We noticed that you're using an unsupported browser. The Tripadvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Winter Park Pet Friendly Rentals

Destination
Revenue impacts this sort order. Learn more

Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 mi
189 rentals in Winter Park.
Renovated Condo near the Slopes and Trails, vacation rental in Winter Park
Renovated Condo near the Slopes and Trails, vacation rental in Winter Park
Renovated Condo near the Slopes and Trails, vacation rental in Winter Park

Renovated Condo near the Slopes and Trails

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps, Pet friendly
More info
Check in
Check out
As seen on
Vrbo.com logo
The Trailhead | Beautifully Furnished Modern Condo In Downtown Winter Park, vacation rental in Winter Park
The Trailhead | Beautifully Furnished Modern Condo In Downtown Winter Park, vacation rental in Winter Park
The Trailhead | Beautifully Furnished Modern Condo In Downtown Winter Park, vacation rental in Winter Park

The Trailhead | Beautifully Furnished Modern Condo In Downtown Winter Park

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Pet friendly
More info
Check in
Check out
As seen on
Vrbo.com logo
Trailhead  721 Pet Friendly pool hot tub, vacation rental in Winter Park
Trailhead  721 Pet Friendly pool hot tub, vacation rental in Winter Park
Trailhead  721 Pet Friendly pool hot tub, vacation rental in Winter Park

Trailhead 721 Pet Friendly pool hot tub

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps, Pet friendly
More info
Check in
Check out
As seen on
Vrbo.com logo
Family/ Pet Friendly Downtown Winter Park Condo 3BD/2BA, vacation rental in Winter Park
Family/ Pet Friendly Downtown Winter Park Condo 3BD/2BA, vacation rental in Winter Park
Family/ Pet Friendly Downtown Winter Park Condo 3BD/2BA, vacation rental in Winter Park

Family/ Pet Friendly Downtown Winter Park Condo 3BD/2BA

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps, Pet friendly
More info
Check in
Check out
As seen on
Vrbo.com logo
Tipsy Fox | Downtown Winter Park and Ski Resort!, vacation rental in Winter Park
Tipsy Fox | Downtown Winter Park and Ski Resort!, vacation rental in Winter Park
Tipsy Fox | Downtown Winter Park and Ski Resort!, vacation rental in Winter Park

Tipsy Fox | Downtown Winter Park and Ski Resort!

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps, Pet friendly
More info
Check in
Check out
As seen on
Vrbo.com logo
New creek side chateau guest suite!  Booking for summer NOW! With hot tub!, vacation rental in Winter Park
New creek side chateau guest suite!  Booking for summer NOW! With hot tub!, vacation rental in Winter Park
New creek side chateau guest suite!  Booking for summer NOW! With hot tub!, vacation rental in Winter Park

New creek side chateau guest suite! Booking for summer NOW! With hot tub!

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Pet friendly
More info
Check in
Check out
As seen on
Vrbo.com logo
Trailhead  211 shared hot tub, vacation rental in Winter Park
Trailhead  211 shared hot tub, vacation rental in Winter Park
Trailhead  211 shared hot tub, vacation rental in Winter Park

Trailhead 211 shared hot tub

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps, Pet friendly
More info
Check in
Check out
As seen on
Vrbo.com logo
216 Sawyer w/ Private Hot Tub, vacation rental in Winter Park
216 Sawyer w/ Private Hot Tub, vacation rental in Winter Park
216 Sawyer w/ Private Hot Tub, vacation rental in Winter Park

216 Sawyer w/ Private Hot Tub

Rental Home
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps, Pet friendly
More info
Check in
Check out
As seen on
Vrbo.com logo
Best Value Luxury Townhome in Lakota across from Ski Resort, Private Hot Tub!, vacation rental in Winter Park
Best Value Luxury Townhome in Lakota across from Ski Resort, Private Hot Tub!, vacation rental in Winter Park
Best Value Luxury Townhome in Lakota across from Ski Resort, Private Hot Tub!, vacation rental in Winter Park

Best Value Luxury Townhome in Lakota across from Ski Resort, Private Hot Tub!

