Compare Kissimmee Cottage Rentals

Featured Kissimmee Cottages

$812 nightly

$920 total

Dec 29 - Dec 30

Total with taxes and fees

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 barbecue grills and a garden.

Pool

Kitchen

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.

Pool

Hot Tub

At this cottage, guests enjoy an outdoor pool, a gym, and a hot tub. Additional amenities include an arcade/game room and laundry facilities.

Pool

Hot Tub

This cottage features an outdoor pool, a lazy river, and a gym. You can take advantage of free parking if you drive. This family-friendly cottage also has free WiFi in public areas.

Pool

Kitchen

Our Retro Mod Pod-Disney & Old Town Minutes Away!

Guests of this cottage have access to an outdoor pool, a gym, and a hot tub. Transportation is made easy with limo/town car service. Other amenities at this family-friendly cottage include an arcade/game room, laundry facilities, and a garden.

Pool

Hot Tub

Guests of this cottage have access to an outdoor pool, a lazy river, and free WiFi in public areas. You can put free parking to good use if you drive. This family-friendly cottage also has barbecue grills.

Pool

Kitchen

$160 nightly

$179 total

Dec 17 - Dec 18

Total with taxes and fees

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

Pool

Hot Tub

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

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

Kitchen

Dryer

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

Guests staying at this cottage enjoy an outdoor pool, free WiFi in public areas, and a garden. Free parking is included with your stay.

Pool

Kitchen

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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 Kissimmee

Ramada by Wyndham Hotel & Water Park

Kissimmee FL

$61 nightly

$69 total

Jan 7 - Jan 8, 2026

Total with taxes and fees

7/10 Good! (1,621 reviews)

Margaritaville Resort Orlando

8000 Fins Up Circle Kissimmee FL

$176 nightly

$200 total

Jan 6 - Jan 7, 2026

Total with taxes and fees

8.8/10 Excellent! (3,652 reviews)

Kompose Boutique Resort at Theme Parks

7491 W Irlo Bronson Memorial Hwy Kissimmee FL

$89 nightly

$101 total

Dec 17 - Dec 18

Total with taxes and fees

9.4/10 Exceptional! (1,965 reviews)

Cottages

Book a cottage in Kissimmee
Spend your next getaway treating yourself to a quieter, simpler way of life in a private cottage in Kissimmee. 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 Kissimmee better.

Cottage apartments in Kissimmee 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 Kissimmee
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 Kissimmee 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 Kissimmee 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 Kissimmee. 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.

Kissimmee Cottages essential information

Accommodation	1056 Cottages
Lowest Price	$69
Highest Price	$920
Popular accommodation	Encore Swanky, Enchanted Cottage with Pool and Mini-Golf Near Disney, 1 bedroom, private laundry in resort with a pool near Disney!! Kissimmee, Stunning Lakeview Townhome w/ Private Pool!, Our Retro Mod Pod-Disney & Old Town Minutes Away!, 5003 Windermere Avenue, Tiny house close to Disney KISSIMMEE, Amazing Game Room, Harry Potter, Mickey & Princess Room. All new Decor! #7sl1621, Stunning Villa With Themed Room's and Game Room, Right Across From the Club House #7sl9003