Photo by K Bianca

Hillcrest rentals with pool

We found 191 rentals with pool — enter your dates for availability

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October 2025

November 2025

Explore Hillcrest rentals with pools

BEATIFUL ZEN VILLA IN HILLCREST!! Gated AC HotTub Paring KingBed

Sleeps 4 · 1 bedroom · 1 bathroom

New Dream Villa Hillcrest Little Italy Oasis Hot Tub King Bed Fenced AC Parking

Sleeps 2 · 1 bedroom · 1 bathroom

Premier Host

Hillcrest Hideaway one block from downtown action, dog friendly w/ private yard

Sleeps 6 · 2 bedrooms · 2 bathrooms

Stunning Hillcrest San Diego Zen Studio OutdoorLiving HotTub RainShower Jacuzzy

Sleeps 3 · 1 bathroom

Premier Host

San Diego Swimming Pool on Stunning Canyon in Hillcrest Mission Hills -Walkable!

Sleeps 8 · 3 bedrooms · 2 bathrooms

Top rated rentals with pools - Hillcrest

Premier Host

Fabulous cottage

We loved this cottage, in a friendly safe neighbourhood. The courtyard area was perfect for relaxing outdoors in the winter sunshine. Betsy and John were the great hosts and we plan to return on future trips to San Diego.

Wendy C.

Stayed Jan 2022

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