Vacation rentals in Glenwood

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Top-rated vacation rentals in Glenwood

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Superhost

A large tree provides shade in the foreground, while a horse riding arena is visible in the background. The arena is surrounded by a fence, and lush greenery dominates the scene, with distant trees and a hint of fog in the valley below.

Cabin in Los Gatos

4.9 out of 5 average rating, 452 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

A clean bathroom sink area features a polished chrome faucet and decorative soap dispenser. A basket is filled with white towels, and an ornate round mirror hangs above the sink, adding a touch of elegance to the space.

Cabin in Los Gatos

4.99 out of 5 average rating, 923 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 serene pool area is showcased, featuring clear water reflecting the sunlight and surrounding trees. There is a pool cleaner in the water, and a patio area is visible on the edge, providing space for relaxation.

Guest suite in Scotts Valley

4.96 out of 5 average rating, 731 reviews

Snug and Cozy between the Skyline and the Sea

Super private, peaceful, and quiet; an excellent place for the traveler who is excited about exploring the Santa Cruz mountains and coast. Completely private In-law unit with extras needed to make it cozy. Snuggled between Scotts Valley, Felton, and Santa Cruz it's near Henry Cowell Redwoods State Park, 1440 Multiversity, and Mount Hermon Conference Center yet less than an hour from Silicon Valley. The Airbnb cleaning handbook is followed making this one of the cleanest places you’ll stay at!

Guest favorite

A compact bathroom features natural wood paneling and a pitched ceiling. A white toilet and sink are positioned alongside a window that invites natural light. Shelves hold basic toiletries, and decorative towels are displayed nearby.

Guesthouse in Los Gatos

4.83 out of 5 average rating, 571 reviews

Rustic Cottage, Redwoods, Beaches.

Tiny, quaint Cottage sequestered in a Redwood forest. Outdoor Clawfoot Bathtub with Shower under the Stars overlooking a Spring fed creek ! Mature Pond & Marina with sitting areas with Koi and Turtles ! Solar powered lights come on at night! Lighting at the Cottage is Electric, Solar and Battery powered. Lanterns are provided ! There is a Cell Phone & device Charging Station available. No Kitchen or cooking facilities. Summit Market, four miles away, open 7 days a week, hours are 7am to 7pm.

Top guest favorite

A spacious deck is shown in the foreground, with comfortable seating and decorative pillows. Towering redwood trees rise in a dense forest background, surrounded by lush greenery and a woodpile. Sunlight filters through the canopy, creating a serene outdoor setting.

Guest suite in Boulder Creek

4.99 out of 5 average rating, 555 reviews

Enjoy Private Redwoods from Your Bed or the Deck

Come and visit our own private slice of the REDWOOD FOREST with over 40 trees and large deck to enjoy. Hosted Rental Permit 241236 Wake up to fresh mountain air, a view of nature and coffee. After a day of WINE tasting, HIKING, BEACHES, exploration, bring a bottle back & sprawl in comfort reflecting, chatting, or sipping. The perfect little getaway spot. Treat yourself to some nature. A winter fireplace, easy walking and parking makes this scene. 1.5 miles to downtown Boulder Creek and fun!

Guest favorite

An outdoor patio space is presented, featuring a small round table accompanied by two chairs. String lights are hung above, and a separate entrance door is visible. The gray wall contrasts with the red brick, creating a welcoming atmosphere.

Guest suite in San Jose

4.91 out of 5 average rating, 215 reviews

Entire Guest Suite Private Entrance Kitchen & Bath

Whether you’re here for a business trip, traveling for pleasure, visiting your friends/relatives, or looking for a short term rental, our fully furnished unit can offer everything you need! What you’ll get from staying at our converted garage: * Separate entrance with self check-in (keyless entry) * Workspace with high-speed wifi * TV with Netflix * Fully stocked & equipped kitchen * Private bedroom with queen bed, wall closet, high ceiling * Private bathroom * Free parking on premise

Top guest favorite

Guest suite in Los Gatos

4.97 out of 5 average rating, 152 reviews

Ridge Top Get-A-Way and Quiet Dedicated work space

Permit 231319 A quiet, private suite in a stunning ridgetop setting—perfect for relaxation and renewal! This spacious guest suite features two bedrooms, a private spa bathroom, and a secluded deck, private, occupying the entire lower floor of our hilltop home. Enjoy breathtaking forest views and peaceful, star-filled nights, just 20 minutes from Silicon Valley and Monterey Bay's beaches. Guests have their own private entrance and convenient off-street parking.

