House holiday rentals in Hillsborough

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Top-rated house rentals in Hillsborough

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Guest favourite

Home in San Mateo

4.93 out of 5 average rating, 106 reviews

Lovely Mid-Century home near SF, SFO, & Peninsula

Walk through the enclosed atrium sporting a custom mural and stunning red maple in this home dating back to 1956. The spacious house boasts mid-century furniture and art with a wall of glass overlooking the deck with a backdrop of fruit trees. Spacious 2 bedrooms & den with TV converts to a sofa bed. You also have a private office if you're working from home, right off the atrium. Enjoy a lovely dinner in back garden on a cool summer night. Though we love children, our home is not childproof, and we prefer not to host children under 12 years of age, thank you for understanding. This home was built in 1956 by Joseph Eichler and completely remodeled in 2017 with the goal of staying true to its original Mid-Century design while updating the house for modern living. It features a collection of beautiful Mid-Century furniture and art made by the owner and friends. Guests enter through an enclosed atrium that sports a custom mural and stunning red maple. The back yard features a large dining area with a backdrop of fruit tree and a spacious deck overlooking thousands of acres of open space and the Coastal Range. This home has two bedrooms with queen size beds and one bedroom with a full size sofa-bed. The master bedroom has an en suite bathroom with walk-in shower, the other two rooms share a bathroom with a deep tub. There is a spacious, well lit office for your use. One of the best features of this home is it's great room with a wood-burning fireplace, dining room, and kitchen--perfect for entertaining a small group. The backyard features an 8 person outdoor dining table and 6 burner BBQ for your use, as well a large outdoor sofa surrounding a fire pit. The front atrium is another well lit modern get away where you can to sit back and enjoy nature and art. Guests will have access to the entire property including the house and gardens. There is a washer and drier for guest use in the garage. I have a co-host who will be there for you 24/7. The house is in the Highlands neighborhood, which was developed by Joseph Eichler in the mid-1950s. The community center across the street from the property features a great playground for children. San Francisco Airport is 15 minutes away. - Caltrain (Goes up and down to San Francisco and San Jose) - BART (Goes to Downtown San Francisco and East Bay) - Lyft (Use referral code JEN573431) - Uber (Use referral code jcc271ue) Parking in the drive way only (no garage use for cars). TV in one of the bedrooms, not the living room. No parties or events allowed. No curtains in two of the bedrooms, but no one can see into these room as a building wall hides them. 20 minutes to downtown San Francisco We take cleaning in this climate very seriously, we are in full compliance with the cleaning guidelines approved by WHO (Worldwide Health Organization) CDC (Center for Disease Control) and the EPA (Environmental Protection Agency)

3–10 Sep

$971 NZD per night

Guest favourite

Home in Half Moon Bay

4.99 out of 5 average rating, 291 reviews

Stairway to Heaven - 1 bedroom

*UPDATE* this unit is available for 1 or 2 bedrooms. A spacious living room with a fire place, flatscreen TV & a kitchenette with most everything you will need to feel at home including Pete's French Roast Coffee, tea's, etc. A nice large bedroom with a Westin Hotel quality queen bed and lux linens, a large bathroom with a double sink, tub and shower. The private entrance leads to a patio with stunning views and quiet space. We will never be the cheapest, but we do strive to be one of the best!

26 Jun – 3 Jul

$454 NZD per night

Guest favourite

Home in Moss Beach

4.91 out of 5 average rating, 114 reviews

Studio with Private Entrance / Patio / Hot Tub

Relax in this peaceful, private studio after a fun day at the beach or exploring our beautiful coast. 1/2 mile from beach & 7-minute drive to Half Moon Bay or Pacifica! Features include a private fenced patio with access to hot tub, new hybrid queen bed, 55" TV, ceiling fan, central heat/air, kitchenette and private bath/separate shower. The new loveseat is also a comfy sleeper - $50.00 for each additional guest, up to 2 with 4 guests max in unit. Note: EV Charger is $25.00 per use.

