Vacation rentals in Glenwood

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Top-rated vacation rentals in Glenwood

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favorite

A small rustic cabin is nestled among tall trees, providing a sense of seclusion. Sunlight filters through the canopy, casting dappled shadows across the ground. The cabin features a single window framed by green trim, blending harmoniously with the natural surroundings.

Cabin in Los Gatos

4.89 out of 5 average rating, 509 reviews

The Coach House

The Coach House is located on our mountain top horse and lavender farm. We offer youth summer camps so are set up for fun outdoor adventures and activities. Have fun with our horses, goats, and chickens! You can take a 10 min walk over to Nonno's Restaurant for wine/pizza/BBQ and bacchi ball, or take an 8 min drive into Los Gatos, or 15 min to Santa Cruz for the beach and some of the best restaurants and spas around!. Good for couples, solo adventurers, business travelers, kids, & behaved dogs!

Top guest favorite

An A-Frame cabin is surrounded by lush greenery, positioned on elevated ground. A stone pathway leads to the entrance, flanked by wooden railings. The cabin features large glass panels on its façade, allowing natural light to flood the interior. A deck with seating overlooks the nature surroundings.

Cabin in Felton

4.96 out of 5 average rating, 171 reviews

Santa Cruz A-Frame

This unique A-Frame cabin, in a quiet mountain neighborhood with private creek access, was handbuilt in 1965 and remodeled in the summer of 2024. Now a little slice of heaven on the creek in the redwoods. *5-10 min to Henry Cowell Redwoods State Park, Roaring Camp Railroad, Loch Lomond Recreation Area, the Trout Farm Inn, Quail Hollow Ranch + Felton stores. *20 min to Santa Cruz, beach + Boardwalk. *1 min to Zayante Creek Market (EV charger) Find us on social: Insta @SantaCruzAFrame

Guest favorite

A uniquely designed treehouse is elevated among the trees, showcasing large glass windows and wooden beams. A wooden walkway leads up to the structure, enhancing the connection with the surrounding natural environment.

Treehouse in Aptos

4.91 out of 5 average rating, 604 reviews

Peaceful Treehouse with Ocean View

Permit 171035 Featured by Sunset Magazine as a “chic escape,” this Peaceful Treehouse-style retreat blends mid-century design with natural materials like wood and stone for a calming, sanctuary feel. Light pours through floor-to-ceiling windows beneath soaring wooden beams, and Japanese-inspired doors add to the architectural charm. Set high in the trees with ocean views, the home offers three elevated decks including one with a hammock. Perfect for relaxing and enjoying the surrounding canopy.

Top guest favorite

A charming green guesthouse is nestled among towering redwood trees. The structure features multiple windows that bring in natural light, enhancing the connection with the surrounding forest. Sunlight filters through the branches, creating a serene outdoor atmosphere.

Cabin in Los Gatos

4.99 out of 5 average rating, 1,042 reviews

Private Guest-House in the Redwoods

Our custom built guesthouse was completed in 2016. It is situated on 5 redwood-covered acres, 10 minutes south of Los Gatos and 20 minutes from Santa Cruz. We have easy access to hiking and biking trails, world-class wine-tasting, microbreweries, shops, amazing dining, and more! There is something for everyone in our area! We are surrounded by a 35 acre tree farm, so it's very private, yet close to the silicon valley! Our property has a standby generator so we are not affected by power outages.

Top guest favorite

A private yard is surrounded by tall trees, featuring a hot tub with bubbles rising to the surface. A hammock is visible to the side of the yard, alongside two Adirondack chairs. The cabin's entrance is shown, with a window allowing natural light to enter.

Cabin in Boulder Creek

4.98 out of 5 average rating, 131 reviews

Forest Cabin & Hot Tub

Take it easy in this cozy cabin retreat in the Santa Cruz Mountains. 30 minutes from downtown Santa Cruz and beaches. This charming 400 sq. ft. studio is the perfect setting to disconnect from city life and immerse yourself in the redwoods. The cabin features a queen bed, full bathroom, kitchen & BBQ. The private yard includes a hot tub, propane firepit and hammock to fully relax and unwind. Please note the cabin is on a one way, windy road. There is WiFi but no TV or A/C. SCC Permit# 241449

Guest favorite

Cabin in Boulder Creek

4.91 out of 5 average rating, 105 reviews

Either Way Hideaway

Relax and enjoy riverside views in our tranquil Santa Cruz Mountains guesthouse. Cozy by our fire pits, take a dip in a private hot tub and enjoy the sounds of the river flow by. Hike Big Basin, Castle Rock and Henry Cowell State Parks. Close to historic downtown Boulder Creek and the Santa Cruz boardwalk, it’s the perfect base for exploring Santa Cruz county. Immerse yourself in of nature while staying connected and comfortable. Either way, you’ll enjoy your stay! SCC Permit #251382

Top guest favorite

Rows of grapevines stretch across the hillside, with traces of autumn colors visible on the leaves. A picturesque blend of green and gold foliage contrasts against the muted earth tones of the ground, while distant trees and hills are lightly shrouded by morning mist.

