Captiva Island Vacation Packages 2026 from $325

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The Latest Captiva Island vacation packages

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

Stay Inn & Suites

Winkler

Save 100% on your flight

$325

per person

Sep 16 - Sep 22

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

5/10 (1,001 reviews)

The place is good for the price

Reviewed on Jul 31, 2026

Manasota Key Resort

Save 100% on your flight

$624

per person

Sep 20 - Sep 23

found 22 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

9.4/10 Exceptional! (304 reviews)

The Perry Hotel Naples

Save 100% on your flight

$934

per person

Oct 20 - Oct 26

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

9.6/10 Exceptional! (970 reviews)

A great accidental find for a short overnight trip.

Reviewed on Aug 7, 2026

Tween Waters Island Resort & Spa

Save 100% on your flight

$716

per person

Oct 17 - Oct 21

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

8.6/10 Excellent! (1,004 reviews)

Everything excellent Excellent

Reviewed on Aug 7, 2026

Shell Island Beach Club

East End

Save 100% on your flight

$993

per person

Oct 10 - Oct 17

found 1 day ago

Roundtrip flight included

New York (JFK) to Fort Myers (RSW)

9.6/10 Exceptional! (24 reviews)

Great place to stay on the beach! Woman at the front desk was rude!

Reviewed on Jun 7, 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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Jungle Drums

7.0/10 (2 reviews)

You can spend time browsing the exhibits at Jungle Drums in Captiva. Discover the area's beautiful sunsets, or seek out its biking trails.

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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

Aug 9 - Aug 10

Total with taxes and fees

8.6/10 Excellent! (1,006 reviews)

"Everything excellent Excellent"

Reviewed on Aug 7, 2026

South Seas

5400 South Seas Plantation Rd Captiva FL

Fully refundableReserve now, pay when you stay

$367 nightly

$409 total

Sep 7 - Sep 8

Total with taxes and fees

8.4/10 Very Good! (1,004 reviews)

"Beautiful property with excellent amenities—we really enjoyed our stay. One suggestion would be to provide daily housekeeping instead of every other day. Also, while construction is ongoing, it would be appreciated if guests could be assigned rooms farther away from the construction area whenever ..."

Reviewed on Aug 2, 2026

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

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See all 665 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.