Smiling House brings together 3 hand-selected luxury houses in San Diego — each one chosen for its setting, its design and the service around it. San Diego is Southern California's sun-drenched coastal city, where Pacific beaches, golden light and an easy outdoor rhythm define the days. From intimate hideaways for two to expansive homes for family and friends, every house is booked directly with our team — no middle-man, no surprises. Browse the homes below, then speak to a concierge who knows San Diego first-hand about dates, rates and the details that make a stay effortless.
Updated October 2026
There is temporarily no availability for luxury houses to rent in san diego. New homes join the collection regularly — explore the full search or a nearby selection below.
All 61 villas in San Diego
Every home in San Diego that can be booked with Smiling House, as a plain list.
- 25. 4BR Coastal Oasis Near Legoland & Beach
- Ocean View Beachside Villa in San Diego
- Ocean View Villa with Beach Access in San Diego
- 5BR Family Home | Minutes from Downtown San Diego
- 5BR Wellness Villa Sauna, Hot Tub, Gym
- Ocean View Nine Bedroom Villa in San Diego
- Pet-Friendly Retreat in San Diego
- Bayside Patio Retreat in San Diego
- Beachfront Four Bedroom House in San Diego
- Direct Beach Access Retreat in San Diego
- Blue Water View Condo in Prime Coastal Locale
- Central SD Retreat with Hot Tub
- Charming Beachfront Cottage in San Diego
- Charming Urban Escape Near Balboa Park & Airport
- Chic San Diego Oasis with Hot Tub
- Cozy San Diego Hideaway in Historic Mission Hills
- Cumberland St 4BR Home | Near Downtown SD
- Downtown San Diego 1BR | Pool, Balcony & Gaslamp
- Beachfront Four Bedroom Villa in San Diego
- Coastal Family Retreat near Private Beach in San Diego
- Tranquil Outdoor Space Villa in San Diego
- Gaslamp Studio · Private Balcony & King Bed
- Ocean View Six Bedroom Estate in San Diego
- Grand Vista Four Bedroom Villa in San Diego
- Inviting Encinitas Home With Coastal Vibes
- Oceanfront Three Bedroom Villa in San Diego
- Ocean View Six Bedroom Villa in San Diego
- Oceanview Four Bedroom Retreat in San Diego
- Penthouse With Panoramic Ocean Views in San Diego
- 39th-Floor Ocean View Residence in San Diego
- Ocean View Villa Steps to the Beach in San Diego
- Luxury Ocean view Bay view Home
- Ocean View Villa with Heated Pool in San Diego
- Ocean View Three Bedroom Villa in San Diego
- Ocean View Rooftop Deck Villa in San Diego
- Beachside Three Bedroom Retreat in San Diego
- Renovated Beachside Villa in San Diego
- Beachfront Three Bedroom Villa in San Diego
- Oceanfront Beach House in San Diego
- Lavish Six Bedroom Retreat Near San Diego Beach
- Ocean View Five Bedroom Villa in San Diego
- Ocean View Four Bedroom Villa in San Diego
- Ocean View Family Beach House in San Diego
- Oceanview Beachfront Condo in San Diego
- Oceanfront Studio in Heart of La Jolla Cove
- Oceanview Four Bedroom Estate in San Diego
- Outdoor Retreat with Spa in San Diego
- Panoramic Caribbean Views in Whittier
- Panoramic Ocean Sunset Villa in California
- Panoramic Ocean View Villa in San Diego
- RMB II - Island Beach Suite 2Br - Sleeps 8-12
- RMB III: Island Paradise 2Br Deck (Sleeps 10-14)
- Skyline Escape in the Heart of Downtown
- Ocean View Beach House in San Diego
- Spacious Beautiful Home with Stunning Bay Views!
- Oceanfront Three-Bedroom Villa in San Diego
- Stunning View Mission Bay Luxury Home Private Pool
- Chic Modern Beach Farmhouse in San Diego
- Beachside Retreat with Direct Access in San Diego
- Oceanfront Luxury Home in La Jolla
- Sprawling Tuscan Villa in California
Smiling House also offers a concierge for private chefs, transfers, ski instructors, yachts and cars, a VIP Club with first access to new residences and member rates, chalets for sale in the Gstaad region through its real estate division and instantly bookable homes with live availability.
More to rent in San Diego
Houses in other destinations
Frequently asked
How do I book a house in San Diego?
Choose a home below and send an enquiry, or ask to book directly. A Smiling House concierge confirms availability and rates with the owner and handles the booking end to end — you deal with our team, not a faceless platform.
What's included when I rent a house in San Diego?
Every home is fully furnished and privately yours for the stay. Concierge support, and often housekeeping and local recommendations, come as standard; specific services vary by property and are listed on each home's page.
Is it cheaper to book direct with Smiling House?
Booking direct removes the platform mark-ups that sit on OTA listings, and puts you in touch with a team that knows San Diego personally. You get the real home, the real price and a human who answers.
How many houses are available in San Diego?
3 houses are featured here right now. Inventory changes as homes are booked and new ones join, so the collection is always current.