Holiday rentals in San Leandro

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Top-rated holiday rentals in San Leandro

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Top guest favourite
A modern living space showcases a comfortable gray sofa with decorative pillows. A wall-mounted TV is positioned across from the seating area, with a dining table and bar stools visible in the open kitchen. Light wood flooring complements the bright, airy atmosphere.
Guest suite in Hayward
5 out of 5 average rating, 242 reviews

★UNIQUE STAY in the middle of the BAY★ Wifi+MORE!

Comfortable in-law suite located in the “Heart of the Bay.” Just a 5-minute drive to downtown Hayward and BART, 25 min. from OAK Airport, and 35 min. from SFO Airport. In-N-Out, Sprouts, Raising Cane’s, Starbucks and much more are conveniently located just 4 minutes away. Our space is ideal for couples, travelers, and guests looking for a well-located home base. Enjoy easy access to nearby cities, dining, transportation, and experience the Bay Area’s energy and diversity from a central location.

Top guest favourite
A private patio features two chairs with cushions positioned around a small table. Lush greenery surrounds the space, complemented by vibrant flowers in a blue planter. A red awning provides shade, adding a cozy touch to the outdoor area.
Guest suite in Oakmore
4.97 out of 5 average rating, 1,048 reviews

Sunset Spa Suite w/private patio, views & parking

This private suite is a slice of heaven in a woodland setting! Accessed via a flight of garden stairs, it has a private entry, dedicated street parking, a private patio, luxurious large bath with a walk-in shower for 2, large jacuzzi tub for 2, heated floors, A.C., mini fridge, toaster oven, & microwave! The bedroom features a queen-sized bed, table for two, large screen smart TV, and strong fiber optic WIFI signal. Located in a beautiful neighborhood with wonderful hikes just outside the door.

Top guest favourite
A modern kitchen features high-end stainless steel appliances and a spacious island with slick bar stool seating. The well-lit area is complemented by contemporary pendant lights. Double french doors open to a backyard, enhancing the connection between indoor and outdoor living.
Home in Castro Valley
4.95 out of 5 average rating, 129 reviews

The Blue Door Retreat

This hotel-like home has been professionally renovated and designed to maximize the comfort, convenience and enjoyment of your stay. The kitchen has a huge WOW factor w/ stainless high-end appliances, fully stocked, ideal for cooking, entertaining, or baking. Indoor/outdoor living w/ double french doors that both open up to the beautiful backyard space complete with patio furniture, BBQ and firetable, ideal for enjoying our amazing CA weather. Smart TV's in every room for those Netflix nights!

Top guest favourite
A modern building with a green roof is nestled in a lush landscape, surrounded by trees. Scenic views of rolling hills and the bay are visible in the background, offering a serene and natural atmosphere. The driveway leads up to the structure, enhancing accessibility.
Bungalow in Sequoyah
4.95 out of 5 average rating, 101 reviews

Modern 2 bedroom with stunning bay views

Kick back and relax in this calm, stylish space. The Oakland Hills are filled with amazing hiking, this location is great for day trips to Napa (35 miles), San Francisco (11 miles) or Carmel (120 m). Centrally located for work or play. This open concept 2 bedroom is a peaceful break away. Given the open concept design - there is not a lot of privacy between bedrooms, just a big bookcase room divider b/w the rooms. There are a few sitting area's outside and a green roof too! And EV charging.

Guest favourite
A private garden area is framed by wooden fencing, featuring various plants and greenery. A door with a purple frame leads into the guesthouse. The wooden deck enhances the natural setting, contributing to a sense of tranquility and seclusion.
Guest house in Eastmont Hills
4.8 out of 5 average rating, 1,019 reviews

The Purple Door, Private Sanctuary, Epic View

Private guesthouse located in the Oakland Hills with stunning views of the bay. We recognize the importance of privacy, this guesthouse will allow you to have everything you need all while never having to be bothered. The sunset views can be taken in from your bed or the deck. There is a bus stop about 150 yards away if you need, the airport is about a 7 minute ride away, rail (BART) is about 5 minutes and the house is near a freeway for quick access to everywhere in the Bay Area.