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, Pet friendly
More info
Check in
Check out
As seen on
Vrbo.com logo
New Penthouse Villa 282 I Rooftop Hot Tub I Great Views I Best Price I FREE, vacation rental in Winter Park
New Penthouse Villa 282 I Rooftop Hot Tub I Great Views I Best Price I FREE, vacation rental in Winter Park
New Penthouse Villa 282 I Rooftop Hot Tub I Great Views I Best Price I FREE, vacation rental in Winter Park

New Penthouse Villa 282 I Rooftop Hot Tub I Great Views I Best Price I FREE

Rental Home
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps, Pet friendly
More info
Check in
Check out
As seen on
Vrbo.com logo
Walkable, Dog-Friendly, Downtown Condo with Fast WiFi, Shared Pool, & Hot Tub, vacation rental in Winter Park
Walkable, Dog-Friendly, Downtown Condo with Fast WiFi, Shared Pool, & Hot Tub, vacation rental in Winter Park
Walkable, Dog-Friendly, Downtown Condo with Fast WiFi, Shared Pool, & Hot Tub, vacation rental in Winter Park

Walkable, Dog-Friendly, Downtown Condo with Fast WiFi, Shared Pool, & Hot Tub

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps, Pet friendly
More info
Check in
Check out
As seen on
Vrbo.com logo
Winter Park Condo w/ Fireplace - 4 Mi to Slopes!, vacation rental in Winter Park
Winter Park Condo w/ Fireplace - 4 Mi to Slopes!, vacation rental in Winter Park
Winter Park Condo w/ Fireplace - 4 Mi to Slopes!, vacation rental in Winter Park

Winter Park Condo w/ Fireplace - 4 Mi to Slopes!

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps, Pet friendly
More info
Check in
Check out
As seen on
Vrbo.com logo
Unique dog-friendly townhome with hot tub & fireplace - walk to shops & eateries, vacation rental in Winter Park
Unique dog-friendly townhome with hot tub & fireplace - walk to shops & eateries, vacation rental in Winter Park
Unique dog-friendly townhome with hot tub & fireplace - walk to shops & eateries, vacation rental in Winter Park

Unique dog-friendly townhome with hot tub & fireplace - walk to shops & eateries

Rental Home
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps, Pet friendly
More info
Check in
Check out
As seen on
Vrbo.com logo
Luxury Condo 412 I Pool I Club House I Hot Tub I Views I Best Price I FREE, vacation rental in Winter Park
Luxury Condo 412 I Pool I Club House I Hot Tub I Views I Best Price I FREE, vacation rental in Winter Park
Luxury Condo 412 I Pool I Club House I Hot Tub I Views I Best Price I FREE, vacation rental in Winter Park

Luxury Condo 412 I Pool I Club House I Hot Tub I Views I Best Price I FREE

Rental Home
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps, Pet friendly
More info
Check in
Check out
As seen on
Vrbo.com logo
Pet friendly luxurious 3 bedroom in downtown!, vacation rental in Winter Park
Pet friendly luxurious 3 bedroom in downtown!, vacation rental in Winter Park
Pet friendly luxurious 3 bedroom in downtown!, vacation rental in Winter Park

Pet friendly luxurious 3 bedroom in downtown!

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps, Pet friendly
More info
Check in
Check out
As seen on
Vrbo.com logo
Pet Friendly 1 bedroom, downtown location, private patio, vacation rental in Winter Park
Pet Friendly 1 bedroom, downtown location, private patio, vacation rental in Winter Park
Pet Friendly 1 bedroom, downtown location, private patio, vacation rental in Winter Park

Pet Friendly 1 bedroom, downtown location, private patio

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps, Pet friendly
More info
Check in
Check out
As seen on
Vrbo.com logo
Mountain Lodge - Half a Mile to Winter Park Resort, vacation rental in Winter Park
Mountain Lodge - Half a Mile to Winter Park Resort, vacation rental in Winter Park
Mountain Lodge - Half a Mile to Winter Park Resort, vacation rental in Winter Park

