Gulf Pines Vacation Packages

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Top Holiday Package Deals in Gulf Pines

Price found within the past 48 hours. Click for updated prices.
Matanzas Inn Bayside Resort and Marina

Matanzas Inn Bayside Resort and Marina

3 out of 5
Price was CA $782, price is now CA $538 per person
CA $538
per person
Jul 9 - Jul 12
found 15 hours ago
Roundtrip flight included
Buffalo (BUF) to Fort Myers (RSW)
9.4/10 Exceptional! (1,010 reviews)
From Penny ( who didn't know she was a You Tube star.lol a video from a previous stay took a video and praised her..which made our decision to stay also..)at the front desk to the cleaners, the grounds, pool,hot tub, our room ,the food everything was excellent just what we where looking for, 2 restaurants and bars, music and great views of the bay with the boats..short walk to the Fort Myers Beach..with shopping, restaurants ,bars and music along the way..went to the upper deck restaurant bar at the hotel on Sat night. and listened to Big Daddy Rich who's a buffalo guy always a good time listening to him sing all our favorites then the waitress comes over.. recognized..our accent..lol..she's from Buffalo also...So we had to order both pizza and wings and we were NOT disappointed... Excellent !. And We are Buffalo Peeps ⛵.We had a Great 44 th. Anniversary get away ..Thanks again Penny 💕

Reviewed on Apr 27, 2026

The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Price was CA $896, price is now CA $557 per person
CA $557
per person
Jul 9 - Jul 12
found 15 hours ago
Roundtrip flight included
Buffalo (BUF) to Fort Myers (RSW)
9.4/10 Exceptional! (758 reviews)
Hard to find parking and valet closes early. Front desk was not helpful at check in and didn’t explain the amenities at all. They did not honor Expedia free drink voucher at stated when I made my reservation. Rooftop bar is very busy and hard to get a reservation or spot at the bar as it is open to the public, but great drinks and views. Room was very nice.

Reviewed on Apr 27, 2026

Mariners Boathouse by Coolvacay

Mariners Boathouse by Coolvacay

3 out of 5
South Island
Price was CA $1,657, price is now CA $1,110 per person
CA $1,110
per person
Jun 18 - Jun 24
found 10 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Fort Myers (RSW)
10/10 Exceptional! (1 review)
Very nice condo. Views are amazing. Nice place. Would recommend.

Reviewed on Mar 6, 2026

The Lighthouse Resort Inn & Suites

The Lighthouse Resort Inn & Suites

3 out of 5
Price was CA $959, price is now CA $645 per person
CA $645
per person
Jul 9 - Jul 12
found 15 hours ago
Roundtrip flight included
Buffalo (BUF) to Fort Myers (RSW)
8.6/10 Excellent! (1,626 reviews)
Great resort & great person & staff

Reviewed on Apr 26, 2026

Hyatt Vacation Club at Coconut Cove, Bonita Springs

Hyatt Vacation Club at Coconut Cove, Bonita Springs

4 out of 5
Price was CA $1,163, price is now CA $813 per person
CA $813
per person
Jul 9 - Jul 12
found 15 hours ago
Roundtrip flight included
Buffalo (BUF) to Fort Myers (RSW)
9/10 Wonderful! (843 reviews)
This resort was awesome. The shuttle to the boat then to the beach was amazing. On the way to the beach, we encountered 4-5 dolphins following the boat. The lazy river was nice just cold. The resort itself was clean, staff was friendly and helpful, and the rooms were also clean and spacious.

Reviewed on Apr 21, 2026

Where to stay in Gulf Pines

Find the best Gulf Pines areas and neighborhoods for the activities you enjoy most. Learn more about Gulf Pines
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Mid Island

2 out of top 10 points of interest in this area

While visiting Mid Island, you might make a stop by sights like Periwinkle Way and Sanibel Island Southern Beach.

Find hotels in Mid Island

Gulf Pines Hotel Deals

Holiday Inn Express Cape Coral-Fort Myers Area by IHG

Holiday Inn Express Cape Coral-Fort Myers Area by IHG

2.5 out of 5
1538 Cape Coral Pkwy E Cape Coral FL
Fully refundable
The price is CA $143 per night from May 10 to May 11
CA $143
CA $160 total
May 10 - May 11
includes taxes & fees
9.2/10 Wonderful! (1,428 reviews)
Amazing place to stay away from home. If you need anything justa ask the front desk and they will bring to you.

