
Holiday rentals in Pillar Point
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Top-rated holiday rentals in Pillar Point
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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.
4.96 out of 5 average rating, 200 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!
4.99 out of 5 average rating, 414 reviews
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.
4.99 out of 5 average rating, 198 reviews
Ocean-View Moss Beach Coastal Retreat
Newly built guest suite located just north of Half Moon Bay in Moss Beach, known for its dramatic bluffs and natural beauty. Oriented toward the ocean, the suite offers up-close views of the Pacific, open horizon, and expansive coastal sky from the deck and living areas, creating a seamless indoor-outdoor connection. The suite is attached to our home and thoughtfully planned for privacy, with a separate entrance and no shared living spaces. Minutes from beaches, coastal trails, and dining.
5.0 out of 5 average rating, 105 reviews
Walk to the Beach from this Ocean Front Home
Your beachfront escape awaits you. Come immerse yourself in the serenity of this Pacific Ocean retreat gracefully set in a secluded beach just 25 mins south of San Francisco. This 2 bed / 2 bath home features breathtaking ocean views and direct beach access just a few steps down. The hot tub overlooking the ocean, fire pits and a putting green complete this idyllic space. Comfortably sleeps 4 adults on 2 king beds and 2 high quality airbeds are provided for total sleeping for 6.
4.92 out of 5 average rating, 298 reviews
Luxury Ocean Front & Harbor View Home
Nestled in the quaint fishing village of Princeton by the Sea, just a mile north of Half Moon Bay, this stunning property is the perfect destination for your next coastal retreat. The two-bedroom, three-bathroom beautiful space sleeps up to 6 people and features spectacular views of Pillar Point Harbor and Half Moon Bay throughout the common areas and bedrooms. This is the ultimate in coastal luxury, featuring modern appliances and an open floor plan through all the common areas.
4.95 out of 5 average rating, 165 reviews
Seal Cove Beach House - Shelter Here
A great place to relax. Beautiful views, scenic hikes on quiet trails, tide pool exploration. Newly rebuilt house above Seal Cove Beach in Moss Beach, CA. 2 bedrooms, 2 full baths, a large great room, fully equipped modern kitchen and large deck all with expansive ocean views. Beach access and beautiful Fitzgerald Marine Reserve Park one block north of house. WiFi, 2 TV's, ample street parking. Moss Beach is between Pacifica and Half Moon Bay with great beaches and hiking.
4.87 out of 5 average rating, 258 reviews
Oceanview Penthouse, Stylish, Walking to Beach
A perfect romantic getaways to this stylish indoor/outdoor Penthouse! We are 10 mins walk to beaches and 15 mins walk to award winning restaurants. There are a lot of fun activities: spending your days on the beach, exploring the hiking, biking, golfing, surfing, kayaking, paddle boarding or just simply kick back relax in this quiet and picturesque property with a panoramic ocean view, enjoying the sunset and the beautiful garden. We are 30 mins to SF or 60 mins to Santa Cruz.
4.96 out of 5 average rating, 422 reviews
New- Stunning Oceanfront "Pelican Bluffs"
Perched on a dramatic oceanfront bluff, Pelican Bluffs fuses modern comfort with coastal charm. Gaze at pelicans gliding over crashing waves, create masterpieces in the the gourmet kitchen, enjoy playful havens for family time, and find workspaces where inspiration abounds. End your day, gathered around the gorgeous fire pit as the fiery sunset turns into a canopy of stars and unforgettable memories see additional photos section for prior reviews from an earlier host
4.98 out of 5 average rating, 110 reviews
Oceanfront Oasis, Sunsets & Crashing Waves
The Bluffs Oceanfront Oasis awaits you. Our beautifully appointed home sits right on the cliff boasting crashing waves and endless sunsets. Start your day in the zen room for a bit of yoga and meditation or take a leisurely walk on the beach trail right out the back gate. After dining out or in, end your evening with something special while seated at the firepit over looking the Pacific. Come for a romantic getaway, a weekend of golf or a family fun filled vacation.
4.95 out of 5 average rating, 151 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.
4.86 out of 5 average rating, 340 reviews
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.
4.92 out of 5 average rating, 177 reviewsPopular amenities for Pillar Point holiday rentals
Other great holiday rentals in Pillar Point

Sea Wolf Bungalow
4.99 out of 5 average rating, 135 reviews
Private Cottage House - Walk to Beaches Harbor
4.88 out of 5 average rating, 107 reviews
Relaxing Getaway with Breathtaking Ocean Views
4.93 out of 5 average rating, 215 reviews
Cozy, creekside guest suite with private entrance
4.98 out of 5 average rating, 347 reviews
Fabulous Beach Get Away - Brand New Beach House
5.0 out of 5 average rating, 159 reviews
Spectacular California Ocean Front Home!
5.0 out of 5 average rating, 59 reviews
Castle Beach Retreat | Hot Tub, Pool Table, Games
4.98 out of 5 average rating, 49 reviews
Coastside Haven-Modern 5BR, Walk to Beach, Firepit
5.0 out of 5 average rating, 31 reviewsDestinations to explore
- San Francisco Holiday rentals
- San Jose Holiday rentals
- Mammoth Lakes Holiday rentals
- Santa Barbara Holiday rentals
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- Oakland Holiday rentals
- Sacramento Holiday rentals
- Reno Holiday rentals
- Monterey Holiday rentals
- Fresno Holiday rentals
- Santa Cruz Holiday rentals
- Three Rivers Holiday rentals
- Stanford University
- Santa Cruz Beach
- Santa Cruz Beach Boardwalk
- Golden Gate Park
- Muir Woods National Monument
- Moscone Center
- Golden Gate Bridge
- Capitola Beach
- Oracle Park
- University of California-Berkeley
- Levi's Stadium
- SAP Center
- Henry Cowell Redwoods State Park
- Mission Dolores Park
- Rio Del Mar Beach
- Pier 39
- University of California San Francisco
- Six Flags Discovery Kingdom
- California’S Great America
- Bernal Heights
- Oakland Arena
- Palace of Fine Arts
- Big Basin Redwoods State Park
- Rodeo Beach





