Holiday rentals with a kayak in San Francisco Peninsula

Apartment in San Francisco

A cozy living area features wood-paneled walls and beams, illuminated by natural light. A comfortable couch is positioned near large windows that showcase a city skyline view. A rustic wooden coffee table adds charm, while a small side table complements the space.

4.98 out of 5 average rating, 104 reviews

Peaceful Studio in the Trees

Private Studio with a beautiful view, surrounded by urban nature. The studio is cozy and cabin-like with everything you need to enjoy your visit. The neighborhood is peaceful and quiet for a city setting. Duboce Triangle is a gorgeous, central neighborhood in San Francisco and arguably one of the best! Our walking score is 98. Enjoy Victorian houses and tree-lined walks to coffee shops, parks, restaurants, fitness studios, events, work, and easy access to public transit for all the sightseeing.

4.94 out of 5 average rating, 108 reviews

A light-filled living area features floor-to-ceiling windows providing panoramic views of the bay. A contemporary glass table is surrounded by stylish chairs, and a plush sofa adds comfort. Greenery from a potted plant enhances the natural ambiance.

Condo in Emeryville

Lux Water View with Balcony Minutes -San Francisco

Luxury Waterfront Retreat | Breathtaking Panoramic Views Wake up to stunning, panoramic water views from every room and balcony in this spa-like, resort-style haven! Whether you're seeking a romantic getaway, executive retreat, or a peaceful stay for remote work or travel nursing, this luxurious space offers the perfect escape. Free onsite parking, 24/7 security patrol for your peace of mind Trader Joe's, restaurants, San Francisco, UC Berkeley, Emeryville Marina & access to Silicon Valley

5 out of 5 average rating, 58 reviews

A cozy bedroom is presented with a wooden accent wall and large windows on either side, allowing natural light to flood the space. The bed features decorative pillows and a colorful throw blanket, complemented by a small potted plant on the side.

Cabin in Bonny Doon

Eclectic Escape

The perfect stay for adventure seekers and relaxation enthusiasts. (Permit 251052) Unwind with yard games and bbq, soak up the sun from the deck or relax in a hammock under redwood shade. Cozy up by the fireplace, enjoy forest views through skylights, or watch movies on the big screen. Explore hiking trails just steps away, vast mountain biking trails (10 min), or hit the beach and surf (13 min). Indulge in wine tasting at a local mountain vineyard nestled amongst the redwood giants (5 mins).

Guest suite in Boulder Creek

A serene river flows gently through a lush forest, surrounded by vibrant green foliage. Smooth rocks emerge from the water, which reflects the surrounding greenery. The scene conveys a peaceful natural environment, ideal for relaxation and exploration.

4.89 out of 5 average rating, 1,066 reviews

Redwood Riverfront Getaway

We are nestled in the beautiful California Redwood forest next to the San Lorenzo River. Guests can enjoy our private guest suite with its own entrance and full bathroom. Our property features tall trees, seasonal river swimming on our private beach, fishing, kayaking, and exploring. We are close to downtown Boulder Creek, minutes away from Santa Cruz, wine tasting, hiking, fine dining, and the coastline. We have no hidden fees and even offer a full return of our cleaning fee. Permit #181307

Guest suite in San Rafael

A spacious studio is shown with a queen bed, plush bedding, and a decorative throw blanket. A work desk is positioned next to a light-colored sofa, while sliding glass doors lead to a private deck. Natural light fills the room, highlighting the wooden flooring.

4.94 out of 5 average rating, 106 reviews

Comfy studio, deck, sep. entrance, a/c. Near S.F.

Cozy studio with comfy queen bed and linens. Separate entrance. Private bathroom, beautiful deck and yard. Perfect home base to relax between touring SF or visiting Marin and adjacent areas. Close to SF, nature, hiking, beaches, bay, excellent restaurants. Convenient location 3 min from 101. One hour from Sonoma & Napa wine country. We have A/C-rare in this area.Backyard shared w/ host and friendly dog. Heads up: some construction in rest of house in 6/25. Prob not very loud or early or late.

4.9 out of 5 average rating, 214 reviews

A serene hot tub is surrounded by lush greenery, offering a private retreat. The hot tub is covered, with gentle wind chimes hanging above. Potted plants add a natural touch, enhancing the tranquil outdoor setting, while views of the waterfront are visible beyond.

