San Diego Homes Worth Coming Back to

Stay Classy Homes offers a handpicked set of well-designed homes across San Diego. Real hospitality, no surprises. Book direct and save.

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Featured Listings

Stunning Villa w/ Pool Pickleball Movie Gym Sauna!

4.9 (19)

Rancho Santa Fe, California

6 bedrooms•7 baths

$4,138for 3 nights•Sep 20 – Sep 23

Panoramic Ocean Views! | Direct Access to Beach

5.0 (67)

San Diego, California

2 bedrooms•2 baths

$1,444for 3 nights•Oct 19 – Oct 22

Oceanfront Home w/ Panoramic Sunset From the Patio

Encinitas, California

3 bedrooms•2 baths

Sunset Balcony View! | Kids Playset | Sleeps 10

4.9 (73)

San Diego, California

4 bedrooms•3 baths

$1,013for 3 nights•Sep 28 – Oct 1

Pool, Jacuzzi and Canyon Views! | 10 Min to Beach

4.9 (27)

San Diego, California

5 bedrooms•3 baths

$2,149for 3 nights•Sep 27 – Sep 30

La Jolla Luxury | Designer Home w/ Pool & Jacuzzi!

5.0 (11)

La Jolla, California

4 bedrooms•4 baths

$3,023for 3 nights•Sep 20 – Sep 23

The Shell House w/ Game Room | Steps to the Bay!

5.0 (7)

San Diego, California

5 bedrooms•4 baths

$1,508for 3 nights•Sep 21 – Sep 24

New Luxury Townhome Steps to Mission Beach/Bay!

4.8 (29)

San Diego, California

3 bedrooms•2 baths

$1,160for 3 nights•Sep 20 – Sep 23

Walk to Balboa Park and Little Italy for Dinner!

4.8 (72)

San Diego, California

4 bedrooms•2.5 baths

$902for 3 nights•Sep 28 – Oct 1

The Pacific Lookout | Panoramic Bay & Ocean Views!

5.0 (14)

San Diego, California

4 bedrooms•2.5 baths

$1,127for 3 nights•Oct 26 – Oct 29

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What Guests Say

Trusted by Travelers

4.8

4717 reviews

First thing foremost the host is very responsive and very kind, accomodating, The property is quiet and clean. I would recommend this 11/10.

Julius

Stayed in September 2026

Very clean and relaxing. Kitchen was fully stocked with pots, pans, etc. Craig was incredibly helpful and responsive.

Sarah

Stayed in September 2026

Great host and home. It's excellent for families!

Tricy

Stayed in September 2026

We had such a nice stay! Location was amazing and the house was spacious and clean. We hope to be back soon!

Ryan

Stayed in September 2026

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