Winter Park Vacation Rentals from AED 722: Search Short-Term Rentals

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Our top choices for Winter Park vacation rentals

A deck with a circular fire pit surrounded by Adirondack chairs, overlooking a snowy landscape with trees and mountains.

1. Chic Winter Park Studio w/ Community Hot Tub

Winter Park

Kelley

AED 876 total

includes taxes & fees

10 Nov - 11 Nov

A modern living room with a stone fireplace, wooden walls, a large flat-screen TV, a dark wooden entertainment unit, a grey sofa, and a large window with a view of trees.

2. Beaver Village Unit #0332 Remodeled 1 Bedroom vaulted ceiling & private deck

Winter Park

Shannon

AED 906 total

includes taxes & fees

7 Nov - 8 Nov

A modern building with a hot tub and lounge chairs on a wooden deck.

3. Cozy, 1 bed Condo, 2 Blocks from Downtown, on Bus Rt Short Term License # 004821

Winter Park

Mikinzie D.

AED 862 total

includes taxes & fees

7 Nov - 8 Nov

A pool area with lounge chairs and a towel rack, surrounded by a building with a view of a snowy mountain.

4. Walk to Gondola · Alpine Slide & Village

Winter Park Village

Lee J.

A spacious kitchen with wooden cabinets, a granite countertop, and a built-in dishwasher.

5. Beaver Village Unit #2032R Vaulted Ceilings views of Winter Park Resort

Winter Park

Dawn C.

AED 906 total

includes taxes & fees

8 Nov - 9 Nov

Modern mountain resort buildings nestled beside a flowing river, surrounded by evergreen forests and dramatic peaks.

6. Fraser Crossing 3518 remodeled studio gas fireplace and views

Winter Park Village

Alfonso

AED 812 total

includes taxes & fees

7 Nov - 8 Nov

A multi-story hotel with a ski lift in the background, surrounded by snow-covered trees and a clear sky.

7. Ski-in Ski-Out Zephyr Mountain Lodge Condo with Hot Tub next to Gondola

Winter Park Village

Ila B.

8. Pool Hot Tub Free Garage · Remodeled Studio

Winter Park

Eric E.

AED 722 total

includes taxes & fees

7 Nov - 8 Nov

A living room with a stone fireplace, a television, a sofa with patterned cushions, and a large window overlooking a snowy landscape.

9. Meadow Ridge Court 9 Unit 4 Updated interior in this 1 bedroom, private patio

Fraser

Caleb M.

AED 855 total

includes taxes & fees

7 Nov - 8 Nov

A modern kitchen with wooden cabinets, a built-in island with stools, a flat-screen TV above the island, and a fireplace.

10. Waterside West A303 Ideal and modern 1 bedroom - open floor plan and mt views

Fraser

Sarah S.

AED 832 total

includes taxes & fees

7 Nov - 8 Nov

A hotel room with a large bed, a wooden headboard, and a view through a sliding glass door to the outside.

11. Micro Guest Suite Downtown Winter Park GREAT LOCATION

Winter Park

Faith R.

AED 909 total

includes taxes & fees

6 Dec - 7 Dec

A wooden cabin with a snow-covered porch, surrounded by trees with yellow leaves.

12. Madge’s Studio - Pets Welcome

Fraser

Carrie B.

AED 566 total

includes taxes & fees

19 Nov - 20 Nov

A multi-story hotel with a ski slope in the background.

13. Zephyr Mountain Lodge

Winter Park Village

Carl

AED 917 total

includes taxes & fees

7 Nov - 8 Nov

A resort with multiple buildings, a swimming pool, and snow-covered surroundings.

14. Meadow Ridge 18-4 Cozy 1 bedroom, ground floor, remodeled, clubhouse amenities

Fraser

Kami

AED 859 total

includes taxes & fees

19 Nov - 20 Nov

Dive into the clubhouse indoor oasis, where exposed wood beams frame crystal-clear waters and natural light creates the perfect retreat.

