Best Vacation Rentals in Woodside

Set in the heart of Silicon Valley, Rosewood Sand Hill unfolds over 16 acres near the Santa Cruz Mountains. The urban retreat charms both business and leisure travelers with resort amenities and a relaxed translation of luxury. Each air-conditioned guest room at our hotel is a haven of comfort and luxury. Equipped with a flat-screen HDTV with satellite channels and movies on demand, walk-in closets, bathrobes and slippers, and Nespresso coffee machines, our rooms are designed to cater to your every need. Step out onto your private terrace or balcony, furnished for your comfort, and enjoy breathtaking views of the gardens, pool area, or the Santa Cruz Mountains. The building's architecture features neutral hues complimented by rich wood tones of walnut, cherry, and cedar. Guests can also enjoy our in-room dining, housekeeping, and turn-down service. Overnight laundry and dry cleaning services are also available. Overnight shoeshine is complimentary. Valet parking is also available. At Rosewood Sand Hill, we understand that dining is an integral part of your stay. That's why we offer a variety of dining options to cater to every palate. Madera restaurant, with its menu of regional cuisine and locally grown produce, offers a dining experience like no other. The relaxing dining room, with its sweeping views of the local Santa Cruz Mountains, sets the perfect backdrop for a memorable meal. For a quick bite, Madera Bar and our outdoor pool offer a selection of light meals, sandwiches, and snacks. Explore various experiences designed to deepen connections and forge enduring memories, like test-driving our onsite Lucid Air and taking our electric Bluejay Bikes to discover our breathtaking surroundings. Embark on unforgettable cycling adventures in the heart of the Bay Area. Explore the stunning Skyline Boulevard, a haven for road cyclists, while staying at Rosewood Sand Hill. The Rosewood Sand Hill fitness center is equipped with state-of-the-art equipment, including cardiovascular, weight, and Kinesis machines. Group fitness classes are offered throughout the week in the Movement Studio. If guests prefer, professional trainers are available for private sessions.

Balcony/Terrace • Tv • Hot Tub • Restaurant • Transportation/Shuttle • Breakfast • Pool • Oceanfront • Other • Internet • Business Services • Accessibility

Luxury hotel with 2 restaurants and a full-service spa
This smoke-free hotel features 2 restaurants, a full-service spa, and an outdoor pool. Free WiFi in public areas and a free area shuttle are also provided. Additionally, a health club, a bar/lounge, and a poolside bar are onsite.
Rosewood Sand Hill offers 121 accommodations, which are accessible via exterior corridors and feature iPod docking stations and DVD players. Beds feature Frette Italian sheets and premium bedding. 50-inch flat-screen televisions come with premium satellite channels and pay movies. Guests can make use of the in-room coffee/tea makers and minibars. Bathrooms include separate bathtubs and showers, bathrobes, slippers, and designer toiletries.

Guests can surf the web using the complimentary wireless Internet access (speed: 100+ Mbps (good for 1–2 people or up to 6 devices)). Business-friendly amenities include laptop-compatible safes and phones; free local calls are provided (restrictions may apply). Additionally, rooms include hair dryers and irons/ironing boards. Housekeeping is offered daily and hypo-allergenic bedding can be requested. Renovation of all guestrooms was completed in June 2020.

The recreational activities listed below are available either on site or nearby; fees may apply.

- "One of my favorite places to stay when I am in the area working. " - "Good" - "Very nice property. Service is excellent " - "Everything about the check-in experience, from the information about reservations we had made, to the on-site amenities were clearly described to us. The staff were very open and welcome, which contributed to a fantastic stay." - "Beautiful classy modern spacious quiet luxurious … what a great resort! Highly recommended no hesitation we will go back again. "

Log-Cabin Home Retreat - Walk to Restaurants Trails Hiking & Biking offers accommodations in Palo Alto, 19 miles from Shoreline Amphitheatre and 28 miles from San Jose Convention Center. There's an outdoor fireplace and guests can use free Wifi and free private parking. This vacation home includes 3 bedrooms, a living room and a TV, an equipped kitchen with a dining area, and 2 bathrooms with a bath and a washing machine. Towels and bed linen are provided in the vacation home. There's also a seating area and a fireplace. The nearest airport is San Francisco International Airport, 24 miles from the vacation home.

