Vacation rentals in Winter Park - HomeToGo base64Hash

Vacation rentals in Winter Park - HomeToGo

Vacation rentals in Winter Park

Browse 3,734 available vacation homes and compared across 13 trusted partners

Price per night
- Up to $100
- $100 - $199
- From $200
Accommodation types
- Condo
- Cabin
- House
Distance to center
- 1 mi
- 2 mi
- 3 mi
Rating
- 4.5+
- 4+
Booking Options
- Instant Booking
Services
- Pool
- Hot tub
- WiFi
- Fireplace
- Kitchen
- Washing machine
- TV
- Balcony/patio
- Parking
- Microwave
- Dishwasher
- Air conditioning
- Sauna
- Yard
- Crib
Show more
Accommodation type
- Pet-friendly
- No smoking
- No pets
- Wheelchair access
Activities
- Grill
- Fishing

Top 15 most Recommended Vacation Rentals in Winter Park

Discover your ideal Winter Park vacation rental with real-time comparisons of 3,744 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

Vacation Rentals With Fireplaces

Vacation houses with Balconies or Patios

Vacation rentals and apartments with air conditioning

Budget-friendly rental options

Enjoy affordable vacation rentals in Winter Park offering exceptional value for money

Top-Rated Vacation rentals in Winter Park

Book the highest-rated Winter Park vacation rentals, rated by real guests for comfort, location, cleanliness, services and value for money

Discover real guest reviews to help you choose the perfect stay in Winter Park

How are reviews collected?

Jane K.

Guest verified by HomeToGo

Absolutely wonderful. New, convenient, and beautifully appointed with new, clean appliances, and plenty of sunshine. Hot tub and fire pit make for a nice social gathering spot. Very quiet. Loved the Nordic ski and hiking available right outside our door!

Why choose HomeToGo?

Securely pay and stay your way

Choose local, trusted payment methods, plus trip insurance and add-on services.

Award-winning customer service

Experience seamless, hands-on support for any booking questions or concerns.

Verified reviews

Trust in the quality and comfort of your stay with verified guest reviews.

Price clarity, no surprises

Spend your budget exactly as planned by comparing thousands of providers.

Smart search made simple

Transform vacation planning into a joy with advanced, AI-powered search tools.

Find your dream stay

Explore 15 million+ rentals, the world’s biggest selection of vacation homes.

Popular Features & Amenities in Winter Park

Pet-friendly (603)
Pool (1,295)
Hot tub (2,391)
WiFi (3,621)
Fireplace (3,311)
Kitchen (3,565)
Washing machine (2,619)
TV (3,604)
Balcony/patio (1,433)
Parking (1,134)
No smoking (3,494)
Grill (1,812)

Winter Park is a good vacation spot if you want an accommodation with a pool, as 35% of the properties have one. Condo with pools in Winter Park are a wonderful choice for groups of 6 and have an average cost of $504 per night. nearly half of Winter Park's rentals with pools are located within two miles of water, spend your days lounging by the pool or the waterfront.

Price and Availability Index in Winter Park

Click on any bar to see price and availability information

Vacation Rental Price Information in Winter Park

The price graph will give you the average nightly price for the upcoming months of the year in Winter Park. The average nightly rate for vacation homes can go up to $619 (12/20 – 12/27) in Winter Park. Winter Park is most affordable in May (5/9 – 5/16), when average accommodation prices are $556 a night.

Rental availability information in Winter Park

The availability graph shows the most competitive months to book a vacation rental in Winter Park. The week with the lowest percentage of available accommodations is in October (10/24 – 10/31). It is easier to find a rental in a week of December (12/13 – 12/20), as only 25% of the accommodations are booked.

Ski the slopes and savor superb views with Winter Park vacation homes

Spacious cabin rentals and modern condo vacation rentals in Winter Park put you near all the action on the ski resort's mountainside. Enjoy the woodsy locale and proximity to Colorado's scenic nature.

What are the best activities for families in Winter Park?

Young mountaineers

Beyond ski school, children can enjoy tubing, ice skating, and snowshoeing. In summer, Winter Park, despite a name reminiscent of endless snow, is just as exciting. The resort's alpine slide is the longest of its kind in mountainous Colorado. Kids can fly down the hill in joy on the safe yet thrilling track.

