Vacation rentals in Cupertino

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Top-rated vacation rentals in Cupertino

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

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Top guest favourite

Home in Half Moon Bay

5 out of 5 average rating, 112 reviews

Fabulous Beach Get Away - Brand New Beach House

Amazing Newly Built Beach House. Wake-up in this beautiful beach house in a tranquil neighborhood just a short stroll to the beach, walking trails, and restaurants. This beautifully decorated, two story home is perfect for your next beach get away! This house is fully equipped with TV, fireplace, new cozy beds, outdoor fire pit and BBQ, and much more. Enjoy this town which features horseback riding, fishing, boating, surfing, quaint downtown with shops, wine tasting, restaurants and much more.

Top guest favourite

Guesthouse in Boulder Creek

4.99 out of 5 average rating, 219 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.

Guest favourite

Treehouse in Half Moon Bay

4.98 out of 5 average rating, 103 reviews

Paradise Treehouse & Heavenly Cabin

A soulful and energetic paradise. Beautiful, private, peaceful & wild surroundings complimented with modern luxuries and comfort. A stunning, unique, & unrivaled experience sure to impact you deeply. Soak in the outdoor tub while you plan your next adventure. Just minutes from the beach, amazing hiking, views and biking. Outfitted with organic latex mattresses, down comforters, top of the line appliances, smoking fast internet and a spectacular wifi sound system with world class acoustics.

Top guest favourite

Home in Pacifica

4.97 out of 5 average rating, 100 reviews

Coastal Retreat w/ Ocean Views

Welcome to your dream coastal retreat! This stunning 4bd, 3ba modern home boasts breathtaking ocean views. Just minutes from the beach and a short drive to San Francisco, it's perfect for surfing, hiking, and relaxing. Unwind in the backyard hot tub after a day of exploring! Whether you're here to catch waves, explore trails, or simply relax with loved ones, our clean and stylish home offers the ideal setting for lasting memories. Book your stay and experience the ultimate luxury getaway!

Superhost

Home in Ben Lomond

4.94 out of 5 average rating, 139 reviews

Central Coast; Meadow, Hot Tub, Polite Pets Welcom

VR#111596 Seemingly remote & private yet so close to everything, single level home with massive deck on 2 1/2 acres backs to park and trails. The cook’s kitchen & herb garden overlook our meadow. The hot tub, outdoor living room & garden shower are just a few of the surprises you will uncover. The 350 heritage oak tree with 10,000 sq ft canopy is a magnet for wildlife. Ask about detached office if you need to work from home; the internet is great. Polite well trained pets OK.

Guest favourite

Tiny homes in Half Moon Bay

4.85 out of 5 average rating, 654 reviews

Small Beach Cottage Near the Coastal Trail

This is the perfect place for a getaway near the beach. Tiny House provides you and your dog comfort and privacy in a quiet neighborhood close to the dog friendly Poplar Beach. We provide the basics to prepare small meals in our kitchenette. You have close access to miles of coastal trails, great shopping and dining in downtown (1 mile away). Ritz Carlton is just 2 miles South of us. The Harbor also has great options for dining. Many trails for hiking and biking very close by.

Superhost

Home in Brisbane

4.9 out of 5 average rating, 101 reviews

Luxurious Bayview Treehouse: Hot Tub, 15 min to SF

Immerse yourself in an architectural gem that balances modern elegance and rustic allure. Our four-bedroom, three-bathroom sanctuary is your secluded escape amidst expansive greenery, a canvas for unforgettable moments. Just 10 minutes from SFO Airport and 15 minutes from dynamic San Francisco, our home is your launchpad to exploration. The Bay Bridge graces the view from your private balcony and hot tub, framing your stay with an awe-inspiring vista.

Guest favourite

Home in Boulder Creek

4.87 out of 5 average rating, 143 reviews

Victorian Cottage in the Redwoods

Historic Landmark 1899 Queen Anne Victorian Cottage near downtown Boulder Creek , Ca. Walking distance to bus, downtown restaurants, Wild Roots Market, hiking trails, San Lorenzo River. Recently remodeled 1 Bdrm 1 Bath with shower and bathtub Full kitchen Vitamix Organic Coffee Nearby Restaurants Beaches Surfing Mountain Biking Henry Cowell Redwoods State Park Roaring Camp & Big Trees Narrow Gauge Railroad Santa Cruz Boardwalk Wild Roots Market

Guest favourite

Apartment in Campbell

4.94 out of 5 average rating, 253 reviews

Victorian Experience Downtown Campbell King Bed

Light streams through the picture window, bathing the room in a golden glow. As you bask in the sun’s warm gift, the taste of morning's first cup of coffee kisses your lips, awakening your senses. You take a deep breath, feeling grateful to have found the perfect oasis—a thoughtfully designed retreat in the heart of downtown Campbell. Whether you’re here for work or relaxation, this space invites you to unwind and savor the moment.

Guest favourite

Apartment in Menlo Park

4.97 out of 5 average rating, 147 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

Home in Half Moon Bay

4.99 out of 5 average rating, 146 reviews

Beautiful Seaside Retreat.

Enjoy the vast ocean views in this beautifully updated craftsman style home, one of the originals in the neighborhood. Stunning views from almost all of the windows of the house and the large deck will remind you that you are on vacation. Comfortable beds, modern kitchen, tasteful design and an amazing location close to beaches, harbor, trails, restaurants. bars, and cafes make tis place the perfect get away.

Guest favourite

Guesthouse in Felton

4.96 out of 5 average rating, 184 reviews

Redwood Cottage & Hot Tub

Enjoy this quaint, peaceful redwood retreat in the Santa Cruz Mountains. This small cottage comes with a private hot tub, outdoor shower, propane fire pit and hammock. You'll be 10 minutes to downtown Felton and 25 minutes to Santa Cruz beaches. The cottage is on a shared property and next door to the main house.