Captiva Island Vacations 2025/2026 from CA $377

Captiva Island flight + hotel packages

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

Hilton Garden Inn Ft Myers

Villas

CA $377

per person

Nov 14 - Nov 17

just found

Roundtrip flight included

Toronto (YYZ) to Fort Myers (RSW)

Stay at this 3-star business-friendly hotel in Fort Myers. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Barbara B Mann Hall and Bell Tower Shops are located nearby.

Inn on Fifth

Old Naples

CA $1,252

per person

Oct 22 - Oct 27

found 21 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Fort Myers (RSW)

Stay at this 4-star spa hotel in Naples. Enjoy a full-service spa, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Fifth Avenue South and Naples Pier are located nearby.

Hyatt Place Fort Myers/at The Forum

The Forum

CA $529

per person

Nov 17 - Nov 22

found 7 hours ago

Roundtrip flight included

Toronto (YYZ) to Fort Myers (RSW)

Stay at this 3-star business-friendly hotel in Fort Myers. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Calusa Nature Center and Planetarium and Topgolf are located nearby.

Edison Beach House

CA $654

per person

Nov 14 - Nov 17

just found

Roundtrip flight included

Toronto (YYZ) to Fort Myers (RSW)

Stay at this 3.5-star beach aparthotel in Fort Myers Beach. Enjoy free parking, a beach locale, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Key West Express and Times Square are located nearby.

The Perry Hotel Naples

CA $1,123

per person

Nov 17 - Nov 22

found 7 hours ago

Roundtrip flight included

Toronto (YYZ) to Fort Myers (RSW)

Stay at this 4.5-star luxury hotel in Naples. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Popular attractions Vanderbilt Beach and Barefoot Beach are located nearby.

Top Captiva Island hotels deals

Tween Waters Island Resort & Spa

15951 Captiva Drive, Captiva, FL

CA $241

CA $318 total

Sep 28 - Sep 29

includes taxes & fees

Stay at this 3-star beach resort in Captiva. Enjoy free parking, 2 outdoor pools, and a full-service spa. Popular attractions Captiva Beach and Captiva Chapel By the Sea are located nearby.

On private beach

Pool

South Seas Resort

5400 South Seas Plantation Rd, Captiva, FL

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Stay at this 3.5-star beach resort in Captiva. Enjoy 3 outdoor pools, 6 restaurants, and a private beach. Popular attractions Jungle Drums and McCarthy's Marina are located nearby.

On private beach

Pool

South Seas Bayside Villa 5130: Your Perfect Island Retreat

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Stay at this vacation home in Captiva. Enjoy free WiFi, patios, and cable/satellite TV service. Popular attractions McCarthy's Marina and Jungle Drums are located nearby.

Pool

Hot tub

South Seas Bayside Villa 4222

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Stay at this vacation home in Captiva. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions McCarthy's Marina and Jungle Drums are located nearby.

Pool

Hot tub

South Seas Beach Villa 2418 Coastal Luxury

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Book a stay at this beach vacation home in Captiva. Enjoy free WiFi, a beach locale, and patios. Popular attractions Jungle Drums and McCarthy's Marina are located nearby.

Pool

Kitchen

Your Beachfront Oasis Awaits

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Book a stay at this beach vacation home in Captiva. Enjoy free WiFi, private pools, and a beach locale. Popular attractions Alison Hagerup Beach Park and Jungle Drums are located nearby.

Pool

Hot tub

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See all available properties in Captiva Island

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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

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 CA $377. 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.