15. Beaver Village Unit #0232R Modern 1 bedroom condo close to downtown & clubhouse

Winter Park

Katherine H.

AED 906 total

includes taxes & fees

7 Nov - 8 Nov

Unwind in the cozy clubhouse living room with a crackling fireplace, comfortable leather seating, and warm wood accents perfect for relaxing evenings.

16. Beaver Village Unit #1612R Remodeled king bed and rich leather furnishings

Winter Park

Sean C.

AED 906 total

includes taxes & fees

8 Nov - 9 Nov

A kitchen with granite countertops, wooden cabinets, and a dining area with a table and chairs.

17. Beaver Village Unit #0931R Located in WP Minutes from Winter Park Resort

Winter Park

Simon M.

Sink into plush leather seating at the clubhouse by your crackling fireplace, where warm wood accents create the perfect après-ski retreat.

18. Beaver Village Unit #0412R Wonderful 1 bed unit the perfect mountain getaway!

Winter Park

Ryan L.

AED 906 total

includes taxes & fees

8 Nov - 9 Nov

A building with a sign reading "Founders Pointe."

19. Top Floor Ski-In / Ski-Out Studio Condo at the base of Winter Park Resort

Winter Park Village

Tonya T.

AED 881 total

includes taxes & fees

7 Nov - 8 Nov

A spacious living area with a white sofa, a coffee table, and a TV mounted on the wall.

20. Hi Country Haus Unit 1803 1 bedroom, private deck, walk to Main Street

Winter Park

Dale K.

AED 882 total

includes taxes & fees

7 Nov - 8 Nov

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Top Winter Park Hotel Reviews

Fraser Crossing Founders Pointe

10/10 Excellent

"Nice place in the mountains to stay"

The Trailhead | Beautifully Furnished Modern Condo In Downtown Winter Park

10/10 Excellent

"The best place to stay in Winter Park! The location is great, the property is beautiful and the host is the best! Very responsive when I had a “senior moment” and couldn’t find my check-in instructions. Hated to leave, will definitely be back"

Creekside Luxury Retreat • 8BR • Walk to Shops, Dining & Shuttle • Sleeps 22

10/10 Excellent

"Fantastic location right by a creek. The house was clean and well organized with some fun games like ping pong & pool as well. Also, walkable to the winterpark town!Our group really enjoyed our stay here. House manager was also great & prompt in resolving, when we had a hot tub issue. Overall, highly recommend."

Renovated Condo near the Slopes and Trails

8/10 Good

"Clean and convenient location. More than adequate for our needs, though the plastic mattress covers in the bunk room were not ideal. Cumbersome approach to 2nd floor up slightly sloped stairs and a door that opens to the unit on the wrong side. Current renovations are lovely…keep going!"

Luxury Downtown Condo - Private Hot Tub! Walk to Dining and Ski Bus...

10/10 Excellent

"The location was great. The house was very clean. The amenities were great from the towels for the hot tub to the well-equipped kitchen. We were a party of 10 and we ate most of our meals because it was comfortable, fun and easy to accommodate all the cooks in the kitchen. We did Elevation Everest, lots of Downhill MTB and hikes. If we ever come back to Winter Park, we will surely stay here again. I forgot my Dyson hairdryer and I’m sure Bob is shipping it back to me now."

A Frame Club

8/10 Good

"Clean and comfortable. Great location, close to action. Super cute. Moose wandered through the property while we were there! The reasons it didn’t get 5 stars: -Breakfast was odd. Pre built burritos, grab and go, for one hour. Tasty, but just odd. -Staff repeatedly told us the restaurant was open for dinner. We sat there for 10 minutes without being acknowledged by anyone. So we left. -No bathroom fan."

Frequently asked questions

Can I find vacation rentals in Winter Park?