Mountain Lodge - Half a Mile to Winter Park Resort

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, Pet friendly
More info
Check in
Check out
As seen on
Vrbo.com logo
Spacious Home w/Mountain Views, Free WiFi, Private Hot Tub, Chef's Dream, vacation rental in Winter Park
Spacious Home w/Mountain Views, Free WiFi, Private Hot Tub, Chef's Dream, vacation rental in Winter Park
Spacious Home w/Mountain Views, Free WiFi, Private Hot Tub, Chef's Dream, vacation rental in Winter Park

Spacious Home w/Mountain Views, Free WiFi, Private Hot Tub, Chef's Dream

Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps, Pet friendly
More info
Check in
Check out
As seen on
Vrbo.com logo
2 BR 1-1/4 Bath Dog friendly, Hi Country Haus 1st Flr WP Condo by river, vacation rental in Winter Park
2 BR 1-1/4 Bath Dog friendly, Hi Country Haus 1st Flr WP Condo by river, vacation rental in Winter Park
2 BR 1-1/4 Bath Dog friendly, Hi Country Haus 1st Flr WP Condo by river, vacation rental in Winter Park

2 BR 1-1/4 Bath Dog friendly, Hi Country Haus 1st Flr WP Condo by river

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps, Pet friendly
More info
Check in
Check out
As seen on
Vrbo.com logo
New Ground Level Riverfront Suite - Walk to Village!, vacation rental in Winter Park
New Ground Level Riverfront Suite - Walk to Village!, vacation rental in Winter Park
New Ground Level Riverfront Suite - Walk to Village!, vacation rental in Winter Park

New Ground Level Riverfront Suite - Walk to Village!

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps, Pet friendly
More info
Check in
Check out
As seen on
Vrbo.com logo
Second-floor condo with fireplace, hot tub & indoor pool - dog-friendly, vacation rental in Winter Park
Second-floor condo with fireplace, hot tub & indoor pool - dog-friendly, vacation rental in Winter Park
Second-floor condo with fireplace, hot tub & indoor pool - dog-friendly, vacation rental in Winter Park

Second-floor condo with fireplace, hot tub & indoor pool - dog-friendly

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps, Pet friendly
More info
Check in
Check out
As seen on
Vrbo.com logo
Winter Park Condo - Minutes to Slope & Downtown!, vacation rental in Winter Park
Winter Park Condo - Minutes to Slope & Downtown!, vacation rental in Winter Park
Winter Park Condo - Minutes to Slope & Downtown!, vacation rental in Winter Park

Winter Park Condo - Minutes to Slope & Downtown!

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps, Pet friendly
More info
Check in
Check out
As seen on
Vrbo.com logo
New Slopeside Luxury Villa 135 I Hot Tub I Ski Views I Best Price I FREE, vacation rental in Winter Park
New Slopeside Luxury Villa 135 I Hot Tub I Ski Views I Best Price I FREE, vacation rental in Winter Park
New Slopeside Luxury Villa 135 I Hot Tub I Ski Views I Best Price I FREE, vacation rental in Winter Park

New Slopeside Luxury Villa 135 I Hot Tub I Ski Views I Best Price I FREE

Rental Home
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps, Pet friendly
More info
Check in
Check out
As seen on
Vrbo.com logo
Mountain Comfort in Esteemed Rendezvous, vacation rental in Winter Park
Mountain Comfort in Esteemed Rendezvous, vacation rental in Winter Park
Mountain Comfort in Esteemed Rendezvous, vacation rental in Winter Park

Mountain Comfort in Esteemed Rendezvous

Rental Home
4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps, Pet friendly
More info
Check in
Check out
As seen on
Vrbo.com logo
Trailhead 212 Downtown walk to bars, restaurants, vacation rental in Winter Park
Trailhead 212 Downtown walk to bars, restaurants, vacation rental in Winter Park
Trailhead 212 Downtown walk to bars, restaurants, vacation rental in Winter Park

