Photo by Kerry Ciulla

Skyway vacation rentals

We found 85 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.

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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 in Skyway?
In Skyway, vacation houses are the most common type of rental, with several options available throughout the area. These properties typically feature spacious layouts, multiple bedrooms, fully equipped kitchens, and outdoor spaces for relaxing after a day of exploring the beautiful Colorado scenery. Ideal for families or groups, they provide a comfortable and inviting atmosphere for a mountain getaway.
How much does it cost to rent a vacation home in Skyway?
Prices for vacation rentals in Skyway vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Skyway to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Skyway vacation house rentals?
You can find great discounts on house rentals in Skyway on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
What are popular rental amenities in Skyway?
In Skyway, popular rental amenities often include balconies, gardens, and fully equipped kitchens, suiting travelers looking for comfort and convenience. Many properties also boast stunning mountain views, allowing guests to soak in the natural beauty of the area. The location of these rentals typically offers easy access to the surrounding mountains, making them ideal for those seeking outdoor adventures.
Can I find family house rentals in Skyway?
In Skyway, Colorado, there are several family-friendly rental options available, providing a great base for visitors looking to explore the area. The properties often feature spacious living rooms great for family gatherings, fully equipped kitchens that make meal prep a breeze, and outdoor spaces where children can play and adults can relax.

These homes are conveniently located near local attractions, including parks suitable for picnics and outdoor activities. Families can enjoy the beautiful natural scenery and engage in recreational activities such as hiking and biking in the surrounding Rockies.
Are there any Skyway vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Skyway with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Can I find long-stay vacation rentals in Skyway?
A long-stay vacation rental in Skyway is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
When is the best time to visit Skyway for a vacation rental?
The best time to book a vacation rental in Skyway is during the peak season from May to July. This vibrant period attracts outdoor enthusiasts eager to take advantage of the stunning natural surroundings. With warm temperatures typically ranging from the mid-60s to upper 70s Fahrenheit, visitors can fully engage in a range of activities, from hiking the scenic trails to enjoying picnics by the picturesque lakes.

July stands out as the most popular month, offering a lively option as both locals and travelers flock to the area. The pleasant climate makes it an ideal time for outdoor exploration, whether you're biking through lush landscapes or taking in the breathtaking views from the nearby mountains.

For those looking for a more budget-friendly experience, consider planning your visit in December. While this month falls into the low season, it brings a unique charm with the beauty of winter. It's a great time to cozy up in a charming cabin, enjoy snow sports, or simply relish the tranquility of the snowy landscape.

Whether you seek the excitement of the peak summer season or the serene beauty of winter, Skyway offers a range of experiences tailored to your travel preferences.
Are there any remote work vacation rentals in Skyway?
In Skyway, Colorado, there are several vacation rentals suitable for remote work. Many of these accommodations come equipped with essential amenities such as high-speed Wi-Fi and reliable internet service, allowing travelers to maintain productivity during their stay. The properties often feature comfortable workspaces, ranging from designated office areas to cozy nooks where guests can focus on their tasks.

Located amidst the stunning Rocky Mountain scenery, these rentals provide an excellent balance of work and leisure. After a day of meetings, guests can unwind by enjoying outdoor activities, such as hiking or skiing, depending on the season. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a Skyway vacation rental?
Book your Skyway vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Skyway, Colorado, United States of America?
In Skyway, Colorado, visitors can enjoy a range of attractions that highlight the area's natural beauty and outdoor activities. The nearby Rocky Mountain National Park offers breathtaking scenery, hiking trails, and opportunities for wildlife viewing, making it a prime destination for nature enthusiasts. The picturesque town of Estes Park, just a short drive away, features charming shops, restaurants, and access to the park's main entrance.

For those interested in winter sports, the area around Skyway provides easy access to ski resorts like Breckenridge and Keystone, both of which offer excellent skiing and snowboarding options during the winter months. In summer, these resorts transform into hubs for mountain biking, hiking, and scenic chairlift rides, allowing visitors to appreciate the stunning mountain vistas.

Additionally, the local community often hosts seasonal festivals and events, providing a taste of Colorado culture and hospitality. The nearby town of Silverthorne offers shopping and dining options, making it a convenient stop for visitors looking to explore the area further.
Can I change or cancel my Skyway home rental booking on Vrbo?
To find Skyway vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Skyway vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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