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Winter Park Rentals

From $458 per night (USD)
VRBO
Incredible Views of Winter Park - Relax in private hot tub
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
This Lakota property is great for either a winter or summer getaway to the Colorado Rocky Mountains. Three bedroom three ...
From $458 per night (USD)
VRBO
From $156 per night (USD)
Expedia
2BD Condo on the river, walk to town, free ski bus!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
You will enjoy a memorable vacation in my fully furnished, newly remodeled, 2 bedroom/1bath condo. This 710 ft Condo is ...
From $156 per night (USD)
Expedia
From $269 per night (USD)
VRBO
Budget friendly rental 2 bedroom, private deck, river views
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
This lovely Colorado condo in Winter Park is a 2 bedroom unit has 899 square feet of living space and includes a bonus a ...
From $269 per night (USD)
VRBO
From $132 per night (USD)
Expedia
Remodeled 1 bedroom downtown, extra bathroom, clubhouse
Bedrooms:
2
Bathrooms:
1
Sleeps:
4
A 1 bedroom vacation rental with 629 square feet, this unit is spacious, comfortable and on the third and top floor of t ...
From $132 per night (USD)
Expedia
From $187 per night (USD)
VRBO
Mountain Getaway on the Bus Route to Winter Park Resort
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Winter Park short term rental registration number 003436. Welcome to your serene retreat in Winter Park! Discover the p ...
From $187 per night (USD)
VRBO
From $164 per night (USD)
Expedia
Budget priced ground floor 2 bedroom
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
The 2 bedroom 1 bathroom unit has been recently renovated and has 651 square feet of living space. In the living room, a ...
From $164 per night (USD)
Expedia
From $416 per night (USD)
VRBO
High-end 3 bedroom with private deck and spacious floor plan
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
A spacious 1, 023 square feet, on the first floor, this is a premium 3 bedroom rental. In the living room a flat screen ...
From $416 per night (USD)
VRBO
From $683 per night (USD)
Expedia
Mountain townhome with hot tub, porches, & easy access to the slopes
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Home Sweet Hideaway Park Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ente ...
From $683 per night (USD)
Expedia
From $272 per night (USD)
VRBO
Luxury & modern interior - 3 bedroom, views and private deck
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This Winter Park ski condo rental has 1,006 square foot unit is on the 3rd floor of the building and is a wonderfully co ...
From $272 per night (USD)
VRBO
From $206 per night (USD)
Expedia
New interior 2 bedrooms, spacious, close to clubhouse
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
A lovely and comfortable 2 bedroom condo offers a large living room area, access to a private deck, wood burning firepla ...
From $206 per night (USD)
Expedia
From $142 per night (USD)
VRBO
Split interior 2 bedroom, comfortable family rental
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
A lovely townhome with 880 square feet of living space on two interior floors, this 2 bedroom unit is a good family rent ...
From $142 per night (USD)
VRBO
From $157 per night (USD)
Expedia
2 bedroom private balcony offers river view
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
A 3rd floor vacation condo rental has 899 square feet of living space and is comfortably decorated. The main living room ...
From $157 per night (USD)
Expedia
From $408 per night (USD)
VRBO
Family condo rental - 3 bedrooms, river views and much more!
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Welcome to the Spirit of Yukon Condo! This premium 3 bedroom, Hi Country Haus unit encompasses 1,023 square feet all on ...
From $408 per night (USD)
VRBO
From $233 per night (USD)
Expedia
Budget friendly 3 bedroom, ground floor, close to Main Street
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
This Winter Park condo is an end corner unit is on the ground floor offering 1, 060 square feet of living space and many ...
From $233 per night (USD)
Expedia
From $157 per night (USD)
VRBO
Downtown 2 bedroom, private deck, comfortable rental
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This downtown 2 bedroom 2 bathroom unit is on the second floor and offers a large interior space with 1,085 square feet ...
From $157 per night (USD)
VRBO
From $147 per night (USD)
Expedia
5th-Floor With Beautiful Views • Full Kitchen • Elegant New Italian Sleeper Sofa
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Welcome to Your Winter Park Getaway! We’re excited to welcome you to our mountain condo located in the heart of Winter ...
