Gulf Harbor Vacation Packages

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Top Holiday Package Deals in Gulf Harbor

Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Ft Myers

Hilton Garden Inn Ft Myers

3 out of 5
Villas
Price was CA $636, price is now CA $394 per person
CA $394
per person
Nov 7 - Nov 10
found 12 hours ago
Roundtrip flight included
Toronto (YTO) to Fort Myers (RSW)
8.6/10 Excellent! (1,009 reviews)
It was very clean, in a good location, has an outdoor pool, very pleasant staff.

Reviewed on Sep. 6, 2025

LaPlaya Beach & Golf Resort - A Noble House Resort

LaPlaya Beach & Golf Resort - A Noble House Resort

4.5 out of 5
Vanderbilt Beach
Price was CA $4,656, price is now CA $2,044 per person
CA $2,044
per person
Nov 29 - Dec 6
found 11 hours ago
Roundtrip flight included
Toronto (YTO) to Fort Myers (RSW)
8.8/10 Excellent! (1,009 reviews)
The overall experience at the hotel was excellent.

Reviewed on Sep. 2, 2025

Inn on Fifth

Inn on Fifth

4 out of 5
Old Naples
Price was CA $3,743, price is now CA $2,140 per person
CA $2,140
per person
Nov 29 - Dec 6
found 11 hours ago
Roundtrip flight included
Toronto (YTO) to Fort Myers (RSW)
9.4/10 Exceptional! (1,004 reviews)
I enjoyed the Hospitality and spa services and 2nd floor pool absolutely great experience.

Reviewed on Sep. 6, 2025

The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Price was CA $2,637, price is now CA $1,528 per person
CA $1,528
per person
Nov 29 - Dec 6
found 11 hours ago
Roundtrip flight included
Toronto (YTO) to Fort Myers (RSW)
9.6/10 Exceptional! (406 reviews)
It's lovely and clean, but it opened in January; hopefully, it will stay that way in the future. The only issue for me was the prices at the rooftop bar. A glass of wine is $16 for a Sauvignon Blanc, and that bottle is $10 at Costco or Total Wine.

Reviewed on Sep. 6, 2025

Best Western Naples Inn & Suites

Best Western Naples Inn & Suites

2.5 out of 5
Moorings
Price was CA $1,276, price is now CA $862 per person
CA $862
per person
Nov 29 - Dec 6
found 11 hours ago
Roundtrip flight included
Toronto (YTO) to Fort Myers (RSW)
8.2/10 Very Good! (1,001 reviews)
Excellent service, room super clean and quiet. I recommend it.

Reviewed on Sep. 1, 2025

Where to stay in Gulf Harbor

Find the best Gulf Harbor areas and neighborhoods for the activities you enjoy most. Learn more about Gulf Harbor
Naples Botanical Garden which includes a pond and a garden

East Naples

4/5(11 area reviews)

Beaches, shopping, and restaurants are just a few things travelers enjoy about East Naples. Check out Fifth Avenue South or Naples Botanical Garden while you're exploring the area.

Find hotels in East Naples

Gulf Harbor Hotel Deals

Naples Grande Beach Resort

Naples Grande Beach Resort

4.5 out of 5
475 Seagate Drive, Naples, FL
Fully refundableReserve now, pay when you stay
The price is CA $251 per night from Sep 8 to Sep 9
CA $251
CA $347 total
Sep 8 - Sep 9
includes taxes & fees
Naples Grande Beach Resort
Margaritaville Beach Resort Fort Myers

Margaritaville Beach Resort Fort Myers

4 out of 5
251 Crescent Street, Fort Myers Beach, FL
The price is CA $180 per night from Sep 14 to Sep 15
CA $180
CA $255 total
Sep 14 - Sep 15
includes taxes & fees
Margaritaville Beach Resort Fort Myers
Lani Kai Beachfront Resort

