Captiva Island Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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Top Captiva Island Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Landing Apartments near North Fort Myers

Landing Apartments near North Fort Myers

4 out of 5
Hancock
Price was CA $1,547, price is now CA $1,131 per person
CA $1,131
per person
Sep 19 - Sep 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Fort Myers (RSW)
9.4/10 Exceptional! (68 reviews)
I would recommend it to all my friends that would be traveling to Florida it’s been great every time I stayed at landing condo never had any problems at all it’s was what they said it be clean friendly excellent place

Reviewed on Jun 17, 2026

LaPlaya Beach & Golf Resort - A Noble House Resort

LaPlaya Beach & Golf Resort - A Noble House Resort

4.5 out of 5
Vanderbilt Beach
Price was CA $3,055, price is now CA $1,992 per person
CA $1,992
per person
Aug 26 - Sep 2
found 22 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Fort Myers (RSW)
9/10 Wonderful! (1,009 reviews)
La propiedad está muy bien y el servicio es excelente

Reviewed on Jul 12, 2026

Inn on Fifth

Inn on Fifth

4 out of 5
Old Naples
Price was CA $2,364, price is now CA $1,622 per person
CA $1,622
per person
Aug 26 - Sep 2
found 22 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Fort Myers (RSW)
9.4/10 Exceptional! (1,001 reviews)
A great hotel in downtown Naples. Great for couples looking for a getaway.

Reviewed on Jul 14, 2026

GullWing Beach Resort

GullWing Beach Resort

3.5 out of 5
South Island
Price was CA $1,993, price is now CA $1,370 per person
CA $1,370
per person
Sep 19 - Sep 26
found 8 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Fort Myers (RSW)
9.4/10 Exceptional! (955 reviews)
Absolutely gorgeous ocean view suite! Exceeded our expectations! The beach was so nice and easy to walk to. Nice location. Great staff! We’ll definitely be going back!

Reviewed on Jul 11, 2026

Casa Ybel Resort

Casa Ybel Resort

2.5 out of 5
Mid Island
Price was CA $2,134, price is now CA $1,512 per person
CA $1,512
per person
Sep 19 - Sep 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Fort Myers (RSW)
8.8/10 Excellent! (372 reviews)
I loved the unit and property. I also like the food and drinks at the restaurant by the pool. I was a little unhappy w housekeeping as they did not clean our room and provide us w clean towels one day.

Reviewed on Jul 14, 2026

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Captiva Island Hotel Deals

Tween Waters Island Resort & Spa

Tween Waters Island Resort & Spa

3 out of 5
15951 Captiva Drive Captiva FL
Fully refundableReserve now, pay when you stay
The price is CA $395 per night from Aug 3 to Aug 4
CA $395
CA $490 total
Aug 3 - Aug 4
includes taxes & fees
8.6/10 Excellent! (1,007 reviews)
"When looking over the balcony all you see is over grown trees and down below is trash. The elevator was between two buildings and you had to walk to the opposite end just to get to your room. Also the beach is across the street not on the property."

Reviewed on Jul 14, 2026

Tween Waters Island Resort & Spa
South Seas

South Seas

3.5 out of 5
5400 South Seas Plantation Rd Captiva FL
Fully refundableReserve now, pay when you stay
The price is CA $355 per night from Jul 26 to Jul 27
CA $355
CA $570 total
Jul 26 - Jul 27
includes taxes & fees
South Seas
2026 SUMMER REDUCED RATES!! WATERFRONT HOME, IN VILLAGE, POOL, HOT TUB, DOCK!

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

Captiva Island FL
10/10 Exceptional! (37 reviews)
"Beautiful home, pool & view. Host very accommodating."

Reviewed on Jul 12, 2026

Get rates
2026 SUMMER REDUCED RATES!! WATERFRONT HOME, IN VILLAGE, POOL, HOT TUB, DOCK!
See all 671 properties in Captiva Island
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.
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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 does a Captiva Island vacation package cost?
From just CA $1,131, you can tailor your Captiva Island vacation package. Simply combine flights, hotels and car rentals and we'll reward you with discounts.
How do I get a cheap travel package to Captiva Island?
You'll save big if you bundle your car rentals, flights and hotels into a Captiva Island vacation package. Sometimes cheap packages mean fewer options. But that's not the case with Expedia. We offer over 550 airlines and 1,000,000 hotels worldwide, which means you'll always have plenty of options to choose from. Want to save even more? Add some fun activities to your package deal and unlock even bigger bargains! After all, travel is about more than just getting to your destination.
How far in advance should I book my Captiva Island vacation?
While prices change from time to time, we generally recommend reserving your seat as early as possible. Many international airfares can be found on Expedia up to a year in advance. If circumstances have left you booking last minute, you may still get lucky. Low prices to Captiva Island sometimes occur in the weeks prior to departure.
What does an Expedia Captiva Island travel package include?
With Expedia, you can select any combination of flights, car rentals and hotels to build your perfect Captiva Island travel package. Once you've made your booking, you can add on the fun things like day tours and activities. Remember, the more you bundle, the more deals you'll score!
What should I know before booking a Captiva Island travel package?
Discover deals that fit your budget with an Expedia package. Hotels, airfares, rental cars — we've got all of them. You'll save big bucks just by combining your bookings. Whether you're embarking on an adventure in the snow or relaxing on a sunny beach, your ideal getaway is just clicks away.
Can I choose my airline with a Captiva Island Expedia vacation package?
Definitely. Expedia has more than 550 airline partners to pick from globally. With all that choice at your fingertips, finding the perfect carrier to fly you to Captiva Island won't be hard.
If I'm not able to travel, can I cancel my Captiva Island vacation package?
Whether it's your hotel, flight or rental car, you can cancel or amend it. Locked in your Captiva Island vacation package in the last 24 hours? You may be able to make changes at no cost. For older bookings, you may be charged a fee by your hotel, airline or car rental company. For more details, check out our Customer Service Portal. We'll help you every step of the way.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.