20–27 Apr

$265 NZD per night

Guest favourite

Home in San Mateo

4.92 out of 5 average rating, 131 reviews

Andulore Cottage - Near Burlingame Ave - Remodeled

Welcome to Andulore Cottage! Remodeled home in great location in quiet neighborhood. Walk to Burlingame Avenue shops, restaurants and Caltrain Station! This 1944 WWII era cottage has been lovingly restored, updated and renovated while preserving historic detail and charm throughout. Interior decor of this home is styled mid-century transitional. There are three bedrooms, living room, dining room, kitchen, and spacious backyard with beautiful patio with brick BBQ and fireplace.

28 Aug – 4 Sep

$823 NZD per night

Guest favourite

Home in Burlingame

4.91 out of 5 average rating, 149 reviews

Cozy Modern Craftsman Retreat

Private studio with a large outdoor patio. Just a short walk to the dinning and shopping on Burlingame Avenue and also on historic Broadway. Caltrain and Bart are minutes away to get take you to wherever you need to go. Fast wifi and espresso maker provided. Enjoy fresh fruit from our orange tree, and a rosemary bush for those that enjoy cooking. Relax with our large queen bed, recessed dimmable lighting and a large flat panel 4K smart TV w/apps for Netflix, Amazon Video, etc.

19–26 Aug

$297 NZD per night

Superhost

Home in Half Moon Bay

4.97 out of 5 average rating, 109 reviews

Luxury Ocean Front & Harbor View Home

Nestled in the quaint fishing village of Princeton by the Sea, just a mile north of Halfmoon Bay, this stunning new property is the perfect destination for your next coastal retreat. The two bedroom, three bathroom beautiful space sleeps up to 6 people and features spectacular views of Pillar Point Harbor and Halfmoon Bay throughout the common areas and bedroooms. Featuring modern appliances and open floor through all the common areas, this is the ultimate in coastal luxury.

16–23 May

$1,353 NZD per night

Guest favourite

Home in Belmont

4.93 out of 5 average rating, 323 reviews

Hidden French Gem ~ 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

5–12 Sep

$265 NZD per night

Guest favourite

Home in Montara

4.97 out of 5 average rating, 274 reviews

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.

20–27 Jul

$281 NZD per night

Guest favourite

Home in Oakland

4.98 out of 5 average rating, 532 reviews

Private Casita with Stunning View

Relax in a private, fully equipped Casita with stunning views of East Oakland and the Bay. This newly constructed one-bedroom guest house in the quiet Eastmont Hills neighborhood has everything you need to work and play. Enjoy lounging in a hammock on the deck or on the couch streaming movies to a 32" television. Brand new stainless steel gas range and full-sized fridge make cooking a breeze, or you can partake in booming Oakland's restaurant scene.

5–12 Dec

$167 NZD per night

Guest favourite

Home in Redwood City

4.97 out of 5 average rating, 290 reviews

Private suite

Our home offers a private getaway perfect for business or a place to relax outside the city. Enjoy your private deck, complete with jacuzzi, and enter our large, sunny suite. Features Cal-King bed, on suite bath with heated tile flooring and bluetooth shower speaker. On site kitchenette includes mini bar, microwave, toaster oven, coffee maker & fridge/freezer. High speed WIFI connection and desk for workspace. Smart TV with blu ray, DVD, and cable.

22–29 Jun

$297 NZD per night

Superhost

Home in San Mateo

4.81 out of 5 average rating, 142 reviews

MJ@Upscale 3B2B House Close to SFO | 525

Welcome to stay at this stylish 3 bedroom 2 bathroom home in the heart of peninsula! The house is fully renovated and furnished! This house is conveniently located in a quiet residential area, but within 10 min walk to San Mateo's thriving and dynamic retail area for food, entertainment and shopping. Walk to Caltrain or minutes to 92, and 101. San Francisco International Airport is 11 minutes away. Additional $220 cleaning fee per pet

26 May – 2 Jun

$821 NZD per night

Superhost

Home in Half Moon Bay

4.87 out of 5 average rating, 208 reviews

Studio: Hot Tub + ocean view

In-law studio with hot tub and ocean view. Located in a quiet and nice neighborhood, you will be a 10 minutes walk from the beach. The unit has a compact kitchen, ice and coffee machines, toaster and a 65” inch Roku TV. It also has direct TV along with high speed internet. Enjoy your coffee on the patio or relax in the hot tub which is exclusive to you.

6–13 Dec

$312 NZD per night