Captiva Island Vacations from $690

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The Latest Captiva Island vacation packages

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

Wiggins Pass Chalet

4 out of 5
Price was $984, price is now $690 per person
$690
per person
Jan 21 - Jan 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.6/10 Exceptional! (296 reviews)
Staff were super helpful.

Reviewed on Nov 9, 2026

The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Price was $1,958, price is now $1,260 per person
$1,260
per person
Jan 21 - Jan 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.6/10 Exceptional! (1,224 reviews)

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 $3,486, price is now $2,320 per person
$2,320
per person
Jan 21 - Jan 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9/10 Wonderful! (1,003 reviews)
Great resort. Probably the nicest on the entire run of resorts on this beach. And that includes the Ritz-Carlton just upo the way. Obviously, the Ritz is classier, but La Playa felt more exclusive and comfortable. The beach experience is top-notch, with complimentary umbrellas and beach chairs upon request. The bar and restaurant were very good. Drinks are pricey, to be sure, which can add up if you're ordering while relaxing on the beach for days on end. About a 25 minute drive to the best restaurants and shops in Old Town Naples. This was a little far for us, since we didn't have a car and Uber'd whenever we went out. Overall, a very nice experience.

Reviewed on Nov 9, 2026

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

4 out of 5
Price was $1,123, price is now $800 per person
$800
per person
Jan 17 - Jan 22
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Fort Myers (RSW)
9.2/10 Wonderful! (3,490 reviews)
Thanks

Reviewed on Nov 9, 2026

Sunsuites Villas At Sunseeker Resort, Curio By Hilton

Sunsuites Villas At Sunseeker Resort, Curio By Hilton

4 out of 5
Price was $989, price is now $711 per person
$711
per person
Jan 29 - Feb 2
found 14 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Fort Myers (RSW)
9.4/10 Exceptional! (135 reviews)
Beautiful location.

Reviewed on Nov 8, 2026

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See all available trips from Pretty Prairie to Captiva Island
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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

What to do in Captiva Island

Bokeelia: Cabbage Key Nature Cruise

Bokeelia: Cabbage Key Nature Cruise

$85
per adult
Bokeelia: Cabbage Key Nature Cruise
Sanibel Island Jet Ski Tour

Sanibel Island Jet Ski Tour

$299
per traveler
Sanibel Island Jet Ski Tour
See all activities in Captiva Island

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
$340 nightly
The price is $379 total per night from Dec 11 to Dec 12
$379 total
Dec 11 - Dec 12
Total with taxes and fees
8.8/10 Excellent! (1,003 reviews)
"Family of 6 had the best time celebrating an 80th birthday. Resort was welcoming and clean. Beach was perfect. So helpful to have them set up umbrellas and chairs. Restaurant had great service and food. We can’t wait to come back again."

Reviewed on Nov 8, 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
$310 nightly
The price is $346 total per night from Dec 1 to Dec 2
$346 total
Dec 1 - Dec 2
Total with taxes and fees
South Seas
Captiva Beach Villas 🏝 On The Gulf Beach

Captiva Beach Villas 🏝 On The Gulf Beach

Captiva FL
10/10 Exceptional! (174 reviews)
"Great location, beautiful property. Easy walk to the beach! Host was awesome."

Reviewed on Oct 24, 2026

Get rates
Captiva Beach Villas 🏝 On The Gulf Beach
See all 659 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.

Find the Best Captiva Island Vacation Packages

Captiva Island Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Southwest Florida Intl. Airport (RSW)

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Frequently asked questions

How much does a Captiva Island vacation package cost?
A Captiva Island vacation package typically costs around $1,250 per adult for a week-long trip. Lower-priced options start around $800 per adult, while premium packages can reach up to $2,150.

*Package prices shown are the average total cost per adult across Expedia bookings over the past year and may change depending on availability, dates, and demand.
How can I save money on a Captiva Island vacation package?
When you bundle, you can save up to 30%*. To save money on a Captiva Island package, consider traveling during the quieter months or be flexible with your dates to find more options. Bundling your flights and hotel together often unlocks savings compared to booking separately. *Members only. Savings vary.
What's included in a Captiva Island vacation package?
A Captiva Island vacation package lets you combine flights, hotel stays, and rental cars. Nearly all package hotels on Captiva Island offer ocean views, providing direct access to the beaches.

Exactly what's included will vary by hotel and package, so it's worth reviewing the details before you confirm your booking.
How do I find cheap Captiva Island vacation package deals?
The cheapest Captiva Island vacation package deals start around $660 per adult for weekend trips. Separately, April and May typically have the lowest average monthly prices, around $990 to $1,120 per adult, typically for a 4-day trip.

Bundling flights and hotel together also typically saves money on a week-long trip — nearly all Captiva Island vacation package deals include some savings versus booking separately, typically around $210 per adult.

Browse cheap vacation packages in Captiva Island on Expedia to compare current deals.

*Package prices shown are the average total cost per adult across Expedia bookings over the past year and may change depending on availability, dates, and demand.
What is the best time to visit Captiva Island?
The best time for a Captiva Island vacation package is from January through March, which is its most popular period for travelers. This timeframe offers pleasant conditions for enjoying the island's outdoor activities and beaches.

