Holiday rentals in Redwood City

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Top-rated holiday rentals in Redwood City

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
A light and airy living area features a neutral-toned sofa adorned with patterned cushions. A wooden coffee table with magazines sits in front of the couch, while a modern dining area is visible in the background, showcasing stylish bar stools and large windows.
Guest house in Redwood City
4.97 out of 5 average rating, 239 reviews

Mt Carmel Cottage Charmer-Bright, Stylish & Clean

Beautifully well-appointed cottage with a private entrance, designed for comfort, style, and privacy—ideal for couples, solo travelers, and business stays. The space is meticulously maintained to provide a clean, relaxing, and comfortable experience. Located within walking distance to Caltrain (0.9 miles) and downtown Redwood City (0.6 miles), offering access to boutiques, cafes, restaurants, parks, and a movie theater. Seamless access to Palo Alto, San Francisco and the greater Silicon Valley.

Guest favourite
A spacious bed is presented with elegant bedding against a soft beige wall. Natural light filters through a window adorned with horizontal blinds. An inviting entrance door is visible, along with a decorative wall art piece above the bed, adding a touch of style to the room.
Guest suite in Redwood City
4.93 out of 5 average rating, 350 reviews

Beautiful Studio

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. 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. Please note: we have 2 dachshunds very friendly with no access to the studio or entrance.

Top guest favourite
A modern kitchen is highlighted by a spacious granite countertop island with four wooden stools. Natural light pours in through a large window overlooking the garden, illuminating stainless steel appliances and cabinetry. Plants add a touch of greenery to the inviting space.
Guest house in Redwood City
4.99 out of 5 average rating, 124 reviews

Private Cottage near Redwood City and San Carlos Downtowns

Quiet, private two-level garden cottage ideal for business travelers and visiting family. Gig+ high-speed Wi-Fi, workspace, central AC & heat, king-size bed, private entry (24/7), 50” 4K TV, fully equipped kitchen with granite countertops, and guest-exclusive washer and dryer. Bedroom, living area, kitchen, bathroom, and dining / work space. Shared garden with BBQ, teak table and hot tub. Walkable to transit, downtown areas, and a popular breakfast café. Some train and light traffic noise.

Top guest favourite
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.
Guest house in San Carlos
4.99 out of 5 average rating, 829 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.

Top guest favourite
A charming outdoor space features a decorative stone fountain with three tiers, surrounded by lush greenery and colorful flower beds. The mansion's stucco facade and tile roof are visible in the background, complemented by a well-maintained pathway leading to the entrance.
Guest suite in Atherton
4.98 out of 5 average rating, 114 reviews

ADU studio unit in a 2/3 acre Spanish mansion

Kick back and relax in this calm, stylish beautiful mansion. An independent front ADU studio in a brand new modern Spanish style mansion in a 2/3 acre lot in Atherton with completely separate entrance and huge front yard with oak trees and fountain. Only 0.5 mile to 101 freeway and 1 mile to train station, near many high tech companies. A stylish welcoming king bed full Kitchenette large fridge large stove oven range microwave and in the unit washer dryer. Central AC and heat, internet & TV.

Top guest favourite
Home in Redwood City
4.95 out of 5 average rating, 112 reviews

Cozy & Fully Equipped Studio

Welcome to your perfect retreat! Our studio is fully equipped, modern, and super comfortable, offering all the amenities for an unforgettable stay. Whether you’re traveling for business or leisure, this space provides the ideal balance between comfort and convenience. 🛋 Cozy living area: Beautifully decorated with a comfortable sofa, TV 🍽 Fully equipped kitchen 🌿 Private patio: A perfect outdoor space to relax and enjoy fresh air. 🚗 Private parking with independent entrance self check in

Top guest favourite
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.
Guest house in Woodside
4.97 out of 5 average rating, 360 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.

