
Apartment vacation rentals in Hillsborough
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Top-rated apartment rentals in Hillsborough
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Relaxed Apartment with a Patio in The Castro
Brew a cup of coffee in a cozy kitchen with elegant tiling and find a seat on a decked patio wrapped in a leafy garden. Curl up with a book on a modern sofa in a living area boasting colorful paintings, a stocked bookcase, and exposed wood beams. The unit is a private apartment below the main house with a private entrance. There is one bedroom and a pull out queen sofa. There is room for approx four people (2 per bed) and one bathroom. The summer kitchen features a brand new quartz counter top, beautiful spanish tile backsplash, drink refrigerator with freezer, microwave, toaster oven (for light heating), and a full set of dishes and glass ware for pizza night at home. There is closet and shelf space for your extra goods and an iron with an ironing board. It's so close to the action it's not even funny! :-) Guests are invited to use the private patio space just outside of the guest unit. We live right upstairs so fully available to all guests during their stay and only a quick text away. The apartment occupies the remodeled lower level of a house in the historic Castro neighborhood. A vibrant nightlife and dining scene is steps away. Head to the iconic Castro Theatre to see a film or take a scenic stroll to Mission Dolores Park. The Muni is a 7 minute walk that takes you to the BART transport to the airport and downtown and financial district. Several buses that run through this area to the rest of the city. Busy area in terms of Lyft/Uber/cabs. Parking can be a bit tough at times, but we never have too much trouble finding a space a block or less from the house. The neighborhood does however, require a parking permit per day. Unfortunately, I have a limited number of passes and will not be able to offer these with the unit. Please be mindful that tickets may be given, but they are generally more sticklers about street cleaning that daily parking permits. I am currently trying to locate nightly parking facilities nearby. If you can manage here without a car, that would be best.

Modern retreat in the tree tops
Relax in this tranquil space nestled in Oakland Hills. Private inlaw unit furnished with modern furniture and art. Kitchen replete w/microwave-convection oven, induction cooktop, dishwasher, coffeemaker, prep tools and serving items await. Enjoy the electric fireplace, cable TV and high-speed WiFi. Stylish bathroom and comfy bed to refresh and relax. From the off-street parking spot, take the 30 well-lit and stable stairs to this quiet home away from home. No pets or smoking on premises. Enjoy!

Garden studio oasis w/ kitchenette & private entry
Cosy, comfortable, and quiet unit with direct access to a lovely garden. 10 min. from the airport, 30 min. from downtown via express bus. Well-connected, sunny neighborhood. Free street parking. Views of the bay, mature redwood trees, easy to get to attractions. Walking distance to bustling food corridor, with restaurants, cafes, grocery stores, ATMs, pharmacy, salons, library, and more. Blocks from largest park in the city with sweeping views, historic greenhouses, and unique Freeway Greenway.

King-Size Luxury Near Stanford in a Modern 1-BR
Welcome to our newly updated one-bedroom apartment located just 2 miles away from Stanford. This luxurious apartment features a king-size bed, a 55" 4K TV, and fast Wi-Fi to ensure you have a comfortable stay. Whether you're visiting Stanford or the Meta headquarters for a short-term business trip or a long-term stay, our centrally located apartment offers the perfect combination of comfort and convenience. We prioritize exceptional service and hospitality, and we're excited to host you soon!

Modern Oceanview 2-Bed Apartment Home
Located in just 5mins walk from the beach, this freshly renovated apartment home has a style of its own. Yet, it is the Pacific Ocean views and all of its marine life, that captures your attention from the moment you open the front door. Beautiful, fully equipped modern kitchen, with large aisle, from where you could enjoy a cup of morning coffee while gazing at the ocean waves. Spend your evenings on the large outdoor patio with electric BBQ grill while enjoying timeless Pacific sunsets.

Newly Updated Guest Suite w/ Sweeping Ocean Views
A dream getaway that's a stone's throw away from the beach! Step inside this crafted home and you'll be greeted by stunning sunsets and ocean views. The living and dining area allows you to soak in the stunning scenery while enjoying a delicious meal. In the evening lay down on the queen size bed and listen to the waves cradle you to sleep. Walk distance to eateries, supermarket and to the outlook where you may catch glimpses of gray whales and dolphins swimming along the coastline.

Sunlit Oakland Retreat w/ Designer Touches & Deck
Sunlight + greenery + indoor-outdoor flow to the deck. Perfect for remote workers, couples, or friends looking for a calm, design-forward retreat. Not suitable for toddlers. Located in the heart of sought-after Piedmont Avenue district. Why you’ll love it: • Premier Walk Score of 96 – enjoy cafés, boutiques just steps away • Michelin 2-star dining around the corner, along with many local favorites • Gourmet kitchen – fully equipped and stocked • Private deck nestled among mature trees

Gracious Flat in Downtown San Mateo
Don't miss your chance to stay in this historic mansion in downtown San Mateo- with new elegant touches placed throughout the flat, you can enjoy the old with the new. 3 blocks from San Mateo Caltrain, Philz coffee and all that lovely downtown San Mateo has to offer. Includes free parking & shared on site coin-operated laundry facilities. If you're modern urban people who accept noise from the train/other tenants & love the vibrant downtown diversity, this is the perfect place for you.