Reviewed on Apr 27, 2026

Holiday Inn Express Cape Coral-Fort Myers Area by IHG
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 $272 per night from May 18 to May 19
CA $272
CA $371 total
May 18 - May 19
includes taxes & fees
9/10 Wonderful! (2,050 reviews)
Everything was super good. I am very happy with my stay. Thank you.

Reviewed on Apr 27, 2026

Margaritaville Beach Resort Fort Myers
Sanibel Island Beach Resort

Sanibel Island Beach Resort

3 out of 5
1231 Middle Gulf Dr Sanibel FL
Fully refundableReserve now, pay when you stay
The price is CA $285 per night from May 17 to May 18
CA $285
CA $352 total
May 17 - May 18
includes taxes & fees
9.2/10 Wonderful! (1,833 reviews)
Staff was friendly and accommodating!

Reviewed on Apr 27, 2026

Sanibel Island Beach Resort
See all 13,279 properties in Gulf Pines
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
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Frequently asked questions

How much does a Gulf Pines vacation package cost?
The cheapest Gulf Pines vacation package is CA $538, so your dream escape can become a reality — without breaking the bank. Combine flights, hotels and car rentals to custom build a package that matches your traveling style.
How do I get a cheap travel package to Gulf Pines?
Browse and book everything all in one place with our Gulf Pines vacation packages. You'll find bargains on hotels, flights, tours and more that'll keep your hip pocket happy and your adventurous spirit full. And, with more than 550 airlines and 1,000,000 hotel options across the globe to select from, you have countless opportunities to mix and match as you want.
Where should I stay in Gulf Pines?
With lots to explore in Gulf Pines, it's a good idea to book a hotel close to its attractions. Sanibel Island Southern Beach, Bowmans Beach and J. N. Ding Darling National Wildlife Refuge are some good ones to add to your must-see list.
How far in advance should I book my Gulf Pines vacation?
Travelers can normally browse international airfares on Expedia within 12 months of the departure date. Booking last minute? With a bit of luck, it's still possible to nab a cheaper ticket just weeks before your journey.
What does an Expedia Gulf Pines travel package include?
Hotels, rental cars and flights, or any combination of the three — it's totally up to you. Whether you're venturing to Gulf Pines with the family or adventuring with your friends, there's a package to suit every budget and style. Once you've made your booking, why not add on a couple of tours or activities?
What should I know before booking a Gulf Pines travel package?
You'll score impressive savings when you combine your flights, hotels and rental cars into a package. Plus, booking everything in one spot will make your trip planning easier. So why waste money or time? Whether you're organizing a ritzy city getaway or a low-cost family road trip, have a look at our vacation packages today.
Can I choose my airline with a Gulf Pines Expedia vacation package?
With a vacation package, you're the boss. Whether you're looking to fly to Gulf Pines in first class or coach, simply pick from the available airline options. Expedia has access to over 550 airline partners across the world.
If I'm not able to travel, can I cancel my Gulf Pines vacation package?
Certainly, and we'll help you every step of the way. You may be able to cancel or change your Gulf Pines vacation package for free if you booked in the last 24 hours. However, you may incur a fee from your hotel, airline or car rental company if you booked more than 24 hours ago. If your travel plans suddenly change, take a look at our Customer Service Portal for more information.

Discover the most popular places to visit in Gulf Pines

Bowman's Beach

Bowman's Beach

4.5/5(16 reviews)

Relax and revel in a visit to one of the area’s most beautiful beaches, great for swimming, fishing and finding special seashells.

Bowman's Beach
J. N. Ding Darling National Wildlife Refuge

J. N. Ding Darling National Wildlife Refuge

5/5(2 reviews)

See almost anything that flies, swims or crawls in Florida in this protected area. Become acquainted with wildlife while learning about varied species.

J. N. Ding Darling National Wildlife Refuge

Sanibel Island Golf Club

Enjoy a round of golf in Sanibel at Sanibel Island Golf Club. Stroll along the seaside in this family-friendly area, or check out its lively bars.

Sanibel Island Golf Club

Things to do

Southwest Florida Sunset Sail

Southwest Florida Sunset Sail

CA $96
per adult
100% of travellers recommend
Southwest Florida Sunset Sail
Copacetic Day Sail

Copacetic Day Sail

CA $96
per adult
100% of travellers recommend
Copacetic Day Sail
Dolphin Wildlife Cruise Fort Myers Beach

Dolphin Wildlife Cruise Fort Myers Beach

CA $88
per adult
100% of travellers recommend
Dolphin Wildlife Cruise Fort Myers Beach
See all activities in Sanibel
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.