- "A lovely property rather let down by poor mainenance."

Escape to a secluded retreat featuring a queen bed plus spacious sectional sofa that can sleep another two,
total for four people. The ambiance of a wine country getaway with a sprawling yard, heated pool and rejuvenating spa. Enjoy the picturesque setting reminiscent of a lush vineyard. Shower bathroom. Kitchenette with two-hot plate, microwave, dishwasher, coffee maker, tea pot. Take advantage of the salt water pool, spa, and outdoor area exclusively available for your enjoyment.
One large casita with a full bath, pool and hot tub on premises. The house on the property is not part of the rental. You will have exclusive use of casita and backyard while you stay. Four people limit including kids strictly enforced or there will be an additional charge per person. No party use is included. We are an exclusive residential community so big loud parties with music are not allowed.We have cameras on the perimeter property and the number of people strictly enforced.
Pool is salt water, heated. cleaned once a week and occasionally you will see a few leaves on the surface. Auto pool cleaner will pick those up when it turns on during daytime. . The decks and the lawn around your house are your exclusive domain.
You have a kitchenette with a two hot plate, microwave, dishwasher, minifridge (formerly a wine cooler) , coffee maker and a tea pot. We provide to basic plates, cups and wine glasses and utensils for four people. Pot, pan basic kitchen utensils.
A gorgeous secluded backyard with seating area plus a huge covered deck with a dining area, all private for your exclusive use.
Outdoor pool and spa use until 10:30 pm only.

- "Had a contract worker stay here and he was very satisfied, clean and spacious property " - "Great stay, quiet isolated location in the Redwood City hills, beautiful property, fairly simple check-in. Space was large enough for two people, great option for our Stanford recovery." - "A place to quickly crash for a simple adult but definitely not a couple or family. The place could be so much better if hosts would keep better care and clean of it. Sadly wouldn’t recommend.. only positive is the view was nice and location was good for us because of close friends. "

3BR Home Near Stanford Great Back Yard King Bed is located in Menlo Park, just 11 miles from Shoreline Amphitheatre and 23 miles from San Jose Convention Center. Both free Wifi and parking on-site are accessible at the vacation home free of charge. 3BR Home Near Stanford Great Back Yard King Bed features 3 bedrooms, a fully equipped kitchen with a dishwasher and an oven, a washing machine, and 2 bathrooms with a hair dryer. Towels and bed linen are offered in the vacation home. For added privacy, the accommodation features a private entrance. Oracle Park is 31 miles from the accommodation. San Francisco International Airport is 17 miles from the property.

Air Conditioner • Internet • Fireplace/Heating • Security/Safety • Parking

A calming oasis in the heart of Silicon Valley -- spacious yet cozy home with lots of privacy, a lovely garden, set in a family oriented neighborhood.

The owner lives in the home for half the year, ensuring it is meticulously maintained and filled with personal touches that create a warm and welcoming atmosphere. This is not just a rental property—it’s a well-loved home, thoughtfully cared for with attention to detail, so you can enjoy the comfort and charm of a truly unique space.

Originally built by an architect for his own family, it also features a seamless layout for effortless living.

- "Booked this gorgeous abode for a visiting consultant who was coming onsite at Stanford for a 13 night stay. Our guest stressed to us many times that he and his spouse had such a lovely experience as they loved the home and that the hosts were very attentive. Speaking on personal experience with booking, I want to thank Amanda, Kate, and Ted for being such lovely hosts to our guests. Special thank you to Amanda for being so incredibly responsive and taking time to work things out with me when we had to make last minute adjustments to our booking due to my personal error. Highly recommend this accommodation to those looking to be within close proximity of Stanford."

@ Marbella Lane - Elegant and Inviting Home in RWC offers accommodations in Redwood City, 13 miles from Shoreline Amphitheatre and 25 miles from San Jose Convention Center. The property is around 28 miles from Oracle Park, 28 miles from San Francisco City Hall, and 29 miles from Moscone Center. The vacation home features free Wifi and free private parking. The air-conditioned vacation home also provides a flat-screen TV, a fully equipped kitchen with a dishwasher, a seating area, washing machine, and 3 bathrooms with a bath and a shower. For added privacy, the accommodation features a private entrance. Guests can also relax in the garden. The nearest airport is San Francisco International Airport, 14 miles from the vacation home.