Yes, we give you a choice of vacation rentals in Winter Park close to Amaze'n Maze Winter Park, or you can select a more remote option if you want a relaxing stay. Visitors like the ski slopes and majestic mountain landscape in Winter Park. You can also check out the live music while you're visiting.

What are some of the best vacation home rentals that Winter Park has to offer?

Creekside Luxury Retreat • 8BR • Walk to Shops, Dining & Shuttle • Sleeps 22: This highly rated vacation home rental in Winter Park is located on the waterfront and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 8 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation. Other favorite homes for rent in Winter Park are Luxury Downtown Condo - Private Hot Tub! Walk to Dining and Ski Bus... and Large Beautiful Townhome, Private Hot Tub, Near Shuttle Route, In Town, WIFI.

How many vacation rentals are there in Winter Park?

With 341 Expedia vacation rentals, you're sure to find just the right place for your Winter Park stay.

What’s there to see and do in Winter Park?

The Fraser River Trail and Arapaho National Recreation Area are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Amaze'n Maze Winter Park. While here, Winter Park Ski Resort and Trestle Bike Park are other places worth a visit.

What’s a vacation rental in Winter Park like?

A vacation rental is a private property you can stay in for a few weeks or just a few days in Winter Park. Vacation rentals offer extras such as laundry facilities and kitchens so you'll have all the comforts of home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of security away from shared hotel elevators and busy front desks while still allowing you to travel. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular choice for a family trip.

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Check prices for these dates

Our top choices for Winter Park vacation rentals

1. Chic Winter Park Studio w/ Community Hot Tub

2. Beaver Village Unit #0332 Remodeled 1 Bedroom vaulted ceiling & private deck

3. Cozy, 1 bed Condo, 2 Blocks from Downtown, on Bus Rt Short Term License # 004821

4. Walk to Gondola · Alpine Slide & Village

5. Beaver Village Unit #2032R Vaulted Ceilings views of Winter Park Resort

6. Fraser Crossing 3518 remodeled studio gas fireplace and views

7. Ski-in Ski-Out Zephyr Mountain Lodge Condo with Hot Tub next to Gondola

8. Pool Hot Tub Free Garage · Remodeled Studio

9. Meadow Ridge Court 9 Unit 4 Updated interior in this 1 bedroom, private patio

10. Waterside West A303 Ideal and modern 1 bedroom - open floor plan and mt views

11. Micro Guest Suite Downtown Winter Park GREAT LOCATION

12. Madge’s Studio - Pets Welcome

13. Zephyr Mountain Lodge

14. Meadow Ridge 18-4 Cozy 1 bedroom, ground floor, remodeled, clubhouse amenities

15. Beaver Village Unit #0232R Modern 1 bedroom condo close to downtown & clubhouse

16. Beaver Village Unit #1612R Remodeled king bed and rich leather furnishings

17. Beaver Village Unit #0931R Located in WP Minutes from Winter Park Resort

18. Beaver Village Unit #0412R Wonderful 1 bed unit the perfect mountain getaway!

19. Top Floor Ski-In / Ski-Out Studio Condo at the base of Winter Park Resort

20. Hi Country Haus Unit 1803 1 bedroom, private deck, walk to Main Street

Find vacation rentals that suit your style

Top Winter Park Hotel Reviews

Fraser Crossing Founders Pointe

Lakota Dreamcatcher 133 | Dreams Are Made Here | Pet Friendly | Across From Resort

The Trailhead | Beautifully Furnished Modern Condo In Downtown Winter Park

Creekside Luxury Retreat • 8BR • Walk to Shops, Dining & Shuttle • Sleeps 22

Renovated Condo near the Slopes and Trails

Luxury Downtown Condo - Private Hot Tub! Walk to Dining and Ski Bus...

A Frame Club

Large Beautiful Townhome, Private Hot Tub, Near Shuttle Route, In Town, WIFI

Top Floor Ski-In / Ski-Out Studio Condo at the base of Winter Park Resort

Frequently asked questions

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