Trailhead 212 Downtown walk to bars, restaurants

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps, Pet friendly
More info
Check in
Check out
As seen on
Vrbo.com logo
New Luxury Mountain Cabin 77 I Hot Tub I Great Views I Best Price I FREE, vacation rental in Winter Park
New Luxury Mountain Cabin 77 I Hot Tub I Great Views I Best Price I FREE, vacation rental in Winter Park
New Luxury Mountain Cabin 77 I Hot Tub I Great Views I Best Price I FREE, vacation rental in Winter Park

New Luxury Mountain Cabin 77 I Hot Tub I Great Views I Best Price I FREE

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps, Pet friendly
More info
Check in
Check out
As seen on
Vrbo.com logo
Mountain view home with private hot tub, fireplace, WiFi, and washer/dryer, vacation rental in Winter Park
Mountain view home with private hot tub, fireplace, WiFi, and washer/dryer, vacation rental in Winter Park
Mountain view home with private hot tub, fireplace, WiFi, and washer/dryer, vacation rental in Winter Park

Mountain view home with private hot tub, fireplace, WiFi, and washer/dryer

Rental Home
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps, Pet friendly
More info
Check in
Check out
As seen on
Vrbo.com logo
Slopeside Luxury Chalet 113 D I Hot Tub I Great Views I Best Price I FREE, vacation rental in Winter Park
Slopeside Luxury Chalet 113 D I Hot Tub I Great Views I Best Price I FREE, vacation rental in Winter Park
Slopeside Luxury Chalet 113 D I Hot Tub I Great Views I Best Price I FREE, vacation rental in Winter Park

Slopeside Luxury Chalet 113 D I Hot Tub I Great Views I Best Price I FREE

Rental Home
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps, Pet friendly
More info
Check in
Check out
As seen on
Vrbo.com logo
New Luxury Villa 262 I Arcade I Rooftop Hot Tub With Views I Best Price I FREE, vacation rental in Winter Park
New Luxury Villa 262 I Arcade I Rooftop Hot Tub With Views I Best Price I FREE, vacation rental in Winter Park
New Luxury Villa 262 I Arcade I Rooftop Hot Tub With Views I Best Price I FREE, vacation rental in Winter Park

New Luxury Villa 262 I Arcade I Rooftop Hot Tub With Views I Best Price I FREE

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, Pet friendly
More info
Check in
Check out
As seen on
Vrbo.com logo
Large Mountain Home / Private Hot Tub / Shuffleboard / Pet Friendly, vacation rental in Winter Park
Large Mountain Home / Private Hot Tub / Shuffleboard / Pet Friendly, vacation rental in Winter Park
Large Mountain Home / Private Hot Tub / Shuffleboard / Pet Friendly, vacation rental in Winter Park

Large Mountain Home / Private Hot Tub / Shuffleboard / Pet Friendly

Rental Home
8 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps, Pet friendly
More info
Check in
Check out
As seen on
Vrbo.com logo
3 bedroom Sleeps 11, pet friendly & private hot tub!, vacation rental in Winter Park
3 bedroom Sleeps 11, pet friendly & private hot tub!, vacation rental in Winter Park
3 bedroom Sleeps 11, pet friendly & private hot tub!, vacation rental in Winter Park

3 bedroom Sleeps 11, pet friendly & private hot tub!

Rental Home
4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps, Pet friendly
More info
Check in
Check out
As seen on
Vrbo.com logo
Luxury villa with private hot tub and just minutes to WP Resort, vacation rental in Winter Park
Luxury villa with private hot tub and just minutes to WP Resort, vacation rental in Winter Park
Luxury villa with private hot tub and just minutes to WP Resort, vacation rental in Winter Park