From $147 per night (USD)
Expedia
From $221 per night (USD)
VRBO
Ground floor condo with free Wi-Fi, flat screen TV and next to the Fraser River
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
A Winter Park ski deal, this unit has 572 square feet, on the ground floor of the building and is has been designated as ...
From $221 per night (USD)
VRBO
From $164 per night (USD)
Expedia
Couples getaway condo - river views and hardwood flooring
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
A Colorado resort condo rental has a western themed 2 bedroom unit on the third floor of the building providing a wonder ...
From $164 per night (USD)
Expedia
From $323 per night (USD)
VRBO
Ski-in Ski-Out:King in Master; Quiet End Unit; high speed secure internet
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Homey 2 BDR/ 2 BA ski-in/ski-out unit with tons of amenities! PET-FREE - SMOKE-FREE UNIT! HDMI FLAT-SCREEN SMART TV! ...
From $323 per night (USD)
VRBO
From $423 per night (USD)
Expedia
Mountainside Winter Park Ski Home w/ Hot Tub
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
Bring a jacket and hit the slopes in Winter Park. Since this vacation rental features 4 bedrooms, 3 bathrooms, and a fir ...
From $423 per night (USD)
Expedia
From $476 per night (USD)
VRBO
Zephyr Mountain Lodge, Condo | 3 Bedroom (Select-Rated Condo 1609)
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Just 110 feet from the gondola, for the closest stay to mountain adventure, this is a perfect property for you! ...
From $476 per night (USD)
VRBO
From $163 per night (USD)
Expedia
Cozy Winter Park Mountain Retreat w/ Fireplace
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Plan your dream mountain getaway at this 1-bedroom, 1-bath Winter Park vacation rental! Nestled in the heart of the Rock ...
From $163 per night (USD)
Expedia
From $393 per night (USD)
VRBO
Four-story townhome with private hot tub, roof deck & big mountain views
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Lions Gate Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $393 per night (USD)
VRBO
$Ski-In/Ski-Out MountainView-Free Heated Parking\nBldg. C UNIT #4013$
From $167 per night (USD)
Expedia
Ski-In/Ski-Out MountainView-Free Heated Parking\nBldg. C UNIT #4013
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Welcome to Our Ski-in/Ski-out Studio with Stunning Mountain and Pool Views! Property Address: 313 Iron Horse Way, Buildi ...
From $167 per night (USD)
Expedia
Click For Pricing
VRBO
Luxury Condo 611 I Pool I Club House I Hot Tub I Best Price I FREE Adventures Daily
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Exclusive Complimentary Adventures! Winter Park Escapes is the only management company to provide Free activities and eq ...
Click For Pricing
VRBO
From $409 per night (USD)
Expedia
Luxury Villa 865 I Hot Tub I Great Views I Best Price I FREE Adventures Daily
Bedrooms:
3
Bathrooms:
3
Sleeps:
10
Exclusive Complimentary Adventures! Winter Park Escapes is the only management company to provide Free activities and eq ...
From $409 per night (USD)
Expedia
From $128 per night (USD)
VRBO
NEW listing - 1 bedroom, private deck, walk to Main Street
Bedrooms:
2
Bathrooms:
1
Sleeps:
4
Spacious 1 bedroom with a convenient downtown location. The private patio off the living room has a river view. A full k ...
From $128 per night (USD)
VRBO
From $532 per night (USD)
Expedia
Summer Luxury: Slope-side Hideaway in Winter Park
Bedrooms:
4
Bathrooms:
4
Sleeps:
11
Winter Park Short Term Rental Registration NO. 018128 Indulge in alpine luxury at our ski-in/ski-out, bike-in/bike-out ...
From $532 per night (USD)
Expedia
From $244 per night (USD)
VRBO
NEWLY beautiful duplex @ Rendezvous. Minutes to town & resort & AMAZING VIEWS
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Discover the charm of a modern mountain home in Winter Park! As soon as you step through the front door, this mountain r ...
From $244 per night (USD)
VRBO
From $714 per night (USD)
Expedia
Winterfell at Winter Park Resort, New Luxury Home | Private Hot Tub | Stunning Views
Bedrooms:
4
Bathrooms:
4
Sleeps:
12
321 Northwoods Place, Winter Park, Colorado Overlooking the slopes of Winter Park Resort and backing to the Arapahoe Nat ...
