Captiva Island Vacations from $347

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The Latest Captiva Island vacation packages

Price found within the past 48 hours. Click for updated prices.
Quality Inn Fort Myers Cape Coral

Quality Inn Fort Myers Cape Coral

Save 100% on your flight
$347
per person
Nov 7 - Nov 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
7.6/10 Good! (417 reviews)
Agradable

Reviewed on Sep 5, 2026

Resort Harbour Properties

Resort Harbour Properties

Punta Rassa
Save 100% on your flight
$1,020
per person
Nov 7 - Nov 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
9.6/10 Exceptional! (372 reviews)
The property was clean and absolutely gorgeous. The pictures honestly didn't do it justice. The hospitality was great! The communication was top notch, but they weren't too much at all. Great privacy! Beach was steps away from the elevator. The location was wonderful! It was secluded but everything we needed was very close by. Sanibel Island was a 10 minute drive at most! We are only going to stay at this property in the future.

Reviewed on Aug 11, 2026

Matanzas Inn Bayside Resort and Marina

Matanzas Inn Bayside Resort and Marina

Save 100% on your flight
$649
per person
Nov 7 - Nov 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
9.4/10 Exceptional! (1,006 reviews)
The staff was amazing from the front desk, housekeeping and maintenance. Everyone had a smile and greeted you. They made us feel welcomed and that they were happy we were there. You don’t get that much nowadays. Check-in and out after hours was easy. The bartender Tiffany was amazing, another friendly smile. The drinks, food and entertainment was good. The front desk went above and beyond. This place feels like it’s family owned paradise NOT the timeshare your just another number. We chose this place than changed our other reservations to come back here for the rest of our stay. We will definitely recommend this place to family and friends. We will be back again soon.

Reviewed on Sep 5, 2026

Windward Passage Resort

Windward Passage Resort

Save 100% on your flight
$723
per person
Nov 7 - Nov 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
8.6/10 Excellent! (9 reviews)
Clean, beachfront, great staff, close attractions

Reviewed on Sep 5, 2026

The Lighthouse Resort Inn & Suites

The Lighthouse Resort Inn & Suites

Save 100% on your flight
$596
per person
Nov 7 - Nov 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
8.6/10 Excellent! (1,787 reviews)
I gave a good star rating because of my own room, but... I had a beautiful, spacious, updated room with a big private balcony near the larger pool with easy parking right in front of my room. It was noisy but quieted down by bedtime. My sister also stayed at the same time and was given a room in the main building over the bar. Her room was awful. Really run down, smaller, not a nice layout, parking was far away in the crowded main lot, she didnt have a private balcony (there was a table & chairs outside her door on the common area walkway), and it was noisy later into the night. She paid the same price as me and booked directly while I booked through Expedia. So beware, what you get may be luck of the draw!

Reviewed on Sep 6, 2026

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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
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.
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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.
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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.
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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.
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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.
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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 7 - Sep 8
Total with taxes and fees
8.6/10 Excellent! (1,002 reviews)
"Great location for get unique island travel experience . Beautiful ocean view on Restaurant to see incredible sunset. Food was delicious also. Property needs to be maintained . Total price includes resort fee is a bit higher for current property conditions."

Reviewed on Sep 4, 2026

Tween Waters Island Resort & Spa
South Seas

South Seas

5400 South Seas Plantation Rd Captiva FL
Fully refundableReserve now, pay when you stay
$309 nightly
$344 total
Sep 21 - Sep 22
Total with taxes and fees
South Seas
Game Room, Pool, Hot Tub, Walk to Beach | Captiva 5BDR | Coco Mango by AvantStay

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

Captiva FL
9.2/10 Wonderful! (23 reviews)
"The house is spacious, very comfortable and immaculate. Easy walking distance to restaurants, shops and beaches.There were lots of pool floats and beach chairs. It was a perfect house for our family gathering. Would definitely rent it again."

Reviewed on Aug 3, 2026

Get rates
Game Room, Pool, Hot Tub, Walk to Beach | Captiva 5BDR | Coco Mango by AvantStay
See all 661 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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.