Captiva Island Vacation Packages 2026 from $463

Captiva Island flight + hotel vacation packages

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

Stay Inn & Suites

Winkler

$463

per person

Oct 14 - Oct 21

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A business center, express check-out, and dry cleaning are also on offer.

Tween Waters Island Resort & Spa

Save 100% on your flight

$945

per person

Oct 14 - Oct 21

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

$1,025

per person

Oct 19 - Oct 25

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.

Casa Ybel Resort

Mid Island

Save 100% on your flight

$990

per person

Oct 14 - Oct 21

found 1 day ago

Roundtrip non-stop 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.

Manasota Key Resort

Save 100% on your flight

$902

per person

Sep 14 - Sep 19

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

This smoke-free hotel's private beach and marina are among the highlights. Enjoy the outdoor pool and perks like free self parking and free WiFi. A terrace, a picnic area, and laundry facilities are also on offer.

Stay near popular Captiva Island attractions

A beach with white sand and turquoise water. There are colorful Adirondack chairs lined up on the sand.

Captiva Beach

9.2/10 (1,970 reviews)

If a restful vacation is part of your travel plans, Captiva Beach might be the perfect place to seek out during your trip to Captiva. Discover the beautiful sunsets in this relaxing area.

See properties

Frequently asked questions

How much are vacation packages to Captiva Island?

With Travelocity vacation packages, you can experience the sights and sounds of Captiva Island from just $463. Activities, flights and hotels — we've got you. You're bound to save loads just for bundling together your bookings. And with everything taken care of before you even set off, you can sit back, relax and enjoy the adventure.

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

Travelocity is here to help you find a terrific Captiva Island package deal. With more than 400 partner airlines and 1,000,000 properties around the world, you're sure to find the perfect combination.

Why should I purchase my Captiva Island vacation package with Travelocity?

You'll not only save lots, but you can also access our 24/7 support, top-notch service and a Price Match Guarantee. Journey across the globe, discover hidden gems and make long-lasting memories — we'll take care of the little details.

Will I save money on my Captiva Island car rental if I book it with a hotel or flight?

You sure can with our Captiva Island vacation packages. With one of these, there are tons of ways to stretch your travel budget further. Bundle any two or more car, flight, hotel and tour bookings and watch your savings pile up. With your own set of wheels, all the popular sights around Captiva Island are an unforgettable road trip away.