Captiva Island Vacation Packages 2025/2026 from $258

Captiva Island flight + hotel vacation packages

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

Hilton Garden Inn Ft Myers

Villas

Save 100% on your flight

$258

per person

Nov 13 - Nov 17

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

This hotel features an outdoor pool, a 24-hour gym, and a restaurant. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the hot tub and perks like free self parking.

Edison Beach House

Save 100% on your flight

$502

per person

Nov 13 - Nov 17

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

An outdoor pool, free self parking, and free newspapers are featured at this aparthotel. A terrace, a garden, and a picnic area are also on offer.

The Perry Hotel Naples

Save 100% on your flight

$600

per person

Nov 13 - Nov 17

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.

Inn on Fifth

Old Naples

Save 100% on your flight

$508

per person

Oct 29 - Nov 1

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

A full-service spa, a 24-hour gym, and a restaurant are all featured at this eco-certified hotel. Enjoy the outdoor pool and perks like a free beach shuttle. Enjoy the a rooftop terrace and unwind at the bar/lounge and poolside bar.

LaPlaya Beach & Golf Resort - A Noble House Resort

Vanderbilt Beach

Save 100% on your flight

$1,119

per person

Nov 13 - Nov 17

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

This luxury resort features a private beach, a full-service spa, and 2 restaurants. Relax with sun loungers and beach umbrellas, and cool off with a drink at the beachside bar. Enjoy the outdoor pool and visit the 2 bars/lounges and beach bar for drinks.

Top Captiva Island hotels deals

Tween Waters Island Resort & Spa

15951 Captiva Drive, Captiva, FL

$331 nightly

$369 total

Sep 21 - Sep 22

Total with taxes and fees

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.

On private beach

Pool

South Seas Resort

5400 South Seas Plantation Rd, Captiva, FL

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This smoke-free resort features a private beach, a golf course, and a water park. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. There's fun for all ages with a children's pool and a waterslide, and barbecue grills are available on site.

On private beach

Pool

South Seas Bayside Villa 5130: Your Perfect Island Retreat

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A hot tub is featured at this vacation home, along with barbecue grills.

Pool

Hot Tub

South Seas Bayside Villa 4222

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A hot tub is featured at this vacation home, along with barbecue grills.

Pool

Hot Tub

South Seas Beach Villa 2418 Coastal Luxury

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This vacation home features barbecue grills.

Pool

Kitchen

Your Beachfront Oasis Awaits

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A hot tub is featured at this vacation home, along with laundry facilities and barbecue grills.

Pool

Hot Tub

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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.

Popular places to visit

A beautiful sunset with a pair of pelicans on Captiva Island.

Captiva Beach

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.

Turner Beach

If a restful vacation is part of your travel plans, Turner Beach might be the perfect place to seek out during your trip to Wulfert. Stroll along the seaside or discover the area's sunrises.

Alison Hagerup Beach Park

Why not spend a carefree afternoon at Alison Hagerup Beach Park during your travels in Captiva? Discover the beautiful sunsets in this relaxing area.

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 $258. 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.