
House holiday rentals in Woodside
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Top-rated house rentals in Woodside
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Serene Oasis in the midst of Silicon Valley
Gaze out at the beautiful green canyon while having a morning coffee in bed. Head to the fully equipped kitchen to prepare breakfast and enjoy it outside on the balcony, surrounded by the sights and sounds of this stunning hilltop location. Close to 280. Centrally located in Silicon Valley for easy access to both San Jose and San Francisco. Deck/BBQ Lounge Area. Minimal. Enjoy life in the San Carlos hills. Drive about 5 minutes to lively San Carlos downtown for several restaurants and bars. Go hiking in Edgewood, Crestview, or Big Canyon. For a taste of big city life, adventure a bit further to San Francisco. Driving is the best option, I280 and 101 are easily accessible. Cal Train station down the hill - connects all the way from San Francisco to San Jose. Very spacious unit ( approximately 1200 sq.ft )

3 BR Home on Vineyard nr Palo Alto & Stanford
Professionally cleaned detached home nestled among an oak grove, waterfall & vineyard in the hills above Stanford (10 min), Palo Alto (20 min), Menlo Park (10-20 min), Mountain View (25 min) and San Francisco and San Jose. Perfect for families and groups; staycations, off-sites or startups visiting Silicon Valley . See resort-style amenities below. LATEST UPGRADES: better AC, faster internet & WiFi6 for lots of devices & bandwidth. Pickleball lines on tennis court; putting green w/ remote tees.

Newly renovated 2BR/1BA in East Palo Alto
2 bd 1 ba entire unit sharing wall with other units(4 units in the house). Not suitable for people who are too sensitive to privacy . located in city of East Palo Alto ( not part of Palo Alto) , working class neighbor. read” neighborhood ”first. Don’t book if uncomfortable with working class. Only 1 parking spot available, not suitable for guests have 2 cars due to busy street Big floor mirror in 1 bedroom. be caucious if have kids . No oven in the kitchen No party and loud groups allowed

🌞Sunny house with♨️hot tub near🌲Stanford
- Sunny, private backyard with an outdoor table and a hot tub - Easy self check-in and check-out - Dedicated off street parking on the driveway and in the garage - Walking distance to Selby's, a Michelin star restaurant - Fast wifi and desks in each bedroom - Modern, professionally designed interior with central heat and air conditioning - 8 min drive to Stanford University - Easy access to HW 101, El Camino and within mins to Menlo Park and Downtown Redwood City, Caltrain, Costco, Whole Foods.

Walk to the Beach from this Ocean Front Home
Your beachfront escape awaits you. Come immerse yourself in the serenity of this Pacific Ocean retreat gracefully set in a secluded beach just 25 mins south of San Francisco. This 2 bed / 2 bath home features breathtaking ocean views and direct beach access just a few steps down. The hot tub overlooking the ocean, fire pits and a putting green complete this idyllic space. Comfortably sleeps 4 adults on 2 king beds and 2 high quality airbeds are provided for total sleeping for 6.

Hidden French Gem for Fam/Biz~near Caltrain,SFO
Highly welcome respectful travelers to step through the 750ft super quiet European-style private studio with secluded bay view. Curl up in front of the 4K TV for movie nights at this stylish, soundproofed nest with a luxury mattress, washer and dryer! — welcome infant & kids. — Read everything to avoid surprises. — 5 min walks to park, Caltrain/restaurants; 10~13 min drive to SFO/Stanford; 20-25 min SF. — No pets, no smoking/vaping, no party! — book for 3 if need single bed

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).

Luxury Silicon Valley Work & Wellness Oasis
PLEASE CONTACT US FOR SUN–THU DISCOUNTS (2+ NIGHTS). Peaceful upscale 1,500 sq ft Los Altos Hills retreat beside Rancho San Antonio Preserve with private trail access. Ideal for business travelers, couples, and nature lovers. Fast fiber Wi-Fi, dedicated workspace, fireplace, sauna, pool table, full kitchen, plush queen bed. Year-round hot tub, BBQ patio, heated saline pool May–Oct. Minutes to Stanford, Los Altos, Palo Alto, and major tech campuses, dining and shops.