Guest favourite
A modern living area features a dark sectional sofa and a glass-topped coffee table. A small dining table with two chairs is located beside a window. Decorative wall art is displayed above the furniture, and a portable air conditioner is positioned in a corner.
Guest suite in San Lorenzo
4.95 out of 5 average rating, 199 reviews

570 - Cozy & Comfortable 1B1B guesthouse w/parking

This is a newly remodeled adjacent unit of a single family house. It has a Queen bedroom, a nice living room with portable AC, a futon, smart TV, fridge, airfryer, microwave, coffee, basic utensils - 3 mins drive to Bayfair BART station - 15 mins drive to Oakland Airport - 25-min drive to San Francisco - Min away to Hwy 880, 238 & 580 -Mins walk to Walmart, Starbucks, Grocery outlet, restaurants and many more. Our place is perfect for 1-2 guests who want a private relaxing stay.

Guest favourite
The image depicts a serene garden pathway leading to two adjacent cabins, framed by vibrant greenery and flowering plants. A wooden trellis is visible, providing shelter, while soft lighting from the cabins enhances the calm atmosphere. A mixture of stone and mulch surfaces directs attention toward the entrance.
Guest house in Oakland
4.92 out of 5 average rating, 388 reviews

Guesthouse Garden Retreat

Our 'sister guesthouses' consist of two small side-by-side cabins (you get both) located behind our home, nestled in a verdant hillside garden that our friends and family lovingly call ‘Little Tuscany’. Cabin 1 - living room with a well-stocked kitchenette, pull-out couch, table and chairs Cabin 2 - bedroom with a queen-size bed, full bathroom and a private deck Accessed by a private entrance, the cabins are luminous and efficient, designed to meet all your needs.

Guest favourite
Guest suite in Cherryland
4.94 out of 5 average rating, 225 reviews

Private Guest Suites | Fast Wifi & Parking

Enjoy a comfortable and private guest suite perfect for business travelers, couples, or anyone visiting the Bay Area. The space is clean, quiet, and thoughtfully set up so you can relax, work, or explore with ease. The suite features a private entrance, cozy sleeping area, comfortable living space, and convenient amenities to make your stay feel like home. Whether you’re here for work or a quick getaway, you’ll have everything you need for a smooth and restful stay.

Top guest favourite
A private hot tub is shown in the foreground, with soft bubbles visible on the surface. In the background, a modern cabin facade features large glass doors reflecting warm sunset hues, framed by a wooden deck with seating.
Cabin in Sheffield
4.94 out of 5 average rating, 375 reviews

Hike-in Bay Views Cabin w HotTub

Hike up to a well designed, small-but-mighty modern cabin with fast WiFi, your own hot tub and a panoramic view spanning across the bay from the Golden Gate to the San Mateo bridge. 108 stairs lead up to the Aerie, so if you don’t want to get your steps in, this is probably not the space for you! 15 min from OAK and city life, but a world away. Sunsets are glorious here. The Aerie is a special spot just for 1 or 2, so leave the posse behind. Registered guests only.

Top guest favourite
The studio features a cozy sleeping area with a spacious bed, topped with a soft blanket and decorative pillows. Natural light filters through the window, and a desk sits opposite the bed. A welcoming entrance is visible to the left.
Guest suite in San Lorenzo
4.97 out of 5 average rating, 366 reviews

Tiny Casita/Studio | Near Oakland, SF & SJ

Welcome to our <b>Cozy Casita Studio</b> ✨ This charming casita-style studio is a peaceful stay for up to two guests. Enjoy a private entrance, queen bed, kitchenette with mini fridge and microwave, and a full bathroom with standing shower. 🐾 Pet-friendly! The casita is fully private but attached to our home, so occasional household sounds may be heard. Conveniently located minutes from San Francisco, Oakland Airport, and just 30 minutes from San Jose Airport.