Guest favorite

A vibrant yellow caterpillar is positioned on a textured, dark wooden surface, displaying a contrast between its bright color and the rich brown tones of the wood. Lush green leaves are visible in the background, adding to the natural setting.

Guesthouse in Scotts Valley

4.92 out of 5 average rating, 148 reviews

The Hen House Haven

Welcome to The Hen House Haven, a charming retreat where comfort meets modern amenities. Enjoy fresh eggs from our ten friendly hens, though egg availability may vary, especially in winter. Located near the Santa Cruz Beach Boardwalk, Henry Cowell Redwoods, and scenic hiking trails, our cozy studio is perfect for a relaxing getaway or adventure-filled stay. Embrace the serenity and warmth of staying with us, and make yourself at home. We can't wait to host you!

Top guest favorite

The entrance features a welcoming door with multiple glass panes, framed by neutral siding. A small porch area is visible, adorned with a textured mat and complemented by a decorative wall lamp. Nearby, a railing outlines the stairway leading to the entrance.

Guesthouse in Los Gatos

5 out of 5 average rating, 128 reviews

Orchard Cottage in convenient countryside location

Orchard Cottage is a newly refurbished historical home in a rural neighborhood 10 minutes from downtown Los Gatos. Lots of wildlife and local private hiking trails make this location in the Santa Cruz Mountains a peaceful retreat from city life. Enjoy your private deck and yard or visit our ducks for a mini-farm experience. Lots of nearby hiking and wineries, and only 25 minutes to Santa Cruz beaches. Please contact me with any questions!

Guest favorite

Guest suite in Los Gatos

4.93 out of 5 average rating, 281 reviews

Remote Mountain Suite with Hot Tub

One-bedroom attached in-law suite with private entrance- relaxing den with large leather couch, flat screen tv (Roku/no cable) kitchenette w/hot plate and private bath. Mountain location 2.5 miles down a very narrow scenic ridge-top road on 6 beautiful acres of lush vegetation and towering redwood trees. Ideal for a couple or small family looking to explore the Santa Cruz county Mountains, Bay Area and coast without breaking the bank.

Guest favorite

The interior of the yurt features a spacious sleeping area with a queen size bed, adorned with layered bedding and decorative throws. Large windows allow natural light to fill the space, complemented by a circular skylight above. Indoor plants are arranged thoughtfully, enhancing the tranquil environment.

Yurt in Watsonville

4.91 out of 5 average rating, 787 reviews

Mountain Top Yurt in the Redwoods

Peaceful, clean, spacious, beautifully decorated and quiet 24' Yurt completely surrounded by Redwoods on top of the Santa Cruz Mountains. Spend a couple days meditating, reading or writing the next chapter of your memoir. Walking distance to Mount Madonna Retreat Center (open now through reservation only). County Park hiking and horseback riding trails located within 3 miles. Ideal place for photography and mountain/road biking.

Guest favorite

A private hot tub is situated on a wooden deck within a fenced area. Natural light filters through the surrounding trees, enhancing the serene setting. Adjacent to the hot tub, an outdoor shower is partially concealed by a privacy screen.

Guesthouse in Felton

4.96 out of 5 average rating, 190 reviews

Redwood Cottage & Hot Tub

Enjoy this quaint, peaceful redwood retreat in the Santa Cruz Mountains. This small cottage comes with a private hot tub, outdoor shower, propane fire pit and hammock. You'll be 10 minutes to downtown Felton and 25 minutes to Santa Cruz beaches. The cottage is on a shared property and next door to the main house.