Vacation rentals in Hillsborough

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Top-rated vacation rentals in Hillsborough

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Guest favorite

Guesthouse in San Carlos

4.99 out of 5 average rating, 587 reviews

Private Garden Cottage

Relax in our cozy cottage nestled in a serene garden setting, the perfect get-away after a day of business meetings or sightseeing. We are close to major Silicon Valley destinations; 30 minutes from San Francisco, San Jose and the beach in Half Moon Bay —with easy access to Highways 101 and 280, as well as public transportation (SamTrans, Caltrain and BART via Caltrain). Our quiet street is an easy 5-minute walk (0.2 mi) from downtown San Carlos with shops and literally dozens of restaurants.

May 28 – Jun 4

G$31,986 GYD per night

Guest favorite

Guest suite in Belmont

4.95 out of 5 average rating, 101 reviews

Cozy private in-law suite, close to SFO, fast WiFi

Newly renovated, spacious in-law unit in the Belmont hills with a private entrance and Bay views. This adorable space is cozy and great for a weekend respite or remote work. SFO airport is just 15 mins away. Close by Stanford and San Carlos. Short drive to hiking trails and 30 mins away from the Pacific ocean. Easy access to San Francisco and San Jose, via freeway 101, 280, and 92. 🌞 Solar-powered through the day with battery 🔋 back-up at night. No outages and eco-friendly. 🌲

Sep 16 – 23

G$22,999 GYD per night

Guest favorite

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.

Oct 13 – 20

G$31,515 GYD per night

Superhost

Guesthouse in San Mateo

4.92 out of 5 average rating, 145 reviews

Cozy Studio 1B/1B w A/C No Pet in San Mateo

This cozy studio is good for a couple vacation. It is also suitable for business trip with high speed WIFI. It is well equipped with all the amenities you need to enjoy your stay! 15 minutes walk to San Mateo Downtown. 11 minutes walk to Cal Train Station, which takes you to San Francisco in 30 min, and San Jose 45 min. If you have a car, you can reach those popular destinations easily: Hwy 101: 3 min San Francisco Airport: 9 min Apple Palo Alto: 12 miles Stanford: 17 miles

Oct 8 – 15

G$22,374 GYD per night

Guest favorite

Guesthouse in Pacifica

4.98 out of 5 average rating, 370 reviews

NEW Private Studio! Close to SF/SFO/Beach Sanitize

Built in 2020, our guesthouse is a perfect place for romantic getaways and road trips. It has a private entrance, smart lock, whole room UV light sanitizers, hotel-quality bedding, brand-new furniture, and the latest interior designer selection. Staying in the sunbelt of beautiful Pacifica, there are a lot of fun activities nearby: spending your day on the beach, exploring the hiking trails, or road trip along Highway 1. Half Moon Bay, SF, and SFO are around 20 minutes away!

Sep 23 – 30

G$26,550 GYD per night

Guest favorite

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

Jul 19 – 26

G$31,074 GYD per night

Guest favorite

Cottage in San Mateo

4.95 out of 5 average rating, 465 reviews

Entire Private Studio by SFO, AC/Heat/Free Parking

Entire cottage with private entrance. * self check-in with codes * free parking on driveway * AC & heating * 1 queen bed, 1 sofa (converts into twin bed) * fiber speed WiFi * kitchenette with sink, dishes & utensils, microwave, oven, mini fridge, keurig coffee maker, water boiler, NO STOVE * 15 min drive to SFO * 10 min walk to Caltrain * walking distances to restaurants, bars & groceries * located at end of cul de sac in a safe & quiet neighborhood * TV with Chromecast

Sep 15 – 22

G$31,619 GYD per night

Guest favorite

Guest suite in El Granada

4.97 out of 5 average rating, 213 reviews

Cozy, creekside guest suite with private entrance

Cozy, creekside guest suite just blocks from the beach and the picturesque harbor. This one bedroom unit has been completely remodeled with a fully stocked kitchen, a separate eating/work space and a bathroom with a walk in shower. Drink your morning coffee (host provided) on the furnished deck while listening to the sounds of the running creek and the fog horn in the distance. This unit has its own private entrance and is closed off from the rest of the house.

Sep 19 – 26

G$30,461 GYD per night

Guest favorite

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.

Jul 13 – 20

G$33,032 GYD per night

Guest favorite

Apartment in Pacifica

4.94 out of 5 average rating, 664 reviews

Seaside Private Studio! Near SFO, SF and Beach!

Clean Modern Studio apartment with all new furnishings! Completely private studio and private entrance, desk and work area, The Apartment really is beautiful with lots of light. Tons of free parking. Only 10 min walk to the ocean/beach and Pacifica Pier. 14 minute drive to SFO airport and to San Francisco. Close to Highway 1 and 280. Easy walk to bus stop and shopping center with upscale grocery store. Not suitable for children.

Jul 13 – 20

G$22,489 GYD per night

Guest favorite

Guesthouse in San Mateo

4.93 out of 5 average rating, 193 reviews

Charming Private Quiet Backyard Studio

This charming, sunny, secluded backyard studio is located in the heart of San Mateo, near public transportation, freeways, restaurants, shopping, and 15 minutes to SFO. Private entrance, quiet backyard setting, plenty of street parking. Less than a 5-min walk to Safeway, CVS, Starbucks and restaurants. * To my regular guests, the rate increase is due to SM County increasing the tax rate. *

Jul 19 – 26

G$27,571 GYD per night

Guest favorite

Guesthouse in Hillsborough

4.95 out of 5 average rating, 809 reviews

Little Cottage on the Hill

Enjoy a peaceful stay at this charming, secluded detached garden cottage great for a stay-cation or as a work-from-home alternative. Due to the coronavirus, we are taking extra care to disinfect frequently touched surfaces between reservations. The cottage features a queen-sized bed, a fireplace, private bathroom and kitchenette. Perfect for both leisure and Business travelers.

