Tiny house holiday rentals in San Mateo County

4.93 out of 5 average rating, 830 reviews

A warm and inviting bedroom features a spacious bed with soft peach-colored bedding. A decorative pillow with a friendly message is placed at the head of the bed. A small nightstand with a lamp and a vase of yellow flowers adds a cheerful touch to the space.

Cottage in Daly City

Mini cottage near San Francisco & SF airport

Mini cottage w/ free parking. This tiny cottage (<200sf) is located in our beautiful backyard. It is close to everything. A 15 min drive to downtown San Francisco and SF airport. A 15 min walk to Westlake shopping center & BART station to San Francisco. The beautiful unit has a private entrance, one bedroom with a queen bed and a private bathroom. We provide Wi-fi, towels, instant coffee, tea, and snack. More amenities for you to use: TV, microwave, refrigerator, hair dryer & electric kettle

Guest suite in Boulder Creek

A serene river flows gently through a lush forest, surrounded by vibrant green foliage. Smooth rocks emerge from the water, which reflects the surrounding greenery. The scene conveys a peaceful natural environment, ideal for relaxation and exploration.

4.89 out of 5 average rating, 1,066 reviews

Redwood Riverfront Getaway

We are nestled in the beautiful California Redwood forest next to the San Lorenzo River. Guests can enjoy our private guest suite with its own entrance and full bathroom. Our property features tall trees, seasonal river swimming on our private beach, fishing, kayaking, and exploring. We are close to downtown Boulder Creek, minutes away from Santa Cruz, wine tasting, hiking, fine dining, and the coastline. We have no hidden fees and even offer a full return of our cleaning fee. Permit #181307

Guest house in San Carlos

The exterior of a cozy cottage is visible, surrounded by a lush garden filled with various plants and flowers. A stone path leads to the entrance, framed by vibrant greenery. Large windows allow glimpses of the inviting interior, enhanced by a seasonal wreath on the door.

4.99 out of 5 average rating, 766 reviews

Private Garden Cottage

Relax in our cozy cottage nestled in a serene garden setting, the perfect get-away after a day of business meetings or sightseeing. We are close to major Silicon Valley destinations; 30 minutes from San Francisco, San Jose and the beach in Half Moon Bay —with easy access to Highways 101 and 280, as well as public transportation (SamTrans, Caltrain and BART via Caltrain). Our quiet street is an easy 5-minute walk (0.2 mi) from downtown San Carlos with shops and literally dozens of restaurants.

Guest house in Half Moon Bay

The entrance is marked by red steps leading up to a wooden door, framed by lush greenery and bamboo. A colorful mat inscribed with 'HELLO' welcomes guests at the threshold, contributing to the inviting atmosphere of the cottage.

4.82 out of 5 average rating, 530 reviews

Cabin with firepit-near Coastal Trails & Harbor

Beach cottage in village of El Granada w/ocean view from property. Walk to Surfer’s beach, 2-minute drive to harbor. Bike or stroll on the paved coastal bluff trail. Kayak in the harbor. Hiking in the hills behind the cottage in Quarry Park. Full kitchen. Attached covered deck. Cable TV & WIFI. Queen size memory foam bed. Sit around the outdoor firepit at night-see the stars & hear the ocean waves. Boat harbor nearby with seafood restaurants, brew pubs & live music. 3 miles drive to Main St.

Guest house in Half Moon Bay

A sunset casts vibrant orange and purple hues across the sky, reflecting on the ocean's surface. Waves gently lap against a sandy shore, where several birds can be seen near the water's edge. A distant lighthouse is visible on the horizon.

4.92 out of 5 average rating, 441 reviews

Stylish Seaside Cottage - Walking to Beach

A perfect place for romantic getaways! newly built on top of our detached garage, 10mins walk to beach! private entrance, smart lock, modern skylights, quality linens, trendy decor, private deck with splendid ocean view, on-site parking! At the sunny beautiful El Granada, 4miles north of Half Moon Bay, a lot of fun activities: spending your days on the beach, exploring the hiking trails, trying out many local restaurants, or road trip along Highway 1, 30 mins to SF or 60 mins to Santa Cruz.

4.93 out of 5 average rating, 110 reviews

A small, Mediterranean-style guesthouse is depicted, featuring a charming doorway with a glass panel. To the side, a cozy seating area with a wicker chair and cushion is visible. An affectionate dog sits on the ground, surrounded by potted plants, adding a welcoming touch.

