Little Gasparilla Island Vacation Packages 2026 from $450

Little Gasparilla Island flight + hotel vacation packages

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

Mariners Boathouse by Coolvacay

South Island

Save 100% on your flight

$450

per person

Nov 10 - Nov 14

found 6 hours ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

This condo doesn't skimp on freebies - guests receive free WiFi and free self parking. An outdoor pool and laundry facilities are also provided.

The Lighthouse Resort Inn & Suites

Save 100% on your flight

$746

per person

Nov 5 - Nov 9

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

This hotel features 2 outdoor pools, a restaurant, and a bar/lounge. Relax with a drink at the poolside bar and enjoy perks like free self parking and free WiFi. A terrace, a garden, and a picnic area are also on offer.

Tween Waters Island Resort & Spa

Save 100% on your flight

$687

per person

Nov 5 - Nov 9

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

This smoke-free resort features a private beach, a full-service spa, and a marina. Family-friendly amenities include a children's pool and kid-friendly dining, along with kayaking. Free self parking is free for guests, and you can enjoy a meal in one of the 3 restaurants.

The Perry Hotel Naples

Save 100% on your flight

$811

per person

Dec 1 - Dec 5

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

A marina, 2 restaurants, and 2 outdoor pools are all featured at this smoke-free hotel. Unwind with a drink at one of the 2 poolside bars and enjoy freebies like WiFi in public areas and a beach shuttle. Relax with a drink at one of the 2 bars/lounges and enjoy the a rooftop terrace.

Wiggins Pass Chalet

Save 100% on your flight

$873

per person

Dec 1 - Dec 8

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

This aparthotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Traveling on business? Take advantage of the 24-hour business center and free internet in public areas. Free parking, a terrace, and a picnic area are also offered.

Top Little Gasparilla Island hotels deals

Dream Beach House, steps to the Beach and beautiful Sunsets

Placida FL

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This vacation home features laundry facilities.

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

5500 Sunseeker Way Punta Gorda FL

Free Cancellation

Reserve now, pay when you stay

$216 nightly

$242 total

Oct 14 - Oct 15

Total with taxes and fees

A full-service spa, 7 restaurants, and 2 outdoor pools are all featured at this resort. 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 and an off-leash area. Relax with a drink at one of the 2 poolside bars and enjoy the 2 hot tubs and 24-hour gym.

The Suites at Fishermen’s Village

1200 W Retta Esplanade Punta Gorda FL

Free Cancellation

Reserve now, pay when you stay

$160 nightly

$179 total

Oct 6 - Oct 7

Total with taxes and fees

A marina, 2 restaurants, and an outdoor pool are all featured at this smoke-free aparthotel. Relax with a drink at one of the 2 bars/lounges and enjoy free perks like free self parking and WiFi in public areas. A coffee shop, a snack bar/deli, and a picnic area are also on offer.

Sunsuites Villas At Sunseeker Resort, Curio By Hilton

5600 Sunseeker Way Charlotte Harbor FL

Free Cancellation

Reserve now, pay when you stay

$290 nightly

$325 total

Oct 4 - Oct 5

Total with taxes and fees

A full-service spa, 7 restaurants, and 2 outdoor pools are all featured at this hotel. Relax with a drink at one of the 2 poolside bars and get perks like free WiFi. Relax with a drink at one of the 9 bars/lounges and enjoy the 24-hour gym.

Wyvern Hotel, an Ascend Collection Hotel

101 E Retta Esplanade Punta Gorda FL

Free Cancellation

$116 nightly

$130 total

Oct 11 - Oct 12

Total with taxes and fees

This smoke-free hotel features 2 restaurants and 2 bars/lounges. Traveling on business? Take advantage of the free WiFi in public areas and free internet in public areas. Enjoy the a rooftop terrace and perks like free self parking.

Baymont by Wyndham Punta Gorda/Port Charlotte

9035 Mac Drive Punta Gorda FL

Free Cancellation

Reserve now, pay when you stay

$69 nightly

$77 total

Oct 3 - Oct 4

Total with taxes and fees

This motel features an outdoor pool and a gym. Business travelers can take advantage of the free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.

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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 Little Gasparilla Island?

Starting at just $450, hotel and flight packages are a fantastic way to make your vacation budget stretch further. Get ready Little Gasparilla Island — here you come!

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

For the best Little Gasparilla Island package deal, you can't go past Travelocity. Pick from as many as 400 airlines and 1,000,000 properties around the globe to create your ideal trip — it's really that simple.

Why should I book my Little Gasparilla Island vacation package with Travelocity?

Whether you're planning an epic vacation or a last-minute trip, we have plenty of enticing destinations to choose from at a great price. And on top of that, we offer customer support 24/7, superb service and a Price Match Guarantee. Save yourself money and time and reserve your dream vacation today.

Will I save money on my Little Gasparilla Island car rental if I combine it with a hotel or flight?

You certainly can with our Little Gasparilla Island vacation packages. With one of these, there are tons of ways to stretch your vacation budget further. Bundle any two or more car, hotel, flight and tour bookings and see the savings pile up. With your own set of wheels, all the popular attractions around Little Gasparilla Island are a memorable road trip away.

What is there to do in Little Gasparilla Island?

A big-name attraction you can't miss in Little Gasparilla Island is Little Gasparilla Island Beach. After you've been there, spend time meeting the locals and getting in touch with the true essence of this impressive destination.