If you're looking to combine your trip with local events, consider visiting in December for the JOG N JAM Concert or in February for the Super Bowl South Seas Getaways!®.
What types of vacation packages are available in Captiva Island?
Captiva Island, known for its beautiful beaches and outdoor activities, offers several types of vacation packages:
  • Pet-friendly: Tween Waters Island Resort & Spa, rated 8.3 out of 10 by travelers, welcomes pets and provides amenities like a hot tub and an outdoor pool.
  • Beach: Nearly all package hotels in Captiva Island feature ocean views, providing direct access to the destination's primary draw.
  • Family: Tween Waters Island Resort & Spa is a popular choice for families, offering family rooms and an outdoor pool, with travelers frequently praising its great location and pool.
  • Luxury: Nearly all hotels available in Captiva Island vacation packages are in the luxury tier, providing upscale amenities such as spas and on-site restaurants.
Is Captiva Island better suited for a beach vacation or a cultural trip?
Captiva Island is primarily a beach destination, making it an excellent choice for a beach vacation. The island is known for its beautiful beaches, outdoor activities, and scenic views, with nearly all package hotels offering ocean views.

Travelers can enjoy relaxing on stretches of sand like Captiva Beach, about 1 mile from central Captiva Island, or exploring the natural beauty of North Captiva Island Beach, about 2 miles away. The focus here is on sun, sand, and water-based recreation.

Your Captiva Island vacation package will be centered around its natural coastal appeal.
Which airport should I use for a Captiva Island vacation?
For a Captiva Island vacation, the primary gateway is Southwest Florida International Airport (RSW) in Fort Myers, FL, which serves the area. Another option for travelers is Sarasota-Bradenton International Airport (SRQ), offering an alternative for reaching the region.
What are the top things to do in Captiva Island?
A Captiva Island vacation offers a range of outdoor activities centered around its beautiful beaches and waterways:

Beyond the beaches, you can enjoy activities like bike riding, kayaking, and canoeing. Browse and book things to do in Captiva Island on Expedia.
What is the best time to book a Captiva Island vacation package?
Book your Captiva Island vacation package around 10 weeks in advance. It gives you time to secure your preferred flights and hotel while rates are still competitive. Most travelers book between 6 and 15 weeks out.

From March to May are the most popular months for Captiva Island packages, so booking earlier is advisable if you're traveling during those months. If you're planning a spontaneous getaway, Expedia also offers last-minute Captiva Island vacation packages.
How many days do you need for a Captiva Island vacation?
Most Captiva Island vacation packages last around 5 days. This allows ample time to enjoy the island's renowned beaches, like Captiva Beach, and explore its natural beauty. Week-long trips are the most popular, though some travelers opt for shorter weekend getaways, and a select few choose around two weeks to explore more extensively. As a beach destination outside a city, Captiva Island offers a relaxed pace focused on sun, sand, and water activities.
Are Captiva Island vacation package hotels conveniently located?
Captiva Island vacation package hotels are generally well-located, often placing guests close to the island's main attractions and beaches. Tween Waters Island Resort & Spa, rated 8.3 out of 10 by travelers, is a popular option. The island's key attractions, such as Captiva Beach and Turner Beach, are both about 1 mile from central Captiva Island, while Jensen's Marina is about a 15-minute walk away, suggesting hotels are concentrated in these accessible areas. Choosing a Captiva Island vacation package allows you to stay within easy reach of these scenic spots.
Can I change or cancel my Captiva Island vacation package if my plans change?
Yes, you can cancel your vacation package via your itinerary page on Expedia or by contacting customer service. Remember that some packages are fully refundable, but the details vary based on each unique booking. A fully refundable package may depend on how far out from the travel dates you're canceling and what airline you are traveling with.
Do One Key members get extra savings when booking Captiva Island vacation packages?
Yes, members who join our free One Key™ travel rewards program can instantly unlock additional savings and save 10% or more on over 500,000 stays worldwide with Member Prices and over 1 million car rentals.
Does Expedia offer Book Now, Pay Later Captiva Island vacation packages?
Yes, with Expedia's Book Now, Pay Later option, powered by Affirm, you can spread the cost of your Captiva Island vacation over 3, 6, or 12 months. With no late payment fees or hidden costs, it's easy to secure your ideal vacation package as soon as you spot it.
How do I find last-minute vacation packages to Captiva Island?
To find last-minute vacation packages to Captiva Island, explore the last-minute deals section for the latest package offers, including flights, departing in the coming weeks. Being flexible with your travel dates and hotel preferences can help you secure the best prices.
How does free cancellation work on Captiva Island vacation packages?
Free cancellation on a Captiva Island vacation package depends on the specific hotel and rate combination you book. Many bookings allow free cancellation up to a stated deadline (often a few days before travel) where eligible. Read the cancellation terms carefully when reviewing the package, and visit Expedia help center for further details.
Is it cheaper to book a Captiva Island vacation as a package or separately?
An Expedia vacation package could land you great savings when compared to arranging flights and hotels separately. Better still, you can tailor your Captiva Island getaway to match your exact preference. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
Why should I book my Captiva Island vacation package with Expedia?
Booking your vacation package on Expedia makes it easier to get more out of your trip from the start. With a wide choice of hotels, you can compare prices, reviews and amenities all in one place, then bundle your hotel with flights which could help you save even more. Flexible booking options on selected stays also make it easier to plan with confidence.

Explore a world of travel with Expedia

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