From $714 per night (USD)
Expedia
From $400 per night (USD)
VRBO
Luxury Villa 520 I Hot Tub I Great Views I Best Price I FREE Adventures Daily
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Exclusive Complimentary Adventures! Winter Park Escapes is the only management company to provide Free activities and eq ...
From $400 per night (USD)
VRBO
From $298 per night (USD)
Expedia
Arrow 201 Downtown Winter Park
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Arrow 201 in Downtown Winter Park Experience the charm of this well-lit, spacious 2-bedroom, 2-bathroom condo nestled ...
From $298 per night (USD)
Expedia
From $260 per night (USD)
VRBO
90 Hideaway Unit 10 just steps to National Forest Trails
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Beautiful Remodeled Condo just steps to National Forest Trails This charmingly renovated condominium, just a stone's th ...
From $260 per night (USD)
VRBO
From $245 per night (USD)
Expedia
Sanctuary Silverado | Sleeps 8 | Modern + Cozy
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Summary: Indulge in luxury at Sanctuary of Silverado, a beautifully remodeled 2-bedroom condo in Winter Park. Enjoy moun ...
From $245 per night (USD)
Expedia
From $157 per night (USD)
VRBO
Winter Haus! 2 Bedroom Corner Unit in the heart of Winter Park, Colorado.
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Welcome to Winter Haus! This unique unit combines all the best that Winter Park has to offer. Nestled steps away from th ...
From $157 per night (USD)
VRBO
From $389 per night (USD)
Expedia
The Winter Baker. Near the slopes and Walk to Downtown Winter Park!
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Welcome to your ideal Winter Park getaway situated in the heart of downtown. Telemark, the building housing this condo, ...
From $389 per night (USD)
Expedia
From $736 per night (USD)
VRBO
Mary Jane's Dream Home | A True HGTV Dream Home | Private Luxe Lodge
Bedrooms:
4
Bathrooms:
4
Sleeps:
14
- Please note, this home does not have air conditioning, but there is a ceiling fan or portable fan in each room. Welco ...
From $736 per night (USD)
VRBO
From $317 per night (USD)
Expedia
Upscale condo with full kitchen & shared hot tub - walk to gondola
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Zephyr Mountain Lodge #1511 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply e ...
From $317 per night (USD)
Expedia
From $1272 per night (USD)
VRBO
Luxury Villa 510 I Next To Resort I Hot Tub I Great Views I Best Price I FREE Adventures Daily
Bedrooms:
5
Bathrooms:
5
Sleeps:
14
Exclusive Complimentary Adventures! Winter Park Escapes is the only management company to provide Free activities and eq ...
From $1272 per night (USD)
VRBO
From $462 per night (USD)
Expedia
Rocky Revel! New! Luxury Condo DT Winter Park with FREE Shuttle to the Slopes!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Rocky Revel! Don't let the lack of reviews deter you! We recently bought this newly built condo and this is o ...
From $462 per night (USD)
Expedia
From $858 per night (USD)
VRBO
New Luxury Villa 211 I Next To Resort I Hot Tub I Views I Best Price I FREE Adventures Daily
Bedrooms:
4
Bathrooms:
5
Sleeps:
16
Exclusive Complimentary Adventures! Winter Park Escapes is the only management company to provide Free activities and eq ...
From $858 per night (USD)
VRBO
From $412 per night (USD)
VRBO
Cozy Winter Park Stay Perfect for Group Travelers | 2 Units | Hot Tubs Access
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Discover vibrant Winter Park! Immerse in lively downtown beats, epic skiing adventures, and serene mountain trails—all s ...
From $412 per night (USD)
VRBO
From $191 per night (USD)
VRBO
Winter Park Getaway: Cozy Family-Friendly Room Available, Hotel with Hot Tub
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Discover vibrant Winter Park! Immerse in lively downtown beats, epic skiing adventures, and serene mountain trails—all s ...
From $191 per night (USD)
VRBO
From $410 per night (USD)
VRBO
King & Bunk, Gravity Haus, Near Downtown, 2 Units
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Discover vibrant Winter Park! Immerse in lively downtown beats, epic skiing adventures, and serene mountain trails—all s ...
