Family-friendly holiday rentals in Woodmoor

4.96 out of 5 average rating, 311 reviews

The exterior of a charming A-frame cabin features a sloped roof and a welcoming blue facade. A small porch is adorned with potted plants, while a pathway of stone slabs leads through landscaped greenery. Sunlight filters through surrounding trees, enhancing the inviting atmosphere.

Cabin in Palmer Lake

𓃲A-Frame on Palmer Lake𓃲 Firepit┃Foosball┃Grill

★Overlooking Palmer Lake, walkable to the downtown ★Location: 1 mi to Pinecrest Event Center, 20 mins to the Air Force Academy ★Outdoors: kayaking, paddle boarding, fishing, hiking ★YARD: Fenced in w/fire pit, grill, hammock, corn hole, ladder golf, yard dice ★FAMILY FRIENDLY: Pack n play, baby bath, high chair, baby monitors, toys! ★55" Smart TV w/ access to apps like Hulu + Netflix ★Fast Wifi ★Keyless Entry ★Comfortable beds ★Equipped kitchen w/waffle maker, blender + more! ★Free Colorado beer

Indoor spacesFamilyQuiet

4.95 out of 5 average rating, 208 reviews

A spacious deck area is furnished with comfortable seating, including a cozy sectional and armchairs. A table sits at the center, with the surrounding view showcasing a forested landscape and distant mountains under a softly lit sky.

Home in Colorado Springs

✔️Clean★Quiet Home★King Bed★Hot Tub★Scenic Views✔️

Stay in our Newly Built Family Home ✔ 4,800 sq ft Home, Perfect for Longer Stays & Families ✔ Professionally Cleaned & Sanitized ✔ 6-person Hot Tub, Gas Fire Pit & deck with Mountain Views ✔ King Size Bed 🗲Fast WiFi - Ideal for Working Remotely ✔ Fully Equipped Kitchen Upstairs, Kitchenette Downstairs ✔ In-Suite Washer & Dryer ✔ Theater Room with Complementary Netflix on all TVs ✔ 15 Minutes from USAF Academy We know you'll love your stay. Book today to reserve our beautiful home in the woods!

KitchenIndoor spacesWi-Fi

4.96 out of 5 average rating, 216 reviews

The exterior of the home is softly illuminated at night, highlighting the entrance with wooden doors and porch. A welcoming pathway of stone leads to the porch, bordered by lush landscaping and decorative pumpkins. Tall trees surround the area, creating a serene atmosphere.

Apartment in Monument

"Private Suite in the Forest"

This quiet unshared 1 bedroom suite is in a home 1 mile from Monument. Near hiking, the USAF Academy, Ford Amphitheatre, Colorado Springs, Castle Rock, Restaurants/Coffee Shops/Brewery, Spruce Mountain, Fox Run Regional Park, Pike Nat. Forest, and many hiking/Nordic trails. 45 miles so. of Denver. It's squeaky clean, 1 mile from I-25, comfortable, quiet, private, on a beautiful treed lot in the residential community of Woodmoor. Has a private entrance and is unshared space. Guests love it!

FamilyIndoor spacesView

Guesthouse in Palmer Lake

A cozy bedroom features a king size bed with patterned black and white pillows, complemented by a rattan headboard and bench. A decorative antler mount adorns the dark wood wall, while natural light streams in from large windows, enhancing the serene atmosphere.

4.95 out of 5 average rating, 149 reviews

A Retreat in the Woods by a Lake & Mountain Views!

Detached guesthouse with private entrance and deck sleeps 2 ADULTS in huge king size bed + 2 KIDS in loft. Located 2 blocks from PINECREST WEDDING VENUE. Hiking trails, access to Nat'l Forest + mountain reservoir. Tennis court in backyard. Pickle ball rackets provided!Open space in back Palmer Lake is 2 mins away, 2 adult SUPs available to you. Great fishing! Shared (but private) space includes a hot tub, fire pit. A/C available May-September. No smokers, marijuana, or vape users. No pets.

KitchenFamilyBathroom

4.9 out of 5 average rating, 172 reviews

A rustic outdoor seating area features a round wooden table surrounded by four metal-framed chairs, all placed on a flagstone patio. A red umbrella adorned with string lights provides shade, while tall pine trees create a natural backdrop.

Guest suite in Monument

The Adventurer’s Retreat

Are you looking for the perfect place to come back to after a day of adventure or just a quite serene getaway with your family? The large open space offers 2 very comfortable king beds, one is a 100% organic non-toxic pillow top mattress. You will feel like you're at home with a well equipped kitchenette, breakfast nook, and large living space along with a pool table. The apartment will make your stay not only relaxing but also fun. Our property has a playground for kids and pikes peak views!

