Captiva Island Vacation Packages 2026 from $450

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The Latest Captiva Island vacation packages

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

Mariners Boathouse by Coolvacay

South Island

Save 100% on your flight

$450

per person

Nov 10 - Nov 14

found 19 hours 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

The Perry Hotel Naples

Save 100% on your flight

$976

per person

Nov 7 - Nov 13

found 2 days ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.6/10 Exceptional! (1,099 reviews)

Excelent instalation and services

Reviewed on Sep 26, 2026

Windward Passage Resort

Save 100% on your flight

$803

per person

Dec 15 - Dec 20

found 11 hours ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

8.8/10 Excellent! (11 reviews)

Wonderful view of the ocean

Reviewed on Sep 15, 2026

Shell Island Beach Club

East End

Save 100% on your flight

$1,135

per person

Dec 5 - Dec 12

found 1 hour ago

Roundtrip flight included

New York (JFK) to Fort Myers (RSW)

9.6/10 Exceptional! (25 reviews)

This well-equipped apartment overlooks the grounds and swimming pool with views of the beach just yards away. Fully restored after the devastation from hurricane Ian 4 years ago it’s in great shape and we had a wonderful stay. The staff work tirelessly to keep the place as it should be and nothing was too much trouble. I can’t recommend it highly enough.

Reviewed on Sep 6, 2026

Landing Apartments Fort Myers near Eastwood Village

Save 100% on your flight

$572

per person

Nov 7 - Nov 13

found 2 days ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.8/10 Exceptional! (31 reviews)

This place is as beautiful as the pictures. Welcome kit has essentials for a short stay. The place is clean and cozy. Highly recommended.

Reviewed on Sep 4, 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

8.4/10 Very Good! (1,001 reviews)

"staff are the best"

Reviewed on Sep 25, 2026

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.