Entire one-bedroom apartment in the Cow House
Our sunny, modern 1 bedroom 1 bathroom garden apartment is in the quiet "Crocker Amazon" neighborhood of San Francisco. It is 15 minutes from SFO and 35 minutes from the Financial District. Guests have private access to the whole apartment including bedroom, bathroom, living & dining rooms, kitchen, and garden access. Access to major freeways is fast and easy, and mass transit is steps away. One off-street parking spot and laundry are available as needed.

Spacious & Luxurious 1 BR w/Pool & Free Parking
Welcome to our Luxurious 1 bedroom located in Menlo Park! Our unit is situated in the luxurious Anton Menlo Apartments, which boasts a range of amenities for our guests to enjoy during their stay. Our unit features a spacious and fully furnished living area, comfortable Queen size bed, with a large modern bathroom, and a fully equipped kitchen with all the necessary appliances and cookware to prepare your favorite meals.

LuxoStays l! ! Lovely 2BR #SFO #Train #Laundry
*Entire Home-No sharing* Conveniently located! This spacious apartment is only 5min to SFO, 1-2 blocks from Starbucks, Walgreens, and other stores that you'll need! Many restaurants are right around the corner to eat at. Free Shuttles, Caltrain, Samtrans, and freeways are just blocks away. Longer inquiries are very welcome. Inquire even if the calendar is blocked off Send us a message now to secure your booking!

Montara Ocean View Suite
This lovely and comfortable 700 sq. ft. suite adorned in modern art offers stunning views of wild open spaces and the ocean. Just a 3 minute walk to the Montara Light House, beaches and tide pools. If you love the great outdoors this is the perfect retreat to for you to discover the beauty of the California coast. Great local dining and just 30 minutes to San Francisco. Perfect for romantic couples and friends.
Popular amenities for Hillsborough apartment rentals
Weekly apartment rentals

Stylish 1bed/1bath apartment in prime location

Fabulous Artist Flat in the Heart of Potrero Hill

Eclectic Luxury room

Beachfront Ocean Views near SF! (Neptune 2)

Sunny Neighborhood Apartment in Oakland Hills

Spacious and charming 1bd apartment on Ocean Beach

Beautiful Private Garden Apt. Nr. Golden Gate Park

Floating condo 'A' on Sausalito's Richardson Bay.
Private apartment rentals

Luxury Living in Menlo Park!

Charming furnished studio

Hilltop Gem with Stunning View of City and Bay

At Mine - Golden State Park Suite

Brand New Modern Luxury Unit | Walk to Downtown

Hip Garden Retreat Near Alameda Downtown

Private & clean STUDIO 580/680 Tri-Valley

Contemporary Apartment in a 19th Century House
Apartment rentals with a hot tub

Amazing Welcoming Unique Ocean Home

Menlo Park 2bd @ Sandhill near Stanford - Pool, Gym

Zen Japan-inspired Suite - Resort hot tub/pool/gym

SF & Bay views, deck w/hot tub, luxurious studio

NoPa Garden Sanctuary ⭐️ Jacuzzi ⭐️ Walk Everywhere

Claremont View

Plush 1-BR in Mission Bay: 10 min walk from Chase

Apt w/ hot tub 7 minutes from beach (2 guests)
When is the best time to visit Hillsborough?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$37,212 GYD | G$36,376 GYD | G$36,376 GYD | G$35,540 GYD | G$36,376 GYD | G$35,540 GYD | G$36,167 GYD | G$37,631 GYD | G$37,422 GYD | G$37,422 GYD | G$39,721 GYD | G$41,394 GYD |
| Avg. temp | 11°C | 12°C | 13°C | 14°C | 16°C | 17°C | 18°C | 18°C | 19°C | 17°C | 14°C | 11°C |
Quick stats about apartment rentals in Hillsborough

Total vacation rentals
Explore 50 vacation rentals in Hillsborough

Nightly prices starting at
Hillsborough vacation rentals start at G$2,091 GYD per night before taxes and fees

Verified guest reviews
Over 840 verified reviews to help you choose

Family-friendly vacation rentals
10 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
50 of Hillsborough vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Hillsborough rentals

4.8 Average rating
Hillsborough stays are highly rated by guests—averaging 4.8 out of 5!
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- Moscone Center
- Stanford University
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- Golden Gate Park
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- Muir Woods National Monument
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- Golden Gate Bridge
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