Guesthouse holiday rentals in Santa Cruz

4.96 out of 5 average rating, 209 reviews

The cottage is framed by lush greenery and tall trees, featuring a welcoming entrance with steps leading to a porch. A gravel walkway and landscaped areas with plants create a serene outdoor setting, inviting guests to explore.

Guesthouse in Felton

Felton Forest Cottage Near Henry Cowell State Park

Your new weekend retreat! The Cottage is situated on unique forest-farm acreage across the street from Henry Cowell Redwoods State Park, surrounded by redwood fairy circles and a beautiful stream. [Permit #: 181566] Charming, private, and yet handily walkable/drivable to parks surrounding the town of Felton and the Santa Cruz Mountain area. About 1 hour south of San Francisco, we're a quick 14 minute drive down picturesque Highway 9 to downtown Santa Cruz and it's popular beaches and Boardwalk.

Guesthouse in Boulder Creek

A solid entry door is framed by a welcoming blue wall with a plant-filled window. A rustic wooden table, stacked with firewood, offers a natural touch. A welcome mat lies neatly at the threshold, inviting guests into the cozy space.

4.98 out of 5 average rating, 254 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.

4.94 out of 5 average rating, 743 reviews

A spacious sleeping area features a comfortable bed adorned with a white coverlet and decorative pillows. Two windows allow natural light to illuminate the room. A cozy armchair is situated nearby, and the entrance to a kitchen area is visible in the background.

Guesthouse in Santa Cruz

Cozy garden westside king suite STR18-0122

This cool and comfortable private space is a great spot to stay while visiting Santa Cruz. Close to everything yet private with its own private entrance and in a quiet setting with an outdoor sitting area. The neighborhood is old Santa Cruz and close to everything. Don’t forget the comfortable king bed! The best deal in Santa cruz! IMPORTANT NOTE: I am required to collect the city mandated short term rental tax in cash when you arrive because the city of Santa Cruz . Please have it ready.

Guesthouse in Upper Seabright

The exterior features a welcoming entrance with a wooden front door and a bench positioned on a paver path. A well-maintained garden with flowers is visible alongside the house, framed by natural wood fencing, and a large window allows natural light into the interior.

4.94 out of 5 average rating, 200 reviews

Cozy 1-Bedroom duplex in Seabright

Walk to Boardwalk, beach and restaurants. One bedroom duplex located in lower Seabright is cozy and clean. Everything you will need including washer/dryer, cable TV, wifi, etc. There is a full kitchen with gas stove, full size refrigerator, microwave and dishwasher. The bedroom has a queen bed and plenty of storage to unpack. There is a twin sofa sleeper in the living room. Check in is 4 pm and check out is 11 am. We do not host pets. We only host guests with positive host ratings.

4.8 out of 5 average rating, 791 reviews

The cottage is set against a backdrop of the ocean, featuring a terracotta roof and white walls. Palm trees frame the entrance, while vibrant flowers adorn the pathway leading to the door. The expansive view of the water is visible beyond the landscaped garden.

Guesthouse in Aptos

The Cottage Getaway by the Sea

The Cottage Getaway by the Sea is a single level one bedroom stand alone cottage on a cliff over Rio Del Mar Beach w/ 180 degree WOW views of the Monterey Bay. Seasonally enjoy dolphins, whales, & great sunsets! Located in a peaceful neighborhood, this is a perfect place for a quiet romantic getaway or just to read, relax, & enjoy. We are one of the few airbnbs with a California King Bed! Pricing is per night for one; 2nd person +$25 per nite PERMITTED vacation rental #181420

4.96 out of 5 average rating, 313 reviews

Tall redwood trees rise from the forest floor, creating a serene canopy. A distant view of the bay is visible through the trees, with a blanket of clouds resting over the landscape. The sky is clear, contrasting with the lush greenery of the forest.

Guesthouse in Woodside

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.