Luxury villa with private hot tub and just minutes to WP Resort

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, Pet friendly
More info
Check in
Check out
As seen on
Vrbo.com logo
New Luxury Loft 24 I Hot Tub I Great Views I Best Price I FREE Adventures Daily, vacation rental in Winter Park
New Luxury Loft 24 I Hot Tub I Great Views I Best Price I FREE Adventures Daily, vacation rental in Winter Park
New Luxury Loft 24 I Hot Tub I Great Views I Best Price I FREE Adventures Daily, vacation rental in Winter Park

New Luxury Loft 24 I Hot Tub I Great Views I Best Price I FREE Adventures Daily

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps, Pet friendly
More info
Check in
Check out
As seen on
Vrbo.com logo
New Luxury Loft 49 I Rooftop Hot Tub I Lounge I Views I Best Price I FREE, vacation rental in Winter Park
New Luxury Loft 49 I Rooftop Hot Tub I Lounge I Views I Best Price I FREE, vacation rental in Winter Park
New Luxury Loft 49 I Rooftop Hot Tub I Lounge I Views I Best Price I FREE, vacation rental in Winter Park

New Luxury Loft 49 I Rooftop Hot Tub I Lounge I Views I Best Price I FREE

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, Pet friendly
More info
Check in
Check out
As seen on
Vrbo.com logo
Best downtown location, rooftop deck w private hot tub! 1/2 block to ski, vacation rental in Winter Park
Best downtown location, rooftop deck w private hot tub! 1/2 block to ski, vacation rental in Winter Park
Best downtown location, rooftop deck w private hot tub! 1/2 block to ski, vacation rental in Winter Park

Best downtown location, rooftop deck w private hot tub! 1/2 block to ski

Rental Home
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps, Pet friendly
More info
Check in
Check out
As seen on
Vrbo.com logo
Winter Park Cabin - Walk to Main Street & Downtown, vacation rental in Winter Park
Winter Park Cabin - Walk to Main Street & Downtown, vacation rental in Winter Park
Winter Park Cabin - Walk to Main Street & Downtown, vacation rental in Winter Park

Winter Park Cabin - Walk to Main Street & Downtown

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps, Pet friendly
More info
Check in
Check out
As seen on
Vrbo.com logo
Private Hot Tub and Mountain Views!, vacation rental in Winter Park
Private Hot Tub and Mountain Views!, vacation rental in Winter Park
Private Hot Tub and Mountain Views!, vacation rental in Winter Park

Private Hot Tub and Mountain Views!

Condo/Apartment
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps, Pet friendly
More info
Check in
Check out
As seen on
Vrbo.com logo
Luxury Villa 668 I On Pond I Hot Tub I Great Views I Best Price I FREE, vacation rental in Winter Park
Luxury Villa 668 I On Pond I Hot Tub I Great Views I Best Price I FREE, vacation rental in Winter Park
Luxury Villa 668 I On Pond I Hot Tub I Great Views I Best Price I FREE, vacation rental in Winter Park

Luxury Villa 668 I On Pond I Hot Tub I Great Views I Best Price I FREE

Rental Home
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps, Pet friendly
More info
Check in
Check out
As seen on
Vrbo.com logo
Trailhead 812 Pet Friendly Downtown Winter Park, vacation rental in Winter Park
Trailhead 812 Pet Friendly Downtown Winter Park, vacation rental in Winter Park
Trailhead 812 Pet Friendly Downtown Winter Park, vacation rental in Winter Park

Trailhead 812 Pet Friendly Downtown Winter Park

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps, Pet friendly
More info
Check in
Check out
As seen on
Vrbo.com logo
NEW! Luxury Penthouse 4BR/3BA Condo In Heart Of Downtown Winter Park, vacation rental in Winter Park
NEW! Luxury Penthouse 4BR/3BA Condo In Heart Of Downtown Winter Park, vacation rental in Winter Park
NEW! Luxury Penthouse 4BR/3BA Condo In Heart Of Downtown Winter Park, vacation rental in Winter Park

