Gulf Harbor Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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    Plan, book, and manage your trip all in one place

Top Holiday Package Deals in Gulf Harbor

Price found within the past 48 hours. Click for updated prices.
Quality Inn Fort Myers Cape Coral

Quality Inn Fort Myers Cape Coral

2 out of 5
Price was CA $831, price is now CA $542 per person
CA $542
per person
Jan 18 - Jan 23
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Fort Myers (RSW)
7.6/10 Good! (495 reviews)

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 $5,829, price is now CA $3,780 per person
CA $3,780
per person
Jan 26 - Jan 31
found 10 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Fort Myers (RSW)
9/10 Wonderful! (1,003 reviews)
The property is beautiful!!!!! Staff always attentive and polite but never intrusive Food is good but drinks are weak and expensive…just get beer to get your $ worth

Reviewed on Nov 13, 2026

The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Price was CA $3,811, price is now CA $2,534 per person
CA $2,534
per person
Jan 26 - Jan 31
found 10 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Fort Myers (RSW)
9.6/10 Exceptional! (1,224 reviews)
If you are looking for a fantastic resort that’s nearby everything SWFL has to offer. This is the resort for you! I wasn’t sure what to expect booking but it was great. From the staff, to the room, the food and private boat to the beach. Every detail was noted and appreciated. I cannot wait to return! Thank you for making a tough trip into a wonderful one!

Reviewed on Nov 13, 2026

Lani Kai Beachfront Resort

Lani Kai Beachfront Resort

3.5 out of 5
Price was CA $1,681, price is now CA $1,134 per person
CA $1,134
per person
Jan 18 - Jan 23
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Fort Myers (RSW)
8.8/10 Excellent! (2,129 reviews)

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
A wooden pier extending into calm waters at dusk, with two illuminated structures at the end.

East Naples

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

Marriott Sanibel Harbour Resort & Spa

Marriott Sanibel Harbour Resort & Spa

4 out of 5
17260 Harbour Pointe Dr Fort Myers FL
Fully refundableReserve now, pay when you stay
The price is CA $318 per night from Dec 1 to Dec 2
CA $318
CA $405 total
Dec 1 - Dec 2
includes taxes & fees
8.6/10 Excellent! (1,000 reviews)
"I just received a $200 charge on my CC post stay for “Resort Fees” which include things I did not use. Additionally, the resort charges $25/day just to park at a place you already paid to stay at. My room was at the Captiva bldg which is not near the main building. The Captiva building does have ..."

Reviewed on Nov 10, 2026

Marriott Sanibel Harbour Resort & Spa
Margaritaville Beach Resort Fort Myers

Margaritaville Beach Resort Fort Myers

4 out of 5
251 Crescent Street Fort Myers Beach FL
Fully refundableReserve now, pay when you stay
The price is CA $255 per night from Nov 29 to Nov 30
CA $255
CA $356 total
Nov 29 - Nov 30
includes taxes & fees
Margaritaville Beach Resort Fort Myers
Compass by Margaritaville Hotel Naples

Compass by Margaritaville Hotel Naples

4 out of 5
4805 Tamiami Trl N Naples FL
Fully refundableReserve now, pay when you stay
The price is CA $152 per night from Nov 22 to Nov 23
CA $152
CA $203 total
Nov 22 - Nov 23
includes taxes & fees
9.6/10 Exceptional! (1,951 reviews)
"Nice hotel. Not sure how it qualifies as a resort but whatever. Rooms were clean and building was in good shape. I would stay there again."

Reviewed on Nov 13, 2026

Compass by Margaritaville Hotel Naples
See all 12,986 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.
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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 $542. 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.

Things to do

Gulf of Mexico Sunset Cruise from Naples

Gulf of Mexico Sunset Cruise from Naples

CA $89
per adult
88% of travellers recommend
Gulf of Mexico Sunset Cruise from Naples
Naples Florida: Downtown Electric Trike Tour - Family Fun

Naples Florida: Downtown Electric Trike Tour - Family Fun

CA $78
per adult
100% of travellers recommend
Naples Florida: Downtown Electric Trike Tour - Family Fun
Naples: Sightseeing and Dining Cruises

Naples: Sightseeing and Dining Cruises

CA $110
per adult
Naples: Sightseeing and Dining Cruises
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.