Captiva Island Vacation Packages 2026 from $564

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The Latest Captiva Island vacation packages

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

The Lighthouse Resort Inn & Suites

Save 100% on your flight

$564

per person

Dec 10 - Dec 15

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

8.6/10 Excellent! (1,787 reviews)

The Perry Hotel Naples

Save 100% on your flight

$686

per person

Nov 1 - Nov 5

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

9.6/10 Exceptional! (1,099 reviews)

Shutter never works, rooftop bar staff is horrible

Reviewed on Sep 24, 2026

Windward Passage Resort

Save 100% on your flight

$835

per person

Dec 5 - Dec 12

found 1 day ago

Roundtrip flight included

New York (JFK) to Fort Myers (RSW)

8.8/10 Excellent! (11 reviews)

Wonderful view of the ocean

Reviewed on Sep 15, 2026

Tween Waters Island Resort & Spa

Save 100% on your flight

$2,499,072

per person

Dec 4 - Dec 11

found 5 hours ago

Roundtrip flight included

Islip (ISP) to Fort Myers (RSW)

8.6/10 Excellent! (1,005 reviews)

Harbour House At The Inn

Save 100% on your flight

$997

per person

Nov 28 - Dec 4

found 4 hours ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.2/10 Wonderful! (780 reviews)

Easy check-in. Very clean. Quiet. Unit has everything you need. I stay here often and will continue.

Reviewed on Sep 20, 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.

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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.

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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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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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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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

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

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

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

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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.