FamilyIndoor spacesWi-Fi

A cozy living area features two comfortable blue armchairs positioned alongside a small dark table. A decorative painting of deer adorns the wall, complemented by a light-colored backdrop. Natural light filters through partially sheer curtains, enhancing the warm wood flooring.

5 out of 5 average rating, 111 reviews

Mountain View Basement Apartment

Comfy, private, & spacious basement apartment w/separate keyless entrance for easy check-in. Relax on our covered, lit patio with firepit or enjoy breathtaking mountain views from our upstairs deck. Eat & cook in our well-stocked basement kitchenette, where breakfast items, cooking ingredients, spices, & condiments will be provided. Washer/dryer & complimentary laundry supplies provided. After a great night's sleep, explore Colorado Springs or Denver with access to i25 just 5 minutes away.

Indoor spacesKitchenNearby

A modern kitchen and dining area features green cabinets, stainless steel appliances, and a large dining table with bench seating. Red chairs add a pop of color, while natural light fills the space through sliding glass doors leading to an outdoor area.

4.98 out of 5 average rating, 118 reviews

Family Friendly Charming +Clean 5 Bedroom House,

This 5 bedroom house has families and vacation amenities in mind! A small sitting room for coffee or conversation greets you when you walk in the door. The floor plan opens up to the living area that has a cozy couch to watch movies on and an eating area to share a meal. The kitchen is fully stocked with everything you need to prepare a meal together. The upper level has 4 bedrooms and a laundry room. There is a master suite with a king bed and a walk in closet. (no rooms on main level)

Indoor spacesFamilyValue

A spacious home is nestled among tall trees and lush landscaping on a private lot. A paved driveway leads to the entrance, with a welcoming covered front porch framed by vibrant greenery. The bright blue sky features scattered clouds, enhancing the tranquil setting.

4.91 out of 5 average rating, 106 reviews

Near Air Force Academy | 5BR + Pet Friendly + Yard

👑 Main-Level King Suite 🔥 2 Living Areas with Gas Fireplaces 🎮 Foosball Table + Smart TVs 🌿 Walk-Out Basement with Backyard Access 🔥 Fenced Yard with Propane Fire Pit & Grill 💻 Dedicated Workspace for Remote Work 🐾 Pet Friendly 📍 Mins from Downtown Monument & Air Force Academy Whether you're visiting family, attending an event at The USAFA, relocating to the area, or simply exploring Colorado, this spacious retreat offers plenty of room to gather, relax, and make yourself at home.

FamilyKitchenAmenities

4.99 out of 5 average rating, 206 reviews

A custom A-frame cabin is surrounded by tall pines, featuring a sloped roof and large glass windows. A spacious deck with steps leads to outdoor seating and a hot tub, while natural stone landscaping adds to the serene setting.

Cabin in Monument

Cozy A-Frame Retreat /Hot Tub/w-Views, Monument CO

Experience a true Colorado getaway with this custom built Scandinavian inspired A-frame, nestled on the Palmer Divide, located only 15 min to Colorado Spring & 30 min to S Denver. You will feel secluded within the pines with views to die for. You might see wildlife walking by while enjoying a cup of coffee or glass of wine in the hot tub or cozied up in a blanket. First bottle of wine on us! Hiking trails are minutes drive from the cabin. Make sure to relax & make lots of memories. 😊

Indoor spacesKitchenCheck-in

4.99 out of 5 average rating, 159 reviews

A rustic wooden sign displaying the text 'Cutthroat Cove' is mounted on a textured wall. The sign features a simple fish graphic, contributing to a natural and welcoming ambiance.

Guest suite in Monument

Cutthroat Cove- Air Force Academy

Completely relax! Even if you are here for business. Cutthroat Cove is near the entrance to the Air Force Academy but feels like you are living in the woods. Private entrance (with stairs), parking space, one bedroom, one bath with a large living room area. The mini kitchen features a dishwasher, mini-fridge, toaster oven and microwave. The fireplace makes it cozy and warm and sometimes we are visited by large wildlife. Minutes from restaurants and hiking trails.

FamilyKitchenAir conditioning

4.92 out of 5 average rating, 240 reviews

Peaceful Forest feel/Hidden but close/10mi USAFA

3bd 1ba Mountain themed home surrounded by Tall Ponderosa Pines trees frequented by deer/private walk-out onto deck/fire-pit seating area/BBQ grill/Play corn-hole, horseshoes jump on trampoline or kick-back. LOCAL: Beautiful hiking trails, unique shops, quaint eateries, Pubs, 2 Lakes, New amphitheater WEDDING VENUES: Palmer Lake, Monument, Larkspur & Flying Horse/Close to Colorado Springs, Manitou Spgs & CastleRock easy access i-25 Denver Airport 1hr.