Parking • Child Friendly • Internet • Other • Air Conditioner • Guest Services • View • Security/Safety

With 14' vaulted ceiling, hand-hewn beams, diamond plaster interior walls, surrounded with stone walls and lush gardens, you will find yourself immersed in the spirit of a perfect getaway in a 1920 Hollywood resort, yet experience the most exquisite luxury & comforts in the heart of Silicon Valley! Explore and relax in the tranquil natural surroundings this 4-acre oak studded estate has to offer, a tropical conservatory, perfect pool and infinity edge spa. Close to Woodside downtown, Highway 280, Silicon Valley, Sand Hill VC firms, Stanford University and Hospital. A short drive to San Francisco. SFO and SJC are only 25 minutes away.

- "Amazing property! The location is great, in a quant little town and the property itself could not be more beautiful. Every detail is amazing, executed very lovely. Beds are comfortable. Host was very responsive. "

Entire Mountain Cottage Home - Restaurants Amazing Hiking & Biking Trails offers accommodations in Palo Alto, 19 miles from Shoreline Amphitheatre and 28 miles from San Jose Convention Center. There's an outdoor fireplace and guests can use free Wifi and free private parking. This apartment comes with a fully equipped kitchen, a seating area, a dining area, and a TV. Towels and bed linen are available in the apartment. The accommodation has a fireplace. Guests at the apartment will be able to enjoy activities in and around Palo Alto, like cycling. The nearest airport is San Francisco International Airport, 24 miles from Entire Mountain Cottage Home - Restaurants Amazing Hiking & Biking Trails.

- "Overall, it was a delightful time." - "Hidden gem in the woods!" - "Just wonderful!" - "My girlfriend and I cherished every minute in this cozy little place. Total home away from home." - "Beautiful little getaway that would be perfect for a couple. Small fixes will make this 5 stars." - "Cute place"

Find an elegant escape in the heart of Menlo Park when you book this 1-bedroom, 1-bathroom vacation rental cottage. Treat your loved one to a romantic getaway with English countryside elegance — from the patio overflowing with flora and fauna to the pristine landscaped English garden. Head out to walk or bike around Menlo Park or get your retail therapy in at the Stanford Shopping Center. If you fancy a trip to the coast, this cozy cottage is sure to be the place for you.

-- THE PROPERTY --

Furnished Patio | Free WiFi | 2 Mi to Stanford University

Bedroom: Queen Bed

OUTDOOR LIVING: Bistro table, outdoor seating, garden, charcoal grill
INDOOR LIVING: Cable TV, dining table, desk workspace, vaulted ceilings, recessed lighting
KITCHEN: Cooking basics, microwave, drip coffee maker, kettle, dishware/flatware
GENERAL: Central heating & A/C, towels/linens, cleaning essentials, washer & dryer
FAQ: Stairs required, homeowner on-site (main house) w/ shared outdoor spaces
PARKING: Street parking (first come, first served)

-- THE LOCATION --

STANFORD UNIVERSITY (2 miles): Stanford Stadium, Iris & B. Gerald Cantor Center for Visual Arts, Frost Amphitheater, Stanford Maples Pavilion
ATTRACTIONS: Filoli (11 miles), Intel Museum (15 miles), California's Great America (15 miles), Winchester Mystery (20 miles)
DAY TRIPS: San Jose (20 miles), Half Moon Bay State Beach - Venice Beach (23 miles), San Francisco (32 miles), Golden Gate National Recreation Area (38 miles), Big Basin Redwoods State Park (47 miles)
SILICON VALLEY: Facebook (3 miles), Googleplex (7 miles), Intel (15 miles), Apple Park (17 miles), PayPal (17 miles)
AIRPORTS: Norman Y. Mineta San Jose International Airport (18 miles), San Francisco International Airport (18 miles)

-- REST EASY WITH US --

Evolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.