From $410 per night (USD)
VRBO
From $192 per night (USD)
VRBO
Powder Hound, Gravity Haus Winter Park, Ideal Skier’s Retreat, Gym Access
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Discover vibrant Winter Park! Immerse in lively downtown beats, epic skiing adventures, and serene mountain trails—all s ...
From $192 per night (USD)
VRBO
From $170 per night (USD)
VRBO
Rambler Single King, Gravity Haus Winter Park, Gym Access, Downtown Ease
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover vibrant Winter Park! Immerse in lively downtown beats, epic skiing adventures, and serene mountain trails—all s ...
From $170 per night (USD)
VRBO
From $342 per night (USD)
VRBO
Ski In Out Luxury Condo 2403 I Hot Tub I Gym I Ski Views I Best Price I FREE Adventures Daily
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Exclusive Complimentary Adventures! Winter Park Escapes is the only management company to provide Free activities and eq ...
From $342 per night (USD)
VRBO
From $176 per night (USD)
VRBO
Modern Stay Near Downtown Winter Park with Hot Tubs & Gym Access
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover vibrant Winter Park! Immerse in lively downtown beats, epic skiing adventures, and serene mountain trails—all s ...
From $176 per night (USD)
VRBO
From $211 per night (USD)
VRBO
Idlewild King + Twin Bunks, Gravity Haus Winter Park, Outdoor Hot Tub, Central
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Discover vibrant Winter Park! Immerse in lively downtown beats, epic skiing adventures, and serene mountain trails—all s ...
From $211 per night (USD)
VRBO
From $230 per night (USD)
VRBO
Relaxing Mountain Retreat Ideal for Couple Stay | Skiing or Hike Nearby
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Discover vibrant Winter Park! Immerse in lively downtown beats, epic skiing adventures, and serene mountain trails—all s ...
From $230 per night (USD)
VRBO
From $230 per night (USD)
VRBO
Catwalk Double Queen + Bunks, Gravity Haus Winter Park, Mountain Views
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Discover vibrant Winter Park! Immerse in lively downtown beats, epic skiing adventures, and serene mountain trails—all s ...
From $230 per night (USD)
VRBO
From $211 per night (USD)
VRBO
Winter Park Family Escape: Modern Room with Downtown Access | Outdoor Hot Tub
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Discover vibrant Winter Park! Immerse in lively downtown beats, epic skiing adventures, and serene mountain trails—all s ...
From $211 per night (USD)
VRBO
From $179 per night (USD)
VRBO
Hike, Bike, Ski: Winter Park Condo w/ Deck
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Serene Views | Private Deck | In-Unit Laundry | Family Friendly Discover the perfect escape in Winter Park when you sta ...
From $179 per night (USD)
VRBO
From $358 per night (USD)
Expedia
Luxury Mtn Retreat: Family Friendly, Sleeps 10
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Summary: Welcome to Bear Trail Luxury Retreat! This modern mountain home, 2 minutes from Downtown Winter Park, features ...
From $358 per night (USD)
Expedia
From $203 per night (USD)
VRBO
Cute, comfy, well-stocked condo with gorgeous views close to bus stop.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to the powder pad! Our place has all the details to make your mountain getaway a fantastic trip. With 2 inviti ...
From $203 per night (USD)
VRBO
From $280 per night (USD)
Expedia
Exclusive Summer Haven: Winter Park Retreat
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Winter Park Short Term Rental Registration NO. 024018 Experience the ultimate Rocky Mountain getaway at this exceptional ...
From $280 per night (USD)
Expedia
From $315 per night (USD)
VRBO
Select Unit 1710 - 2BR - Zephyr Mountain Lodge
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Gorgeous top floor two bedroom two bathroom condominium at Zephyr Mountain Lodge. Custom cabinets, stainless steel appl ...
From $315 per night (USD)
VRBO
From $395 per night (USD)
Expedia
Basecamp Luxe | Sleeps 10 | Rooftop Hot Tub Fun
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Summary: Basecamp Luxe is a chic 4-bedroom retreat in Winter Park, blending modern style with playful mountain vibes. Un ...
From $395 per night (USD)
Expedia
From $233 per night (USD)
VRBO
Hideaway Park Gem: Pool, Views, Music!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Nestled beside Hideaway Park in downtown Winter Park, our condo provides the perfect blend of relaxation and adventure. ...
