Winter Haven Cottages

Get more for your budget and save up to 50% off select Secret Bargain hotels

Get even more value with CheapTickets Price Guarantee!

Change your flight without a fee on select flights

Check dates for Winter Haven hotels

Cottages in Winter Haven

Encore Swanky

411 Lasso Drive Kissimmee FL

With a stay at this cottage in Kissimmee, you'll be within a 10-minute drive of Walt Disney World® Resort and Mystic Dunes Golf Club.

Pool

Kitchen

Lake Ida Beach Resort

2524 Lake Alfred Rd Winter Haven FL

$75 nightly

$84 total

Jun 15 - Jun 16

Total with taxes and fees

Free Cancellation

Reserve now, pay when you stay

With a stay at Lake Ida Beach Resort in Winter Haven, you'll be on a lake, within a 15-minute drive of LEGOLAND® Florida and Lake Conine.

The Cozy Cottage 1 bedroom plus studio bed and 2 bathrooms in charming Lakeland

Lakeland FL

$116 nightly

$128 total

Jul 15 - Jul 16

Total with taxes and fees

With a stay at this cottage in Lakeland (East Lake Morton), you'll be within a 5-minute drive of RP Funding Center and Polk Museum of Art.

Charming Historic Cottage with Cozy Porch and Garden Retreat

Polk City FL

$182 nightly

$201 total

Jun 15 - Jun 16

Total with taxes and fees

Located in Polk City, this cottage is a 3-minute drive from Fantasy of Flight and 8 minutes from Gen. James A. Van Fleet State Trail.

The Russell Lake House

Winter Haven FL

With a stay at this cottage in Winter Haven, you'll be on the waterfront, within a 15-minute drive of LEGOLAND® Florida and Winter Haven Public Library.

Enchanted Cottage with Pool and Mini-Golf Near Disney

Kissimmee FL

With a stay at this cottage in Kissimmee, you'll be a 3-minute drive from Old Town and 9 minutes from Orlando Vineland Premium Outlets.

Solterra Swanky

5180 Oakbourne Avenue Davenport FL

Located in Davenport (Solterra Resort), this cottage is within a 10-minute drive of ChampionsGate Golf Club and Reunion Resort Golf Course.

It's A Wonderful Life Vacay Home

3000 Salted Rim Rd, Kissimmee, Fl Kissimmee FL

With a stay at this cottage in Kissimmee, you'll be within a 10-minute drive of Walt Disney World® Resort and Mystic Dunes Golf Club.

Luxury 6BR Home w/ Theater + Pool Near Disney

Bismarck Palm Road 8950 Kissimmee FL

With a stay at this cottage in Kissimmee, you'll be within a 10-minute drive of Island H2O Live! and Flamingo Crossings Town Center.

Amazing Game Room, Harry Potter, Mickey & Princess Room. All new Decor! #7sl1621

Nassau Point Trail 1621 Kissimmee FL

Located in Kissimmee, this cottage is within a 15-minute drive of Island H2O Live! and ChampionsGate Golf Club.

2/1 Pet Friendly Spanish Cottage

Lakeland FL

With a stay at this cottage in Lakeland (Lakeshore), you'll be within a 5-minute drive of RP Funding Center and Lake Parker.

Stunning Villa With Themed Room's and Game Room, Right Across From the Club House #7sl9003

Kissimmee FL

Located in Kissimmee, this cottage is within a 15-minute drive of Walt Disney World® Resort and Island H2O Live!.

Pool

Kitchen

Don't see what you're looking for?

See all available properties in Winter Haven

View all properties

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.