Farm stay in Felton

4.94 out of 5 average rating, 159 reviews

Vineyard Retreat with Expansive Mountain View

Vineyard retreat in Santa Cruz Mountains with expansive hilltop views. Situated off the beaten path between Los Gatos & Felton. The perfect place to disconnect, unwind & relax in a rural mountain setting. Our vineyard is 100% natural, no chemicals, pesticides or additives, from the soil to your cup. Please enjoy meandering the rows, soaking in the views and being in nature. Watch the marine layer recede in the morning & enjoy stargazing at night. Pricing is the same for 1-4 guests.

Guest favorite

A wooden cabin is surrounded by tall redwood trees, featuring a large deck that extends around the building. The exterior showcases natural wood tones, with a chimney visible and a large window that invites light into the interior.

Cabin in Soquel

4.93 out of 5 average rating, 206 reviews

Redwood Ridge Retreat by the Sea

Unparalleled redwood seclusion at the top of a sunny ridge with a view of Monterey Bay. Just 10 mins to downtown Soquel and 15 mins to the Santa Cruz beaches. 40 mins to Silicon Valley, a rare property with a Big Sur feel close to everything. Vacation permit #191374. Enjoy cozy wood heat or cool shade provided by surrounding redwood and oaks. Extensive decks for outdoor dining, relaxing, yoga, sunbathing, birdwatching! We are happy to answer your questions!

Top guest favorite

A spacious living area features a large sectional sofa adorned with pillows, positioned near windows allowing natural light. A round dining table with chairs complements the open design, while abstract wall art adds a modern touch to the environment.

Guesthouse in Scotts Valley

4.97 out of 5 average rating, 128 reviews

Treescape, a perfect modern, rustic, SV getaway.

Welcome toTreescape Guest Suite, nestled in Scotts Valley finest neighborhoods, we’re located across the street, from beautiful Glenwood Preserve, & around the corner from 1440 Multiversity. Our remodeled guest suite is only a three-five minute drive, to local restaurants, grocery stores, coffee shops, microbrewery, and more. Treescape is 1 mile to HW-17, 8 miles to Santa Cruz, 10 miles to Natural Bridges State Beach, and 15 miles to Silicon Valley.

Superhost

A round dining table is set for four, featuring red placemats and white dinnerware. Glasses are positioned beside each plate, and stylish utensils are arranged on either side. The wooden chairs are designed with a light finish, complementing the warm tones of the table.

Guest suite in Los Gatos

4.84 out of 5 average rating, 264 reviews

Mountain Gem - $1M VIEW

We are offering a 1-bedroom apartment on the lower level of a 2-unit house. It is located in a very beautiful place and has a huge balcony with a million-dollar view of the Santa Cruz mountains. Close by 17 highway, which can take you to Los Gatos in 10 minutes, and Santa Cruz - in 20. Great for Bay Area business travelers. Ideal for Santa Cruz beach vacationers. 15 minutes to gorgeous nearby wineries. Got everything one needs for a super stay.

Top guest favorite

A private living room features a wooden cabinet and a dark blue armchair beside a window with natural light. A small refrigerator and kettle are visible. A woven rug lies on the wooden floor, with magazines resting nearby, and greenery adds a touch of color.

Home in Upper Seabright

4.89 out of 5 average rating, 691 reviews

Town-and-Nature

Three beautiful, quiet, private and secure rooms within our home, with separate entrance. PLEASE NOTE: It is part of a home, not entire home as listing heading implies, due to Airbnb's limited choices. Lovely garden with outside sitting area. 20 minute footpath/walk to beach through green belt and harbor, great restaurants nearby including three at the beach, short drive to downtown for live music and arts. Host is German, practices acupuncture.

Superhost

An aerial view displays the serene property nestled among towering redwoods. A sparkling pool is surrounded by lush greenery, with a patio and seating area visible in the background. The landscape features diverse plants, enhancing the tranquil atmosphere of this private retreat.

Place to stay in Los Gatos

4.81 out of 5 average rating, 104 reviews

Stay Alpha Home • Modern Redwood Retreat with Pool

Permit 231266 - Nestled in the Santa Cruz mountains is this serene oasis, rustic with modern touches and a stunning pool (the upper pool and main pool are not heated). Embrace yourself with the lush tropical setting and gorgeous redwood groves in this mesmerizing, unique villa. With distance between you and the closest neighbor, it’s perfect for families and nature enthusiasts seeking a rejuvenating retreat. Your redwood getaway awaits!