Photo by Kerry Ciulla

Skyway vacation rentals

We found 81 vacation rentals — enter your dates for availability

Discover a selection of 21 homes and other vacation rentals in Skyway that are perfect for your trip. Vacation rentals offer the amenities you expect for you and your friends, family, or even pets, such as a garden and pool. You're sure to find a rental for everyone's needs, including places that are non-smoking or accessible.

Vacation rentals with weekly discounts - Skyway

Showing deals for:Aug 22 - Aug 29
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Find out more about Skyway

Find out more about Skyway

Why visit Skyway

  1. Outdoor Adventures: Skyway offers breathtaking landscapes ideal for hiking, biking, and enjoying nature.
  2. Skyway Bridge: A must-visit landmark that provides stunning views and a unique experience.
  3. Skyway Park: Perfect for family outings, featuring playgrounds and picnic areas.
  4. Community Events: Engage with locals at various resident events and the popular Skyway 10K.
  5. Charming Neighborhoods: Explore picturesque streets lined with friendly residences, perfect for leisurely strolls.

Top attractions near Skyway

Skyway, Colorado Springs, is perfect for outdoor and family adventures, featuring attractions like waterfalls, golf courses, and entertainment arenas. Visitors can enjoy various activities, including the Skyway Bridge, resident events, the Skyway 10K, and Skyway Park. With a focus on culture and outdoor experiences, this area promises something for everyone, making it an ideal vacation spot for those looking to explore the great outdoors and enjoy local events.

  1. Seven Falls: A stunning series of cascading waterfalls nestled in a picturesque canyon, perfect for outdoor adventures and romantic strolls. Hike the scenic trails to experience the beauty of nature up close.
  2. Pikes Peak Center: A vibrant entertainment venue hosting concerts, theater performances, and family-friendly events. Enjoy a lively atmosphere and diverse programming suitable for all ages.
  3. Broadmoor Golf Club: A prestigious golf course offering breathtaking views and a welcoming environment. Ideal for families and golf enthusiasts, it combines scenic beauty with a friendly atmosphere.

Things to do recommended for couples

For a romantic getaway in Skyway, explore the luxurious Colorado Springs Country Club, enjoy live entertainment at the Colorado Music Hall, or have fun at Adventure Golf and Batting Cages. These experiences offer the perfect blend of relaxation and adventure for couples seeking memorable moments together.

Things to do recommended for families

Your family will love exploring the serene trails of Red Rock Canyon Open Space, just 3 miles from Skyway. Experience the thrill of the U.S. Olympic & Paralympic Training Center, 4 miles away, and enjoy a splashing good time at Great Wolf Lodge Water Park, located 13 miles away.

What do I need to keep in mind when booking a vacation around Skyway

When planning your trip—whether you're traveling with friends, family, pets, or seeking longer accommodations—it's important to prioritize your preferences. Here are some helpful booking tips for using Vrbo.

  • Traveling to Skyway with a group: Think about how many bedrooms you'll require, as well as features like a complete kitchen or outdoor areas for group activities. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to Skyway with young kids: Traveling with young kids can be demanding. It's important to prioritize their comfort and safety, along with finding suitable amenities, like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Skyway: For many families, a vacation isn't truly enjoyable without their furry companion by their side. If that resonates with you, explore Vrbo listings that welcome pets. Many of these pet-friendly accommodations offer feeding bowls and beds, ensuring that every member of the family feels comfortable and at home.
  • Planning for a long term stay visiting Skyway: If you're seeking vacation rentals that offer special rates for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. You might also want to include amenities like a parking space, a well-equipped kitchen, or a private pool in your search.

Where to stay near Skyway

Skyway, nestled in Colorado Springs, offers a delightful mix of outdoor adventures and family-friendly experiences. Explore the scenic neighborhoods, where friendly locals and rich history create a welcoming atmosphere. Don't miss Skyway Drive, lined with charming single-family residences, perfect for leisurely strolls. Nearby, you'll find convenient access to local amenities, including nursing homes and senior citizen services, ensuring a comfortable stay for all visitors. Skyway is a fantastic base for your Colorado exploration!

  • Manitou Springs: Located a mere 4 miles from Skyway, Manitou Springs is a charming city known for its vibrant outdoor and family-friendly activities. Nestled at the foot of Pikes Peak, this community offers a unique blend of history and adventure. Visitors can explore the local recreational areas, hike scenic trails, and enjoy various arena entertainment events. Don't miss the local landmarks such as the inviting urban park and the expansive nature reserve, perfect for a day of exploration amidst stunning natural beauty.
  • Cheyenne Canyon: Just 1 mile from Skyway, Cheyenne Canyon is a picturesque neighborhood that beckons outdoor enthusiasts and families alike. The area is renowned for its breathtaking landscapes and recreational opportunities, including camping and golfing at private clubs. Nature lovers can revel in the tranquility of local parks and the nearby national state park, offering a plethora of hiking and wildlife viewing experiences. Cheyenne Canyon is a fantastic spot to immerse yourself in Colorado's natural beauty while enjoying quality time with loved ones.
  • Broadmoor: Situated 2 miles from Skyway, Broadmoor is an elegant neighborhood that combines outdoor fun with family adventures. Known for its luxurious golf courses and exclusive country clubs, this area is a golfer’s paradise. Beyond golfing, visitors can explore the stunning urban parks and nature reserves that surround Broadmoor. The picturesque setting makes it an ideal location for a leisurely stroll or a family picnic, allowing travelers to connect with nature while enjoying a slice of Colorado's serene lifestyle.

