Photo by Bob Kirschke
Harbor Island holiday rentals
We found 5,973 holiday rentals — enter your dates for availability
Discover a selection of holiday rentals in Harbor Island that are perfect for your trip. Holiday rentals offer the best amenities for you and your friends, family or even pets, such as Wi-Fi and a washer and dryer. What you'll find is a property to rent for everyone's needs, including places that are non-smoking or accessible.
Holiday rentals with weekly discounts - Harbor Island
Showing deals for:14 Nov - 21 Nov
Image gallery for Beautiful Normal Heights Living
1010 out of 10 rating
Exceptional
(57 reviews)
Beautiful Normal Heights Living
San Diego, CA
10% off
Price is S$2,408
S$2,408
S$344 per night
includes taxes & fees
Image gallery for ✈Fully Remodeled Mansion Pool/Jacuzzi☀
9.69.6 out of 10 rating
Exceptional
(96 reviews)
✈Fully Remodeled Mansion Pool/Jacuzzi☀
San Diego, CA
8% off
Price is S$6,852
S$6,852
S$979 per night
includes taxes & fees
Image gallery for Central, Family-Friendly, Clean San Diego 3bed/2bath home w/backyard
9.89.8 out of 10 rating
Exceptional
(10 reviews)
Central, Family-Friendly, Clean San Diego 3bed/2bath home w/backyard
San Diego, CA
7% off
Price is S$2,783
S$2,783
S$398 per night
includes taxes & fees
Image gallery for Relax at this Family Home w/ Solar heated Pool & Game Room. Close to everything!
9.69.6 out of 10 rating
Exceptional
(21 reviews)
Relax at this Family Home w/ Solar heated Pool & Game Room. Close to everything!
San Diego, CA
8% off
Price is S$4,442
S$4,442
S$635 per night
includes taxes & fees
Image gallery for Spacious Ocean Beach Studio w/ Parking - Short Walk to the Beach
9.29.2 out of 10 rating
Wonderful
(12 reviews)
Spacious Ocean Beach Studio w/ Parking - Short Walk to the Beach
San Diego, CA
8% off
Price is S$2,101
S$2,101
S$300 per night
includes taxes & fees
Image gallery for Beachfront Windansea Escape ideal for families
1010 out of 10 rating
Exceptional
(17 reviews)
Beachfront Windansea Escape ideal for families
La Jolla, CA
8% off
Price is S$31,667
S$31,667
S$4,524 per night
includes taxes & fees
Image gallery for Spanish gated Villa w/pool & spa near Mission Bay
9.69.6 out of 10 rating
Exceptional
(32 reviews)
Spanish gated Villa w/pool & spa near Mission Bay
San Diego, CA
6% off
Price is S$5,303
S$5,303
S$758 per night
includes taxes & fees
Image gallery for La Jolla Beach House. 2 Minute Walk to the Beach!
9.49.4 out of 10 rating
Exceptional
(10 reviews)
La Jolla Beach House. 2 Minute Walk to the Beach!
La Jolla, CA
8% off
Price is S$10,679
S$10,679
S$1,526 per night
includes taxes & fees
Image gallery for Top Floor Ocean Front Remodeled Condo
1010 out of 10 rating
Exceptional
(60 reviews)
Top Floor Ocean Front Remodeled Condo
San Diego, CA
8% off
Price is S$4,213
S$4,213
S$602 per night
includes taxes & fees
Image gallery for Near Bay Home with A/C, Bikes, Parking, and Wi-Fi - Mins to Beach!
9.89.8 out of 10 rating
Exceptional
(17 reviews)
Near Bay Home with A/C, Bikes, Parking, and Wi-Fi - Mins to Beach!
San Diego, CA
8% off
Price is S$3,286
S$3,286
S$469 per night
includes taxes & fees
Image gallery for Dog Friendly Cottage with Ocean Beach Charm
1010 out of 10 rating
Exceptional
(52 reviews)
Dog Friendly Cottage with Ocean Beach Charm
San Diego, CA
8% off
Price is S$2,440
S$2,440
S$349 per night
includes taxes & fees
Image gallery for 2-Bedroom Coastal Gem, Just Steps to the Sand
8.08.0 out of 10 rating
Very good
(11 reviews)
2-Bedroom Coastal Gem, Just Steps to the Sand
San Diego, CA
8% off
Price is S$4,195
S$4,195
S$599 per night
includes taxes & fees
Image gallery for Newly Designed 20's Bungalow with a MidCentury Modern Flair
1010 out of 10 rating
Exceptional
(84 reviews)
Newly Designed 20's Bungalow with a MidCentury Modern Flair
San Diego, CA
8% off
Price is S$2,467
S$2,467
S$352 per night
includes taxes & fees
Image gallery for Architectural Masterpiece on Windansea Beach - Family and Pet Friendly!
