Guesthouse vacation rentals in Evergreen, San Jose

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Top-rated guesthouse rentals in Evergreen, San Jose

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Guest favorite

A hot tub is seen surrounded by a softly lit patio, with colorful string lights enhancing the evening ambiance. Lush greenery and a covered seating area are visible in the background, contributing to a relaxing outdoor space.

Guesthouse in Los Gatos

4.92 out of 5 average rating, 358 reviews

Los Gatos/Cambrian COTTAGE-HOT TUB/pvt.parking

This charming cottage, located on the outskirts of Los Gatos in the quiet and safe Cambrian neighborhood, is an ideal retreat away from the busy downtown. We ensure a safe and comfortable stay with rigorous cleaning protocols. The studio features one queen bed, with an additional cot available upon request. Please note that dogs are on the property. All dogs, including service dogs, must have prior consent from the host and provide current vaccinations (rabies, DH2PP, bordetella, leptospiros.

Guest favorite

Natural light floods the cottage through multiple windows, highlighting a wooden table paired with two black chairs. A white door opens to the outdoor area, providing a seamless connection to the exterior. Wooden beams add a touch of character to the ceiling.

Guesthouse in Palo Alto

4.77 out of 5 average rating, 164 reviews

Sunnystay: Bright Garden Palo Alto Studio Cottage

Brand New Remodeled Updated Charming extremely well lit Independent Private Guest cottage with New Bed , Bedding, New Hardwood floors, Remodeled Private bath, Added new Full Kitchen, & Washer Dryer facility in a serene garden setting desirable Crescent Park Palo Alto. Guests have the entire cottage to themselves with a private patio. We have fully upgraded the cottage and addressed all issues from past listing of 3 years ago. Extremely serene and quiet environment, a dream for remote work.

Top guest favorite

Tall redwood trees create a serene forest environment, with their textured trunks standing closely together. Lush green foliage is visible at the base, complementing the rich earth tones of the bark. A stone wall subtly outlines the natural space, adding to the peaceful atmosphere.

Guesthouse in Boulder Creek

4.99 out of 5 average rating, 215 reviews

Digital Nomad Retreat

Imagine yourself in the REDWOOD FOREST and take a breath of mountain air. Only 25 miles from the Silicon Valley, 15 miles from the Santa Cruz Boardwalk, a cozy location tucked in the forest. Many are on the move and can work from anywhere, so why not a beautiful place of your own? A perfect getaway spot central to WINE TASTING, HIKING, BEACHES and even mountain exploration, right from the doorstep. Located only a mile and a half from downtown Boulder Creek, food and window shopping are easy.

Guest favorite

A welcoming entrance to the guest house is shown, featuring a solid black door with glass panels. A stylish doormat greets guests, while surrounding greenery adds a touch of nature. A pathway made of brick leads to the door, enhancing the inviting ambiance.

Guesthouse in Palo Alto

4.91 out of 5 average rating, 187 reviews

Downtown Palo Alto Gem! Cute, Spotless Guest House

We invite you to stay in our private, remodeled guest house. It's an easy walk to the restaurants and shops on University Avenue, in a safe and sought-after neighborhood in Downtown Palo Alto. The guest house was recently renovated and has a gorgeous bay window, air conditioning, two skylights, and a spa-like bathroom. We pride ourselves in keeping it absolutely spotless. The studio cottage is 200 square feet. It’s perfect for a single person but can also accommodate a couple.

Top guest favorite

An outdoor dining area features a long wooden table surrounded by several chairs, suitable for gatherings. Lush greenery and vibrant foliage create a serene environment, complemented by a barbecue grill nearby, inviting outdoor cooking and dining experiences.

Guesthouse in Palo Alto

4.98 out of 5 average rating, 257 reviews

*Airbnb PLUS* Mod Bungalow in Urban Farm Setting

Enjoy a private, high-quality designer experience on a rustic "urban farm". Make yourself at home amidst Mid-Century Modern furniture, a fully-stocked kitchen and luxurious bedding. Grill or hang out on a private patio. Families, friends, or business travelers will appreciate the proximity to downtown Palo Alto, Stanford, and tech companies. Safe and friendly neighborhood. We share fresh eggs from our chickens when in season. Private entrance and off-street parking for one car.

