Little Gasparilla Island Vacation Packages 2026 from $545

Little Gasparilla Island flight + hotel vacation packages

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

Tween Waters Island Resort & Spa

Save 100% on your flight

$545

per person

Oct 25 - Oct 28

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.

Mariners Boathouse by Coolvacay

South Island

Save 100% on your flight

$782

per person

Nov 17 - Nov 23

found 1 day 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.

Landing Furnished Apartments - Naples, FL

Save 100% on your flight

$1,189

per person

Dec 2 - Dec 9

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

This apartment features an outdoor pool and a gym. Traveling on business? Take advantage of the free WiFi in public areas and onsite conference center. There's a rooftop terrace on site, and concierge services and barbecue grills are also offered.

Casa Ybel Resort

Mid Island

Save 100% on your flight

$657

per person

Nov 12 - Nov 16

found 14 hours ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

This hotel features 2 restaurants, 6 outdoor tennis courts, and an outdoor pool. Enjoy beachfront dining and relax with beach cabanas and sun loungers. Relax with a drink at the bar/lounge and enjoy perks like free self parking and free WiFi.

Windward Passage Resort

Save 100% on your flight

$837

per person

Nov 17 - Nov 23

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

This hotel features an outdoor pool and a hot tub. Guests will appreciate free perks like free self parking and WiFi in public areas. Laundry facilities are provided for your convenience.

Top Little Gasparilla Island hotels deals

Dream Beach House, steps to the Beach and beautiful Sunsets

Placida FL

Get rates

This vacation home features laundry facilities.

Kitchen

Washer

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

5500 Sunseeker Way Punta Gorda FL

Free Cancellation

Reserve now, pay when you stay

$143 nightly

$160 total

Oct 1 - Oct 2

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.

Pool

Hot Tub

The Suites at Fishermen’s Village

1200 W Retta Esplanade Punta Gorda FL

Free Cancellation

Reserve now, pay when you stay

$152 nightly

$171 total

Sep 30 - Oct 1

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.

Pool

Kitchen

Sunsuites Villas At Sunseeker Resort, Curio By Hilton

5600 Sunseeker Way Charlotte Harbor FL

Free Cancellation

Reserve now, pay when you stay

$192 nightly

$215 total

Sep 20 - Sep 21

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.

Pool

Spa

Days Inn by Wyndham Port Charlotte/Punta Gorda

1941 Tamiami Trl Port Charlotte FL

Free Cancellation

Reserve now, pay when you stay

$72 nightly

$81 total

Oct 1 - Oct 2

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free on-the-go breakfast, free WiFi, and free self parking. Business travelers can take advantage of the business center. There's an outdoor pool on site, and a 24-hour front desk and a convenience store are also provided.

Pool

Breakfast included

Wyvern Hotel, an Ascend Collection Hotel

101 E Retta Esplanade Punta Gorda FL

Free Cancellation

$112 nightly

$125 total

Sep 27 - Sep 28

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.

Pet friendly

Parking included

Don't see what you're looking for?

See all available properties in Little Gasparilla Island

View all properties

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 $545, 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.