Compare Winter Haven Cottage Rentals

Featured Cottages in Winter Haven

Guests staying at this cottage enjoy an outdoor pool, an arcade/game room, and a terrace. You can put free offsite parking to good use if you drive. Other amenities at this family-friendly cottage include a garden and barbecue grills.

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

Guests of this cottage enjoy features like an outdoor pool, a hot tub, and laundry facilities. Additional amenities include a garden and barbecue grills.

$66 nightly

$73 total

Nov 3 - Nov 4

Total with taxes and fees

Guests of Lake Ida Beach Resort enjoy features like an outdoor pool, free WiFi in public areas, and a terrace. If you drive, put free parking to good use. The 24-hour front desk has multilingual staff ready to assist with sightseeing, directions, and local dining recommendations. Additional amenities include laundry facilities, barbecue grills, and a picnic area.

Enchanted Cottage with Pool and Mini-Golf Near Disney

Guests of this cottage have access to an outdoor pool, a gym, and a hot tub. Other amenities at this family-friendly cottage include an arcade/game room, laundry facilities, and barbecue grills.

"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney

$270 nightly

$302 total

Oct 27 - Oct 28

Total with taxes and fees

Guests staying at this cottage enjoy a hot tub and laundry facilities.

Lakeview Cottage Escape. Close to BOK Tower Gardens, Legoland and Disney

At this cottage, guests have access to barbecue grills.

There's free parking if you drive.

Guests staying at this cottage can enjoy an outdoor pool, a garden, and barbecue grills. Free offsite parking is available if you drive.

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

This cottage features free WiFi in public areas and a garden.

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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.

Hotel Options in Winter Haven

Holiday Inn Winter Haven by IHG

200 Cypress Gardens Boulevard Winter Haven FL

$111 nightly

$124 total

Nov 8 - Nov 9

Total with taxes and fees

9/10 Wonderful! (1,000 reviews)

Best Western Plus Winter Haven Inn & Suites

5801 Roosevelt Dr Winter Haven FL

$130 nightly

$146 total

Oct 12 - Oct 13

Total with taxes and fees

9.6/10 Exceptional! (1,372 reviews)

Staybridge Suites Winter Haven Auburndale by IHG

305 5th St NW and Avenue D NW Winter Haven FL

$134 nightly

$150 total

Oct 18 - Oct 19

Total with taxes and fees

9.8/10 Exceptional! (918 reviews)

Cottages

Book a cottage in Winter Haven
Spend your next getaway treating yourself to a quieter, simpler way of life in a private cottage in Winter Haven. Cozy and charming, cottage rentals are the ideal spot when you want the comforts of home paired with a one-of-a-kind experience. They’re perfect for a single traveler looking for peace and quiet, or small groups who want to get to know Winter Haven better.

Cottage apartments in Winter Haven range from rustic to luxurious, with just about everything in between. Orbitz gives you the best deals on all of them.

Find the best cottages in Winter Haven
City cottages are great if you want a cozy, comfy place to stay without being far from the all the cool spots you want to check out. A cottage makes a great home base for a day filled with adventure in Winter Haven and the surrounding area. Not willing to give up all the comforts of a fine hotel? A luxury cottage turns up the charm while offering perks like room service, cable television, sunken spa tubs and housekeeping.

Stay in a Winter Haven cottage and swap busy days for peaceful evenings. Use the kitchenette or full kitchen to come up with a meal or reheat leftovers from your afternoon in Winter Haven. You may even be able to use a pool and laundry facilities. Whether you’re in the mood for quiet relaxation or a night on the town, a cottage puts you right where you want to be.

Winter Haven Cottages essential information

Accommodation	2410 Cottages
Lowest Price	$73
Highest Price	$302
Popular accommodation	Encore Swanky, The Cozy Cottage 1 bedroom plus studio bed and 2 bathrooms in charming Lakeland, Lake Ida Beach Resort, Enchanted Cottage with Pool and Mini-Golf Near Disney, "Casa Kiwi" Margaritaville Cottage 5 minutes to Disney, Lakeview Cottage Escape. Close to BOK Tower Gardens, Legoland and Disney , It's A Wonderful Life Vacay Home, Solterra Swanky, Amazing Game Room, Harry Potter, Mickey & Princess Room. All new Decor! #7sl1621