Harbor Island Vacation Packages 2026 from $650

Harbor Island flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

The Sofia Hotel

Downtown San Diego

$650

per person

Oct 30 - Nov 4

found 1 day ago

Roundtrip flight included

Boston (BOS) to San Diego (SAN)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Self parking, a coffee shop, and a lobby fireplace are also offered.

Paradise Point Resort & Spa

Mission Bay

Save 100% on your flight

$795

per person

Dec 6 - Dec 12

found 1 day ago

Roundtrip flight included

Boston (BOS) to San Diego (SAN)

This smoke-free resort features a full-service spa, a marina, and 3 restaurants. Family-friendly amenities include mini golf and kid-friendly dining, along with kayaking. Enjoy the 5 outdoor pools and perks like free WiFi.

Legacy Resort Hotel & Spa

Mission Valley

Save 100% on your flight

$690

per person

Dec 2 - Dec 8

found 1 day ago

Roundtrip flight included

Boston (BOS) to San Diego (SAN)

A full-service spa, an outdoor pool, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the gym and unwind at the bar/lounge and poolside bar.

Margaritaville Hotel San Diego Gaslamp Quarter

Downtown San Diego

Save 100% on your flight

$908

per person

Dec 2 - Dec 8

found 1 day ago

Roundtrip flight included

Boston (BOS) to San Diego (SAN)

This hotel features a restaurant, an outdoor pool, and a bar/lounge. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls. You'll appreciate the 24-hour gym, poolside bar, and rooftop terrace.

Urban Boutique Hotel

Downtown San Diego

Save 100% on your flight

$674

per person

Dec 2 - Dec 8

found 1 day ago

Roundtrip flight included

Boston (BOS) to San Diego (SAN)

This hotel doesn't skimp on freebies - guests receive free continental breakfast and free WiFi. Business travelers can take advantage of the 24-hour business center. A picnic area, luggage storage, and concierge services are also on offer.

Top Harbor Island hotels deals

Sheraton San Diego Resort

1380 Harbor Island Dr San Diego CA

Free Cancellation

Reserve now, pay when you stay

$213 nightly

$245 total

Sep 27 - Sep 28

Total with taxes and fees

A marina, 5 restaurants, and 3 outdoor pools are all featured at this smoke-free hotel. Traveling on business? Take advantage of the business center, free WiFi in public areas, and free airport shuttle. Enjoy the 2 hot tubs, and relax with drinks at the bar/lounge and poolside bar.

Pool

Hot Tub

Hilton San Diego Airport/Harbor Island

1960 Harbor Island Drive San Diego CA

Free Cancellation

Reserve now, pay when you stay

$180 nightly

$206 total

Sep 27 - Sep 28

Total with taxes and fees

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. There's a 24-hour gym on site, and laundry facilities and concierge services are also offered.

Pool

Free airport shuttle

Handlery Hotel

950 Hotel Cir N San Diego CA

Free Cancellation

Reserve now, pay when you stay

$111 nightly

$128 total

Sep 23 - Sep 24

Total with taxes and fees

This smoke-free hotel includes 2 restaurants, an outdoor pool, and a hot tub. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the gym and visit the 2 bars/lounges and poolside bar for drinks.

Pool

Hot Tub

Paradise Point Resort & Spa

1404 Vacation Rd San Diego CA

Free Cancellation

Reserve now, pay when you stay

$254 nightly

$292 total

Oct 4 - Oct 5

Total with taxes and fees

Pool

Hot Tub

Best Western Seven Seas

411 Hotel Circle South San Diego CA

Free Cancellation

Reserve now, pay when you stay

$85 nightly

$97 total

Sep 22 - Sep 23

Total with taxes and fees

2 hot tubs, an outdoor pool, and a gym are all featured at this smoke-free hotel. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy a meal from the a restaurant and perks like free self parking.

Pool

Hot Tub

California Suites Hotel

5415 Clairemont Mesa Blvd San Diego CA

Free Cancellation

Reserve now, pay when you stay

$89 nightly

$102 total

Sep 22 - Sep 23

Total with taxes and fees

This hotel features an outdoor pool and a hot tub. Traveling for business? Take advantage of the free WiFi in public areas, express check-out, and conference space. Free self parking, a terrace, and a garden are also offered.

Pool

Hot Tub

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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

How much are vacation packages to Harbor Island?

You can score a great hotel + flight bundle from just $650. With one of our Travelocity vacation packages, a getaway in Harbor Island has never looked so enticing! Save your time and money and then start packing that suitcase.

Where can I get the best vacation package deals for Harbor Island?

There are incredible Harbor Island package deals to be scored with Travelocity. Did you know we partner with 400 airlines and 1,000,000 properties around the world? Remember this when you're ready to tick another destination off your must-visit list.

Why should I purchase my Harbor Island vacation bundle with Travelocity?

We've got 24/7 support, first-rate service and a Price Match Guarantee. Life is all about the journey — and we have exciting destinations for you to journey to in every nook and cranny of the globe. Explore with us and make your hip pocket happy.