Treat kids to a day out fishing at one of the area's child-friendly ponds. The stocked North Pond at Lion's Fishing Ponds is suitable for ages 14 and younger, while the stocked pond at Kaibab Park is for those 15 and under. Casting a line should get some bites!

Where are the unique attractions in Winter Park?

Adrenaline rushes

Winter Park Ski Resort is one of the top, best-known ski resorts in Colorado, not to mention the longest-running, at 75 years old. Explore seven territories of highly varied terrain, from challenging moguls in Mary Jane Territory to backcountry-like Vasquez Ridge.

Colorado has a collection of 53 extra-tall mountains over 14,000 feet, referred to locally as "14-ers." Winter Park is home to a few of these mammoths, with the closest and least difficult pair being Mount Bierstadt and Mount Evans.

Information about vacation rentals in Winter Park

🏡 Vacation rentals available	3,744 rentals
💳 Possible discounts	up to 14%
🌙 Nightly prices starting at	$114
⭐ Popular amenities	Pets allowed, Pool and Hot tub
🐾 Pet friendly homes	597 homes
🏊 Vacation rentals with pools	1,308 homes

11 reviews

Winter Park vacation rentals have an average rating of 4.8/5 on 11 reviews left by travelers.

Frequently Asked Questions

What is the price per night for a vacation rental in Winter Park?

The price of a night's stay in Winter Park starts at $114. Average prices for condos are $592 per night. House rentals in Winter Park cost on average $728 per night.

How many vacation rentals are available to book in Winter Park?

There are currently 3,744 vacation homes from 13 different providers in Winter Park.

What are the most popular amenities for vacation rentals in Winter Park?

If you're looking to book a vacation rental in Winter Park, travelers search for vacation homes with these amenities: Pets allowed, Pool and Hot tub.

How many vacation homes with pools are in Winter Park?

Choose from 1,308 vacation rentals available to book in Winter Park.

Are dogs allowed in vacation rentals in Winter Park?

Yes, there are 597 rentals in Winter Park that allow dogs , with an average nightly price of $588.

Vacation rentals in Winter Park

Price per night

Accommodation types

Distance to center

Rating

Booking Options

Services

Accommodation type

Activities

Top 15 most Recommended Vacation Rentals in Winter Park

House with heated pool & sauna | Lake view | Perfect for remote work

Child-friendly wonderful vacation home with sauna, heated pool & hot tub | Lake view

Vacation home with hot tub, terrace & barbecue | Mountain view

Child-friendly vacation home with sauna, barbeque & terrace | Mountain view

Vacation home with sauna, hot tub & barbecue | Mountain view

Rental apartment with hot tub & barbeque | Mountain view

Rental apartment with hot tub & BBQ | Mountain view

Vacation home with hot tub, barbecue & yard

Children-friendly charming vacation home with BBQ, jacuzzi & yard | Mountain view | Dogs allowed

House with barbecue & jacuzzi

Children-friendly lovely condo with patio, hot tub & barbeque | Mountain view | Good for workation

Child-friendly wonderful vacation home with hot tub & terrace

Vacation home with barbecue & jacuzzi | Mountain view | Suitable for remote work

Holiday apartment with jacuzzi & barbeque

Child-friendly vacation home with barbecue & terrace | Mountain view | Perfect for remote work | Dogs allowed

Vacation Rentals With Fireplaces

Rental apartment with pool & jacuzzi

Family-friendly vacation home with hot tub, grill & patio | River view | Pets are welcome

Cabin with patio, barbecue & hot tub

Vacation houses with Balconies or Patios

Vacation home with heated pool, sauna & jacuzzi | Lake view

Family-oriented lovely vacation home with heated pool, sauna & hot tub | River view

Family-friendly vacation home with jacuzzi, sauna & heated pool | River view | Perfect for remote work

Vacation rentals and apartments with air conditioning

Holiday apartment with hot tub & barbeque | Mountain view

Rental apartment with hot tub

Vacation home with BBQ, hot tub & heated pool | River view