Top guest favorite

A spacious wooden deck is surrounded by towering redwood trees, creating a natural and serene atmosphere. It features a central fire pit with seating arranged around it, ideal for gathering. Additional chairs are positioned for comfort, adding to the inviting outdoor space.

Guesthouse in Woodside

4.97 out of 5 average rating, 255 reviews

SkyHigh Redwoods Retreat with Bay Views

Inhale. Exhale. Relax in this cozy, romantic guesthouse retreat nestled in the redwoods of the Santa Cruz Mountains, overlooking the bay and conveniently located near the famous Alice’s Restaurant on Skyline Blvd in Woodside. The 1 acre gated property has ample parking and privacy. Snuggle in with the wood burning fireplace, prepare meals in the full size kitchen and take in the views of the majestic redwoods right outside the windows with bay views peeking through the trees.

Guest favorite

The modern kitchen features sleek white cabinetry and stainless steel appliances. An eat-in island with seating for two is set with plates and glasses. Natural light is provided by multiple windows, highlighting the quartz countertops and decor elements in the open space.

Guesthouse in Redwood City

4.95 out of 5 average rating, 435 reviews

🌼Modern guesthouse w private patio and ♨️ hot tub

New and modern guesthouse, built in 2018, 20 min walk to downtown Redwood City. The kitchen comes fully equipped with high-end appliances, quartz countertops, Keurig coffee maker, and an eat-in island. In the living room, enjoy the 55" 4K TV with Bose sound on a sectional sofa that doubles as a pull-out bed. Rest well on a premium cal king size bed and enjoy a relaxing dip in the hot tub on your tranquil backyard patio. Unit has washer/dryer, heat/AC, and ensuite bath.

Top guest favorite

Guesthouse in Scotts Valley

4.97 out of 5 average rating, 117 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.

Guest favorite

Guesthouse in Woodside

4.93 out of 5 average rating, 144 reviews

A beautiful Tree house -your own retreat

This charming 2 bedrooms is nestled among the trees in beautiful Woodside, California. This town is 30 minutes from San Francisco and right behind Stanford University. Our tree house is a private, peaceful, modern and very comfortable detached guest house. The house has a fully equip kitchen, BBQ and very peaceful settings where you can enjoy nature hikes and be surrounded by peaceful trees and yet just minutes away from town.

Top guest favorite

A wooden deck features a railing overlooking a serene creek, surrounded by lush greenery. Four metal chairs are positioned along the deck, inviting relaxation. Sunlight filters through the trees, creating a peaceful outdoor setting.

Guesthouse in Woodside

4.99 out of 5 average rating, 536 reviews

Guest House in the Woods

Our guest house is located close to La Honda and Woodside in the North Santa Cruz Mountains. Located in the Redwood forest and looks down onto a beautiful creek from a lovely deck. There are many open space hiking and biking trails within a short drive, and the beach. 5 miles from Alice's Resturant. San Francisco and Santa Cruz are easily accessible. The house has vaulted ceilings and a full kitchen, and laundry.

Guest favorite

A wooden deck is adorned with potted plants and a seating area. A light-colored cabana features an open serving space and is complemented by string lights overhead. The area is surrounded by greenery, offering a sense of privacy and tranquility.

Guesthouse in Atherton

4.88 out of 5 average rating, 125 reviews

Guesthouse near Stanford, Palo Alto, Menlo Park

You’ll love our place because of the ambiance, the privacy, the quiet, the outdoors space, the neighborhood, and the comfy beds. Our guesthouse is good for couples, solo adventurers, business travelers. We live in the primary house on the property. We are close to the CalTrain station (1 mile/10 minutes by bike). We carefully follow enhanced cleaning protocols.

Guest favorite

An outdoor seating area is featured with several metal tables and chairs arranged under a clear blue sky. Mulched ground provides a natural surface, with trees and open grassy fields in the background. The surrounding landscape includes a mix of greenery and distant structures.

Guesthouse in Gilroy

4.89 out of 5 average rating, 410 reviews

Back-to-Eden Guest House on a Farm

Peaceful, comfortable guest house with 3 bedrooms and 2 baths plus spacious living room. Fresh country air, quiet surroundings, beautiful sunrise and sunset. 8-10 people max. Any larger group will need prior arrangement with the host. Super fun animal interaction tour may be available during your stay . Please inquire upon booking regarding joining a tour.