Top guest favourite
A bright living area features a comfortable gray sectional sofa and a stylish armchair, surrounded by natural light from large windows. A decorative electric fireplace is positioned below a wall-mounted TV, with two patterned chairs and a small end table completing the space.
Home in Castro Valley
4.98 out of 5 average rating, 203 reviews

Cheerful 2-bedroom near San Francisco &FW580/238AC

Welcome to Tom & Melissa's a cheerful 2-bedroom 1-bath in a single family house, It is a spacious 1016 sq feet house. Centrally located in the East Bay, and very close to freeway 580 and 238! You're within 30 minutes of San Francisco or 40 minutes of San Jose. Enjoy this spacious residential home with a large private patio, two separate bedrooms, a bright and comfortable living space, and a kitchen, making it a great place for family or couples.

Guest favourite
A modern studio interior showcases a cozy layout, featuring a queen bed with a light patterned comforter and a futon sofa bed. A round coffee table sits on a geometric area rug, with a bright yellow flower pillow adding a pop of color. A vintage red refrigerator is visible in the kitchenette.
Tiny home in Downtown San Leandro
4.9 out of 5 average rating, 105 reviews

10% off for Weekly Stay Studio in Downtown

Welcome to our cozy and newly remodeled studio in Downtown San Leandro. It offers 1 queen bed & 1 futon sofa bed, modern kitchenette and washer & dryer in unit. Located in downtown San Leandro, offers easy access to bart, I-880 & I-580. Secured gated lot. Our team is dedicated to making your experience memorable, and we are available to assist you with any inquiries.

Popular amenities for San Leandro holiday rentals

When is the best time to visit San Leandro?

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Frequently Asked Questions

  • Where should I stay in San Leandro?

    Make yourself at home in San Leandro by choosing from our most frequently booked neighborhoods. We have over 290 vacation rentals in San Lorenzo, over 400 vacation rentals in Heron Bay, and over 590 vacation rentals in Downtown San Leandro.

  • How much does it cost to stay in house rentals in San Leandro?

    Experience the best of San Leandro with our house rentals, starting at about $20 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there house rentals with a dedicated workspace in San Leandro?

    Yes! Work meets play with ease at over 60 house rentals in San Leandro featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there family-friendly house rentals in San Leandro?

    San Leandro has more than 50 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Are there pet-friendly house rentals in San Leandro?

    Four-legged friends are welcome in San Leandro. Choose from more than 20 house rentals for guests traveling with pets.

  • Do house rentals in San Leandro have air conditioning?

    Absolutely! We offer over 30 house rentals with air conditioning in San Leandro. Enjoy a tailored experience with all the comforts you desire.

  • Do guesthouse rentals in San Leandro have wifi?

    Absolutely! We offer over 20 guesthouse rentals with wifi in San Leandro. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in San Leandro have a bbq area?

    Absolutely! We offer over 10 house rentals with a bbq area in San Leandro. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in San Leandro have a gym?

    Absolutely! We offer over 10 house rentals with a gym in San Leandro. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for House Rentals in San Leandro?

    Enhance your stay in our House Rentals with the most popular amenities: over 130 homes with wifi, over 30 homes with air conditioning, over 10 homes with a gym, over 10 homes with a bbq area, and more. Indulge in the ultimate retreat, tailored to your preferences.

Quick stats about holiday rentals in San Leandro

  • Total holiday rentals

    Explore 210 holiday rentals in San Leandro

  • Nightly prices starting at

    San Leandro holiday rentals start at $25 SGD per night before taxes and fees

  • Verified guest reviews

    Over 6,510 verified reviews to help you choose

  • Family-friendly holiday rentals

    70 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 40 rentals that welcome pets

  • Rentals with dedicated workspaces

    100 properties have a dedicated workspace

  • Wifi availability

    200 of San Leandro holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill and Laptop-friendly workspace across San Leandro rentals

  • 4.7 Average rating

    San Leandro stays receive an average rating of 4.7 out of 5 from guests

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