Lani Kai Beachfront Resort

3.5 out of 5
1400 Estero Blvd, Fort Myers Beach, FL
Fully refundableReserve now, pay when you stay
The price is CA $135 per night from Sep 24 to Sep 25
CA $135
CA $182 total
Sep 24 - Sep 25
includes taxes & fees
Lani Kai Beachfront Resort
See all 12,175 properties in Gulf Harbor
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Gulf Harbor vacation package cost?
Choose from any combination of hotels, flights and car rentals, and you can be vacationing in Gulf Harbor from just CA $394. And the more you bundle, the more cash you save. Your dream escape has never been more affordable.
How do I get a cheap travel package to Gulf Harbor?
You'll save tons of cash if you combine your car rentals, hotels and flights into a Gulf Harbor vacation package. Sometimes cheap means fewer options. But that's not the case with Expedia. We offer more than 550 partner airlines and 1,000,000 properties throughout the world, which means you'll always have plenty of options to choose from. Eager to save even more? Add some popular activities to your package deal to unlock even more discounts! After all, travel is about more than simply getting to your destination.
Where should I stay in Gulf Harbor?
Most travelers who visit Gulf Harbor put both Naples Pier and Barefoot Beach on their to-do lists. Why not reserve a hotel right near these fantastic attractions?
What are the top hotels in Gulf Harbor?
Adorable Canal Front Cottage Close To Beach With Boat Ramp and 3b 3ba Tropical Paradise Waterfront Pool House are two of the most well-known properties in Gulf Harbor. Why not look up the rates and facilities at each and then make a decision?
How far in advance should I book my Gulf Harbor vacation?
It's tricky picking the ideal time for airfares, but we generally suggest the earlier, the better. Many international journeys on Expedia become available to compare up to 12 months in advance. If you're unable to do so, don't worry. Cheap prices appear from time to time within a few weeks of departure dates.
What does an Expedia Gulf Harbor travel package include?
Expedia has everything you need to plan your Gulf Harbor trip, but how you structure your package is up to you. Select from any combination of flights, hotels and rental cars. Searching for some experiences or tours to keep you on the go? Once you've made your booking, you can add them on too. Whatever your budget or style, there's a deal to suit your needs.
What should I know before booking a Gulf Harbor travel package?
You can save a tidy sum by bundling your hotels, flights and rental cars. Once you've created your package, you can add on things like tours and activities. Your next unforgettable adventure is only a couple of clicks away.
Can I choose my airline with a Gulf Harbor Expedia vacation package?
Definitely. Expedia has more than 550 airline partners to select from worldwide. With so many choices, finding the ideal carrier to whisk you away to Gulf Harbor will be a snap.
If I'm not able to travel, can I cancel my Gulf Harbor vacation package?
You can. We understand that things don't always go to plan, so we're happy to help if you need to make changes to your Gulf Harbor vacation package. You may be able to cancel or amend your itinerary for free if you've booked in the last 24 hours. Your airline, hotel or car rental company may charge you a fee if your booking was made more than 24 hours ago. Take a look at our Customer Service Portal for further information. Also, be sure to check your itinerary for the finer details on change fees.

Discover the most popular places to visit in Gulf Harbor

Naples Beach

Naples Beach

4.5/5(102 reviews)

Why not spend a carefree afternoon at Naples Beach during your travels in Naples? Stroll along the seaside or visit the shops while you're in the area.

Naples Beach
5th Avenue Shopping District which includes markets, street scenes and a city

Fifth Avenue South

Enjoy many happy hours exploring the variety of shops, dining options and cultural attractions of this popular shopping district in Naples, Florida.

Fifth Avenue South
Naples Pier featuring landscape views and a beach as well as a large group of people

Naples Pier

4.5/5(74 reviews)

Visit this beloved Naples destination to experience the simple charms of the beachfront on a dock that has served the city for more than 100 years.

Naples Pier

Things to do

SEAS The Day with Pure Florida

Naples Sightseeing Boat Tour

CA $88
per adult
98% of travellers recommend
Naples Sightseeing Boat Tour
Cute Manatee

Manatee Sightseeing and Wildlife Boat Tour

CA $96
per adult
90% of travellers recommend
Manatee Sightseeing and Wildlife Boat Tour
Naples Florida: Downtown Electric Moped Tour

Naples Florida: Downtown Electric Moped Tour

CA $82
per adult
100% of travellers recommend
Naples Florida: Downtown Electric Moped Tour
See all activities in Naples
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.