Pet-friendly vacation rentals in Hillsborough

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Top-rated pet-friendly home rentals in Hillsborough

Guests agree: these pet-friendly homes are highly rated for location, cleanliness, and more.

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Guest favorite

Guesthouse in Redwood City

4.93 out of 5 average rating, 300 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.

Guest favorite

Home in Half Moon Bay

4.99 out of 5 average rating, 341 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!

Guest favorite

Rental unit in Point Richmond

4.92 out of 5 average rating, 273 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 ok-site 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.

Guest favorite

Guest suite in Woodside

4.88 out of 5 average rating, 365 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.

Guest favorite

Guest suite in Moss Beach

4.93 out of 5 average rating, 162 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 semi-fenced patio with access to hot tub, new hybrid queen bed, 55" TV, ceiling fan, central heat, 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.

Guest favorite

Camper/RV in Half Moon Bay

4.98 out of 5 average rating, 228 reviews

Airstream Coastal Hideaway (Sunset)

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 2023 Airstream. Fully loaded with all the amenities to make your glamping experience perfect. Fire pit, outside BBQ, outside griddle, Heat, 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.

Superhost

Tiny home in Half Moon Bay

4.85 out of 5 average rating, 633 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.

Guest favorite

Guest suite in Half Moon Bay

4.94 out of 5 average rating, 247 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.

Guest favorite

Guesthouse in Woodside

4.97 out of 5 average rating, 210 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.

Guest favorite

Guesthouse in Woodside

4.93 out of 5 average rating, 130 reviews

A beautiful Tree house -your own retreat

This charming 2 bedrooms is nestled among the trees in beautiful Woodside, California. This town is 30 minutes from San Francisco and right behind Stanford University. Our tree house is a private, peaceful, modern and very comfortable detached guest house. The house has a fully equip kitchen, BBQ and very peaceful settings where you can enjoy nature hikes and be surrounded by peaceful trees and yet just minutes away from town.

Guest favorite

Camper/RV in Half Moon Bay

4.99 out of 5 average rating, 143 reviews

Beachfront California Coast Airstream_Luxury (NEW)

This spectacular location comes fully equipped with the 'top of the line' 28 foot' Airstream, (Big Sur & Tommy Bahama class limited edition) with horizontal flip rear tail door for seamless indoor/outdoor living. Overlooking a stunning beach, perched high on a cliff this one of a kind experience boasts breathtaking views of the California coastline and Pacific Ocean to create an unforgettable magical experience of a lifetime.

Guest favorite

Guesthouse in La Honda

4.95 out of 5 average rating, 412 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.