From $233 per night (USD)
VRBO
From $176 per night (USD)
Expedia
WinterPark*Ski*CoffeeBar*Pets+*CommunalHotTub
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Cozy Winter Park Abode: Your ideal alpine retreat just 3 miles from Winter Park Ski Resort! This designer condo offers m ...
From $176 per night (USD)
Expedia
From $302 per night (USD)
VRBO
NEW LISTING! Value Unit 1422 - 2BR - Zephyr Mountain Lodge
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Stay just 110 feet from the gondola for unbeatable access to mountain adventures! This cozy two-bedroom, two-bathroom c ...
From $302 per night (USD)
VRBO
From $1515 per night (USD)
Expedia
Canopy House | Large & Luxe | Stunning Ski In Ski Out Chalet
Bedrooms:
4
Bathrooms:
4
Sleeps:
12
Discover unparalleled mountain living at Canopy House, a mountain haven nestled amongst the trees in Winter Park. This l ...
From $1515 per night (USD)
Expedia
From $217 per night (USD)
VRBO
Cozy Rustic Condo with Scenic Views & Modern Amenities in Winter Park
Bedrooms:
3
Bathrooms:
3
Sleeps:
10
Viking Alpine Haven Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter you ...
From $217 per night (USD)
VRBO
From $377 per night (USD)
Expedia
210 Sawyer with Private Hot Tub
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
No matter the season—winter, spring, summer, or fall—you'll love our newly renovated mountain retreat. In winter, you're ...
From $377 per night (USD)
Expedia
From $640 per night (USD)
VRBO
4-bedroom Modern Mtn Vacation
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
A Stylish Escape w/ excellent location to all Winter Park and Fraser has to offer. 4 miles to Winter Park Resort, ~20 mi ...
From $640 per night (USD)
VRBO
From $377 per night (USD)
Expedia
Comfy condo next to Gondola
Bedrooms:
2
Bathrooms:
3
Sleeps:
9
Welcome to your perfect mountain getaway! Nestled in the heart of the charming Winter Park Ski Resort, our comfy Condo o ...
From $377 per night (USD)
Expedia
From $311 per night (USD)
VRBO
4BR Mountain Escape Family Friendly, Sleeps 10
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Summary: Escape to the mountains in a modern, upscale home 2 minutes from Downtown Winter Park that features 4BR/3.5BA, ...
From $311 per night (USD)
VRBO
From $286 per night (USD)
Expedia
Luxury Modern Condo w/ Hot Tub and Views!
Bedrooms:
3
Bathrooms:
3
Sleeps:
10
Winter Park Short Term Rental Registration NO. 024870 Experience the perfect blend of luxury and convenience in this stu ...
From $286 per night (USD)
Expedia
From $271 per night (USD)
VRBO
The AlpenGlow House: Private Hot Tub Retreat with Stunning Mountain Views!
Bedrooms:
3
Bathrooms:
3
Sleeps:
10
***BRAND NEW LISTING***Discover your perfect mountain retreat in our beautifully furnished 3-bedroom, 3.5-bathroom townh ...
From $271 per night (USD)
VRBO
From $369 per night (USD)
Expedia
Lakota Lookout private hot tub
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Lakota Lookout Mountain View Townhome | Hot Tub Welcome to your ideal mountain retreat in Winter Park, Colorado! This ...
From $369 per night (USD)
Expedia
From $178 per night (USD)
VRBO
Peaceful 1-bedroom mountain condo in Winter Park
Bedrooms:
2
Bathrooms:
1
Sleeps:
4
Relax in this cozy and stylish retreat after enjoying a day in the mountains. The spacious and updated one-bedroom cond ...
From $178 per night (USD)
VRBO
From $318 per night (USD)
Expedia
New 2BD/2BA Condo - in Winter Park! Walk to restaurants & steps from bus line!
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Brand new build in Timber Fox/ROAM community with fully stocked gourmet kitchen that opens up to the living and dining a ...
From $318 per night (USD)
Expedia
From $241 per night (USD)
VRBO
Trailhead 322 Shared Hot Tub, Pool, Private Balcony, and Grill
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Accommodating up to eight guests, the condo includes two bedrooms and a hallway sleeping nook. The master bedroom featur ...
