Compare Winter Park Cottage Rentals

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Featured Winter Park Cottages

Orlando Lakefront Tiny House Community

Orlando Lakefront Tiny House Community

3 out of 5
3405 N Orange Blossom Trail, Orlando, FL
Orlando Lakefront Tiny House Community features free WiFi in public areas, express check-out, and a terrace. A stay here includes free parking. Additional amenities include laundry facilities, a picnic area, and a garden.
Tiny Hidden Cottage

Tiny Hidden Cottage

$131 nightly
The price is $144 total per night
$144 total
Oct 5 - Oct 6
Total with taxes and fees
Guests staying at this cottage enjoy features like a water park.
2BR COTTAGE IN SANFORD HISTORIC DISTRICT

2BR COTTAGE IN SANFORD HISTORIC DISTRICT

Guests staying at this cottage have access to laundry facilities, a garden, and barbecue grills.
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!

The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!

$317 nightly
The price is $352 total per night
$352 total
Oct 6 - Oct 7
Total with taxes and fees
Guests of this cottage enjoy access to a water park, laundry facilities, and barbecue grills. Other amenities at this family-friendly cottage include a living plant wall and a garden.
5003 Windermere Avenue

5003 Windermere Avenue

3 out of 5
5003 Windermere Avenue,, Kissimmee, FL
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.
LAKEFRONT - kayak, fish, paddleboard, canoe, HOT TUB, golf -near Orlando

LAKEFRONT - kayak, fish, paddleboard, canoe, HOT TUB, golf -near Orlando

Guests staying at this cottage enjoy a water park, a hot tub, and laundry facilities. This smoke-free cottage also has barbecue grills.
End of the summer special! Guesthouse with lake view and private pool

End of the summer special! Guesthouse with lake view and private pool

$243 nightly
The price is $268 total per night
$268 total
Oct 12 - Oct 13
Total with taxes and fees
This cottage features an outdoor pool and laundry facilities.
Downtown Cottage

Downtown Cottage

$164 nightly
The price is $181 total per night
$181 total
Oct 12 - Oct 13
Total with taxes and fees
At this cottage, guests have access to features like laundry facilities.
Modern Townhome W/private Pool & Free Water Park!

Modern Townhome W/private Pool & Free Water Park!

4 out of 5
5009 Windermere Avenue, Kissimmee, FL
This cottage features an outdoor pool, a lazy river, and a gym. A stay here includes free parking. This family-friendly cottage also has free WiFi in public areas.
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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 Park

    Hyatt Regency Orlando International Airport

    Hyatt Regency Orlando International Airport

    9300 Jeff Fuqua Boulevard, Orlando, FL
    $179 nightly
    The price is $201 total per night from Oct 6 to Oct 7
    $201 total
    Oct 6 - Oct 7
    Total with taxes and fees
    9.4/10 Exceptional! (3,642 reviews)
    Marriott's Grande Vista

    Marriott's Grande Vista

    5925 Avenida Vista, Orlando, FL
    $87 nightly
    The price is $98 total per night from Oct 26 to Oct 27
    $98 total
    Oct 26 - Oct 27
    Total with taxes and fees
    8.8/10 Excellent! (3,254 reviews)
    Universal's Cabana Bay Beach Resort

    Universal's Cabana Bay Beach Resort

    6550 Adventure Way, Orlando, FL
    $138 nightly
    The price is $155 total per night from Nov 4 to Nov 5
    $155 total
    Nov 4 - Nov 5
    Total with taxes and fees
    8.8/10 Excellent! (5,343 reviews)

Cottages

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

Cottage apartments in Winter Park 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 Park
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 Park 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 Park 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 Park. 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 Park Cottages essential information

Accommodation
274 Cottages
Lowest Price
$98
Highest Price
$352
Popular accommodation
Orlando Lakefront Tiny House Community , Tiny Hidden Cottage , 2BR COTTAGE IN SANFORD HISTORIC DISTRICT, The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!, 5003 Windermere Avenue, LAKEFRONT - kayak, fish, paddleboard, canoe, HOT TUB, golf -near Orlando, End of the summer special! Guesthouse with lake view and private pool, Downtown Cottage, Modern Townhome W/private Pool & Free Water Park!

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