NEW! Luxury Penthouse 4BR/3BA Condo In Heart Of Downtown Winter Park

Condo/Apartment
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps, Pet friendly
More info
Check in
Check out
As seen on
Vrbo.com logo
New Luxury River Front Villa 110 I Rooftop Lounge I Hot Tub I Views I FREE, vacation rental in Winter Park
New Luxury River Front Villa 110 I Rooftop Lounge I Hot Tub I Views I FREE, vacation rental in Winter Park
New Luxury River Front Villa 110 I Rooftop Lounge I Hot Tub I Views I FREE, vacation rental in Winter Park

New Luxury River Front Villa 110 I Rooftop Lounge I Hot Tub I Views I FREE

Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps, Pet friendly
More info
Check in
Check out
As seen on
Vrbo.com logo
New Luxury Townhome 1 I Arcade I Hot Tub I Views I Best Price I FREE Adventures, vacation rental in Winter Park
New Luxury Townhome 1 I Arcade I Hot Tub I Views I Best Price I FREE Adventures, vacation rental in Winter Park
New Luxury Townhome 1 I Arcade I Hot Tub I Views I Best Price I FREE Adventures, vacation rental in Winter Park

New Luxury Townhome 1 I Arcade I Hot Tub I Views I Best Price I FREE Adventures

Rental Home
4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps, Pet friendly
More info
Check in
Check out
As seen on
Vrbo.com logo
Pet friendly 2 bedroom, walk to Main Street, forest view, vacation rental in Winter Park
Pet friendly 2 bedroom, walk to Main Street, forest view, vacation rental in Winter Park
Pet friendly 2 bedroom, walk to Main Street, forest view, vacation rental in Winter Park

Pet friendly 2 bedroom, walk to Main Street, forest view

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Pet friendly
More info
Check in
Check out
As seen on
Vrbo.com logo
Luxury Villa 558 I Great Views I Hot Tub I Best Price I FREE Adventures Daily, vacation rental in Winter Park
Luxury Villa 558 I Great Views I Hot Tub I Best Price I FREE Adventures Daily, vacation rental in Winter Park
Luxury Villa 558 I Great Views I Hot Tub I Best Price I FREE Adventures Daily, vacation rental in Winter Park

Luxury Villa 558 I Great Views I Hot Tub I Best Price I FREE Adventures Daily

Rental Home
2 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps, Pet friendly
More info
Check in
Check out
As seen on
Vrbo.com logo
Beautiful Rustic Home, 4 BDR + Bonus!, vacation rental in Winter Park
Beautiful Rustic Home, 4 BDR + Bonus!, vacation rental in Winter Park
Beautiful Rustic Home, 4 BDR + Bonus!, vacation rental in Winter Park

Beautiful Rustic Home, 4 BDR + Bonus!

Rental Home
5 bedrooms
3 bathrooms
Sleeps 16
Match: Sleeps, Pet friendly
More info
Check in
Check out
As seen on
Vrbo.com logo
Lakota Dreamcatcher 133 | Dreams Are Made Here | Pet Friendly | Across From, vacation rental in Winter Park
Lakota Dreamcatcher 133 | Dreams Are Made Here | Pet Friendly | Across From, vacation rental in Winter Park
Lakota Dreamcatcher 133 | Dreams Are Made Here | Pet Friendly | Across From, vacation rental in Winter Park

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

Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps, Pet friendly
More info
Check in
Check out
As seen on
Vrbo.com logo
Dog Friendly Townhouse w/Private Deck, Gas Grill, vacation rental in Winter Park
Dog Friendly Townhouse w/Private Deck, Gas Grill, vacation rental in Winter Park
Dog Friendly Townhouse w/Private Deck, Gas Grill, vacation rental in Winter Park

Dog Friendly Townhouse w/Private Deck, Gas Grill

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Pet friendly
More info
Check in
Check out
As seen on
Vrbo.com logo
Pet friendly, family getaway in the mountains; private hot tub, close to town, vacation rental in Winter Park
Pet friendly, family getaway in the mountains; private hot tub, close to town, vacation rental in Winter Park
Pet friendly, family getaway in the mountains; private hot tub, close to town, vacation rental in Winter Park