From $241 per night (USD)
VRBO
From $236 per night (USD)
Expedia
Comfortable 3 bedroom, private deck, close to downtown
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
This charming and welcoming townhome, featuring an in-home sauna, offers ample space and a retro aesthetic, making it an ...
From $236 per night (USD)
Expedia
From $621 per night (USD)
VRBO
Luxury Villa 308 I Next To Resort I Hot Tub I Great Views I Best Price I FREE adventures Daily
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Exclusive Complimentary Adventures! Winter Park Escapes is the only management company to provide Free activities and eq ...
From $621 per night (USD)
VRBO
Click For Pricing
Expedia
Downtown Winter Park! 4BR Condo with Scenic Views
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Summary: Welcome to Rhapsody Retreat, a sophisticated 4BR condo in downtown Winter Park, part of Elysian’s exclusive col ...
Click For Pricing
Expedia
From $263 per night (USD)
VRBO
Downtown Winter Park Gem | Walk to Everything!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Winter Park Short Term Rental Registration NO. 024872 Escape to this serene and modern second-floor condo in the heart o ...
From $263 per night (USD)
VRBO
From $766 per night (USD)
Expedia
Charming 4BR Chalet with Hot Tub & Mountain Views
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Summary: Experience modern comfort in this spacious 3,000 sq ft Winter Park chalet, perfect for families or groups up to ...
From $766 per night (USD)
Expedia
From $142 per night (USD)
VRBO
MODERN NEW BUILD IN WINTER PARK-steps from trail.beautiful ski in out.1 br+den.
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
**Charming New Build in Winter Park - Steps from the Trail!** Discover the charm of Winter Park in this inviting 1-bedr ...
From $142 per night (USD)
VRBO
From $666 per night (USD)
Expedia
Winter Park Resort Luxury Getaway with Hot Tub
Bedrooms:
4
Bathrooms:
4
Sleeps:
12
Winter Park Short Term Rental Registration NO. 024876 Welcome to Ironhorse Manor, a luxurious woodland retreat nestled i ...
From $666 per night (USD)
Expedia
From $670 per night (USD)
VRBO
Adventure Awaits: Bike & Hot Tub
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to your perfect winter getaway at Zephyr Mountain Lodge! This charming condo is ideally located just steps from ...
From $670 per night (USD)
VRBO
From $254 per night (USD)
Expedia
Amenities Deck Level | Walk to Gondola | WP Resort
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Ski Mountain Condo, located in Winter Park Resort's Fraser Crossing Building, Includes Resort Amenities and Ski ...
From $254 per night (USD)
Expedia
From $207 per night (USD)
VRBO
Founders Point Studio! Base of Winter Park Resort!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: Welcome to our charming studio at Founders Point, located just steps away from the base of Winter Park Ski Reso ...
From $207 per night (USD)
VRBO
From $192 per night (USD)
Expedia
Spacious 1BR, Fireplace, Amenities Deck | WP Resort | Ski-in/out
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: Escape to the serene beauty of Winter Park with a stay at this delightful 1-bedroom, 1-bath condo, perfect for ...
From $192 per night (USD)
Expedia
From $158 per night (USD)
VRBO
Condo w/ Spas & Pool: 3 Mi to Winter Park Resort!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Nearby Trails | 3 Mi to Fraser Tubing Hill Centrally located in Winter Park, this cozy 1-bedroom, 1-bath vacation renta ...
From $158 per night (USD)
VRBO
From $289 per night (USD)
Expedia
New Luxury Condo 3409 I Hot Tub I AC I Great Views I Best Price I FREE Adventures Daily
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Exclusive Complimentary Adventures! Winter Park Escapes is the only management company to provide Free activities and eq ...
From $289 per night (USD)
Expedia
From $589 per night (USD)
VRBO
Stunning Views! 4BR Oasis w/ Decks in Winter Park
Bedrooms:
5
Bathrooms:
4
Sleeps:
10
Summary: Experience alpine luxury in this 2,500 sq ft retreat from Elysian’s exclusive collection. - Perfect for 10 gue ...
