Vacation rentals in Hillsborough, CA

Best Vacation rentals and Airbnb offers in Hillsborough, CA

@ Marbella Lane - Adorable and Quiet Studio

Holiday Home, Hillsborough

@ Marbella Lane - Adorable and Quiet Studio is a holiday home in Hillsborough, with a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About @ Marbella Lane - Adorable and Quiet Studio

@ Marbella Lane - Adorable and Quiet Studio is a holiday home in Hillsborough, with a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, dryer, and heating.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $951.

From$86/night

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Beautiful centralized home away from home

Apartment, Hillsborough

Beautiful centralized home away from home is a apartment in Hillsborough, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings,…

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About Beautiful centralized home away from home

Beautiful centralized home away from home is a apartment in Hillsborough, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, dryer, and tv.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $884.

From$88/night

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Elegant charming unit close to everything

Apartment, Hillsborough

Elegant charming unit close to everything is a apartment in Hillsborough. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time…

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About Elegant charming unit close to everything

Elegant charming unit close to everything is a apartment in Hillsborough. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, hot tub, dryer, and tv.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $930.

From$93/night

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Dandy retreat convenient location

Guest House, Hillsborough

Dandy retreat convenient location is a guest house in Hillsborough, with kitchen access and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Dandy retreat convenient location

Dandy retreat convenient location is a guest house in Hillsborough, with kitchen access and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, dryer, and tv.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,027.

From$105/night

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Browse Vacation Rentals with a Pool in Hillsborough, CA

Add a pool to the search when you want an easy place to cool off between outings.

Secluded freestanding house in the delightful grape garden, private spa and pool

Cottage, Hillsborough

Secluded freestanding house in the delightful grape garden, private spa and pool is a cottage in Hillsborough, with pet-friendly space and pool access. This stay gives travelers a…

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About Secluded freestanding house in the delightful grape garden, private spa and pool

Secluded freestanding house in the delightful grape garden, private spa and pool is a cottage in Hillsborough, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, hot tub, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,544.

From$162/night

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Hillsborough Haven: Private Pool, Hot Tub & Scenic Views in a gated House.

Holiday Home, Hillsborough

Hillsborough Haven: Private Pool, Hot Tub & Scenic Views in a gated House. is a holiday home in Hillsborough, with pool access and kitchen access. This stay gives travelers a comfortable…

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About Hillsborough Haven: Private Pool, Hot Tub & Scenic Views in a gated House.

Hillsborough Haven: Private Pool, Hot Tub & Scenic Views in a gated House. is a holiday home in Hillsborough, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, hot tub, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,774.

From$335/night

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Stonewood Private Luxury Guest House

Guest House, Hillsborough

Stonewood Private Luxury Guest House is a guest house in Hillsborough, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Stonewood Private Luxury Guest House

Stonewood Private Luxury Guest House is a guest house in Hillsborough, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, kitchen, with kitchen, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,124.

From$382/night

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Coastal Charm: Ocean Views, Hot Tub, Fire Pit Near Tide Pools, Surfing, & SFO

Holiday Home, Hillsborough

Coastal Charm: Ocean Views, Hot Tub, Fire Pit Near Tide Pools, Surfing, & SFO is a holiday home in Hillsborough, with pool access, easy beach access, and kitchen access. This stay gives…

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About Coastal Charm: Ocean Views, Hot Tub, Fire Pit Near Tide Pools, Surfing, & SFO

Coastal Charm: Ocean Views, Hot Tub, Fire Pit Near Tide Pools, Surfing, & SFO is a holiday home in Hillsborough, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, hot tub, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,692.

From$413/night

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Best Hillsborough, CA vacation rentals with parking

Find vacation rentals that make arriving by car easier.

Beautiful newly remodeled home near SFO

Holiday Home, Hillsborough

Beautiful newly remodeled home near SFO is a holiday home in Hillsborough, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Beautiful newly remodeled home near SFO

Beautiful newly remodeled home near SFO is a holiday home in Hillsborough, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,731.

From$176/night

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Marbella Lane - Bright and Cozy Home near SFO

Holiday Home, Hillsborough

Marbella Lane - Bright and Cozy Home near SFO is a holiday home in Hillsborough, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings,…

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About Marbella Lane - Bright and Cozy Home near SFO

Marbella Lane - Bright and Cozy Home near SFO is a holiday home in Hillsborough, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, parking, paid parking, and tv.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,928.

From$208/night

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Marbella Lane - Bright and Cozy Home near SFO

Holiday Home, Hillsborough

Marbella Lane - Bright and Cozy Home near SFO is a holiday home in Hillsborough, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Marbella Lane - Bright and Cozy Home near SFO

Marbella Lane - Bright and Cozy Home near SFO is a holiday home in Hillsborough, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,145.

From$212/night

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@ Marbella Lane – Cozy 2BR + Studio Duplex Home

Holiday Home, Hillsborough

@ Marbella Lane – Cozy 2BR + Studio Duplex Home is a holiday home in Hillsborough, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for…

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About @ Marbella Lane – Cozy 2BR + Studio Duplex Home

@ Marbella Lane – Cozy 2BR + Studio Duplex Home is a holiday home in Hillsborough, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,400.

From$234/night

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Best Pet-Friendly Vacation Rentals in Hillsborough, CA

Bring your pet along with stays that welcome four-legged travelers.

Cozy Affordable Private Rooms near Grand Ave Miller

Apartment, Hillsborough

Cozy Affordable Private Rooms near Grand Ave Miller is a apartment in Hillsborough, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring…

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About Cozy Affordable Private Rooms near Grand Ave Miller

Cozy Affordable Private Rooms near Grand Ave Miller is a apartment in Hillsborough, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $648.

