Captiva Island Vacations from $536

Book a Hotel + Flight or Car together to unlock savings

Photo by Anthony Ball
  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 when you book a flight and hotel together*
  • Find the right fit

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

    Plan, book, and manage your trip all in one place

The Latest Captiva Island vacation packages

Price found within the past 48 hours. Click for updated prices.
Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

Save 100% on your flight
$536
per person
Dec 10 - Dec 14
found 10 hours ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.2/10 Wonderful! (3,301 reviews)
The Perry Hotel Naples

The Perry Hotel Naples

Save 100% on your flight
$972
per person
Nov 27 - Dec 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.6/10 Exceptional! (1,099 reviews)
Tween Waters Island Resort & Spa

Tween Waters Island Resort & Spa

$2,393,682
per person
Dec 1 - Dec 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
8.6/10 Excellent! (1,005 reviews)
My husband and I were able to check in right on time. We were given a helpful overview of the property, a map, and list of the numerous amenities (complimentary kayaks, bikes, beach towels, pools and hot tubs, as well as the many restaurants, shops, rentals, and beach services) and opening and closing times said amenities. Prices for amenities and rentals were reasonable in my opinion. The restaurants range in price from reasonable to upscale dining. Our room was exactly as pictured. The entire property including the private beach - which was just across the road - were exceptionally clean. My only complaint was our bed was very firm for our tastes. The Gulf side beach was gorgeous. We saw many shore birds and dolphins. The bay side features a large marina and manatees in the cove. All staff we encountered were very friendly and helpful. We stayed in mid September and it appeared that most of the rooms were filled, but it was still very relaxing, quiet, and uncrowded. The location is excellent. It's easy to find off the main road through the islands and it's only a short drive to the attractions and beaches in both Sanibel and Captiva. Overall I would recommend and would stay here again.

Reviewed on Sep 20, 2026

Matanzas Inn Bayside Resort and Marina

Matanzas Inn Bayside Resort and Marina

Save 100% on your flight
$612
per person
Dec 6 - Dec 12
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.4/10 Exceptional! (1,006 reviews)
Mariners Boathouse by Coolvacay

Mariners Boathouse by Coolvacay

South Island
Save 100% on your flight
$869
per person
Nov 27 - Dec 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.8/10 Exceptional! (13 reviews)
Very nice place, our 2nd time here and we still love it

Reviewed on Sep 7, 2026

Don't see what you're looking for?
See all available trips from Columbus to Captiva Island
View all trips

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
A starry night sky over rocky terrain.
Photo by Noel Benadom

Turner Beach

9.4/10 (63 reviews)
If a restful vacation is part of your travel plans, Turner Beach might be the perfect place to seek out during your trip to Captiva. Discover the beautiful sunsets in this relaxing area.
See properties
A sandy beach with footprints and tire tracks, palm trees, and a clear sky.
Photo by Norwegian Girl

Alison Hagerup Beach Park

8.4/10 (17 reviews)
Why not spend a carefree afternoon at Alison Hagerup Beach Park during your travels in Captiva? Discover the beautiful sunsets in this relaxing area.
See properties

Jensen’s Marina

9.2/10 (36 reviews)
Explore the waterfront of Jensen’s Marina and enjoy activities such as biking in Captiva. Amble around the area's beautiful beaches or seek out the kayaking spots.
See properties

Captiva Chapel By the Sea

8.6/10 (28 reviews)
You can find out about the history of Captiva with a visit to Captiva Chapel By the Sea. Discover the area's beautiful sunsets, or seek out its biking trails.
See properties

McCarthy's Marina

9.0/10 (47 reviews)
Explore the waterfront of McCarthy's Marina and enjoy activities such as biking in Captiva. Discover the area's beautiful sunsets, or seek out its kayaking spots.
See properties

Captiva Island Hotel Deals

Tween Waters Island Resort & Spa

Tween Waters Island Resort & Spa

15951 Captiva Drive Captiva FL
Fully refundableReserve now, pay when you stay
$311 nightly
$346 total
Sep 28 - Sep 29
Total with taxes and fees
8.6/10 Excellent! (1,002 reviews)
"My husband and I were able to check in right on time. We were given a helpful overview of the property, a map, and list of the numerous amenities (complimentary kayaks, bikes, beach towels, pools and hot tubs, as well as the many restaurants, shops, rentals, and beach services) and opening and closing ..."

Reviewed on Sep 20, 2026

Tween Waters Island Resort & Spa
South Seas

South Seas

5400 South Seas Plantation Rd Captiva FL
Fully refundableReserve now, pay when you stay
$328 nightly
$366 total
Oct 8 - Oct 9
Total with taxes and fees
8.4/10 Very Good! (1,002 reviews)
"This place was absolutely incredible. Our room was right on the water and immaculate. The resort is huge and has its own trolley. They also have a waterpark and another pool with waterslides. Amazing stay!"

Reviewed on Sep 21, 2026

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

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

Captiva FL
9.2/10 Wonderful! (16 reviews)
"Need to make it easier to find the unit. We were up and down the stairs looking for the room 2121 reason couldn't find it because the plaque on the building showing the room numbers was off until I called the company . Otherwise enjoyed my stay ."

Reviewed on Sep 20, 2026

Get rates
Beach Villa 2121: Your Exclusive Two-Story Beach Villa with Direct Gulf Views
See all 657 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)

More vacations you might like

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.