Winter Haven using one of the methods below:

  • View our selection of featured holiday rentals in Lakeland - Winter Haven
  • Use the map to find apartments and other holiday homes in the Lakeland - Winter Haven neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Lakeland - Winter Haven while they last

Look no further and take a look at our great range of rental properties in Lakeland - Winter Haven!