Walkthrough
Living Room View
Living Room View
Location: Cypress Point
Location: Cypress Point
Dining Area
Dining Area
Kitchen
Kitchen
Entry
Entry
Bar and shuffleboard table
Bar and shuffleboard table
Living Room
Living Room
Primary Bedroom
Primary Bedroom
Primary Bathroom
Primary Bathroom
Second Bedroom
Second Bedroom
Second Bathroom
Second Bathroom
Third Bedroom
Third Bedroom
Third Bathroom
Third Bathroom
Fourth Bedroom
Fourth Bedroom
Fourth Bathroom
Fourth Bathroom
Fifth Bedroom
Fifth Bedroom
Exterior
Exterior
Overview
Overview
Concours Week!
Concours Week!
View
View
Yard
Yard
Upper deck
Upper deck
Primary Bedroom Closet
Primary Bedroom Closet
Laundry
Laundry
Dining Room
Dining Room
Living Room View
Living Room View
Nearby beach
Nearby beach
Dining Area
Dining Area
Foyer
Foyer
Living Room
Living Room
Living Room
Living Room
Living Room
Living Room
Living Room
Living Room
Primary Bedroom
Primary Bedroom
Primary Bathroom
Primary Bathroom
Fourth Bathroom
Fourth Bathroom
Fourth Bathroom
Fourth Bathroom
Exterior facing Cypress Course
Exterior facing Cypress Course
Concours Week!
Concours Week!
View
View
No Air Conditioning
No Air Conditioning
View at Pebble Beach
View at Pebble Beach
Layout
Layout
$899-$3,999/night (+tax & fees)

5 night min stay

Includes tax & fees

Cypress Point - Pebble Beach

 5 Bedroom Ocean View House

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. less ↑

  5,000 sf

  Sleeps 10

  5 bedroom

  4 Full, 1 Half

Your Host:

Michael Wiederholt

(831) 601-0532 or (831) 521-6638

Ask a Question

Amenities

Kitchen - Full
Laundry - In Unit
Linens Provided
Cleaning Supplies
Laundry Detergent
Shampoo, Conditioner, Soap
Paper Towels, Tissues, TP
Hair Dryer
Iron and Ironing Board
Gas Fireplace
Jetted Tub in Bath
Parking - Off Street
Garage (2)
Luxury

View/Location

Ocean View
Golf Course Front
Golf Course View
Near the ocean

Beds

King Bed (3)
Queen Bed
Twin/Single Bed (2) — XL Twin Trundle

Communication

Internet - Wireless [Free]
Telephone
Free Local Calls
Computer
Desk
Printer

Activities

Beach - 5 Min Walk
Golfing Nearby
Day Spa - Nearby

Outdoor

Deck/Patio
BBQ Grill [Gas/Electric] - Private

Kitchen

Cooking Utensils/Dishes Provided
Refrigerator - Full Size
Refrigerator - Bar Size
Dishwasher
Microwave
Ice Maker
Catering Available
Blender
Toaster
Coffee Maker — Cuisinart 12 cup and DeLonghi espresso/cappuccino maker

Entertainment

TV - HDTV (5)
CD Player
iPod Port
Telescope

Suitability

Bedroom on Ground Floor
Entry Level - No Stairs
Honeymoon Spot
No Pets Allowed
Smoking Not Allowed

21 Guest Reviews

Review

Having come into Carmel for our daughter's wedding, Cypress Point was the perfect house for the occasion. All the rooms overlook the ocean and golf course. The mid-century modern style plays perfectly into the location, and overall feel of the area. I loved the former homeowner Loma's trophy and personal items. It speaks to the history the house hosted over the years. The house was clean and well appointed. There was ample parking as we had several cars. The grounds were well kept and the flowers were beautiful. Overall, I would recommend this house to anyone staying in the area. less

— Julie J., Stayed April 26, 2026

Review

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. less

— William, Stayed March 17, 2026

Review

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 less

— Malcolm , Stayed August 21, 2025

Review

My Family has lived in Pacific Grove since the 1940’s…I’ve lived in Pebble Beach and Carmel off and on my entire life…my Wife’s Family is from Canada…I am a car guy and used the Rennsport Reunion to gather my in-laws for a Family reunion. This home is a classic Pebble Beach home that introduced the classic Pebble Beach lifestyle that I grew up with! We will definitely rent this wonderful home, for car week, or another occasion , again! Thank you for sharing this great home with us! Aloha! less

— Hannu, Stayed October 10, 2023

Review

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! less

— Peter, Stayed January 09, 2023

Review

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

— benjamin, Stayed December 17, 2022

Review

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. less

— Marc, Stayed March 22, 2022

Review

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!! less

— Stephanie, Stayed September 15, 2021

Review

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. less

— Marc, Stayed May 18, 2021

Review

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. less

— John, Stayed April 12, 2021

Review

This home is in a wonderful location with views of the ocean from every room. From enjoying coffee on the balcony in the morning to rounding out our evening by the fire, this house has something for everyone. A well stocked kitchen and all the amenities and more that you would need. The rental agency were very helpful and easy to work with. We will certainly be back. less

