Book Holiday Homes in Lakeland - Winter Haven

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Featured Holiday Homes in Lakeland - Winter Haven

The Berkley, Orlando

The Berkley, Orlando

4 out of 5
8545 W. Irlo Bronson Highway, Kissimmee, FL
With a stay at The Berkley, Orlando in Kissimmee, you'll be within a 10-minute drive of Walt Disney World® Resort and Mystic Dunes Golf Club.
The Berkley, Orlando
Orlando Renters

Orlando Renters

3.5 out of 5
8285 Champions Gate Blvd, Kissimmee, FL
When you stay at Orlando Renters in Kissimmee, you'll be next to a golf course, a 3-minute drive from ChampionsGate Golf Club and 9 minutes from Mystic Dunes ...
Orlando Renters
Formosa Valley Resort by UNE Homes

Formosa Valley Resort by UNE Homes

4 out of 5
Formosa Vly Pl, Kissimmee, FL
With a stay at Formosa Valley Resort by UNE Homes in Kissimmee, you'll be a 3-minute drive from Mystic Dunes Golf Club and 8 minutes from Walt Disney World® ...
Formosa Valley Resort by UNE Homes
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Encore Resort

Encore Resort

4 out of 5
101 Lasso Drive, Kissimmee, FL
Located in Kissimmee, this vacation home is within a 15-minute drive of Walt Disney World® Resort and Disney's Hollywood Studios®.
Encore Resort
Kissimmee Maingate Area Pool Homes by SVV

Kissimmee Maingate Area Pool Homes by SVV

3.5 out of 5
Kissimmee
With a stay at Kissimmee Maingate Area Pool Homes by SVV in Kissimmee, you'll be within a 15-minute drive of Walt Disney World® Resort and Old Town.
Kissimmee Maingate Area Pool Homes by SVV
Big Pool&Spa/Themed rooms/Private yard/ CLOSE TO EVERYTHING, Lakeview,Playground

Big Pool&Spa/Themed rooms/Private yard/ CLOSE TO EVERYTHING, Lakeview,Playground

Kissimmee
When you stay at this vacation home in Kissimmee, you'll be on the waterfront, a 3-minute drive from Mystic Dunes Golf Club and 8 minutes from Walt Disney World® ...
Big Pool&Spa/Themed rooms/Private yard/ CLOSE TO EVERYTHING, Lakeview,Playground
Home w/ Pool, Hot Tub & Game Room, 6 Mi to Disney!

Home w/ Pool, Hot Tub & Game Room, 6 Mi to Disney!

Kissimmee
With a stay at this vacation home in Kissimmee (Lindfields), you'll be within a 15-minute drive of Walt Disney World® Resort and Old Town.
Home w/ Pool, Hot Tub & Game Room, 6 Mi to Disney!
The Bear's Den Resort Orlando

The Bear's Den Resort Orlando

5 out of 5
7880 Nicklaus Clubhouse Lane, Kissimmee, FL
With a stay at The Bear's Den Resort Orlando in Kissimmee (Reunion), you'll be within a 10-minute drive of Reunion Resort Golf Course and Mystic Dunes Golf ...
The Bear's Den Resort Orlando
☼ Luxury Home * Private Pool ☼ 3 Miles from Disney - 200 5-Star Reviews ★ ★★ ★★

☼ Luxury Home * Private Pool ☼ 3 Miles from Disney - 200 5-Star Reviews ★ ★★ ★★

Kissimmee
Located in Kissimmee, this vacation home is within a 15-minute drive of Walt Disney World® Resort and Old Town.
☼ Luxury Home * Private Pool ☼ 3 Miles from Disney - 200 5-Star Reviews ★ ★★ ★★
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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.

Lakeland - Winter Haven Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Lakeland - Winter Haven vacation homes are the perfect way for you to wing it.

Holiday houses in Lakeland - Winter Haven let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Lakeland - Winter Haven in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Lakeland - Winter Haven adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Lakeland - Winter Haven with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Lakeland - Winter Haven vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Lakeland - Winter Haven Holiday Homes essential information

Accommodation
977 Holiday Homes
Lowest Price
AU$211
Highest Price
AU$331
Popular accommodation
The Berkley, Orlando, Orlando Renters, Formosa Valley Resort by UNE Homes, Encore Resort, Kissimmee Maingate Area Pool Homes by SVV, Big Pool&Spa/Themed rooms/Private yard/ CLOSE TO EVERYTHING, Lakeview,Playground, Home w/ Pool, Hot Tub & Game Room, 6 Mi to Disney!, The Bear's Den Resort Orlando, ☼ Luxury Home * Private Pool ☼ 3 Miles from Disney - 200 5-Star Reviews ★ ★★ ★★

Top trending hotels in Lakeland - Winter Haven

The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

4 out of 5
14501 Grove Resort Avenue, Winter Garden, FL
Fully refundableReserve now, pay when you stay
The price is AU$331 per night from 5 Jan to 6 Jan
AU$331
includes taxes & fees
5 Jan - 6 Jan 2025
Located in Four Corners, The Grove Resort & Water Park Orlando is on a lake, a 1-minute drive from Surfari Water Park and 11 minutes from Orange County National ...
The Grove Resort & Water Park Orlando
Hilton Vacation Club Mystic Dunes Orlando

Hilton Vacation Club Mystic Dunes Orlando

7600 Mystic Dunes Lane, Kissimmee, FL
The price is AU$211 per night from 12 Jan to 13 Jan
AU$211
includes taxes & fees
12 Jan - 13 Jan 2025
Located in Kissimmee, Hilton Vacation Club Mystic Dunes Orlando is within a 15-minute drive of Disney's Hollywood Studios® and Disney Springs™.
Hilton Vacation Club Mystic Dunes Orlando
Margaritaville Resort Orlando

Margaritaville Resort Orlando

4 out of 5
8000 Fins Up Circle, Kissimmee, FL
Fully refundableReserve now, pay when you stay
The price is AU$307 per night from 5 Jan to 6 Jan
AU$307
includes taxes & fees
5 Jan - 6 Jan 2025
With a stay at Margaritaville Resort Orlando in Kissimmee, you'll be within a 15-minute drive of Walt Disney World® Resort and Old Town.
Margaritaville Resort Orlando
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Hilton Vacation Club Aqua Sol Orlando West

Hilton Vacation Club Aqua Sol Orlando West

4 out of 5
17777 Bali Blvd, Winter Garden, FL
Fully refundableReserve now, pay when you stay
The price is AU$258 per night from 4 Jan to 5 Jan
AU$258
includes taxes & fees
4 Jan - 5 Jan 2025
Located in Four Corners, Hilton Vacation Club Aqua Sol Orlando West is within a 15-minute drive of Walt Disney World® Resort and ChampionsGate Golf Club.
Hilton Vacation Club Aqua Sol Orlando West
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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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^Subject to availability and chosen travel dates.