From $589 per night (USD)
VRBO
From $416 per night (USD)
Expedia
New Luxury Loft 219 I Private Hot Tub I Great Views I Best Price I Discounted Attractions
Bedrooms:
3
Bathrooms:
3
Sleeps:
10
This brand new luxury vacation home has one of the best locations and views available in the heart of downtown Winter Pa ...
From $416 per night (USD)
Expedia
From $261 per night (USD)
VRBO
New Headwaters Condo 206 I Great Views I Best Price I FREE Adventures Daily
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Exclusive Complimentary Adventures! Winter Park Escapes is the only management company to provide Free activities and eq ...
From $261 per night (USD)
VRBO
From $412 per night (USD)
Expedia
New Luxury Chalet 366 I Hot Tub I Great Views I Best Price I FREE Adventures Daily
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Exclusive Complimentary Adventures! Winter Park Escapes is the only management company to provide Free activities and eq ...
From $412 per night (USD)
Expedia
From $446 per night (USD)
VRBO
Cozy 3-bedroom townhome in beautiful Winter Park with great views, WiFi
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Escape to this lovely townhome in picturesque Winter Park. With 3 queen beds and 1 twin bed spread across 3 bedrooms, th ...
From $446 per night (USD)
VRBO
From $900 per night (USD)
Expedia
Mountain Majesty | Sleeps 14 | Hot Tub + Sauna
Bedrooms:
4
Bathrooms:
5
Sleeps:
14
Summary: Welcome to Mountain Majesty – your private villa retreat high in the Winter Park peaks! -6BR, 5.5BA – sleeps 1 ...
From $900 per night (USD)
Expedia
From $449 per night (USD)
VRBO
Catwalk | Double Queen + Twin Bunks at Gravity Haus Winter Park, Parking
Bedrooms:
2
Bathrooms:
2
Sleeps:
12
Discover vibrant Winter Park! Immerse in lively downtown beats, epic skiing adventures, and serene mountain trails—all s ...
From $449 per night (USD)
VRBO
From $452 per night (USD)
VRBO
Escape to the Mountains: Relaxing Retreat with Double Queens + Twin Bunks
Bedrooms:
2
Bathrooms:
2
Sleeps:
12
Discover vibrant Winter Park! Immerse in lively downtown beats, epic skiing adventures, and serene mountain trails—all s ...
From $452 per night (USD)
VRBO
From $873 per night (USD)
VRBO
Slopeside Custom Chalet I 2 Hot Tubs I Fire Tables I Views I Best Price I FREE Adventures Daily
Bedrooms:
3
Bathrooms:
5
Sleeps:
14
Exclusive Complimentary Adventures! Winter Park Escapes is the only management company to provide Free activities and eq ...
From $873 per night (USD)
VRBO
From $277 per night (USD)
Expedia
Spacious home w/ kitchen, wifi, great views, deck & convenient location
Bedrooms:
3
Bathrooms:
3
Sleeps:
9
Trailside Tranquility Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter y ...
From $277 per night (USD)
Expedia
From $280 per night (USD)
VRBO
Ski In Ski Out Condo Dripping in Style | Fraser Crossing 3526
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Settle into style at Fraser Crossing 3526, a beautifully curated two-bedroom condo just steps from Winter Park Resort. F ...
From $280 per night (USD)
VRBO
From $650 per night (USD)
Expedia
Riverside Reserve | Sleeps 10 | Views+Arcade Fun
Bedrooms:
5
Bathrooms:
4
Sleeps:
10
Summary: Wake up to the sound of Vasquez Creek in this luxury 4BR townhome in downtown Winter Park. Just a 5-min drive t ...
From $650 per night (USD)
Expedia
From $349 per night (USD)
VRBO
Mountain escape, minutes from Winter Park resort and town. Hot tub access.
Bedrooms:
2
Bathrooms:
3
Sleeps:
9
Your cozy getaway awaits in Winter Park at this soothing house. With 3 bedrooms including 1 king bed, 2 queen beds, and ...
From $349 per night (USD)
VRBO
From $349 per night (USD)
Expedia
3BR Mountain Retreat in the Heart of Winter Park with Private Hot Tub
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Welcome to 106 Willows Way, a beautifully appointed three-bedroom, three-bathroom home in downtown Winter Park. Designed ...
From $349 per night (USD)
Expedia

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