The Pearl
Mid-century modern meets coastal California cool. Think low platform beds, Parachute linens, vintage artwork of Japanese Ama pearl divers, and terrazzo bathrooms. Communal and pool-forward, with a weekly dive-in movie night setting the tone.
Book the Pearl Suite if you want a private balcony directly facing the pool cinema screen — it's the best seat in the house for movie night
Why It Matters
One of San Diego's most distinctive small hotels — a legitimately cool renovation of a 1960s roadside motel, with the Ponyboy restaurant (from Addison alumni) elevating the dining scene to something worth booking around. Oyster-shaped saltwater pool is genuinely unique.
A 23-room mid-century motel turned sharp boutique hotel in San Diego's Point Loma neighborhood. Originally built in 1959 as the Sportsman's Lodge, renovated and reimagined by Casetta Group with a contemporary coastal aesthetic that keeps the bones intact — rock walls, two-story exterior corridors, and that iconic oyster-shaped saltwater pool at the center of it all. The vibe here is laid-back and social, not precious. It draws locals and in-the-know travelers equally.
Where You'll Stay
6 room types available
Classic Pearl
The standard room at 230 sq ft. King bed on a natural wood platform, Parachute linens, writing desk, and vintage art on the walls. Shower-bath combo in the ensuite. No outdoor space, but comfortable and stylishly done for the price point.
KingGrand Pearl
250 sq ft with a private terrace or balcony for genuine indoor-outdoor flow. Natural wood platform King bed with Parachute linens, writing desk, custom vintage furnishings and original art. Walk-in rain shower in the ensuite. Solid upgrade from Classic Pearl for anyone who wants outdoor space.
KingMini Pearl
The smallest room on property at just 112 sq ft — be warned, it is genuinely compact. But it packs in a raised Queen bed with Parachute linens, custom bathrobes, designer furnishings, and a walk-in shower. Good for solo travelers or couples who plan to spend most of their time poolside.
QueenPearl Suite
The hotel's flagship suite and the biggest room on property at 360 sq ft. Lounge area with designer furnishings, vintage pieces, original art, and local ceramics. Private balcony overlooking the pool deck — the best view in the house for Dive-In Movie nights. Pull-out sofa makes it handy for small groups or wedding parties. Walk-in rain shower in the ensuite bathroom. Parachute Home linens throughout.
KingQueen Pearl ADA
ADA-accessible room at 230 sq ft. Queen bed with Parachute linens, writing desk, vintage furnishings, and a roll-in rain shower for full accessibility. Same thoughtful design touches as the other rooms.
QueenQueen Pearl Plus
At 260 sq ft, this is the roomiest Queen option and sleeps up to four thanks to a pull-out sofa. Queen bed with Parachute linens, writing desk, vintage furnishings and original art, shower-bath combo ensuite. A practical pick for families or friends traveling together.
QueenThe Property
Eat & Drink
1 venue on property
Restaurant
On Property
How you'll actually spend your days.
Beach cruiser bikes available to borrow free of charge from the front desk. The hotel sits a block from America's Cup Harbor, making for easy, flat rides along Shelter Island's harbor path. More ambitious cyclists can push up Catalina Boulevard toward Cabrillo National Monument.
Weekly Wednesday outdoor movie screenings projected on a large screen above the oyster-shaped pool. Guests can watch from the pool, poolside hammock chairs, or tables at Ponyboy. Films run the range from Jaws to Ratatouille to The Incredibles. Dinner and drinks from Ponyboy available poolside. Reservations recommended via Resy.
Every Tuesday, groups of exactly four guests get a rotating shared dinner menu for $100 total — an unusually good-value format at a restaurant of this caliber. Menu changes monthly. Available from 5PM to close.
The centerpiece of the hotel: the original 1950s oyster-shaped saltwater pool, heated and usable year-round. Surrounded by open cabanas, hammock chairs, floaties, and towel service. Poolside dining and bar service available from Ponyboy (Wed–Sun). A bamboo-enclosed outdoor rain shower sits nearby.
A Matterport 3D virtual tour of the hotel is available on the official website for pre-arrival browsing.
Amenities & Practical Info
The details that matter for planning.
Private dining and event space available. Options include semi-private poolside patio and full buyout for weddings and corporate events.
Free Wi-Fi throughout the hotel and in all guest rooms.
Bar service available poolside from Ponyboy, Wednesday through Sunday.
Organic MoonCloth Designs x Casetta bath amenities provided in all rooms.
Smart TVs and Bluetooth stereos in all guest rooms.
Premium Parachute Home bed and bath linens in all guest rooms.
Minibars stocked with curated snacks and drinks in all guest rooms.
Limited on-site self-parking available on a first-come, first-served basis at $20 per night. Not guaranteed.
Blink EV charging stations on-site. Parking is complimentary for EV drivers.
The Pearl does not have an on-site fitness center or spa. Guests looking for these amenities will need to seek them off-property.
Original 1950s oyster-shaped saltwater pool, heated, open year-round. Complete with hammock chairs, open cabanas, floaties, and towel service.
Curated retail shop through the Casetta Group offering artisan goods and hotel-branded merchandise.
Front desk staffed around the clock.
Luggage storage available at the property.
Beach cruiser bikes available free of charge from the front desk.
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