Cypress Point - Pebble Beach House - Oceanview Luxury at Cypress Point
With dramatic ocean views from the entire top floor, this luxury estate is located on the first hole of Cypress Point—one of the most exclusive golf courses in the world. "Champagne at Five" was the original owners' motto, and it's easy to see why: this home was made for entertaining. Drive down a private lane onto a circular driveway with parking for over a dozen cars…a rarity in Pebble Beach. Double doors open to a light-filled entryway and a large living room with wall-to-wall glass. Skylights spill sunshine throughout the open floor plan, while travertine-like flooring increases the feeling of warmth, spaciousness and calm. Built in the 50s by legendary golfer Loma Smith, this mid-century modern was brought back to life by a talented design team who honored the original—while incorporating every modern luxury. The living room—with a large fireplace and 56" Smart TV—overlooks the golf course and a vast swath of the Pacific. Two love seats, a ten-foot sofa, four armchairs, and cushions on the hearth supply ample seating. The bar—with TV, full-sized refrigerator, double sink, and a second prep kitchen—features a wall of trophies, photos and memorabilia that illuminate this home's place in Pebble Beach history and the golden age of golf. In the kitchen, the designers retained the retro feel with the original Geneva cabinetry, while updating it with solid surface countertops and stainless steel appliances, including two Kitchenaid convection ovens with warming drawers, a five-burner gas cooktop, a built-in desk and a 42" table for casual dining. The formal dining room seats 12. In the Master Suite (with ocean, forest, and golf course views), two upholstered chairs invite conversation or contemplation, while a luxurious Serta iComfort King bed guarantees restful nights. The walk-in closet—with ten individual closets (hanging, drawers, accessories)—is a testimony to another era, and the perfect spot for a bride-to-be to prepare for her special day. The master bath has double sinks, a walk-in shower, and a new jetted tub. A second guest room off the entry has ocean views, a King bed, reading chair, and a built-in TV. The en suite bath—with its original pink decor—is a nostalgic nod to the past. On the opposite end of the upper floor, a soothing seafoam palette in the third guest room mirrors the ocean views. This suite has a King bed, a bath with a tub/shower, and a small vanity set in grey and white Carrera marble. Downstairs, two bedrooms share a spacious bath with a double vanity, large walk-in shower, and a separate toilet compartment. The first bedroom, decorated in sunny yellows, has two extra-long twin trundle beds. Pass through the bedroom and bath to enter a Queen bedroom (with a second, private entrance via a covered stairway to the upper floor). The Cypress Point estate features an oversized two car garage, a laundry room with extra capacity washer/dryer, and televisions in all bedrooms, living room, kitchen and bar. The covered, 900 square foot ocean view upper deck has a barbecue, two chaise lounge chairs, and two outdoor dining tables with seating for eight.
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Amenities
Kitchen
Washing machine
Dryer
Outdoor space
Parking available
Sea view
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Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has not indicated whether there is a smoke detector on the property
Property Registration Number VR000643
About the area
Pebble Beach
Located in Pebble Beach, this holiday home is next to a golf course and by the sea. Pebble Beach Golf Links and Fisherman's Wharf are worth checking out if an activity is on the agenda, while those wishing to experience the area's natural beauty can explore Carmel Beach and Monterey Bay. Check out an event or a game at WeatherTech Raceway Laguna Seca, and consider making time for Monterey Bay Aquarium, a top attraction not to be missed. Spend some time exploring the area's activities, including golfing.
Monterey, CA (MRY-Monterey Peninsula) - 16 min drive
Restaurants
Roy's at Pebble Beach - 10 min drive
Carmel Valley Coffee Roasting Company - 10 min drive
Belas DFAC - 11 min drive
Carmel Bakery and Coffee Company - 10 min drive
The Bench - 10 min drive
Frequently asked questions
Is Cypress Point - Pebble Beach House - Oceanview Luxury at Cypress Point pet-friendly?
No, pets are not allowed at this property.
How much does it cost to stay at Cypress Point - Pebble Beach House - Oceanview Luxury at Cypress Point?
As of 4 Apr, 2026, prices found for a 1-night stay for 2 adults at Cypress Point - Pebble Beach House - Oceanview Luxury at Cypress Point on 14 Apr, 2026 start from S$1,208, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.
How much is parking at Cypress Point - Pebble Beach House - Oceanview Luxury at Cypress Point?
On-site parking is available at the property.
What time is check-in at Cypress Point - Pebble Beach House - Oceanview Luxury at Cypress Point?
Check-in begins at 3:00 PM.
What time is check-out at Cypress Point - Pebble Beach House - Oceanview Luxury at Cypress Point?
Checkout is at 11:00 AM.
Where is Cypress Point - Pebble Beach House - Oceanview Luxury at Cypress Point located?