Guesthouse in Scotts Valley

A spacious sleeping area is highlighted by a large bed featuring white bedding. Two windows allow natural light to fill the room, offering views of greenery. A small table with two stools is positioned near the windows, and modern lighting fixtures complement the overall design.

4.92 out of 5 average rating, 181 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!

Guesthouse in Almaden Valley

An outdoor area features a serene pool surrounded by blooming flowers and lush greenery. The distant horizon showcases a sparkling view of the city lights below, under a clear evening sky transitioning from dusk to night.

4.97 out of 5 average rating, 1,001 reviews

Cabana in Sierra Azul Open Space Preserve

Nestled in the Sierra Azul Mountain Range in Los Gatos, we enjoy AMAZING unobstructed views of the Entire Silicon Valley... San Francisco to Gilroy from 1700ft altitude! This private retreat is perfect for relaxing and rejuvenating, surrounded by forest, streams and wildlife! Relax in complete solitude, refresh with chemical-free, great tasting spring water and crisp clean air high above the smog of Silicon Valley! Great Hiking/Biking Trails at your backdoor!

Guesthouse in Upper Seabright

A cozy living space is presented with a daybed adorned with an assortment of colorful pillows, complemented by a natural wood coffee table. Light enters through large windows, highlighting a vibrant piece of wall art. A small desk and chair are positioned nearby.

4.91 out of 5 average rating, 713 reviews

Sunny Harborside Bungalow

Private small cozy 1 br/1ba bungalow. This space boasts a taste of Latin American beach, Spanish tile floors and wood furniture. Kitchenette with an induction burner and xl toaster oven (no range) , full size fridge, private patio seating, umbrella, tropical plants. Bathroom with a small shower. Curtained off bedroom with full closet, queen bed. Living room has day bed/couch with twin mattress for 3rd guest. Plz read “other details to note” before booking.

4.89 out of 5 average rating, 646 reviews

A light-filled living area features a comfortable gray sofa and a smart TV on a modern stand. French doors open to the outdoors, while a decorative plant adds a touch of greenery. A brown chair and a white rug complete the inviting space.

Guesthouse in Santa Cruz

Santa Cruz Guesthouse Surrounded by Redwoods

Get back in touch with nature in a farmhouse-style property next to abundant woodlands and hiking trails (Permit 181242). It's an airy, skylit space with honey-colored hardwood floors and a well-equipped kitchen. Bathe in a claw-foot tub and relax on a wooden porch. Please note that this house shares the property with the owners who live in the main house, and an Airstream. The property is also serviced by landscapers and pest services.

Guesthouse in Scotts Valley

A cozy sleeping area features a spacious bed with a dark blue quilt and multiple patterned pillows. Framed artwork depicting serene landscapes adorns the walls, while a small nightstand with an orange lamp adds a pop of color.

4.9 out of 5 average rating, 135 reviews

The Hideaway: Sunny 2BR Apartment in the Redwoods

Welcome to our spacious 2-bedroom, 1-bath apartment in the heart of the Redwoods! With towering trees all around, you'll feel like you're truly escaping into nature. Enjoy the beautiful scenery and fresh air from the comfort of your own oversized deck, complete with an outdoor dining table and umbrella with lights - perfect for relaxing after a day of exploring.

4.98 out of 5 average rating, 220 reviews

The entrance showcases a welcoming door with four rectangular windows above an intricate design. The door is painted in a soft green shade, framed by white siding and complemented by a modern black pendant light hanging from the eaves.

Guesthouse in Santa Cruz

Modern Cottage in Santa Cruz

Adventure awaits you here in Santa Cruz! Whether you’re coming to enjoy the hiking of nearby Henry Cowell Redwoods State Park or heading down to Pleasure Point for a surf, we’re close to it all! Here you’ll find the perfect place to get some R&R after a busy, adventure filled day. Keep it simple at this peaceful and centrally-located spot.

