Captiva Island Vacation Packages 2026 from $466

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The Latest Captiva Island vacation packages

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

Latitude 26 Waterfront Resort & Marina

Save 100% on your flight

$466

per person

Oct 31 - Nov 7

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

8.6/10 Excellent! (1,009 reviews)

The Lighthouse Resort Inn & Suites

Save 100% on your flight

$546

per person

Oct 31 - Nov 7

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

8.6/10 Excellent! (1,781 reviews)

Tween Waters Island Resort & Spa

Save 100% on your flight

$894

per person

Nov 1 - Nov 7

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

8.6/10 Excellent! (1,011 reviews)

So nice to have the benefit of being able to enjoy both the beach side and bay side.

Reviewed on Aug 31, 2026

The Perry Hotel Naples

Save 100% on your flight

$881

per person

Oct 31 - Nov 5

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.6/10 Exceptional! (1,074 reviews)

Overall a great experienced.... even got room view upgraded because of my birthday!

Reviewed on Aug 31, 2026

Casa Ybel Resort

Mid Island

Save 100% on your flight

$962

per person

Oct 31 - Nov 7

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

8.8/10 Excellent! (412 reviews)

The property is super convenient the beaches across the street a volleyball pool and then a huge lighted pool. The rooms were very clean older but clean and very comfortable. Mine felt like a little apartment tiki bar downstairs is great. The food is good. The drinks were good. They do play music until about midnight so if you don’t like music till that time, this isn’t the place for you lol. We will definitely stay here again.

Reviewed on Aug 30, 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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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

15951 Captiva Drive Captiva FL

Fully refundableReserve now, pay when you stay

$311 nightly

$346 total

Sep 1 - Sep 2

Total with taxes and fees

8.6/10 Excellent! (1,005 reviews)

"So nice to have the benefit of being able to enjoy both the beach side and bay side."

Reviewed on Aug 31, 2026

South Seas

5400 South Seas Plantation Rd Captiva FL

Fully refundableReserve now, pay when you stay

$290 nightly

$324 total

Sep 7 - Sep 8

Total with taxes and fees

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

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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.