Top guest favourite
A private outdoor area is enclosed by wooden fencing, featuring a wooden gate and a trellis overhead. Lush greenery and flowering plants are visible throughout the space, with decorative seating positioned near a small water feature, enhancing the natural setting.
Guest house in Redwood City
4.93 out of 5 average rating, 101 reviews

Sunny Cottage in Redwood City

This charming petite maison will have you at bonjour! Surrounded by greenery and flooded with natural light, this spacious cottage has everything you need for a work stay or vacation getaway. Private entrance and patio, outdoor seating, spacious indoors with a modest living room, kitchen, bathroom, and bedroom with workspace. Ample street parking just a few steps from entrance. Located close to downtown Redwood City and easy access to both the 280 and 101 freeways.

Top guest favourite
An inviting outdoor patio is displayed, featuring a round table surrounded by six cushioned chairs. A vibrant red front door complements the neutral siding of the cottage, while lush greenery and colorful plants frame the entrance, enhancing the welcoming atmosphere.
Guest house in San Carlos
4.99 out of 5 average rating, 177 reviews

Silicon Valley Oasis

Experience elegance and comfort in our spacious, 500 sq ft studio cottage, located in the heart of Silicon Valley. Newly built in a classic Craftsman style, it features wooden casement windows, a private garden with Adirondack chairs, and a fully-equipped kitchen with an Italian range. Enjoy a plush queen-sized bed, a cozy sectional for cinema-like experiences on a 65" TV with in-ceiling speakers, and lightning-fast Wi-Fi. Perfect for a luxurious and memorable stay.

Top guest favourite
An inviting deck area features two white lounge chairs adorned with pillows, positioned near a door leading into the studio. A light-colored rug lies in front of the entrance, while a wooden railing offers a view of the surrounding greenery.
Guest house in San Carlos
4.99 out of 5 average rating, 144 reviews

Delightful Hideaway in San Carlos

Fully equipped executive studio in the heart of Silicon Valley. This studio is ideal for accommodating executives, visiting doctors and nurses and other professions that might require long term stays. Visitors will enjoy the warm family-friendly environment and delightful garden setting. It is also well-suited for those on vacation who delight in visiting the nearby cities, as well as those who have families close by and want to have their own private spot.

Guest favourite
A resort-style pool surrounded by lounge chairs is visible, with modern apartment buildings framing the scene. The area is bright and airy, showcasing a leisure space ideal for relaxation, with neatly landscaped greenery along the pool's edge.
Flat in Menlo Park
4.95 out of 5 average rating, 171 reviews

Charming 2BR Apartment near tech Giants & Stanford

Welcome to our Luxurious 2 bedroom located in Menlo Park! Our unit is situated in the luxurious Anton Menlo Apartments, which boasts a range of amenities for our guests to enjoy during their stay. Our unit features a spacious and fully furnished living area, two comfortable bedrooms, a pair of modern bathrooms, and a fully equipped kitchen with all the necessary appliances and cookware to prepare your favorite meals.

Top guest favourite
A spacious bedroom features vaulted wooden ceilings and large glass sliding doors leading to an outdoor deck. A comfortable bed is flanked by two bedside tables with lamps. A decorative painting hangs above the bed, and a wooden dresser adds functional storage.
Guest house in Woodside
4.99 out of 5 average rating, 585 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.

Popular amenities for Redwood City holiday rentals

When is the best time to visit Redwood City?

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Avg. price$210 SGD$214 SGD$213 SGD$207 SGD$220 SGD$232 SGD$218 SGD$222 SGD$211 SGD$200 SGD$196 SGD$206 SGD
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Frequently Asked Questions

  • What are the best places to stay in Redwood City?

    Vacation rentals in Redwood City’s downtown or nearby neighborhoods provide easy access to local restaurants, galleries, and parks. Many options feature amenities for families, groups, or pet owners.

  • What are the best things to do in Redwood City with kids?

    Explore playgrounds at Red Morton Park or discover interactive exhibits at the San Mateo County History Museum. Many families enjoy community events, movie nights, and locally organized festivals.

  • What are some of the best things to do in Redwood City?

    Tour the San Mateo County History Museum, spend time in Red Morton Park, and explore public art installations downtown. Seasonal community festivals add lively touches throughout the year.

  • How is the weather in Redwood City?