Situated in Pebble Beach, this golf holiday home is within a 10-minute walk of 17-Mile Drive and Cypress Point Golf Club. Fan Shell Beach and Lone Cypress Pine are also within 1 mile (2 km).
Reviews
9.8
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Me and my friends' have been attending the Pebble Beach Concourse since 1995
We have been renting a house since 2005
Have to say this is the best house we have every stayed in for the concourse
The home was perfect location, clean, great floor plan and unbelievable views of the golf course and bay
Michael and his staff did a wonderful job taking care of us
We will be back !
Regards
My family and I were in town for a family funeral. This house was accommodating for 10 of us and absolutely beautiful. Large deck facing the golf course and water. Lots of places to sleep. Neighborhood was so nice. Great communication with host. Hope we can stay again sometime in the future.
This property was amazing. The house was perfect for our sales team and their customers as they attended the AT&T Pebble Beach Pro-Am. The views from the house were incredible. One of our guests described it as the 20-million-dollar views. The house was big enough for our group of 10, our private chef dinners, and keeping everyone entertained. The house was spotless and comfortable. I would highly recommend this house for any group wanting to stay near Pebble Beach.
The best experience we’ve had in renting vacation homes! The beautiful home, THE VIEW was amazing out of every important room, it was very comfortable and clean.
Debra was always ready to help if a problem arose .
Wish I could give Cypress Point 10 stars!
We’ll be back!
Wow! What a wonderful home. My hubby and I traveled with two other couples. Each bedroom was so very comfortable and having our own bathroom was so nice. The living space and bar area were just perfect. The kitchen was nicely stocked and plenty of room for the six of us to enjoy cooking dinners together. The views are over the top. We can't wait to go back.
Toby P.
Stayed 5 nights in Jun 2022
Verified
2/10 Terrible
Kait M.
4 Aug, 2025
Liked: Location
Disliked: Cleanliness, check-in, listing accuracy
Deceptive listing
We were shocked and deeply unsettled upon arrival at this home. The listing included 42 photos, yet none showed a massive 30-foot shrine room—filled wall to wall with trophies, paintings, personal photos, and multiple urns belonging to the deceased former homeowner, who we later learned had died in the house. The room is adjacent to the main living room in the center of the home.This was not a small oversight or personal decor preference—it was an overwhelming and emotionally heavy memorial space that completely altered the feel of the home. We arrived late in the day with children in tow, had nowhere else to go on such short notice, and were forced to stay one night. Despite the property manager acknowledging the omission and allowing us to leave early, we were still charged 2,500 for one night.We ended up changing our flights and cutting our trip short entirely due to the lack of alternative accommodations that could fit our family.Travelers deserve full transparency when booking a property, especially when it involves something this significant. This should absolutely have been disclosed in the listing and shown in the photos. I hope future guests are given the full picture before booking.
Prepare for your jaw to drop when you step inside this fantastic glass from top to bottom the whole length of the house because the views of the ocean are mesmerizing to say the least !!! Grampa was the man on this one ! Everyone had their own bedroom with full bathroom. My whole family was soooo amazed at the view of the ocean. It almost brought tears to our eyes each time you looked out. From the first thing you see when you get out of bed to the last before bed. There is a tall tree and bush area in front of the living room that blocked some of the view. The house was built in the 60’s and for the most part has not changed. This was both good and sometimes bad. Some of the sliding glass doors have rusted shut, but several were still operational at the time of my stay. September 2025. The water control valves were different. In a couple of the bathrooms and showers the cold turned on opposite modern righty tighty lefty loosey, but we quickly adapted. There were some small items that I contacted the property manager about and they were quickly handled. I highly recommend that you do not trespass on the Cypress point golf course property that is right in the backyard. They probably will prosecute. I asked at the pro shop if my granddaughter could practice on their driving range and putting area. They said in a NO uncertain tone that we were not allowed by club rules ! A disappointing response since we were mere steps away and that they were both free of any golfers. Oh well
fonerules
Stayed 6 nights in Sep 2025
From a partner site
10/10 Excellent
Wil H.
17 Mar, 2026
Perfection on the Peninsula
Our stay on Monterey Peninsula was truly memorable and the fantastic accommodations was the perfect setting for our family! The house was eclectic and made us imagine the wonderful get togethers during the Crosby Clambake! The views of the white foam of the crashing blue waves was mesmerizing from all the rooms and the spacious back patio. The house was well stocked and we had no problem finding anything we needed during our 5 night stay. We were intrigued at the beautiful trophies and history in the trophy room and the shuffleboard table was an unexpected delight as we had games every night! Even our 3 year old quickly learned the game and constantly was challenging the older family members. Finally, the proximity to 17 mile drive was amazing and we enjoyed our walks down to beautiful vistas and beaches so close to the house. Thanks again.
Wil H.
From a partner site
10/10 Excellent
Peter A.
