Vacation rentals in San Gregorio

4.91 out of 5 average rating, 417 reviews

Poplar Beach Getaway: Family-Friendly, Near Beach!

Family-friendly, relaxed home in a quiet residential neighborhood - 1/2 block from the blufftops, a 10-minute stroll to lovely Poplar Beach, and 1/2 mile from scenic Main Street restaurants, shops, and cafes. 3 bedrooms with queen beds, two baths, a living area, a well-equipped kitchen, a spacious kid-friendly den, and a backyard with a new deck ensure you all have room to spread out and relax after a fun day at the beach or exploring the area. Short drive to San Francisco, Santa Cruz, San Jose.

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A modern living area features a sectional sofa complemented by a glass coffee table. Large sliding doors provide natural light and a view of the outdoor space. A sleek fireplace adds warmth to the room, with a stylish area rug enhancing the comfortable setting.

5.0 out of 5 average rating, 156 reviews

Fabulous Beach Get Away - Brand New Beach House

Amazing Newly Built Beach House. Wake-up in this beautiful beach house in a tranquil neighborhood just a short stroll to the beach, walking trails, and restaurants. This beautifully decorated, two story home is perfect for your next beach get away! This house is fully equipped with TV, fireplace, new cozy beds, outdoor fire pit and BBQ, and much more. Enjoy this town which features horseback riding, fishing, boating, surfing, quaint downtown with shops, wine tasting, restaurants and much more.

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A bright living room is visible, featuring a comfortable sofa with striped accents, a coffee table made of natural wood, and an inviting fireplace below a flatscreen TV. Large windows provide natural light and views of the outside, complemented by tasteful wall art and decorative elements.

4.96 out of 5 average rating, 195 reviews

Stairway to Heaven - 2 bedroom

PLEASE NOTE, we live in a 3 story home and this unit is on the lower level of our home. Also available in a 1 bedroom, this suite features a spacious living room with a fire place, flatscreen TV & a kitchenette with most everything you will need to feel at home. A nice large bedroom with a quality queen bed & linens, a large bathroom with a double sink, tub and shower. The private entrance leads to a patio with stunning views and quiet space. There is a second sunning patio do dine and rest.

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A welcoming living room features high ceilings and large windows allowing natural light to fill the space. A comfortable sofa with blue and yellow pillows faces a wooden coffee table, while decorative armchairs and a flat-screen TV complete the inviting atmosphere.

4.99 out of 5 average rating, 413 reviews

Half Moon Bay Coastal Home Walk Beach & Harbor SPA

Coastal Vacation House is a short 10 minute walk to Surfers Beach, Pillar Point Harbor & Sam's Chowder House! 15 miles/ 30 mins to San Francisco! Just a few blocks from the best restaurants, shops & Marina! Near ocean bluffs ( Mavericks) & Coastal Trail perfect for hiking, walking, bike riding. Short drive to downtown Half Moon Bay shops! Ideal for holidays & entertaining family on vacation! Fun for everyone including kids! The 2,100 sq ft home is cozy & roomy for a relaxing weekend in HMB!

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4.97 out of 5 average rating, 127 reviews

A tranquil pond is featured, with a fountain creating playful water spray that catches glimmers of sunlight. Surrounding greenery and trees are visible, while the ocean horizon is faintly seen in the distance, blending with the soft hues of a sunset.

Cottage in Pescadero

Bean Hollow West Cottage

This lovely 2 bedroom 2 bath cozy cottage is a great place to stay while exploring the beautiful coast of No. California. The cottage is tucked away in silence interrupted only by the faint sound of the distant ocean. It has a spectacular ocean view surrounded by a peaceful pond, incredible sunsets, lots of trees and wildlife. Sits 5 minutes from Bean Hollow Beach and many others minutes away between Half Moon Bay and Santa Cruz. This cottage is safe and private with beautiful outdoor living.

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Treehouse in Half Moon Bay

A bright interior space features large windows allowing natural light to fill the area. Colorful cushions in various shades are arranged on the floor, complemented by wooden accents and an open ceiling design that highlights the natural surroundings.