Popular amenities for Santa Cruz guesthouses

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-Friendly guesthouses

Guesthouse in Monte Sereno

The cottage exterior features a charming design with a slate stone patio and a round dining table with two chairs. Glass double doors provide access, and large windows offer views of the surrounding greenery. The roof is intricately shaped, complementing the natural setting.

4.98 out of 5 average rating, 446 reviews

Quiet Poolside Cottage for Solitude

4.83 out of 5 average rating, 581 reviews

Tall redwoods provide a natural canopy, creating a serene atmosphere with dappled sunlight filtering through the leaves. A forest floor of soft mulch and green undergrowth complements the tranquil setting, inviting exploration and reflection.

Guesthouse in Los Gatos

Rustic Cottage, Redwoods, Beaches.

4.94 out of 5 average rating, 227 reviews

A studio space features sloped ceilings with natural light from skylights. A full-sized bed is dressed in patterned linens, accompanied by a 43-inch smart TV on a low wooden console. A single armchair with an ottoman is positioned near a dark dresser.

Guesthouse in Hensley

Private Entrance Studio with in-unit bathroom

Guesthouse in Willow Glen

The exterior of the studio is framed by a stone facade, featuring large glass doors that open to reveal a cozy interior. Plush seating and a dining table are visible inside, with the gourmet kitchen in the background. Natural light brightens the space, enhanced by the greenery outside.

4.99 out of 5 average rating, 211 reviews

TheStudio in Willow Glen (San Jose) CA-95125

4.96 out of 5 average rating, 446 reviews

The entrance to the studio cottage is framed by lush greenery, with steps leading up to an open door. Natural light spills into the interior, showcasing wooden accents and inviting outdoor space. Paved stones create a pathway, bordered by a wooden fence.

Guesthouse in Sunnyvale

Private cottage in a garden

Guesthouse in Santa Clara

4.94 out of 5 average rating, 102 reviews

Guest House w/King Bed and Parking in Santa Clara

A private entrance is visible, featuring a white door with decorative glass. A small window is positioned to the right, allowing natural light. A potted plant provides a touch of greenery, and a wooden fence creates a sense of privacy.

4.85 out of 5 average rating, 110 reviews

Adorable cottage in Burbank area of San Jose

4.92 out of 5 average rating, 104 reviews

A spacious yard features a children's play structure with a slide and swings, accompanied by a patio seating area under a shade umbrella. Lush green grass enhances the outdoor setting, surrounded by wooden fencing for privacy.

Guesthouse in Sunnyvale

Sunnyvale2B/1B/Family/Free EV Charging/AC/WiFi/PKG

Guesthouses with a patio

Guesthouse in Moss Landing

The entrance to a rustic studio features a covered porch with white wicker chairs and a hanging chair. Light-colored flooring leads into the interior where a cozy sleeping area can be seen, enhancing the warm welcome of this private space.

4.9 out of 5 average rating, 139 reviews

Artsy&Private UNIT C

4.96 out of 5 average rating, 115 reviews

A bright kitchen area features white cabinetry and modern appliances, including a stove, refrigerator, and washer/dryer unit. A small rug adds a touch of warmth to the space. Countertops are clear and equipped with essential cooking items, creating a functional and inviting cooking environment.

Guesthouse in Japantown

Cozy Private 1B1B Cottage near Japantown

A bright living area features a dark leather sofa adorned with decorative pillows, accompanied by a wooden coffee table. A small table with two chairs is positioned beside a large window, allowing natural light to illuminate the space. A floor lamp and decorative plant enhance the room's inviting feel.

4.94 out of 5 average rating, 167 reviews

Newly built stylish guesthouse

4.99 out of 5 average rating, 117 reviews

A spacious deck features two wooden directors' chairs positioned around a small circular table. Lush greenery lines the perimeter, creating a natural backdrop. A sunshade is partially visible, offering protection from the sunlight.

