
Photo by Kerry Ciulla
Skyway holiday lettings
We found 83 holiday rentals — enter your dates for availability
Discover a selection of 19 homes and other holiday rentals in Skyway that are perfect for your trip. Holiday rentals offer the best amenities for you and your friends, family or even pets, such as a fireplace and garden. You'll be able to choose a property to rent to meet everyone's needs, including places that are non-smoking or accessible.
Holiday rentals with weekly discounts - Skyway
Showing deals for:1 Aug - 8 Aug
Image gallery for Stylish Spacious Retreat in Skyway - Broadmoor Area w/Mtn Views Park Quiet

1010 out of 10 rating
Exceptional
(7 reviews)
Stylish Spacious Retreat in Skyway - Broadmoor Area w/Mtn Views Park Quiet
Colorado Springs, CO
8% off
Price is £3,462
£3,462
£495 per night
includes taxes & fees
Image gallery for Broadmoor Retreat | Hot tub & New Furniture

9.49.4 out of 10 rating
Exceptional
(26 reviews)
Broadmoor Retreat | Hot tub & New Furniture
Colorado Springs, CO
7% off
Price is £2,672
£2,672
£382 per night
includes taxes & fees
Image gallery for 10 minute walk to the Broadmoor, plenty of parking and fast internet STR-0522

1010 out of 10 rating
Exceptional
(12 reviews)
10 minute walk to the Broadmoor, plenty of parking and fast internet STR-0522
Colorado Springs, CO
7% off
Price is £2,796
£2,796
£399 per night
includes taxes & fees
Image gallery for Colorado Springs , Cheyenne Mountain, Broadmoor ,Westside, Skyway

9.89.8 out of 10 rating
Exceptional
(10 reviews)
Colorado Springs , Cheyenne Mountain, Broadmoor ,Westside, Skyway
Colorado Springs, CO
15% off
Price is £763
£763
£109 per night
includes taxes & fees
Image gallery for Nestled in Cheyenne Canyon and one minute walk to the Broadmoor hotel!

9.89.8 out of 10 rating
Exceptional
(12 reviews)
Nestled in Cheyenne Canyon and one minute walk to the Broadmoor hotel!
Colorado Springs, CO
7% off
Price is £1,496
£1,496
£214 per night
includes taxes & fees
Image gallery for Perfect vacation home with amazing outdoor space, pet and handicapped friendly!

1010 out of 10 rating
Exceptional
(15 reviews)
Perfect vacation home with amazing outdoor space, pet and handicapped friendly!
Colorado Springs, CO
12% off
Price is £1,217
£1,217
£174 per night
includes taxes & fees
Image gallery for 1BR-Colorado Cottage Charm-Hiking and Broadmoor

9.89.8 out of 10 rating
Exceptional
(40 reviews)
1BR-Colorado Cottage Charm-Hiking and Broadmoor
Colorado Springs, CO
7% off
Price is £1,513
£1,513
£216 per night
includes taxes & fees
Image gallery for Rustic-Modern Townhome A in Ivy Wild/Downtown

9.49.4 out of 10 rating
Exceptional
(49 reviews)
Rustic-Modern Townhome A in Ivy Wild/Downtown
Colorado Springs, CO
8% off
Price is £1,189
£1,189
£170 per night
includes taxes & fees
Image gallery for Genuine Santa Fe Adobe Casita

1010 out of 10 rating
Exceptional
(51 reviews)
Genuine Santa Fe Adobe Casita
Colorado Springs, CO
8% off
Price is £1,357
£1,357
£194 per night
includes taxes & fees
Image gallery for Cheyenne Bluff! Walk to Ivywild Bristol Brewery!