    Redwood City experiences mild winters around 42–59°F (6–15°C) and warm, dry summers near 58–77°F (15–25°C). Rain is rare from June through September, so layers and sun protection are helpful for outdoor activities.

  • When is the best time to visit Redwood City?

    Late spring through early fall is often recommended for comfortable temperatures between 56–77°F (13–25°C) and minimal rainfall. Outdoor festivals and community gatherings are common during these seasons.

  • What are the best places to visit in Redwood City?

    The San Mateo County History Museum and local parks like Red Morton Park are frequently suggested. Downtown Redwood City has art, dining, and historic architecture to explore.

  • What are some hiking trails in Redwood City?

    Edgewood Park and Natural Preserve features scenic trails through oak woodlands and grasslands. Pulgas Ridge Preserve is also mentioned for dog friendly hikes and panoramic viewpoints.

  • What are some family activities we can do in Redwood City?

    Families can explore playgrounds, join library storytimes, or visit the San Mateo County History Museum. Seasonal festivals and outdoor movie nights are frequently mentioned as welcoming options.

  • What are some of the best day trip ideas from Redwood City?

    Locals often suggest exploring coastal beaches, hiking preserves in the hills, or discovering museums and gardens in nearby towns around the Peninsula. Nature parks just outside Redwood City provide hiking and wildlife viewing.

  • Are there any pet friendly accommodations available in Redwood City?

    Many vacation rentals in Redwood City welcome pets, especially in neighborhoods with access to outdoor spaces and walking trails. Look for listings that mention pet friendly amenities or fenced yards.

  • What are some local tips for visiting Redwood City?

    Explore downtown’s historic blocks on foot, and take advantage of frequent public events. Locals often suggest visiting parks early for quieter walks and checking community calendars for ongoing festivals.

  • What is Redwood City known for?

    Redwood City is known for its lively downtown, historic courthouse, and community events. The city has a tradition of hosting outdoor concerts, festivals, and cultural celebrations throughout the year.

  • What are the best hidden gems to explore in Redwood City?

    Locals often mention the Pulgas Water Temple, art murals tucked throughout downtown, and scenic spots in Edgewood Park. Small neighborhood cafes and bookstores also draw those seeking quieter moments.

  • What are the best foods to try in Redwood City?

    Redwood City has diverse cuisine, with locally rooted Mexican, Italian, and Southeast Asian flavors often recommended. Farmers markets provide fresh produce, pastries, and regional specialties.

  • What should I bring for a trip to Redwood City?

    Pack light layers, as Redwood City’s weather is generally mild but can shift between cool mornings and warmer afternoons. Comfortable shoes are often suggested for exploring parks, downtown areas, and nearby trails.

  • What is the nightlife in Redwood City like?

    Redwood City has a lively downtown area with bars, lounges, and entertainment venues featuring live music and performances. Locals often gather in public spaces for seasonal events or outdoor concerts.

  • What are the most popular events or festivals in Redwood City?

    Redwood City has summer outdoor concerts, a Fourth of July parade, and frequent downtown cultural celebrations. Community arts nights and seasonal markets are often suggested by locals for their lively atmosphere.

  • Are there family friendly vacation rentals in Redwood City?

    Redwood City has a selection of family friendly vacation rentals, often including homes with extra bedrooms, living spaces, and amenities suitable for children. Many neighborhoods feature parks and playgrounds nearby.

Quick stats about holiday rentals in Redwood City

  • Total holiday rentals

    Explore 1,700 holiday rentals in Redwood City

  • Nightly prices starting at

    Redwood City holiday rentals start at $13 SGD per night before taxes and fees

  • Verified guest reviews

    Over 62,340 verified reviews to help you choose

  • Family-friendly holiday rentals

    580 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 440 rentals that welcome pets

  • Holiday rentals with a pool

    300 properties feature pools

  • Rentals with dedicated workspaces

    900 properties have a dedicated workspace

  • Wifi availability

    1,670 of Redwood City holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill and Laptop-friendly workspace across Redwood City rentals

  • 4.8 Average rating

    Redwood City stays are highly rated by guests – averaging 4.8 out of 5!

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