From$69/night

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Cozy Affordable Private Rooms near Grand Ave Miller

Apartment, Hillsborough

Cozy Affordable Private Rooms near Grand Ave Miller is a apartment in Hillsborough, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area,…

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About Cozy Affordable Private Rooms near Grand Ave Miller

Cozy Affordable Private Rooms near Grand Ave Miller is a apartment in Hillsborough, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, pet friendly, pets friendly, parking, and paid parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $648.

From$69/night

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20%OFF! Chic Home with Expansive big Backyard

Holiday Home, Hillsborough

20%OFF! Chic Home with Expansive big Backyard is a holiday home in Hillsborough, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About 20%OFF! Chic Home with Expansive big Backyard

20%OFF! Chic Home with Expansive big Backyard is a holiday home in Hillsborough, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,674.

From$171/night

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Remodeled 2BR in Downtown San Mateo

Apartment, Hillsborough

Remodeled 2BR in Downtown San Mateo is a apartment in Hillsborough, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring…

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About Remodeled 2BR in Downtown San Mateo

Remodeled 2BR in Downtown San Mateo is a apartment in Hillsborough, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,060.

From$218/night

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Best Hillsborough, CA vacation rentals with a kitchen

Compare stays with kitchen access for longer trips and easier meals.

Miller Apartments

Guest House, Hillsborough

Miller Apartments is a guest house in Hillsborough, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Miller Apartments

Miller Apartments is a guest house in Hillsborough, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, kitchen, with kitchen, parking, and onsite parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $646.

From$69/night

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246C - Large Studio w/ Kitchenette, Laundry & Deck

Apartment, Hillsborough

246C - Large Studio w/ Kitchenette, Laundry & Deck is a apartment in Hillsborough, with outdoor space, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About 246C - Large Studio w/ Kitchenette, Laundry & Deck

246C - Large Studio w/ Kitchenette, Laundry & Deck is a apartment in Hillsborough, with outdoor space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,228.

From$129/night

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RUSTIC/MODERN DESIGN, OASIS CITY GETAWAY/NEAR SFO

Holiday Home, Hillsborough

RUSTIC/MODERN DESIGN, OASIS CITY GETAWAY/NEAR SFO is a holiday home in Hillsborough, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring…

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About RUSTIC/MODERN DESIGN, OASIS CITY GETAWAY/NEAR SFO

RUSTIC/MODERN DESIGN, OASIS CITY GETAWAY/NEAR SFO is a holiday home in Hillsborough, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,827.

From$186/night

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Sparkling Clean Luxury Suite near SF/SFO/BART/CalTrain + EV + Free Parking +WiFi

Apartment, Hillsborough

Sparkling Clean Luxury Suite near SF/SFO/BART/CalTrain + EV + Free Parking +WiFi is a apartment in Hillsborough, with parking and kitchen access. This stay gives travelers a comfortable…

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About Sparkling Clean Luxury Suite near SF/SFO/BART/CalTrain + EV + Free Parking +WiFi

Sparkling Clean Luxury Suite near SF/SFO/BART/CalTrain + EV + Free Parking +WiFi is a apartment in Hillsborough, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, kitchen, with kitchen, kids friendly, and kids friendly videos or books.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,820.

From$190/night

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Our Favorite Family-Friendly Vacation Rentals in Hillsborough, CA

Plan a trip with stays that give families more room to spread out.

NEWLY FURNISHED! RECENTLY RENOVATED! CUTE SPACE! CLOSE TO SFO!

Cottage, Hillsborough

NEWLY FURNISHED! RECENTLY RENOVATED! CUTE SPACE! CLOSE TO SFO! is a cottage in Hillsborough, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for…

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About NEWLY FURNISHED! RECENTLY RENOVATED! CUTE SPACE! CLOSE TO SFO!

NEWLY FURNISHED! RECENTLY RENOVATED! CUTE SPACE! CLOSE TO SFO! is a cottage in Hillsborough, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,220.

From$122/night

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Private and charming Bay Area home. Centrally located to all Bay Area cities!

Cottage, Hillsborough

Private and charming Bay Area home. Centrally located to all Bay Area cities! is a cottage in Hillsborough, with easy beach access, parking, and kitchen access. This stay gives travelers a…

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About Private and charming Bay Area home. Centrally located to all Bay Area cities!

Private and charming Bay Area home. Centrally located to all Bay Area cities! is a cottage in Hillsborough, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,234.

From$144/night

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Peaceful Family Friendly 2-bed 2-bath Entire Apt Unit in Belmont Hill

Apartment, Hillsborough

Peaceful Family Friendly 2-bed 2-bath Entire Apt Unit in Belmont Hill is a apartment in Hillsborough, with pool access, parking, and kitchen access. This stay gives travelers a comfortable…

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About Peaceful Family Friendly 2-bed 2-bath Entire Apt Unit in Belmont Hill

Peaceful Family Friendly 2-bed 2-bath Entire Apt Unit in Belmont Hill is a apartment in Hillsborough, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,505.

From$170/night

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ANDULORE COTTAGE - Near Burlingame Ave - Remodeled - Spacious Backyard Retreat

Holiday Home, Hillsborough

ANDULORE COTTAGE - Near Burlingame Ave - Remodeled - Spacious Backyard Retreat is a holiday home in Hillsborough, with parking, kitchen access, and a quieter setting. This stay gives…

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About ANDULORE COTTAGE - Near Burlingame Ave - Remodeled - Spacious Backyard Retreat

ANDULORE COTTAGE - Near Burlingame Ave - Remodeled - Spacious Backyard Retreat is a holiday home in Hillsborough, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,588.

From$280/night

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