Pet friendly, family getaway in the mountains; private hot tub, close to town

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps, Pet friendly
More info
Check in
Check out
As seen on
Vrbo.com logo
� PET-FRIENDLY | Lakota Antlers 300 | Alpenglow Hot Tub Views | Game Room!, vacation rental in Winter Park
� PET-FRIENDLY | Lakota Antlers 300 | Alpenglow Hot Tub Views | Game Room!, vacation rental in Winter Park
� PET-FRIENDLY | Lakota Antlers 300 | Alpenglow Hot Tub Views | Game Room!, vacation rental in Winter Park

� PET-FRIENDLY | Lakota Antlers 300 | Alpenglow Hot Tub Views | Game Room!

Rental Home
4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps, Pet friendly
More info
Check in
Check out
As seen on
Vrbo.com logo
Cozy Downtown Condo with Jacuzzi 5 Min from Resort, vacation rental in Winter Park
Cozy Downtown Condo with Jacuzzi 5 Min from Resort, vacation rental in Winter Park
Cozy Downtown Condo with Jacuzzi 5 Min from Resort, vacation rental in Winter Park

Cozy Downtown Condo with Jacuzzi 5 Min from Resort

Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, Pet friendly
More info
Check in
Check out
As seen on
Vrbo.com logo
…
Showing results 1-50 of 1,226

Winter Park Vacation Rentals
Looking for family ski fun, or golf and mountain biking within 90 minutes of Denver? Year-round, a money-saving Winter Park vacation rental is your quickest road from Denver to Rocky Mountain recreational fun. Don’t want to drive the 90 minutes from the Denver airport to your money-saving Winter Park vacation rental? The old Rio Grande Scenic Railroad Company weekend ski train may be out of operation. But you can still kickback and enjoy the Rocky Mountain scenery from the comfort of Amtrak’s California Zephyr. Allow at least 2 hours for the daily rail journey between Denver Union Station and Fraser-Winter Park station.
Railroad Starts Winter Park
The railroad started it all. Winter Park came into existence way back when the railroad constructed the Rocky Mountains/Moffat Tunnel and workers needed places to live in this rugged mountain wilderness. The City of Denver launched Winter Park as a ski resort in 1940 by constructing a ski tow at West Portal. Today there are 25 lifts servicing 143 designated ski trails on about 3,000 acres, of which over a third is off-piste terrain. And money-saving vacation rental homes, apartments, townhouses, and condos make Winter Park a comfortable year-round family resort.
Winter Fun
Winter Park usually kicks off skiing before Thanksgiving, as there are 26 trails and about 300 acres for the snowmaking machines. As the snow accumulates and winter season gets into full swing, your money-saving vacation rental also becomes your portal to glade skiing, cross-country skiing, snow cycling, snowboarding, snowshoeing, Snowcat tours and NASTAR racing. Guided touring opportunities abound for the whole family to learn about the native Rocky Mountain plants and animals. For vacation DVDs and training purposes, the Ski and Ride School rents helmet cams to capture the mogul runs and downhill action.
Summer Fun
Golf at Grand Elk, Headwaters, or one of the 9-hole courses up the highway near Granby. From Granby, it is a short drive to Rocky Mountain National Park. The kids will enjoy rounds of mountainside mini-golf and the Alpine Slide. Meanwhile fly fish the Fraser River. Wade in or take a boat to fish the Colorado River, while the kids practice clowning and juggling at Winter Park Circus Camp. Mountain bike, rollerblade or picnic along the five-mile Fraser River Trail. Checkout Trestle Bike Park, which has hosted Mountain States Cup cross country racing, slalom, downhill, and super D.
More Winter Park Fun
The whole family will enjoy the Old West post office and stage stop at Cozens' Ranch House Museum. Cowboy sing-a-long campfires and mountain man storytelling will leave the kids spellbound. Learn astronomy at the two-hour Star Safaris produced by the University of Colorado's Fiske Planetarium. Then relax at your money-saving Winter Park vacation rental, before your next adventure.