Guesthouse in San Carlos

Delightful Hideaway in San Carlos

A newly constructed guest house is displayed, featuring a modern design with a sloped roof and solar panels. The exterior includes a combination of white stucco and dark accents. A landscaped area with grass and gravel pathways leads to the entrance, complemented by a tree and outdoor seating.

4.96 out of 5 average rating, 116 reviews

Garden Cottage w/ Hot Tub • 3 mi. to SJC

4.89 out of 5 average rating, 143 reviews

A spacious studio is displayed, featuring a light-filled sleeping area with a cozy bed, adorned with crisp white linens and decorative pillows. A small dining table with two chairs is positioned nearby, along with a stylish desk and chair. Soft lighting enhances the overall warmth of the space.

Guesthouse in Palo Alto

Palo Alto Cottage: Privacy, Comfort & Convenience

4.93 out of 5 average rating, 230 reviews

A welcoming entrance to the studio is framed by wooden fencing and highlighted by a sign that reads 'Park Studio.' Large terracotta pots with blooming flowers and lush greenery add a touch of nature, creating an inviting atmosphere.

Guesthouse in Menlo Park

Charming, modern, restorative, private studio

Guesthouse in Willow Glen

A bright living area features a light grey sofa with decorative pillows, paired with a round black coffee table. A teal armchair is positioned nearby. Large windows with striped shades allow natural light to fill the space, complemented by a tall indoor plant.

4.94 out of 5 average rating, 101 reviews

Adorable 2 bed guesthouse walk to Willow Glen DWTN

Guest house rentals with a washing machine and dryer

4.93 out of 5 average rating, 346 reviews

The guesthouse entrance is framed by a neatly landscaped area, featuring a spacious path made of stone tiles leading to the front door. Elegant wrought iron railings and manicured greenery enhance the inviting setting under clear blue skies.

Guesthouse in Evergreen

Evergreen Valley Hillside retreat

Guesthouse in The Willows

A private patio area is featured, furnished with two seating areas and a central table. An umbrella provides shade, while potted plants add greenery to the space. The wooden fence offers privacy, and the stone floor is complemented by a textured outdoor rug.

4.99 out of 5 average rating, 148 reviews

Quaint Cottage Near Downtown Palo Alto

Guesthouse in Almaden Valley

5 out of 5 average rating, 112 reviews

Newly Built | Modern 1BR/1BA Private Cottage

Superhost

A light-filled living area features a fold-out sofa bed and a wooden dining table surrounded by four chairs. A wall-mounted TV is visible, along with a small coffee station on a dark table. A doorway leads to the bathroom, and a window provides natural light.

Guesthouse in Downtown San Jose

4.78 out of 5 average rating, 519 reviews

Beautiful private guest house in downtown San Jose

Superhost

A charming outdoor patio area features a round table surrounded by four decorative chairs. Lush greenery decorates the space, including potted plants and foliage. Two turquoise doors are complemented by wall-mounted lanterns and classical sculptures, creating a peaceful setting for relaxation.

Guesthouse in Monte Sereno

4.84 out of 5 average rating, 166 reviews

Private Cozy Suite Los Gatos - Saratoga

4.98 out of 5 average rating, 330 reviews

A cozy seating area features a brown leather sofa accompanied by a white throw pillow, positioned on a soft, light rug. A glass coffee table sits in front, while two modern chairs with metallic frames are positioned at a nearby desk. Natural light enters through a window, illuminating the space.

Guesthouse in Campbell

Downtown Campbell Executive Cottage

4.98 out of 5 average rating, 232 reviews

A cozy living area features a stylish brown leather sofa and a round dining table accompanied by black chairs. Large glass doors invite natural light and provide views of the shared backyard. A modern kitchen is situated in the background, enhancing the open layout.

Guesthouse in Hensley

Private Abodu Guesthouse in Downtown San Jose

An exterior view of the cottage showcases a spacious patio area, featuring a dining set with an umbrella. The home is painted in a light color, complemented by a well-manicured garden. A stone fountain stands to the side, adding to the tranquil outdoor setting.