Indoor spacesFamilyAccuracy

5 out of 5 average rating, 211 reviews

The exterior of a modern two-story guest house is shown, featuring large windows and a combination of light and dark materials. The structure is situated amidst tall pine trees on a gravel driveway, with a single carport located beneath the upper level.

Home in Colorado Springs

Private Guest House in the Forest

Our family has lived on this gorgeous, treed 5-acre property for over twenty years. Back then we were considered the outskirts of town. Now we have amazing amenities just a couple of miles up the road. We've dreamed of building this guest house for years and are now proud to announce "We're open for business!" I've been designing and building custom homes for 25 years. This home represents all of my best ideas and style. You're going to love it!

Indoor spacesKitchenGetting around

Popular amenities for Woodmoor family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

The kitchen features white cabinetry with sleek silver handles and a granite countertop. An island with a wooden accent provides additional workspace. Modern appliances, including a refrigerator and oven, are visible. Soft lighting illuminates the space, creating a bright and functional cooking area.

4.98 out of 5 average rating, 153 reviews

HOT TUB! Amazing Mountain views! Newly Remodeled

Indoor spacesFamilyAccuracy

4.96 out of 5 average rating, 224 reviews

A hot tub is positioned on a deck, offering scenic views of the surrounding mountains and greenery. The bubbling water contrasts with the natural landscape, while a wooden railing provides a boundary to the spacious outdoor area.

Cabin in Palmer Lake

Hot Tub | walk to trails & lake | Pet Friendly

FamilyIndoor spacesAir conditioning

4.98 out of 5 average rating, 268 reviews

Cabin in Florissant

Retreat at Mydnyt Mountain•Hot Tub•No Chores

KitchenFamilyDecor

4.98 out of 5 average rating, 127 reviews

The chalet's A-frame structure is framed by tall pine trees, showcasing large windows that invite natural light. A gentle plume of smoke is rising from the chimney, indicating a warm interior. The outdoor deck offers a seating area for relaxation amidst a scenic mountain setting.

Cabin in Woodland Park

Scenic Views, HotTub, Firepit, 2 Decks, Dogs YES

Indoor spacesFamilyWi-Fi

5 out of 5 average rating, 110 reviews

Guest suite in Monument

The Fly-by! Mountain&Lake view; Hot Tub+MiniGolf

FamilyIndoor spacesCheckout

Natural light fills a spacious living area with large windows, showcasing greenery outside. A comfortable sofa adorned with blankets is complemented by two modern armchairs. A wooden dining table is set nearby, with decorative touches including a potted plant and a wall-mounted shelf.

4.94 out of 5 average rating, 144 reviews

Secluded Chalet in the Pines Hot tub Wrapped porch

FamilyKitchenNearby

4.97 out of 5 average rating, 153 reviews

A secluded cabin is set among tall trees, featuring multiple outdoor decks and a covered porch area. The structure showcases wooden siding and a chimney, with lush green grass leading up to it, inviting a sense of tranquility and connection to nature.

Cabin in Woodland Park

Design Cabin Private Ridge Hike Stargazing Hot Tub

Indoor spacesKitchenLocation

4.98 out of 5 average rating, 129 reviews

A modern A-frame cabin is nestled in a snowy landscape, showcasing a spacious deck and a luxurious hot tub. Nearby, a geodesic dome offers a unique stargazing experience. The backdrop features a starry sky, enhancing the serene mountain setting.

Cabin in Florissant

Modern A-Frame w/ Hot Tub + Stargazing Dome

Indoor spacesKitchenCheck-in

Family- and pet-friendly home rentals

4.95 out of 5 average rating, 267 reviews

A wooden sign labeled 'Blue Spruce' stands in front of a log cabin, surrounded by tall trees and natural greenery. The cabin features a green roof and large windows, allowing a view of the serene outdoor environment. A path leads from the sign to the entrance.

Cabin in Manitou Springs

Keithley Pines Blue Spruce Cabin

KitchenIndoor spacesDecor

4.97 out of 5 average rating, 173 reviews

The exterior of the cozy cabin is shown with a welcoming door framed by warm outdoor lights. Two metal chairs and a small table are placed on the patio, scattered with autumn leaves. The surrounding trees hint at a tranquil wooded setting.

Cabin in Cripple Creek

Lucky Llama A-Frame|Views |Fireplace|Dogs Welcome!

Indoor spacesKitchenTV

4.85 out of 5 average rating, 308 reviews

A scenic view captures the surrounding landscape, featuring rolling hills and distant mountains under a partly cloudy sky. Lush greenery and wild grasses fill the foreground, with trees framing the edges of the image. A peaceful natural setting is evident.