Oct 6 – 13

G$27,707 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Hillsborough vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Hillsborough's top sights

Limon Rotisserie Burlingame8 locals recommend

Crepevine14 locals recommend

RASA11 locals recommend

Copenhagen Bakery & Cafe24 locals recommend

Mingalaba Restaurant28 locals recommend

Sawyer Camp Trail54 locals recommend

Other great vacation rentals in Hillsborough

Guest favorite

Guest suite in San Mateo

4.94 out of 5 average rating, 206 reviews

Luxury King Bed & Spa Bathroom

Jul 6 – 13

G$40,357 GYD per night

Guest favorite

Guesthouse in La Honda

4.95 out of 5 average rating, 381 reviews

Bicycle Shack @ La Honda Pottery

Apr 5 – 12

G$24,237 GYD per night

Guest favorite

Guesthouse in Belmont

4.97 out of 5 average rating, 363 reviews

A Comfortable & Private Guest House

Mar 28 – Apr 4

G$22,822 GYD per night

Guest favorite

Guesthouse in Woodside

4.96 out of 5 average rating, 156 reviews

Mountain Retreat

Sep 4 – 11

G$27,406 GYD per night

Guest favorite

Apartment in El Granada

4.87 out of 5 average rating, 401 reviews

Studio near Harbor/Half Moon Bay

Jun 3 – 10

G$25,255 GYD per night

Guest favorite

Apartment in Burlingame

4.97 out of 5 average rating, 403 reviews

Home away from home in wonderful Burlingame

Oct 5 – 12

G$35,445 GYD per night

Guest favorite

Condo in Hillsborough

5.0 out of 5 average rating, 8 reviews

Breathtaking View Modern 1b1b on Top of the World

Sep 6 – 13

G$30,744 GYD per night

Superhost

Guest suite in San Mateo

5.0 out of 5 average rating, 26 reviews

Top floor private Suite with amazing views

Jun 7 – 14

G$27,818 GYD per night

Show all

Quick stats about vacation rentals in Hillsborough

Total rentals
200 properties
Rentals with dedicated workspaces
100 properties have a dedicated workspace
Rentals with a pool
20 properties have a pool
Pet-friendly rentals
40 properties allow pets
Family-friendly rentals
60 properties are a good fit for families
Total number of reviews
6K reviews

Frequently Asked Questions

How much does it cost to stay in guesthouse rentals in Hillsborough?
Experience the best of Hillsborough with our guesthouse rentals, starting at about $90 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do apartment rentals in Hillsborough have air conditioning?
Absolutely! We offer over 20 apartment rentals with air conditioning in Hillsborough. Enjoy a tailored experience with all the comforts you desire.
Are there Hillsborough vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 20 vacation homes with pools in Hillsborough, available on Airbnb. Make a splash and soak up the sun in style!
Do house rentals in Hillsborough have a kitchen?
Absolutely! We offer over 70 house rentals with a kitchen in Hillsborough. Enjoy a tailored experience with all the comforts you desire.
Are there pet-friendly vacation rentals in Hillsborough?
Four-legged friends are welcome in Hillsborough. Choose from more than 40 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Hillsborough?
Yes! Work meets play with ease at over 100 vacation rentals in Hillsborough featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do guesthouse rentals in Hillsborough have free parking?
Absolutely! We offer over 10 guesthouse rentals with free parking in Hillsborough. Enjoy a tailored experience with all the comforts you desire.
Do guesthouse rentals in Hillsborough have wifi?
Absolutely! We offer over 10 guesthouse rentals with wifi in Hillsborough. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly vacation rentals in Hillsborough?
Hillsborough has more than 60 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Where should I stay in Hillsborough?
Make yourself at home in Hillsborough by choosing from our most frequently booked neighborhoods. We have over 580 vacation rentals in Parrot Drive Area, over 870 vacation rentals in Lakeview, and over 700 vacation rentals in Hillsborough Heights.

Vacation rentals in Hillsborough

Top-rated vacation rentals in Hillsborough

Vacation rentals for every style

Houses

Apartments

Hotels

Popular amenities for Hillsborough vacation rentals

Stay near Hillsborough's top sights

Other great vacation rentals in Hillsborough

Guest suite in San Mateo

Guesthouse in La Honda

Guesthouse in Belmont

Guesthouse in Woodside

Apartment in El Granada

Apartment in Burlingame

Condo in Hillsborough

Guest suite in San Mateo

Quick stats about vacation rentals in Hillsborough

Total rentals

Rentals with dedicated workspaces

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Frequently Asked Questions

How much does it cost to stay in guesthouse rentals in Hillsborough?

Do apartment rentals in Hillsborough have air conditioning?

Are there Hillsborough vacation rentals on Airbnb with pools?

Do house rentals in Hillsborough have a kitchen?

Are there pet-friendly vacation rentals in Hillsborough?

Are there vacation rentals with a dedicated workspace in Hillsborough?

Do guesthouse rentals in Hillsborough have free parking?

Do guesthouse rentals in Hillsborough have wifi?

Are there family-friendly vacation rentals in Hillsborough?

Where should I stay in Hillsborough?

Destinations to explore