Pet-friendly holiday rentals in Hillsborough

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.

Apartment w hot tub / forest & ocean view

Slow living on the farm. Welcome to Coop d’État Farm Retreat on Kings Mountain—set among old-growth redwoods with ocean views, a fire pit & a private hot tub. The apartment sits on our working glamping property, where chickens roam, goats graze, dogs stand guard, and our cats supervise from afar. We’re a 10-minute walk to the Purisima Open Space trail network. This cozy apartment occupies the lower floor of our home & includes a private entrance and parking, access to a shared picnic & BBQ area.

Cozy 2 Bedroom Home, Dog Friendly, w/Private Yard

Home is dog friendly! Cozy 2 bedroom [Queen Beds] home, one bath, centrally located, private entry, lots of natural light, private fenced backyard, cafe lights, space for kids, pets to run around. Beach access trail on Mori Point 1/2 block away, 1/2 mile walk down the trail to Sharp Park Beach, you may see whales from the shore! Sharp Park Golf Course is one block walking distance. 15 min to SFO | 20 min to downtown San Francisco, private driveway and lots of free street parking available!

Stairway to Heaven - 1 bedroom

PLEASE NOTE- we live in a 3 story home and this unit is on the lower level of our home. Also available in a 2 bedroom, this suite features a spacious living room with a fire place, flatscreen TV & a kitchenette with most everything you will need to feel at home. A nice large bedroom with a quality queen bed & linens, a large bathroom with a double sink, tub and shower. The private entrance leads to a patio with stunning views and quiet space. There is a second sunning patio do dine and rest.

Walk to Beach - Remodeled Coastal Home Safe Town

This remodeled coastal home offers 3 bedrooms & 1 bathroom and fits up to 8 guests, where you can enjoy a peaceful and relaxing stay near the beach and shopping center. Enjoy the beatiful countryside away from city. Only 20 minutes drive to SF, SFO. What You'll Love: ✔ Stylish – thoughtfully designed with modern decor and cozy furnishings ✔ "The Simpson" Arcade game - Kids' favorite ✔ Enjoy 10 minute walk to Pacifica State Beach ✔ Sleeps up to 8 Comfortably – 3 bedrooms (4 beds) + 1 sofa bed

Curated Studio w/ Hot Tub & Outdoor Bath

Stay in a modern space curated by Oakland artists! This spacious studio features reclaimed barn wood throughout with eclectic modern furnishings. Snuggle up in the queen sized Casper mattress with luxurious spa quality sheets. Working while traveling? We've got gigabit wi-fi. Couples will enjoy the garden hot tub & outdoor bath with dual shower heads. Just looking to relax? Take a dip in our private outdoor bathing tub. Gated off-street parking & anytime contactless checkin are included too!

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.

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.

Montara Beach Getaway

Peace and quiet awaits at our Montara Beach Getaway. Enjoy hiking, biking, and nice walks on the beach right out the front door. We are located 2 blocks from Montara State Beach, and across the street from open space with miles of hiking trails. Enjoy this 1 bedroom unit with a comfortable queen bed and a full kitchen in the living area. The couch also folds out to accommodate extra guests. To help you unwind there is a hot tub right outside your door. Come enjoy our beautiful Coastside.

Oceanview Penthouse, Stylish, 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.

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.

Entire Private Coastal Retreat - Spectacular Ocean

Guest will enjoy the privacy of being the only residence on the premises - Your own private coastal retreat with spectacular ocean front views. A fully stocked gourmet kitchen with chef’s appliances, ample cookware, basic spices and condiments, luxurious linens and bedding, beach towels, blankets, board games, Apple TV and Netflix, and toiletries for your stay.