Guest house in Palo Alto

Peaceful & Safe Garden Guesthouse in Midtown PA

Recently painted, our quiet, safe, very clean and quaint Mediterranean style guesthouse, is located in a landscaped yard underneath a Redwood tree, and is suitable for only 1 guest. You can conveniently walk to Midtown neighborhood cafés, great eateries and markets. Quickly access the Stanford campus, Silicon Valley companies, San Antonio Shopping areas, and California Ave Caltrain Station by car. You're welcome to enjoy our backyard, nap in the hammock or work on the patio with WiFi access.

Guest house in Mountain View

A spacious bed is placed against a light-colored wall, accented by a decorative pillow featuring a geometric pattern. A bedside table holds a tissue box, while a lamp adds soft lighting. Natural light illuminates the room from a nearby open door.

4.99 out of 5 average rating, 112 reviews

Charming Peaceful New Studio in Mtn View

Our guest(s) can enter thru a well landscape garden to the studio's private entrance. Once inside, you can relax and enjoy a newly remodeled studio with a kitchenette, a washer/dryer combo unit, one queen size bed plus a spacious full bathroom. The studio also has a work friendly chair/desk, which can double as dining table, and two comfortable accent sofas for reading, chatting, etc. Pls check our other Airbnb unit < https://www.airbnb.com/rooms/7699331> if this studio is not available.

4.96 out of 5 average rating, 107 reviews

The exterior view of a modern guesthouse is presented, featuring bright white walls and a contrasting yellow trim. Large windows allow natural light into the interior, and a well-maintained lawn is visible in front, bordered by wooden fencing for privacy.

Home in Redwood City

Sunny 🌞 guesthouse near Stanford 🌲 w/private patio

Enjoy a stylish experience at this brand new, centrally-located 1 bed/1 bath guesthouse. Private driveway for off street parking with free EV charger. Sunny patio and lawn area for outdoor dining/ outdoor living space. Dedicated desk and free fiber internet/WiFi to work from home. Quiet, centrally located neighborhood walking distance to grocery, restaurants including Michelin star Selby’s & KL Wine store. 10 mins drive to Stanford 5 mins drive to Menlo Park DT 5 mins drive to RWC

4.96 out of 5 average rating, 275 reviews

The guest house is presented with a charming Tudor-style exterior, featuring a pitched roof and decorative wooden beams. Large glass doors provide a view into the interior space, framed by a covered porch supported by sturdy beams. Lush landscaping and a vibrant red entry gate enhance the inviting ambiance.

Home in San Carlos

The Perfectly Appointed Modern English Guest House

Relax and unwind in this newly constructed guest house. Completed in 2019 it offers all the amenities of a 5-star hotel suite with the privacy and ambiance of a quaint English Tudor home. Located just 2 blocks from charming downtown San Carlos in the “City of Good Living”. We are 30 minutes from San Francisco, San Jose and the beach in Half Moon Bay —with easy access to Highways 101 and 280, as well as public transportation (SamTrans, Caltrain and BART via Caltrain).

Place to stay in San Mateo

A scenic outdoor area is visible, featuring a trampoline alongside a grassy space. A deck extends toward the water, where a blue kayak and a boat with a cover are stationed. A shaded seating area is located nearby, with a view of the serene lake.

4.9 out of 5 average rating, 109 reviews

Cottage on the Water -SUP,Kayaking,Canoeing

Private Club House Water Front. Free use of stand-up paddle board, kayak, and canoe. Private entrance with Smartlock and wifi. Modern studio with full bathroom. and the kitchenette area is fully furnished for light cooking. Conveniently located near grocery, Target, Trader Joes, and restaurants. 5 minutes from Downtown San Mateo, and 10 minutes from SF Airport. Looking to get away from the bay area without actually leaving, nice escape.

4.97 out of 5 average rating, 501 reviews

A well-lit guestroom features a queen-size bed with floral bedding. A spacious loveseat sofa is positioned near a sliding glass door that opens to the backyard. A small coffee table rests in front of the sofa, and a portable air conditioner is visible in the corner.

Guest house in Pacifica

Elegant Guesthouse in Garden Close to SF/SFO/Beach

Built in 2020, our guesthouse is the perfect place for couples or solo travelers. It has a private entrance, smart lock, hotel-quality bedding, brand-new furniture, and the latest interior design selections. Staying in the sunbelt of beautiful Pacifica, there are a lot of fun activities nearby: spending your day on the beach, exploring the hiking trails, or road trip along Highway 1. Half Moon Bay, SF, and SFO are around 20 minutes away!