1010 out of 10 rating
Exceptional
(94 reviews)
Architectural Masterpiece on Windansea Beach - Family and Pet Friendly!
La Jolla, CA
8% off
Price is S$15,227
S$15,227
S$2,175 per night
includes taxes & fees
Image gallery for Pacific Beach Studio #1973 Close to beach, bay and more!
9.29.2 out of 10 rating
Wonderful
(7 reviews)
Pacific Beach Studio #1973 Close to beach, bay and more!
San Diego, CA
8% off
Price is S$1,346
S$1,346
S$192 per night
includes taxes & fees
Image gallery for Beach Bungalow 1 with Private Outdoor yard
9.49.4 out of 10 rating
Exceptional
(101 reviews)
Beach Bungalow 1 with Private Outdoor yard
La Jolla, CA
7% off
Price is S$2,951
S$2,951
S$422 per night
includes taxes & fees
Image gallery for La Jolla Cove Modern Luxury in Exclusive Location
1010 out of 10 rating
Exceptional
(14 reviews)
La Jolla Cove Modern Luxury in Exclusive Location
La Jolla, CA
11% off
Price is S$5,950
S$5,950
S$850 per night
includes taxes & fees
Image gallery for Ocean Front 3BR with Best Private Patio!
9.89.8 out of 10 rating
Exceptional
(28 reviews)
Ocean Front 3BR with Best Private Patio!
San Diego, CA
8% off
Price is S$7,212
S$7,212
S$1,030 per night
includes taxes & fees
Image gallery for Beach 2 Blocks * Ocean Views * A/C
9.89.8 out of 10 rating
Exceptional
(93 reviews)
Beach 2 Blocks * Ocean Views * A/C
San Diego, CA
7% off
Price is S$10,235
S$10,235
S$1,462 per night
includes taxes & fees
Image gallery for The Key Lime Oasis, Gorgeous Second-Story Unit!
9.49.4 out of 10 rating
Exceptional
(94 reviews)
The Key Lime Oasis, Gorgeous Second-Story Unit!
San Diego, CA
8% off
Price is S$5,133
S$5,133
S$733 per night
includes taxes & fees
Image gallery for POOL * Remodeled Single Level House * Ocean & City Views
1010 out of 10 rating
Exceptional
(18 reviews)
POOL * Remodeled Single Level House * Ocean & City Views
San Diego, CA
7% off
Price is S$2,993
S$2,993
S$428 per night
includes taxes & fees
Image gallery for Ocean/Sunset Views, Modern, Sunset Cliffs/Point Loma near OB, PLNU, Thurs Club
1010 out of 10 rating
Exceptional
(57 reviews)
Ocean/Sunset Views, Modern, Sunset Cliffs/Point Loma near OB, PLNU, Thurs Club
San Diego, CA
7% off
Price is S$2,323
S$2,323
S$332 per night
includes taxes & fees
Image gallery for Newly Updated Retro Beach Rental
9.89.8 out of 10 rating
Exceptional
(88 reviews)
Newly Updated Retro Beach Rental
San Diego, CA
12% off
Price is S$2,340
S$2,340
S$334 per night
includes taxes & fees
Image gallery for 3 Levels of Water Front • A/C • 5 Outdoor Spaces
9.69.6 out of 10 rating
Exceptional
(14 reviews)
3 Levels of Water Front • A/C • 5 Outdoor Spaces
San Diego, CA
7% off
Price is S$20,976
S$20,976
S$2,997 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Harbor Island
🌟Breathtaking 180º Views | Family+Work | Hot Tub | 💖of San Diego🌴 |5⭐️reviews
Sleeps 14 · 6 bedrooms · 4 bathrooms
1010 out of 10
Exceptionalexceptional
63 reviews(63 reviews)
Luxury 5BD/4BA Mission Hills/Stunning Rooftop + Skyline Views
Sleeps 14 · 5 bedrooms · 4 bathrooms
9.49.4 out of 10
Exceptionalexceptional
203 reviews(203 reviews)
The Gathering Place | Family Favorite | Central SD
Sleeps 8 · 4 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
10 reviews(10 reviews)
Modern upscale home, 2bd 2bth, Pr Patio, 1 Blk>Zoo
Sleeps 6 · 2 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
42 reviews(42 reviews)
Sunset Suite: 3-bedroom apartment with gorgeous sunset views near Dog Beach
Sleeps 8 · 3 bedrooms · 2 bathrooms
9.09.0 out of 10
Wonderfulwonderful
2 reviews(2 reviews)
Maven by AvantStay | 5 Minutes to the Beach! Ocean Views & Spacious Design
Sleeps 15 · 5 bedrooms · 3+ bathrooms
9.09.0 out of 10
Wonderfulwonderful
14 reviews(14 reviews)
Top rated rentals - Harbor Island
Would definitely stay again!
1010 out of 10
Exceptionalexceptional
269 reviews(269 reviews)
Peace of mindOur Book with Confidence guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value