Harbor Island Vacation Packages 2025/2026 from $335

Harbor Island flight + hotel vacation packages

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

Sand Castle Inn

$335

per person

Jan 10 - Jan 15

found 1 day ago

Roundtrip flight included

Denver (DEN) to San Diego (SAN)

This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. A picnic area, express check-in, and express check-out are also on offer.

The Sofia Hotel

Downtown San Diego

Save 100% on your flight

$467

per person

Dec 10 - Dec 16

found 1 day ago

Roundtrip flight included

Boston (BOS) to San Diego (SAN)

A restaurant and a 24-hour gym are featured at this hotel. 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.

Fairmont Grand Del Mar

Carmel Valley

Save 100% on your flight

$1,035

per person

Jan 10 - Jan 15

found 1 day ago

Roundtrip flight included

Denver (DEN) to San Diego (SAN)

This luxury hotel features a golf course, a full-service spa, and 6 restaurants. There's fun for all ages with a children's club and a children's pool, and babysitting is an added bonus. Traveling on business? Take advantage of the 24-hour business center, express check-out, and valet parking.

Margaritaville Hotel San Diego Gaslamp Quarter

Downtown San Diego

Save 100% on your flight

$516

per person

Dec 10 - Dec 16

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.

Pacific View Inn

Pacific Beach

Save 100% on your flight

$389

per person

Jan 10 - Jan 15

found 1 day ago

Roundtrip flight included

Denver (DEN) to San Diego (SAN)

Free WiFi in public areas, a terrace, and express check-out are available at this hotel. Enjoy a day at the beach surfing, or relax with beach umbrellas. Luggage storage is also provided.

Top Harbor Island hotels deals

Sheraton San Diego Resort

1380 Harbor Island Dr, San Diego, CA

Free Cancellation

Reserve now, pay when you stay

$158 nightly

$182 total

Nov 23 - Nov 24

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 Mission Valley

901 Camino Del Rio S, San Diego, CA

Free Cancellation

Reserve now, pay when you stay

$114 nightly

$131 total

Nov 16 - Nov 17

Total with taxes and fees

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

Pool

Hot Tub

Hampton Inn & Suites by Hilton San Diego SeaWorld

3888 Greenwood St, San Diego, CA

Free Cancellation

Reserve now, pay when you stay

$119 nightly

$137 total

Nov 16 - Nov 17

Total with taxes and fees

This hotel features an outdoor pool and a gym. Business travelers can take advantage of the free WiFi in public areas. Enjoy the hot tub and free buffet breakfast each morning.

Pool

Hot Tub

Pendry San Diego

550 J Street, San Diego, CA

Free Cancellation

Reserve now, pay when you stay

$295 nightly

$342 total

Nov 30 - Dec 1

Total with taxes and fees

A full-service spa, 3 restaurants, and an outdoor pool are all featured at this smoke-free hotel. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Make the most of the 24-hour gym and a rooftop terrace, and relax with drinks at one of the 3 bars/lounges.

Pool

Hot Tub

Hard Rock Hotel San Diego

207 5th Ave, San Diego, CA

Free Cancellation

Reserve now, pay when you stay

$229 nightly

$265 total

Nov 23 - Nov 24

Total with taxes and fees

A nightclub, 2 restaurants, and an outdoor pool are all featured at this smoke-free hotel. Enjoy a meal in one of the 2 coffee shops/cafes and perks like free WiFi. Enjoy the 24-hour gym and unwind at the bar/lounge and poolside bar.

Pool

Free WiFi

Courtyard by Marriott San Diego Downtown Little Italy

1646 Front St, San Diego, CA

Free Cancellation

$114 nightly

$132 total

Nov 27 - Nov 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 free WiFi in public areas and free internet in public areas. Enjoy the 24-hour gym and conveniences like a 24-hour front desk and concierge services.

Pool

Pet friendly

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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.

Popular places to visit

San Diego Zoo

See nature up-close and personal at one of the country’s largest and most educational zoos.

San Diego Convention Center

During your trip, find out what's happening at San Diego Convention Center, a top convention center in San Diego. Experience the area's acclaimed art scene and entertainment choices.

Mission Bay

Beaches and islands, amusement parks and water sports, bonfires, and sunsets: this outdoor playground buzzes both on land and in the water.

Frequently asked questions

How much are vacation packages to Harbor Island?

You can score a great hotel + flight bundle from just $335. 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.