Pet-friendly vacation rentals in Hillsborough

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Top-rated pet-friendly home rentals in Hillsborough

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Guest favorite

Guesthouse in Redwood City

4.93 out of 5 average rating, 298 reviews

Soak up the Serenity on the Patio of a Charming Cottage

Light the fire pit and dress for dinner in the vine-covered garden at a peaceful retreat with a soothing waterfall. Zen beachy decor and coastal paintings set the scene indoors, with abundant natural light enhancing easy open-plan living. Pets are welcome with a small cleaning fee of a $50 (one time fee) and additional pets $25 (one time fee). The main room is 12'x17'. Closet is 6 1/2' long. Bathroom 4'x5 1/2' + shower 3'3" x 3'3". kitchen 4 1/2' x 8". Simple breakfast served. Your own private entrance, plenty of parking on the street, nice neighborhood. We are available if you have any questions or need information on the area. 2 night minimum please. The cottage is tucked away off the street in a quiet, safe neighborhood where residents walk their dogs in pleasant weather. Nearby downtown Redwood City is home to shops and groceries and freeways and public transportation are within easy reach. There is a bus that runs at the corner of our block, it would take you to downtown Redwood City or travel down the El Camino Real. There is a train depot downtown as well. Pets - 2 small dogs in the main house, 2 outdoor cats.

Jan 5 – 12

G$22,696 GYD per night

Guest favorite

Apartment in Richmond

4.92 out of 5 average rating, 217 reviews

Point Richmond Top Floor Studio with Bay views

Beautiful private top (3rd) floor Pt. Richmond Studio Apartment Amenities include: Beautiful views overlooking the SF Bay, Golden Gate and San Rafael bridges, and Mt Tamalpais. Enjoy the sunset sipping a glass of wine Queen bed , kitchen, HD TV, Wifi, frig, gas stove, oven, microwave, approx 450sf. Free off-street parking. Safe area. 5 minute walk to downtown Pt. Richmond Centrally located: 15 min drive to Marin or Berkeley, 35 min to SF or Sausalito, and 1 hour to the wine country.

Apr 9 – 16

G$29,846 GYD per night

Guest favorite

Home in Half Moon Bay

4.98 out of 5 average rating, 314 reviews

Half Moon Bay Coastal Home Walk Beach & Harbor SPA

Coastal Vacation House is a short 10 minute walk to Surfers Beach, Pillar Point Harbor & Sam's Chowder House! 15 miles/ 30 mins to San Francisco! Just a few blocks from the best restaurants, shops & Marina! Near ocean bluffs ( Mavericks) & Coastal Trail perfect for hiking, walking, bike riding. Short drive to downtown Half Moon Bay shops! Ideal for holidays & entertaining family on vacation! Fun for everyone including kids! The 2,100 sq ft home is cozy & roomy for a relaxing weekend in HMB!

Feb 25 – Mar 4

G$114,431 GYD per night

Guest favorite

Guest suite in Woodside

4.89 out of 5 average rating, 340 reviews

Stay Nestled in Ancient Redwoods in Silicon Valley

Welcome to our 6-acre home, High Ground, & have our kid and pet friendly carriage house to yourself! The large studio apt with separate entrance has stunning views of ancient redwood trees + the Bay/Mount Diablo. Immediate hiking trails, wildlife, minutes to: Alice's restaurant (5), Michelin-rated Village Pub (15) highway 280 (15) Palo Alto/Menlo Park/Half Moon Bay/Ocean (30), SFO (35) San Francisco (45). Perfect for a northern CA retreat, business in the Valley or sight-seeing in San Fran.

Jun 19 – 26

G$25,861 GYD per night

Guest favorite

Guest suite in Los Gatos

4.93 out of 5 average rating, 254 reviews

Remote Mountain Suite with Hot Tub

One-bedroom attached in-law suite with private entrance- relaxing den with large leather couch, flat screen tv (Roku/no cable) kitchenette w/hot plate and private bath. Supplied with bottle of wine and breakfast essentials. Mountain location 2.5 miles down a very narrow scenic ridge-top road on 6 beautiful acres of lush vegetation and towering redwood trees. Ideal for a couple or small family looking to explore the Santa Cruz county Mountains, Bay Area and coast without breaking the bank.

Oct 8 – 15

G$24,760 GYD per night

Guest favorite

Home in Moss Beach

4.91 out of 5 average rating, 115 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.

Jan 18 – 25

G$32,261 GYD per night

Guest favorite

Camper/RV in Half Moon Bay

4.96 out of 5 average rating, 169 reviews

Coastal Airstream (Sunrise) - new listing

On 9 private acres overlooking the stunning Beach and Pacific ocean from a breathtaking cliff top view. Stunning sunrises and sunset greet you in this fully equipped new 2022 Airstream. Fully loaded with all the amenities to make your glamping experience perfect. Fire pit, outside BBQ, outside griddle, A/C and fully stocked kitchen. Comes will full bathroom with shower. Truly a rare experience and located within 10 mins of Half Moon Bay shopping. Beach access short walk or drive.

Dec 9 – 16

G$71,465 GYD per night

Guest favorite

Guest suite in Half Moon Bay

4.94 out of 5 average rating, 179 reviews

New! Oceanview Penthouse, Walking to Beach

A perfect romantic getaways to this stylish indoor/outdoor Penthouse! We are 10 mins walk to beaches and 15 mins walk to award winning restaurants. There are a lot of fun activities: spending your days on the beach, exploring the hiking, biking, golfing, surfing, kayaking, paddle boarding or just simply kick back relax in this quiet and picturesque property with a panoramic ocean view, enjoying the sunset and the beautiful garden. We are 30 mins to SF or 60 mins to Santa Cruz.

Mar 14 – 21

G$44,226 GYD per night

Guest favorite

Guesthouse in Woodside

4.97 out of 5 average rating, 156 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.

Dec 4 – 11

G$39,994 GYD per night

Guest favorite

Guest suite in Fremont

4.96 out of 5 average rating, 225 reviews

Clean and comfy 2 bedroom private entry

Relax in this private guest suite with a private entry tucked away in a central, quiet neighborhood in Fremont. This guest suite contains 2 separated bed rooms, 1 living room, and 1 full bathroom. Perfect for parties looking for a quiet and safe stay. We offer complimentary snacks, and adjustable A/C, additional fan, and fast internet. For pets, we do charge an additional fee, however provide a towel, clean bed, and water and food bowl as an additional amenity!

Dec 22 – 29

G$26,228 GYD per night

Guest favorite

Guesthouse in La Honda

4.95 out of 5 average rating, 383 reviews

Bicycle Shack @ La Honda Pottery

My place is close to miles of hiking and biking trails in county parks and openspace, great views, the beach and not far from the Peninsula, S.F. and Santa Cruz. You’ll love my place because of the location, the people, the ambiance, the outdoors space and that it is a self contained small cabin with a tiny deck.. My place is good for couples, solo adventurers, and furry friends (pets). Perfect for hikers and bikers.

Mar 28 – Apr 4

G$24,277 GYD per night

Guest favorite

Condo in Redwood City

4.93 out of 5 average rating, 105 reviews

Cozy Entire 1-Bedroom Condo in Redwood City

Beautiful condo, offering peace, comfort and privacy for your travel needs. Great location for couples, families, solo & business travelers. Family friendly neighborhood, peaceful, clean and safe. Professionally maintained and cleaned. Close to boutiques, coffee, restaurants, parks, downtown redwood city & just a few minutes from Palo Alto. Easy access to San Francisco, San Jose and the Silicon Valley.

Mar 12 – 19

G$36,765 GYD per night