Captiva Island Vacation Packages 2026 from $466

Captiva Island flight + hotel vacation packages

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

Latitude 26 Waterfront Resort & Marina

Save 100% on your flight

$466

per person

Oct 31 - Nov 7

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

A marina and an outdoor pool are featured at this smoke-free motel. Enjoy a meal from the restaurant and perks like free continental breakfast and free self parking. Free WiFi in public areas, a picnic area, and express check-in are also on offer.

The Lighthouse Resort Inn & Suites

Save 100% on your flight

$546

per person

Oct 31 - Nov 7

found 1 day ago

Roundtrip 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.

The Perry Hotel Naples

Save 100% on your flight

$1,458

per person

Nov 3 - Nov 9

found 1 day ago

Roundtrip non-stop 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.

Tween Waters Island Resort & Spa

Save 100% on your flight

$894

per person

Nov 1 - Nov 7

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.

Matanzas Inn Bayside Resort and Marina

Save 100% on your flight

$606

per person

Oct 31 - Nov 7

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the hot tub and perks like free self parking and free WiFi. A terrace, a picnic area, and luggage storage are also on offer.

Top Captiva Island hotels deals

Tween Waters Island Resort & Spa

15951 Captiva Drive Captiva FL

Free Cancellation

Reserve now, pay when you stay

$311 nightly

$346 total

Sep 1 - Sep 2

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

5400 South Seas Plantation Rd Captiva FL

Free Cancellation

Reserve now, pay when you stay

$290 nightly

$324 total

Sep 7 - Sep 8

Total with taxes and fees

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. You'll find 5 restaurants and 6 outdoor pools on site, along with a bar/lounge to unwind.

On private beach

Pool

Game Room, Pool, Hot Tub, Walk to Beach | Captiva 5BDR | Coco Mango by AvantStay

Captiva FL

Get rates

A hot tub is featured at this vacation home, along with laundry facilities and concierge services. Barbecue grills are provided for your convenience.

Pool

Hot Tub

Beach Villa 2121: Your Exclusive Two-Story Beach Villa with Direct Gulf Views

Captiva FL

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This vacation home featured laundry facilities and barbecue grills.

Pool

Kitchen

Captiva Beach Villas 🏝 On The Gulf Beach

Captiva FL

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An outdoor pool is featured at this condo, along with laundry facilities and barbecue grills.

Pool

Kitchen

Beach Villa 2217: Your Island Escape with Stunning Gulf Views!

Captiva FL

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This condo features barbecue grills.

Pool

Kitchen

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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.

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.

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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 $466. 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.