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Captiva Vacation Packages

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A road with a 'Welcome to Captiva' sign, palm trees, and a speed limit sign of 25 mph.

Captiva
Florida
United States of America
North America
Hotwire.com

Captiva Flight + Hotel Packages

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

Olde Marco Island Inn and Suites

3 out of 5

Save 100% on your flight

Price was $830, price is now $540 per person

$540

per person

Dec 3 - Dec 8

found 19 hours ago

Roundtrip flight included

Hartford (BDL) to Fort Myers (RSW)

Stay at this hotel in Marco Island. Enjoy free WiFi, free parking, and 4 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Marco Beach and Pelican Pier Marina are located nearby.

The Perry Hotel Naples

4.5 out of 5

Save 100% on your flight

Price was $1,695, price is now $959 per person

$959

per person

Dec 11 - Dec 15

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

Book a stay at this luxury hotel in Naples. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Popular attractions Vanderbilt Beach and Barefoot Beach are located nearby.

Tween Waters Island Resort & Spa

3 out of 5

Save 100% on your flight

Price was $1,107, price is now $674 per person

$674

per person

Nov 10 - Nov 14

found 1 day ago

Roundtrip flight included

Hartford (BDL) to Fort Myers (RSW)

Book a stay at this beach resort in Captiva. Enjoy free parking, 2 outdoor pools, and a full-service spa. Popular attractions Bowman's Beach and Captiva Beach are located nearby.

Casa Ybel Resort

2.5 out of 5

Save 100% on your flight

Price was $1,029, price is now $691 per person

$691

per person

Nov 10 - Nov 14

found 1 day ago

Roundtrip flight included

Hartford (BDL) to Fort Myers (RSW)

Book a stay at this beach hotel in Sanibel. Enjoy free WiFi, free parking, and 2 restaurants. Popular attractions Sanibel Island Southern Beach and Bowman's Beach are located nearby.

50 yard walk to sand and Gulf of America

Reviewed on Sep 28, 2026

Sanctuary Point by Avantstay Waterfront Pool + Spa Kayak + Fishing Dock Near Beaches

3 out of 5

Save 100% on your flight

Price was $1,736, price is now $1,227 per person

$1,227

per person

Dec 2 - Dec 9

found 9 hours ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

Stay at this cottage in Bonita Springs. Enjoy free parking, balconies, and in-room washers/dryers. Popular attractions Bonita Springs Public Beach and Barefoot Beach are located nearby.

Spinnaker Inn of Naples

2 out of 5

Price was $825, price is now $592 per person

$592

per person

Dec 9 - Dec 13

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

Book a stay at this business-friendly hotel in Naples. Enjoy free WiFi, free parking, and cable TV channels. Our guests praise the clean rooms in our reviews. Popular attractions Tiburon Golf Club and Fifth Avenue South are located nearby.

Mariners Boathouse by Coolvacay

3 out of 5

Price was $860, price is now $616 per person

$616

per person

Nov 10 - Nov 14

found 1 day ago

Roundtrip flight included

Hartford (BDL) to Fort Myers (RSW)

Book a stay at this beach condo in Fort Myers Beach. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Key West Express and Bonita Springs Public Beach are located nearby.

Very nice place, our 2nd time here and we still love it

Reviewed on Sep 7, 2026

Windward Passage Resort

2 out of 5

Price was $1,384, price is now $994 per person

$994

per person

Dec 17 - Dec 22

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

Book a stay at this beach hotel in Fort Myers Beach. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Key West Express and Lynn Hall Memorial Park are located nearby.