9 Jan, 2023
Cypress Point New Year
Cypress Point was the perfect place to celebrate the New Year with family. This immaculately maintained midcentury home is in a stunning location with views of Fanshell Beach across the #1 Fairway of Cypress Point Club. With the New Year's Storm, the waves were even more epic than usual.
Our party of three adults and five children ages 8-14 had more than enough room. The open floorplan is ideal for a larger group. The three upstairs bedrooms are large with the same epic views as the living, dining and kitchen. Even the two downstairs bedrooms are a nice size.
The home is a great base camp for adventures as well, as it's a short drive to Carmel, Pacific Grove and Monterey. The Lodge and Market at Pebble Beach is even closer - about a five minute drive for quick last-minute needs.
I highly recommend Cypress Point not only for families, but for couples or friend groups golfing or visiting for the Concourse. We can't wait to go back!
Peter A.
From a partner site
10/10 Excellent
Ben D.
17 Dec, 2022
👍
Spent 10 nights here in December with my large family. Perfect location. Off hole 1 of Cypress. Ocean views. Privacy.
House is a fabulous mid century modern. Maintained wonderfully.
Will book again
Wonderful time celebrating a birthday and golfing.
Phil C.
Stayed 7 nights in Jul 2022
From a partner site
10/10 Excellent
Marc D.
22 Mar, 2022
Cypress Point property always a winner
Our 5th time renting this unique property, so yes, we love it. No better view from all of the upper floor bedrooms, living room, dining room, and kitchen. Very clean, comfortable bedding, and well equipped kitchen.
Rental agent, Debra Ryll always easy to work with. Never any problem with the financial part of renting and now that there is keyless entry to the property you don't have to stop at the office to pick up keys.
Yes, we will be back again.
Amazing house on Cypress Golf Course off of 17 mile drive
Amazing space where family of 10 adults could really spread out in the 4,000sf mid century modern architectural gem. From the 5 bedrooms, 4 1/2 bathrooms, dining room with seating for 12, huge living room with fireplace with amazing views from all upstairs rooms. Beautiful bar area complete with all bar essentials/fridge/cocktail glasses. Vintage American Shuffleboard table provided lots of entertainment. Plenty of parking for us with our three cars. Highly recommend a stay here. We will be back!
The views from this house were spectacular. The house is situated about halfway between the lodge at Pebble Beach and Spanish Bay. It's close enough to Carmel to enjoy their restaurants and galleries.
The house itself is clean and well equipped. Our property manager, Debra Ryll was excellent in helping our family enjoy this home.
Jim C.
Stayed 5 nights in Sep 2021
From a partner site
10/10 Excellent
Gayle S.
30 Sept, 2021
CARMEL
This breathtaking property was even more then we expected. The home was well equipped and extremely clean. The Living space was large and furnished with the mid century style of the home. Views were exceptional of the golf course and the ocean. Great location with Carmel Village only 10 minutes away. Would definitely return!!
Gayle S.
Stayed 5 nights in Sep 2021
From a partner site
10/10 Excellent
Stephanie A.
15 Sept, 2021
Peaceful oasis
This was our third visit to this property and it never disappoints! This time we discovered how very well stocked the kitchen was - we found a juicer, waffle maker, various storage containers, every type of glass you can imagine (martini, shot, white wine, red wine…) you name it they have thought of everything! I’ve already booked our next stay!!
We gathered with our adult children to be together and could not have picked a more perfect setting. Thank you for sharing your beautiful home with us.
We loved every minute of our stay. The house was immaculate well supplied, and had a spectacular view. We will definitely return in the future.
Maureen F.
Stayed 5 nights in May 2021
From a partner site
10/10 Excellent
Marc D.
18 May, 2021
Our home away from home in Pebble Beach
Just stayed for 8 nights at the Cypress Point home, our 4th stay at this awesome home.
The view from all of the rooms never gets tiring. Bedrooms are comfortable. Kitchen well equipped with utensils, dishes, pots, and pans. Home was very clean.
Bar area with the shuffleboard table is the place to be day or night.
Already looking forward to another stay next year.
Marc D.
From a partner site
10/10 Excellent
John R.
12 Apr, 2021
Cali Cool
Our family vacation at Cypress point in April 2021. The area/home was everything we anticipated and more. I am so in love with the fact the home has been updated but with someone who had a good eye on decorating to keep the mid century modern california cool house. We just loved. Can't say enough.
Mid-century modern spacious house ideal for viewing ocean from three bedrooms,. sitting room, dining room, kitchen. Low profile, comfortable furniture reupholstered keeps the low profile and the view as the protagonist.
Dr. Jill M.
Stayed 9 nights in Mar 2021
About the host
Hosted by Michael Wiederholt
Languages:
English
Premier Host
They consistently provide great experiences for their guests