4.99 out of 5 average rating, 155 reviews

Paradise Treehouse & Heavenly Cabin

A soulful and energetic paradise. Beautiful, private, peaceful & wild surroundings complimented with modern luxuries and comfort. A stunning, unique, & unrivaled experience sure to impact you deeply. Soak in the outdoor tub while you plan your next adventure. Just minutes from the beach, amazing hiking, views and biking. Outfitted with organic latex mattresses, down comforters, top of the line appliances, smoking fast internet and a spectacular wifi sound system with world class acoustics.

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4.97 out of 5 average rating, 379 reviews

Tall redwood trees rise from the forest floor, creating a serene canopy. A distant view of the bay is visible through the trees, with a blanket of clouds resting over the landscape. The sky is clear, contrasting with the lush greenery of the forest.

Guesthouse in Woodside

SkyHigh Redwoods Retreat with Bay Views

Inhale. Exhale. Relax in this cozy, romantic guesthouse retreat nestled in the redwoods of the Santa Cruz Mountains, overlooking the bay and conveniently located near the famous Alice’s Restaurant on Skyline Blvd in Woodside. The 1 acre gated property has ample parking and privacy. Snuggle in with the wood burning fireplace, prepare meals in the full size kitchen and take in the views of the majestic redwoods right outside the windows with bay views peeking through the trees.

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A spacious grassy yard is surrounded by lush gardens, showcasing colorful flowers and greenery. A seating area with wooden chairs is situated near a fountain, providing a tranquil spot to enjoy the views. The sky displays varying shades of blue, contributing to the serene atmosphere.

4.86 out of 5 average rating, 338 reviews

Oceanfront w/ Direct Beach Access + New Hot Tub

This private oceanfront retreat offers direct beach access, lush gardens, and a spacious lawn. Walk to restaurants, music venues, and galleries nearby. Relax in the hot tub with ocean views or gather around the fire pit at sunset. Surfer’s Beach and Princeton Harbor are just north, and the Coastal Trail passes by for scenic biking and walking. Enjoy surfing, golfing, horseback riding, swimming—or simply unwind with a cocktail while watching the sunset.

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Superhost

The image showcases a modern Airstream parked on a sandy area overlooking the ocean. A large retractable awning extends over an outdoor seating arrangement that includes a fire pit surrounded by chairs. Lush green grass and a wooden fence frame the scene, highlighting the coastal setting.

Camper/RV in Half Moon Bay

4.95 out of 5 average rating, 240 reviews

Beachfront California Coast Airstream_Luxury (NEW)

This spectacular location comes fully equipped with the 'top of the line' 28 foot' Airstream, (Big Sur & Tommy Bahama class limited edition) with horizontal flip rear tail door for seamless indoor/outdoor living. Overlooking a stunning beach, perched high on a cliff this one of a kind experience boasts breathtaking views of the California coastline and Pacific Ocean to create an unforgettable magical experience of a lifetime.

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4.99 out of 5 average rating, 593 reviews

A spacious bedroom features vaulted wooden ceilings and large glass sliding doors leading to an outdoor deck. A comfortable bed is flanked by two bedside tables with lamps. A decorative painting hangs above the bed, and a wooden dresser adds functional storage.

Guesthouse in Woodside

Guest House in the Woods

Our guest house is located close to La Honda and Woodside in the North Santa Cruz Mountains. Located in the Redwood forest and looks down onto a beautiful creek from a lovely deck. There are many open space hiking and biking trails within a short drive, and the beach. 5 miles from Alice's Resturant. San Francisco and Santa Cruz are easily accessible. The house has vaulted ceilings and a full kitchen, and laundry.

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4.91 out of 5 average rating, 175 reviews

Home in Montara

Entire Private Coastal Retreat - Spectacular Ocean

Guest will enjoy the privacy of being the only residence on the premises - Your own private coastal retreat with spectacular ocean front views. A fully stocked gourmet kitchen with chef’s appliances, ample cookware, basic spices and condiments, luxurious linens and bedding, beach towels, blankets, board games, Apple TV and Netflix, and toiletries for your stay.

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The living room features a light-filled space with large windows on either side, framed by minimalist decor. A modern fireplace serves as a focal point, complemented by a surfboard mounted above. Comfortable seating is arranged around a neutral-toned coffee table on a textured area rug.