-- POLICIES --

- No smoking
- No pets allowed
- No events, parties or large gatherings
- Additional fees and taxes may apply
- Photo ID may be required upon check-in
- NOTE: the homeowner lives on site with 2 chihuahuas, in a completely separate unit, with some shared outdoor amenities
- NOTE: Stairs are required to enter the property

- "This is a cute little two room cabin, set amidst several beautiful small garden areas. Although over all on the small side, the rooms were completely adequate in space to effortlessly move around. Owners were there part of the time and were very helpful. Sitting in the garden with a champagne breakfast was heavenly." - "Loved our stay! We used this as a home base to move my daughter into her dorm - it's very conveniently located close to campus. Though it's in a quiet neighborhood, many amenities are nearby - a Safeway, many restaurants, and Stanford Shopping Center. The cottage itself is tucked behind the owner's home, but access is easy, and includes an adorable (very friendly) canine welcoming committee. If dogs aren't your thing, don't worry, these dogs won't bother you at all, but are happy to receive a tummy rub if you wish. The cottage itself was spotless, with a modern, well-supplied kitchen and bathroom. The queen-sized bed was very comfy, and nights were wonderfully quiet and peaceful, with lovely gardens and outside sitting areas around you. Though we didn't need it, there is A/C, as well as a washer and dryer, and TV with cable. The owners are super friendly if you need them, but the cottage feels very private if you don't. Ample street parking is available with little street traffic. Would stay again! "

11 miles from Shoreline Amphitheatre in Menlo Park, Updated Menlo Park English Tudor Garden Cottage! features accommodations with access to a spa center. Free Wifi is offered throughout the property and private parking is available on site. The vacation home features 1 bedroom, a fully equipped kitchen with an oven and a microwave, a washing machine, and 1 bathroom with a hair dryer. Towels and bed linen are available in the vacation home. For added privacy, the accommodation features a private entrance. Guests can relax in the garden at the property. San Jose Convention Center is 23 miles from Updated Menlo Park English Tudor Garden Cottage!. San Francisco International Airport is 17 miles from the property.

- "Nice well furnished cottage in Menlo Park" - "Charming Cottage Escape Near Stanford: Perfect for a Relaxing Stay" - "A lovely cottage in a leafy quiet neighborhood, it had everything I needed and was perfectly clean."

Enjoy a private, comfortable stay in silicon valley in a fully equipped cottage with wonderful bay views. Located 15 minutes away from Stanford and 25 miles from San Francisco, this home is suitable for 3 adults or a small family of 4.

This sunny, quiet and clean cottage has a king bed and a queen sized futon. An extra twin mattress can be placed upon request, and all necessary linens are provided to make your stay comfortable.

The cottage has air conditioning and heating systems, as well as a ceiling fan. There is a dining table and a work desk, as well as ample room for storage. It has a fully equipped kitchen including microwave, coffee maker, toaster oven, cooking and dining utensils. A full bathroom equipped with hairdryer and toiletries, Wi-Fi, flat screen TV with Cable and DVD player are also included.

The cottage has private access and a furnished outdoor lounge patio with a beautiful view of the San Francisco Bay area. There is private parking, no need to park on the street. Linen and cleaning services are available upon request, with an additional charge. Laundry facilities are available on premises, with use upon request.

Your privacy is valued, so you can access the cottage independently and you will be provided with your own entry code/key. A package with basic information about the area (favorite local restaurants, entertainment, markets, hospitals, pharmacies) will be awaiting you upon arrival. However, if you were to need indications about the area, or any additional help, we are happy provide them.

The home is located strategically in a safe, green neighbourhood in the heart of silicon valley, 5 minutes away from downtown amenities, movie theaters, shops and hospitals. There is a large natural reserve with beautiful hiking trails walking distance from our house. One of the main connecting highways between San Francisco and San Jose (280) is 5 minutes away. Less than 10 minutes away is the Redwood City Caltrain Station that connects you to the entire Bay Area including SFO, San Francisco and Bart if you wish to cross the Bay. There is a bus line a 15 minute walk away, and buses in the area easily connect you to neighboring locations such as Menlo Park and Palo Alto.

- "Absolutely incredible place to stay for relaxing and unwinding. Can not recommend staying here enough. We will be staying here anytime we are traveling to the San Francisco Area. Beyond impressed and thrilled with our getaway." - "Highly recommend! Great hosts..." - "Well maintained, clean and comfortable with lovely view." - "Really enjoyed my stay. Nice little patio to sit and enjoy the view, had everything I needed for my solo stay. Would come back."

