Holiday rentals with lake access in Milpitas

High-End Lakeview Cottage in Los Gatos

Nestled just 4 minutes from downtown Los Gatos, be one of the first to experience this unique guest cottage. Everything has been done to the highest level of detail, from the Wolf Range & Sub-Zero Refrigerator, wide plank 100+ year reclaimed flooring, marble counters, to the hand-chiseled travertine front patio. Wake-up to a view of the crew team on the 'lake' and wild birds flying overhead. This is not your typical Airbnb and is for the highly discerning looking for a home away from home.

View · Outdoor spaces · Family

Either Way Hideaway

Relax and enjoy riverside views in our tranquil Santa Cruz Mountains guesthouse. Cozy by our fire pits, take a dip in a private hot tub and enjoy the sounds of the river flow by. Hike Big Basin, Castle Rock and Henry Cowell State Parks. Close to historic downtown Boulder Creek and the Santa Cruz boardwalk, it’s the perfect base for exploring Santa Cruz county. Immerse yourself in of nature while staying connected and comfortable. Either way, you’ll enjoy your stay! SCC Permit #251382

Nearby · View · Comfort

Perfect home with pool for family vacations!

Relax with the whole family at this peaceful and gorgeous home. There is one step down to the living room and family room. Step has been marked with bright tape so you do not miss it. We do not offer to heat the pool during fall and winter seasons. The weather is to cold and heater can not keep up with a guarantee temperature. The jacuzzi is available all year and heats up fast. The house does not have AC. It usually dose not get hot in this area so all the homes were built without AC

Outdoor spaces · Nearby · Location

Vineyard Retreat with Expansive Mountain View

Vineyard retreat in Santa Cruz Mountains with expansive hilltop views. Situated off the beaten path between Los Gatos & Felton. The perfect place to disconnect, unwind & relax in a rural mountain setting. Our vineyard is 100% natural, no chemicals, pesticides or additives, from the soil to your cup. Please enjoy meandering the rows, soaking in the views and being in nature. Watch the marine layer recede in the morning & enjoy stargazing at night. Pricing is the same for 1-4 guests.

View · Nearby · Indoor spaces

The Red Edit w/AC | Scarlet Retreat, Deck & Views

Welcome to The Red Edit — a bold and stylish 2BR, 1BA retreat in Castro Valley. Designed with vibrant scarlet tones and modern touches, this cozy home is perfect for families, couples, or creatives. Enjoy a spacious living room, a fully equipped kitchen, and a private deck with outdoor seating and sweeping city views. Whether you're exploring nearby parks and cafes or simply relaxing in our unique space, this unforgettable stay invites you to recharge and make lasting memories.

View · Nearby · Sleep quality

Lake Chabot Villa | Private • Pool+Spa • Game Room

This inviting 3-bedroom, 2-bath home is perfect for families, groups, and business travelers looking for comfort and space. Enjoy our dedicated game space featuring a full-size pool table, bar seating. Large glass doors open to the backyard and pool area, bringing in natural light and creating a seamless indoor-outdoor experience. Step outside to a private backyard featuring a swimming pool and lounge area, surrounded by lush greenery, ideal for unwinding after a long day.

Nearby · Outdoor spaces · Pool

Cozy Studio near Palo Alto & Stanford | Quiet WFH

A private, curated studio by the Bay Trail, just minutes from Stanford, Google, Meta and Silicon Valley. Features a full kitchen, in-unit laundry, private bathroom, separate entry, free parking, wifi and a workspace. ✨ Designed and curated by a professional interior designer and tech-industry hosts, balancing comfort, efficiency, and calm. ❤️ More than just a place to stay — a place to feel at home in Palo Alto. Note: The studio is attached to a separately occupied home.

Nearby · Family · Decor

Spacious 3BR Home Near San Francisco

Spacious 3-Bedroom Home Near San Francisco Welcome to our comfortable 3-bedroom, 2-bath home in Castro Valley, ideal for families visits, business travelers, tech professionals, traveling nurses and extended stays. This 1,300 sq ft home features central A/C, fast WiFi, a fully equipped kitchen and comfortable beds. Located in a quiet, safe neighborhood. We maintain a peaceful, respectful environment. Parties, events, loud music, smoking, and drug use are not permitted.

Nearby · View · Condition

Private Updated In-Law Studio Near Lake Chabot

The studio was recently refreshed with updated finishes, improved lighting, and a clean, modern layout. Escape to our cozy & modern private in-law suite in a quiet Castro Valley neighborhood. Perfect for 2 guests, this studio features a private entrance, kitchenette, and a comfy queen bed. Enjoy easy self check-in and a private patio. You're just one mile from the beautiful hiking and kayaking at Lake Chabot. High-speed WiFi included for work or streaming.

Nearby · View · Quiet

Peaceful Retreat w/ Views + Gated Parking

This romantic retreat is perched on a sunny ridge with sweeping views of the bay, surrounding hills, and spectacular sunsets. Farm vibes with California natives, fruit trees, redwoods, and outdoor space to enjoy. No shared walls, behind our family home inside a secure gate with door-side parking. Super quiet in a safe, residential neighborhood. Convenient to everything in the Bay. Perfect home base for visiting family, work trips and extended stays.

Nearby · Outdoor spaces · Location

Lagoon Living Offsite + Family Retreat!

► Wake up to water views in the heart of Silicon Valley ► Centrally located: ✈ SFO: 10 mins. SF: 25 mins. Palo Alto, Mountain View, Cupertino & San Jose: 25 mins ► Maid services during stay ► Enjoy sunny weather in our one-of-a-kind backyard w/ deck, sauna, BBQ, garden, casita (office + extra bedroom), dock & SUPs ► Set up for relaxing, cooking & grilling, with sauna and pizza oven ► Blazing fast internet (360mbps) throughout the property + backyard

Outdoor spaces · Nearby · Parking

Lagoonfront Retreat: 3BR House Near SFO

Our stunning Airbnb listing offers both convenience and relaxation. 5min to multiple supermarkets and 15mins to SFO. Enjoy breathtaking views of the lagoon, modern decor, a fully-equipped kitchen, two comfortable living areas, and three cozy bedrooms with high-quality linens. We provide high-speed Wi-Fi, working desks, and heating for your comfort. We look forward to hosting you and helping you make the most of your stay in this beautiful area.

Nearby · View · Bathroom