The Chandelier Studio
Newly remodeled with private bathroom, kitchenette, and entry. Located in one of the most desirable areas of Redwood City known as Woodside Plaza. This is a quiet and pleasant community with tree line streets. We offer a very comfortable and spacious studio, quality linens, YoutubeTV, Netflix, Amazon Prime, Roku, Wifi. Equipped with central AC and Heater. Comfortable queen bed. Minutes away from Stanford hospital Futon converts to extra bed, bedding available.

Canyon Oak House: Private, tranquil with trees
Looking for a serene getaway in San Carlos/mid peninsula? Tranquil, professionally cleaned retreat with lots of breathing space perched among the trees in Devonshire Canyon, San Carlos, CA. Enjoy evening sun on the large deck, wake up to the birds in the trees or a family of deer in the garden. Conveniently close to downtown San Carlos but feels like you're in the country. FAST WIFI. CLOSE TO 280 AND 101. We will consider pets (additional cleaning fee applies).

A private beachy pad in Montara
Welcome to Chez Sage! Your own private apartment get-away, with a private deck and ocean views, is just 30 minutes south of San Francisco. The entrance to your private apartment leads you up the stairs to a deck with an ocean peek. Enter your home away from home and relax in the window seat to gaze at Montara Mountain or eat breakfast on the island with peeks of the ocean. Once you're settled, it's just a short stroll to watch the sunset from the beach.

Sea Wolf Bungalow
If you're looking for the most spectacular views on the San Mateo Coast, come to Sea Wolf Bungalow. Located just 20 minutes southwest of San Francisco and 7 miles north of Half Moon Bay, this historic cabin sits on its on own point with sweeping views of the Pacific. Enjoy whale watching, the beach, surfing, fishing, golf, hiking and the fabulous dining of the coastal area.
Popular amenities for Woodside house rentals
House rentals with a pool

Summer-house/OASIS on quiet street in ROCKRIDGE!

Beautiful Large 4BR Home with POOL

Large Home in Palo Alto w/Pool

Little Poolside House near Downtown Mountain View!

Mission style, w. Pool, Hot tub, walk to downtown

Luxury 4-Suite Carbon-Neutral Home With Pool

Country Club Living on Golf Course & amazing views

Private Oasis with Pool and Fire Pit
Weekly house rentals

2BR House + Patio + Office near Apple and Main St.

Super Private Hidden Redwood City House and Garden

Redwood Treehouse Retreat

12-Min From SFO, Tastefully Designed, Work Station

NEW! Woodside Retreat: Gorgeous Views & Hot Tub

Palo Alto Modern Retreat

Cozy 3B/2B House Redwood City

1BR/1BA Duplex (C) near Castro/Caltrain Mtn View
Private house rentals

Beautiful Home near Stanford w/ Private Garden

Chique 2-bedroom home near Stanford Hospitals

Serene & Charming Home in Atherton border

Serene & Peaceful Getaway in Redwood City

Stafford Place

Peaceful Redwood Retreat by the Coast

Cozy 2 Bedroom with Large Deck

Stylish Executive King 1BR w/ AC | Walk 2 train/DT
When is the best time to visit Woodside?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $514 NZD | $505 NZD | $522 NZD | $505 NZD | $531 NZD | $584 NZD | $618 NZD | $587 NZD | $529 NZD | $548 NZD | $543 NZD | $545 NZD |
| Avg. temp | 10°C | 12°C | 13°C | 15°C | 17°C | 19°C | 20°C | 20°C | 20°C | 18°C | 13°C | 10°C |
Quick stats about house rentals in Woodside

Total holiday rentals
Explore 50 holiday rentals in Woodside

Nightly prices starting at
Woodside holiday rentals start at $68 NZD per night before taxes and fees

Verified guest reviews
Over 1,730 verified reviews to help you choose

Family-friendly holiday rentals
30 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wi-Fi availability
50 of Woodside holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Woodside rentals

4.9 Average rating
Woodside stays are highly rated by guests—averaging 4.9 out of 5!
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- Rentals with a washing machine and dryer Woodside
- Rentals with outdoor seating Woodside
- Rentals with pools Woodside
- Guesthouse rentals Woodside
- Family-friendly rentals Woodside
- Private suite rentals Woodside
- Rentals with a hot tub Woodside
- Rentals with a patio Woodside
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