14 miles from Shoreline Amphitheatre in Woodside, Exquisite Estately Villa provides accommodations with access to a hot tub. With mountain views, this accommodation offers a terrace and a swimming pool. The homestay features rooms with air conditioning, free private parking, and free Wifi. At the homestay, the units are equipped with a desk. Rooms have a coffee machine and a private bathroom with a walk-in shower and bathrobes, while some rooms also boast a fully equipped kitchen. At the homestay, units have bed linen and towels. Guests at the homestay can enjoy hiking nearby, or make the most of the garden. San Jose Convention Center is 24 miles from Exquisite Estately Villa. San Francisco International Airport is 18 miles from the property.

- "Beautiful place and great location" - "Qian's estate in Woodside is one of the most exquisite and idyllic settings in the Bay Area. The acc" - "Beautiful and restful location, short walk to coffee, dinner and groceries."

Reminiscent of a 1920's Hollywood villa, enjoy the aesthetics of that romantic age, yet experience 5 star luxury pampering & the most modern of comforts. Explore and relax in the tranquil natural surroundings this 4-acre oak studded estate has to offer, a tropical conservatory, perfect pool and infinity edge spa. Close to Woodside, Highway 280, Silicon Valley, Sand Hill VC firms, Stanford University and Hospital. A short drive to San Francisco. SFO and SJC are only 25 minutes away.

- "We truly enjoyed our stay in this studio located on a beautiful property near the heart of Woodside. The kitchen with marble counters was well outfitted, the living space was refined and comfortable, and the king bed was sumptuous. We had access to the pool and patio areas, which were gorgeous. The hosts were highly responsive. I highly recommend a visit." - "We had a lovely time in Qian’s luxurious guest suite. It was very clean, tidy and thoughtfully appointed. The grounds are stunning and we enjoyed relaxing in the spa and just sitting outside. Qian was warm, inviting, and responsive We would stay here again."

Beautiful Studio is located in Redwood City, just 12 miles from Shoreline Amphitheatre and 25 miles from San Jose Convention Center. This apartment is 29 miles from Oracle Park and 30 miles from Moscone Center. The apartment also offers free Wifi and free private parking. The air-conditioned apartment consists of 1 separate bedroom, 1 bathroom with bathrobes and a hair dryer, and a seating area. There is a dining area and a kitchen complete with an oven, a microwave, and a toaster. Additional in-room amenities include wine or champagne. Guests at the apartment will be able to enjoy activities in and around Redwood City, like hiking. The nearest airport is San Francisco International Airport, 15 miles from Beautiful Studio.

- "Like home." - "This was my second stay at his property. I liked it so well the first week I stayed I rented it for a second week."

STONEWOOD GUEST HOUSE is a luxury private guest house on a gated estate. It is a completely separate house and has a private entrance. It's newly remodeled with high-end finishes & furnishings, garage & parking. It has 2 bedrooms, 2 bathrooms, & private patio w/table, lounge chairs, fountain, & grill. No detail has been left out including a fully stocked gourmet kitchen, dishwasher, front loading washer & dryer, fireplace, flat screen tv's with premium cable in the living room and both bedrooms, luxurious linens (bedding & towels), plenty of closet space with hangers, ceiling fans, blue tooth speakers, alarm clock with sleep sound machine, hair dryers, dedicated work space with color printer/scanner/ paper/toner & basic office supplies, wireless internet, original artwork, and basic amenities (shampoo/ conditioner, shower gel, q-tips, cotton balls, bathroom tissue, facial tissues, laundry detergent, dish detergent, fire extinguishers, smoke alarms, carbon monoxide alarms, first aid kit, etc.). The main house has several wooded acres, a pool, & pond with fish and turtles.

Woodside is a beautiful upscale neighborhood known for its horses and bicycling (road & mountain). The house is located in the heart of Woodside with easy freeway access, it's in close commutable distance to all airports (SFO, SJC, & OAK), San Francisco, San Jose, and the coast. Its just, minutes from Stanford, Redwood City, Palo Alto, Menlo Park, San Carlos, & Mountain View.

