Captiva Island Vacation Packages 2026 from $553

Captiva Island flight + hotel vacation packages

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

Manasota Key Resort

Save 100% on your flight

$553

per person

Sep 14 - Sep 17

found 1 day ago

Roundtrip non-stop 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.

LaPlaya Beach & Golf Resort - A Noble House Resort

Vanderbilt Beach

Save 100% on your flight

$1,328

per person

Sep 1 - Sep 8

found 1 day ago

Roundtrip non-stop 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.

A Wave From it All

Siesta Isle

Save 100% on your flight

$1,744

per person

Sep 14 - Sep 20

found 1 hour ago

Roundtrip non-stop flight included

Columbus (CMH) to Fort Myers (RSW)

This vacation home features 6 beach bars and an outdoor pool. Guests will appreciate free perks like free self parking and WiFi in public areas. A picnic area, barbecue grills, and a virtual front desk are also on offer.

Casa Ybel Resort

Mid Island

Save 100% on your flight

$1,289

per person

Aug 27 - Sep 3

found 1 day 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.

The Perry Hotel Naples

Save 100% on your flight

$857

per person

Aug 27 - Sep 3

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.

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

Aug 2 - Aug 3

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

$377 nightly

$420 total

Jul 27 - Jul 28

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

2026 SUMMER REDUCED RATES!! WATERFRONT HOME, IN VILLAGE, POOL, HOT TUB, DOCK!

Captiva Island FL

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This vacation home features an outdoor pool and a hot tub. Families will appreciate the playground and barbecue grills. A garden and laundry facilities are also provided.

Pool

Hot Tub

Beach Villa 2313, Upscale and Beautiful Beach Front Condo with Gorgeous Gulf

Captiva FL

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This condo featured laundry facilities and barbecue grills.

Pool

Kitchen

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

Captiva FL

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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 2117: Beachfront Luxury on Captiva

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 $553. 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.