Cottage in Palmer Lake

Completely Remodeled Historical Cottage

Indoor spacesFamilyBackyard

4.92 out of 5 average rating, 113 reviews

A bright living area is highlighted by large windows allowing natural light to fill the space. Comfortable seating is positioned near the windows, while a round dining table is set for meals. A well-equipped kitchen is visible in the background, featuring modern appliances.

Loft in Palmer Lake

Crow's Nest

FamilyKitchenValue

Guesthouse in Colorado Springs

A cozy cabin features a distinctive sloped roof and is surrounded by tall trees. The exterior is constructed from natural wood, complementing the forest setting. A stone fire pit and several outdoor benches are positioned in front of the cabin, providing a welcoming outdoor space.

4.95 out of 5 average rating, 132 reviews

Cozy Fishing Cabin in Black Forest

KitchenFamilyCheck-in

4.97 out of 5 average rating, 237 reviews

Cabin in Florissant

Whimsical Dreams Cabin | Firepit | Kids Fort

KitchenIndoor spacesWalkability

Earthen home in Colorado Springs

The exterior of a unique earthship home is framed by lush greenery and tall pine trees. Large glass windows reflect the surrounding landscape, allowing natural light to illuminate the earth-toned structure. A black door is visible at the front, alongside a small seating area.

5 out of 5 average rating, 209 reviews

Off-grid, Earthen home in the forest!

Indoor spacesKitchenSleep quality

Guest suite in Colorado Springs

A cozy basement suite is presented, featuring a sectional couch and a wall-mounted television. Shelves filled with books occupy one wall, while a dry bar with seating is visible nearby. Soft lighting contributes to a relaxed ambiance within the space.

4.94 out of 5 average rating, 330 reviews

Private, Spacious Basement Suite in N CO Springs

KitchenIndoor spacesHiking

Family-friendly home rentals with a pool

4.98 out of 5 average rating, 46 reviews

A serene outdoor patio area features a table complemented by comfortable chairs, surrounded by lush greenery. A small waterfall pond is visible in the background, framed by tall trees and a clear sky, offering a peaceful natural setting.

Home in Larkspur

Forest Retreat, 2 floors, 3 bedrooms w/Hot Tub Spa

KitchenFamilyAmenities

Guesthouse in Colorado Springs

An indoor pool area features a 35 ft heated swimming pool underneath a spacious glass enclosure. Two swan-shaped pool floats rest on the water, while lounge chairs are positioned along one side, providing a relaxing atmosphere. Natural light streams through the large glass walls.

4.91 out of 5 average rating, 154 reviews

Urban Float - Heated Indoor Pool/HotTub & Firepit

Indoor spacesFamilyGetting around

Apartment in Colorado Springs

A bright living area is furnished with a green sofa and a white slipcovered couch. A wooden coffee table sits in front. A dining table is positioned near a window, allowing natural light to illuminate the space. Decorative plates and a world map adorn the wall.

4.92 out of 5 average rating, 279 reviews

Quite spacious Apt w/Game Table, Pool, Bball court

Indoor spacesFamilyHiking

4.88 out of 5 average rating, 103 reviews

A spacious living area features a comfortable sectional sofa, a flat-screen smart TV mounted on the wall, and a coffee table. Fresh greenery adds a touch of nature, while a ceiling fan provides airflow. The adjoining kitchen space is subtly visible in the background.

Apartment in Castle Rock

Rocky Mountain Haven w/ king bed | pool & hot tub

Indoor spacesKitchenBarbecue

4.91 out of 5 average rating, 89 reviews

An open living space showcases wooden cabinetry and a high ceiling with exposed beams. A spacious seating area includes a sectional couch and a coffee table. A dining table that seats six is visible, along with a wood-burning stove providing warmth.

Home in Colorado Springs

Cheerful home w/pool & hot tub in quiet area

Indoor spacesKitchenComfort

4.88 out of 5 average rating, 133 reviews

An outdoor patio area is highlighted by a wooden frame, providing shelter over a dining table and seating. A hot tub is situated nearby, surrounded by lush greenery and tall trees, creating a serene environment for relaxation.

Home in Woodland Park

Sunshine Mountain , experience true Colorado!

FamilyIndoor spacesCleanliness

The exterior of a two-story home is displayed, showcasing a well-maintained backyard with a semi-inground heated pool surrounded by white lounge chairs. A deck with stairs leads to the entrance, while a sunroom is visible beneath the windows. Neatly trimmed greenery frames the area.

5 out of 5 average rating, 30 reviews

Spacious, Mountain Views, Heated Pool, & Sunroom!

Indoor spacesFamilyPool