- "Will be back soon!" - "Great short stay and Great hostess!" - "Very nice property with lots of extras" - "This property is so conveniently located to the quaint downtown of Woodside and also within just a few minutes to Palo Alto, Stanford Mall, and Stanford Campus. Lisa, the property owner, was the best hostess - from the reservation process to the details of her beautiful Guest House. The Guest house is nestled between redwoods and eucalyptus trees. Food, drinks, and snacks were provided. Fully equipped home just in case you were to forget anything. Beautiful furnishings, comfortable beds, soft fluffy towels, TVs in all rooms, and a quiet and private backyard with beautiful patio furniture. Don't even think about it...just make the reservation. Hope all of you enjoy as much as we did. Purpose of our trip this time was to seek medical treatment at Stanford however we would come back for a long weekend trip to shop or watch a Stanford football game."

With 17' vaulted ceiling, hand-hewn beams, reclaimed wood sidings, surrounded with stone walls and lush gardens, you will find yourself immersed in the spirit of a perfect getaway in a cabin resort in Wyoming, yet experience the most exquisite luxury & comforts in the heart of Silicon Valley! Explore and relax in the tranquil natural surroundings this 4-acre oak studded estate has to offer

- "The property is beautiful but even more importantly, working with Qian was great. She is responsive and attentive." - "Enjoyed our stay in Woodside at this beautiful, clean property. Great location, an easy walk to restaurants. Super close to Palo Alto which is where I had business to attend. Overall, would recommend the property and would stay there in the future." - "Beautiful property. Loved staying there and there is so much to do around there and so many restaurants and shops to visit. Loved the bakery in the morning and the grocery store was fantastic."

Studio with a private entrance, your own private kitchen, dining area and all cooking utensils, fully equipped.
TV 50” with roku, netflix, amazon prime through WiFi.
The studio has its own separate heating unit and AC.
Bath robes and feather down-quality linen.
Well insulated, wheelchair ok
Code operated, lock door
Minutes away from Stanford.
We use eco-friendly cleaning products.
Easy parking always available.
Comfortable queen bed.
The space
Close to fine restaurants and shopping
Guest access
Host always available to the request of the guest.
Other things to note
Designated parking in front of your estudio.

- "Used mainly for sleeping. Great location for visiting family in Woodside" - "The apartment was very clean and comfortable. It is in a lovely residential area but close to shopping. Our daughter lives in Redwood Coty and it was a 10 minute bike ride to her apartment. We would definitely stay here again." - "Bathroom and Kitchen are very updated. Large closet and the bed is very comfortable. Private entry and convenient to anyplace around Stanford, Atherton and Redwood City."

This luxurious, peaceful home in the heart of Silicon Valley is surrounded by lovely trees. A mere 30 min. S. of San Francisco, close to Stanford, Sand Hill, the ocean and more! Great dining & entertainment nearby. Excellent hiking & biking. Enjoy 2 comfy bedrooms with private bathrooms and a pull-out couch in the office with 1/2 bath. This get-away-from-it-all is the perfect place to unwind, or even work!

- "We really enjoyed our stay. The location and amenities were great!" - "Excellent" - "We needed a place near Stanford for graduation; the location of the home was very convenient to 280 and easily accessible. The property itself was very nice and the surroundings equally as pleasant. Would very much recommend this home and would love stay again in the future." - "Great location, very nice place, responsive host. We would definitely stay there again! "

Reminiscent of a 1920's Hollywood villa, enjoy the aesthetics of that romantic age, yet experience 5 star luxury pampering & the most modern of comforts. Explore and relax in the tranquil natural surroundings this 4-acre oak studded estate has to offer. 2 Luxury suites joined in one for larger group gathering! One offers a King bed and private bath perfect for 2, while the other sleeps 2-4 and has a kitchen. These 2 suites are quite separate from each other. Booking this space gives you both suites.

2 of 3 deluxe suites below:
https://www.vrbo.com/2341118?unitId=2907476
https://www.vrbo.com/3987627
https://www.vrbo.com/2339871?unitId=2906223

- "The setting was absolutely beautiful and very peaceful but still close (walking distance) to a good grocery store and several restaurants The house was very comfortable and beautifully decorated The host Qian was incredibly kind and responded quickly to any questions or requests we had We like the place so much we plan to return again" - "We loved the accessibility and serenity of this property. Host were responsive and cordial. We would definitely stay again."