— Carmel, Stayed August 03, 2020

Review

Our third stay at this wonderful house for our golf vacation. We usually book two nights at the Inn at Spanish Bay so we can obtain tee times, then book this house for the rest of the week so we can enjoy a relaxing and extravagant week. The view is unbeatable. The bar area with the shuffleboard table is the area everyone gravitates to day or night. The kitchen is extremely well stocked with just about every utensil, pot, or pan you need to make gourmet meals. Lastly, Monterey Rentals (agent Debra Ryll) makes the entire rental process easy and stress free. While we booked for 5 nights, because Monterey County shut down the restaurants, bars, and stores because of the Corona virus, we asked to leave a day early and our last night's fee was promptly credited. If you are thinking of renting this house, do not hesitate. less

— Marc, Stayed March 22, 2020

Review

The house was so fabulous that we returned for a second year and a longer stay. Great location, exceptional views, too many amenities to list. Responsive rental agency to any maintenance issues, none that impacted our stay in any way. A true mid-century gem, loads of space for entertaining, comfortable beds, full service kitchen with a pantry full of supplies. It’s just the best! less

— Vicki, Stayed July 14, 2018

Review

This was our second stay at this home and once again it did not disappoint. We stayed for a week. The view from every room on the main level is unbeatable. The home was very clean and the furniture was in immaculate condition. The beds are comfortable and the bath towels very plush. The kitchen is stocked with just about every cooking utensil, pots and pans, and small appliances that you will need to make anything. During our first stay two years ago we remarked to the rental agent that it would be nice to have lounge chairs for the deck and sure enough, there were two lounge chairs waiting for us when we arrived. This is a spectacular home. You will not be disappointed if you choose to stay here. less

— Marc, Stayed March 23, 2018

Review

Perfect house for couples or a group. The views don't disappoint. Well appointed rental property in excellent condition with many guest amenities, good location to shopping, dining and golf. The large common rooms and ample guest rooms allow for gathering and privacy, when needed. The shuffleboard table and bar area were perfect for entertaining our friends. We chose to stay in some evenings to enjoy this house and hope to return. less

— Vicki, Stayed July 10, 2017

Review

We loved staying at Cyprus again. Beautiful place and especially works for us because of its proximity to the golf club. The only thing I can think of is a simpler TV system.Even when you follow the instructions the living room TV doesn't always come on.Not a big problem but an annoyance. Thanks for all your help less

— William b harrison, Stayed October 21, 2016

Review

Stayed in Cypress Point house on #1 Fairway for a week in September. The house and stay could not have been nicer, exceeded expectations. Very relaxing, great location and view. Owner did a wonderful job with updated remodeling while keeping the house true to the time period it was built, well done! less

— Jim , Stayed September 27, 2016

Review

Wonderful house. Stayed a week and wish it could have been longer. How satisfied were we? Rented the place again for next year while we were still there. Great retro design with interesting finds around the house such as 1950's record players and rotary dial phone. Bedrooms and bathrooms comfortable. Kitchen well stocked with pots, pans, appliances. As a previous reviewer mentioned, evening activity centered around the bar and shuffleboard table. Views from the entire length of the house that cannot be beat. Location convenient to all of the Pebble Beach Resort properties. The only thing missing were some lounge chairs for the deck--I hope that the owner may get some prior to our visit next year, because it would nice to be able to enjoy the view relaxing outside on a lounger. You will not be disappointed with this house. less

— Marc, Stayed March 24, 2016

Review

I have been staying in the Pebble Beach area for 13 years and have rented multiple homes. The Cypress home is perfect for a quiet serene setting with beautiful views of the ocean, Cypress Point golf club and Bird Rock. Coffee on the back deck in the morning is memorable. Updated bathrooms, kitchen and cooking supplies is a bonus. Would definitely recommend this home. Do not let Google Maps mislead you, this home is directly on Cypress Point. less

— Brendan, Stayed December 18, 2015

Review

The home is in good condition, though the most outstanding feature is the view along one entire side of the house. We had a wonderful time and hope to return within the next few months. Our new favorite on the peninsula!

— Joseph, Stayed November 02, 2015

Review

The home was absolutely perfect! Best view, amazing location, gorgeous bedrooms and linens, so much fun for the kids and just lovely. We were sad to leave and can't wait to stay here again, thank you!!

— Nancy, Stayed August 30, 2015

You're Inquiring About

Cypress Point - Pebble Beach

09/30/2026 → 09/30/2026
2 guests

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Michael Wiederholt

Call: (831) 601-0532 or (831) 521-6638

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