Best time to go to Skyway

If you're planning a trip to Skyway, it's a good idea to check both the weather and property rates. The warmest month is July.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudiness
January26.2°F (-3.2°C)No Rain (Dry)Sunny
February27.0°F (-2.8°C)No Rain (Dry)Mostly Sunny
March36.3°F (2.4°C)No Rain (Dry)Mostly Sunny
April43.3°F (6.3°C)Light RainMostly Sunny
May52.5°F (11.4°C)Light RainMostly Sunny
June64.9°F (18.3°C)Light RainSunny
July68.7°F (20.4°C)Light RainMostly Sunny
August67.1°F (19.5°C)Light RainSunny
September61.3°F (16.3°C)No Rain (Dry)Sunny
October46.9°F (8.3°C)No Rain (Dry)Sunny
November36.0°F (2.2°C)No Rain (Dry)Sunny
December26.8°F (-2.9°C)No Rain (Dry)Sunny

Booking with Vrbo is a breeze

Are you trying to save on your next getaway? Keeping your travel dates flexible can help, as prices often vary. Additionally, opting for a longer stay typically leads to significant savings. To discover the perfect Vrbo property that fits your budget, take advantage of our filters to sort by price, location, and type of vacation rental.

Unlock savings with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash™ on the total booking amount. Being the planner truly has its perks! When you join our travel rewards program, One Key, you'll gain access to exclusive member discounts and earn OneKeyCash™ on eligible bookings. Sign up today and begin enjoying your savings!

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board offers a user-friendly area to plan new trips, continue from where you last stopped, or manage your travel arrangements. You can easily view your saved or booked properties, which are organized into categories like Potential, Upcoming, and Current Trips. To begin using Trip Boards, simply visit: https://www.vrbo.com/en-ca/trips.

Frequently asked questions

What is the most popular type of vacation rental accommodation in Skyway?
According to our research, cabins are considered the most popular type of property in Skyway. But as you know, everyone’s idea of an epic trip can vary. Vrbo has vacation homes of all shapes and sizes, and we’ll help you find your ideal match.
How much does it cost to rent a vacation rental in Skyway?
The average price for a vacation home in Skyway is determined by a number of factors, including time of year, length of stay and property type. Whether you’re in search of a sprawling house with room for friends and family or an apartment just for the two of you, just add your travel dates to see some great-value stays.
How much does it cost to rent a beach house in Skyway?
Prices for beach houses in Skyway may differ depending on the size and type of the property and when you’re traveling. All you have to do is enter your travel dates into Vrbo and how many guests to view your vacation rental options and prices. From there you can use our filter tool to narrow your search by ratings, nearby activities and more.
Are there pet-friendly vacation rentals in Skyway?
With seven vacation rentals that welcome pets, your furry best friend can join you on your Skyway break. Use the filter tool to browse our pet-friendly vacation rentals and find the pawfect pad on Vrbo.
What are popular rental amenities in Skyway?
Some of the most popular rental amenities people prefer in Skyway are a barbecue grill, a garden and a fireplace. Whether you’re hitting the road with family, pals or even pets, Vrbo vacation rentals include the best amenities for ultimate relaxation with the people closest to you.
Are there large group vacation rentals in Skyway?
Yes, there are five vacation properties in Skyway that can sleep five or more people. From family getaways to special occasions like birthday parties, these stays have ample space to chill out with the people that matter the most.
Are there vacation rentals in Skyway that welcome kids?
With six family-friendly vacation homes to select from in Skyway, now is a great time to introduce the little ones to the pleasures of travel. Just click on our “Properties good for families” filter to discover stays packed with amenities ideal for families on the move, like living rooms, patios, hot tubs and entertainment areas.
What are the top attractions for families in Skyway?
Bear Creek Nature Center will keep the kids happy during your Skyway vacation. This family-friendly attraction is situated within close proximity of the center.
Can I find two-bedroom vacation rentals in Skyway?
Skyway has two two-bedroom vacation rentals that you can choose from. Discover a vacation home with all the comfort and privacy you need at a price that’s hard to resist on Vrbo.
How can I find vacation rentals with air conditioning in Skyway?
Select your travel dates and then make use of our filters to view vacation rentals with air conditioning in Skyway on Vrbo. With four air-conditioned properties on offer here, you can look forward to a cool and comfortable trip.
How old do you have to be to rent a vacation rental in Skyway?
We recommend you check with the Skyway vacation rental you’d like on Vrbo as the minimum age varies. However, generally it’s 16, 18 or 21.
How long can I rent a vacation rental in Skyway for?
The amount of time you can stay in a Skyway vacation rental for is down to the property. Just tap in your dates of travel to view available options that offer long-term stays. They come with all the things you need to make your extended vacation more comfortable and enjoyable, like kitchens and backyards. Some vacation homes may also offer weekly or monthly discounted prices, so you can stick around for longer for less.
Does Vrbo offer discounts for vacation homes in Skyway?
On Vrbo, we’ve got plenty of fabulous deals and discounts for Skyway. Browse our newly listed homes, as well as our weekly and monthly discounts on vacation rentals. Whether you’re looking for a mini vacay or an extended escape, Vrbo offers lots of options for every budget and style.

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