9.09.0 out of 10 rating
Wonderful
(10 reviews)
Cheyenne Bluff! Walk to Ivywild Bristol Brewery!
Colorado Springs, Colorado
6% off
Price is £2,063
£2,063
£295 per night
includes taxes & fees
Image gallery for Rustic-Modern Townhome B in Ivy Wild/Downtown

8.68.6 out of 10 rating
Excellent
(35 reviews)
Rustic-Modern Townhome B in Ivy Wild/Downtown
Colorado Springs, CO
8% off
Price is £1,189
£1,189
£170 per night
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find the best place to stay - Skyway
Genuine Santa Fe Adobe Casita
Sleeps 4 · 3 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
51 reviews(51 reviews)
Broadmoor Retreat | Hot tub & New Furniture
Sleeps 8 · 4 bedrooms · 2 bathrooms
9.49.4 out of 10
Exceptionalexceptional
26 reviews(26 reviews)
Hiker's Hideaway! Nature Escape, BBQ & Pit Trails
Sleeps 6 · 3 bedrooms · 2 bathrooms
8.28.2 out of 10
Very goodvery good
10 reviews(10 reviews)
5 Mi to Area Attractions: Home w/ Hot Tub
Sleeps 10 · 4 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
1 review(1 review)
Serenity Skyline Lodge
Sleeps 12 · 5 bedrooms · 3+ bathrooms
1010 out of 10
Exceptionalexceptional
20 reviews(20 reviews)
Broadmoor Area Home Great for Families and Pets!
Sleeps 10 · 4 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
93 reviews(93 reviews)
- Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
- More quality timeFrom booking to staying, the whole process is simple and enjoyable
- All the privacy of homeEnjoy full kitchens, pools, gardens and more
- More for lessMore space, more privacy, more amenities — more value
Frequently asked questions
What is the most popular type of holiday rental accommodation in Skyway?
Based on our data, houses are the most desirable type of holiday rental in Skyway. But as you’d expect, everyone’s idea of an awesome trip can differ. Vrbo has holiday rentals of all shapes and sizes, and we’ll help you locate the best fit for your needs.
How much does it cost to rent a holiday rental in Skyway?
The average price for a holiday home in Skyway is determined by several factors, like time of year, length of stay and property type. Whether you’re dreaming about a villa with space for extended family or a cosy cottage ideal for just you and the kids, just add your travel dates to discover stays with great value.
How much does it cost to rent a beach house in Skyway?
Prices for beach houses in Skyway differ depending on the style and size of the property and when you’re travelling. All you need to do is enter your travel dates into Vrbo and the number of guests to view your rental options and prices. From there you can use our filter tool to tailor your search results by ratings, nearby activities and more.
Are there pet-friendly holiday rentals in Skyway?
Happily, yes. Take your pick of six holiday rentals that allow pets in Skyway on Vrbo. Our cuddly best friends deserve a getaway too, so simply use our search function for pet-friendly holiday rentals to find a perfect pad where your pup can be near his favourite humans.
What are popular rental amenities in Skyway?
A garden, a fireplace and a barbecue grill rank as the most popular rental amenities in Skyway. Whether you’re travelling by yourself, with your better half or a group of dear friends, Vrbo can help you find a holiday rental that fits your tastes with all the conveniences you’re looking for.
Are there large group holiday rentals in Skyway?
With two Skyway holiday properties that can accommodate five or more people, you can bring a few extra family members or friends along. Whether you’re planning a casual gathering or a celebratory event, we’ll help you book a comfortable space to match the occasion.
Are there holiday rentals in Skyway that welcome kids?
Skyway has six family-friendly holiday homes to choose from. And finding a stay that welcomes youngsters is a cinch with Vrbo’s “Properties good for families” filter. As well as having the entire place to yourselves, you’ll also get perks and conveniences such as multiple bedrooms, pools and kitchens.
What are the top attractions for families in Skyway?
Keeping the kids happy during your Skyway holiday is a breeze with these cool family-friendly attractions:
- Cheyenne Mountain Zoo
- Seven Falls
- Glen Eyrie Castle
How can I find holiday rentals with air conditioning in Skyway?
Skyway has four holiday rentals where you’ll be able to wind down in air-conditioned comfort. To locate a property on Vrbo that offers this perk, enter your preferred travel dates and use the handy filter tool to select the “air conditioning” box.
How old do you have to be to rent a holiday rental in Skyway?
The minimum age can differ between properties on Vrbo, so be sure to check the rules of the holiday rental in Skyway you’re interested in. But usually, it’s 16, 18 or 21.
How long can I rent a holiday rental in Skyway for?
It really depends on the Skyway property. To see all available options offering extended stays, simply type your dates and number of people into the Vrbo search page. You can look forward to having the place to yourself, along with home comforts such as air conditioning, a kitchen and an outdoor space where your little ones can play. Keep your eyes open for any long-term stays that offer weekly or monthly discounts.