Villa in San Rafael

Waterfront Marin Retreat with Pool & Hot Tub

5,000 sq ft waterfront luxury villa right at the edge of the canal with private access to the water. Enjoy the heated pool and hot tub, or grab the kayak or paddle board and get on the water from your own dock. The home is 20 mins from San Francisco and Sonoma, has easy access to the 101 freeway, and close to China Camp State Park for hiking or downtown San Rafael. The five bedrooms are perfect for retreats, family vacations, or company off-sites. The spa-like environment is a true getaway.

4.93 out of 5 average rating, 187 reviews

A serene view of the lagoon is captured during sunset, showcasing soft pastel colors reflecting on the calm water. The shoreline is visible along with a wooden deck extending over the water. Clouds swirl gently in the evening sky, enhancing the tranquil atmosphere.

Home in Bolinas

Bolinas Beach Home

One-of-a-kind house that is over the Bolinas Lagoon with 180 degree views of the lagoon, beach, and Mt. Tamalpais. The beach is 250 ft away. House is furnished with high end Restoration Hardware and Design Within Reach furniture. Relax on the deck, watch the tide go in-and-out, and marvel at the seals, birds, and wildlife. There is a canoe, 2 stand-up paddle boards, beach towel, fishing rods, and crab pot available for use. And of course fast WiFi for streaming and video calls.

4.89 out of 5 average rating, 167 reviews

Home in San Rafael

Bayfront Oasis | Deck, Fire Pit, Kayaks – Near Win

Experience waterfront living in Marin County! This sunlit retreat features a private dock, kayaks, paddleboard, and stunning views. With 3 bedrooms, 2 baths, and spacious living areas, up to 8 guests can relax in comfort. Enjoy the fire pit, BBQ, and nearby trails. Between San Francisco & Wine Country. Security deposit, rental agreement, and ID required. Pets allowed with approval. Two parking spots provided, no off-street parking allowed per city laws. Driveway is 22ft long.

Houseboat in Bethel Island

Two individuals are seen paddleboarding on calm waters, with one standing upright and the other kneeling. Lush greenery and a rocky shoreline are visible in the background under a partly cloudy sky.

4.9 out of 5 average rating, 141 reviews

Unique & Rustic Waterfront houseboat- w/Kayaks

Let the summer air take you in as you sit waterfront watching the sea lions make their migration through the labyrinth of California waterways. Pick up a harbor provided fishing pole to test your luck at the evening catch.. if the fish prove to allusive that evening enjoy a short stroll down to main street for dining at one of the many great island restaurants! Celebrating a Birthday?! Let us know! Birthday Signs and We literally roll out the Red Carpet to your cabana!

5 out of 5 average rating, 6 reviews

An open-concept kitchen and dining area are presented, featuring white cabinetry and stainless steel appliances. Sunlight streams in through large windows, illuminating the dining table with black chairs. A sliding door leads to a deck with views of surrounding trees, creating a bright and airy space.

Cabin in Los Gatos

Hideaway, Luxury Homestead

Relax and recharge at this secluded cottage in Los Gatos. Whether you’re here to reconnect with nature, hike the trails, camp under the stars, or explore the Bay Area, we have everything for a worry-free stay! With nature trails on-site and the Saratoga Gap down the road, you won’t have to go far from the vacation rental for adventure. Come evening, unwind in the outdoor bathtub, and admire the amazing views from the pond deck at this peaceful place to stay.

4.9 out of 5 average rating, 10 reviews

An open kitchen space features modern appliances, including a stainless-steel refrigerator and oven. Light wood beams stretch across the ceiling, while a large window allows natural light to illuminate the area. A comfortable seating area is visible through an adjoining doorway.

Home in Montara

Shenoa By-The-SEA

This ocean-view cottage was featured in Coastal Living Magazine. With views of the Pacific and Montara Mountain, Shenoa-by-the-Sea features vaulted ceilings with skylights that fill the space with natural light. The pergola-covered back deck offers a lovely outdoor living area with a fire pit, perfect for relaxing. Beach access is less than half a mile north at Montara State Beach. The cottage is adjacent to Highway 1 so you will hear some traffic noise.