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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.

Casa Ybel Resort

2.5 out of 5

Save 100% on your flight

Price was $817, price is now $532 per person

$532

per person

Nov 9 - Nov 12

found 15 hours ago

Roundtrip non-stop 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.

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.

Matanzas Inn Bayside Resort and Marina

3 out of 5

Save 100% on your flight

Price was $1,378, price is now $879 per person

$879

per person

Dec 17 - Dec 22

found 1 day ago

Roundtrip flight included

Hartford (BDL) to Fort Myers (RSW)

Stay at this hotel in Fort Myers Beach. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Key West Express and Estero Boulevard Beach are located nearby.

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 1 day 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.

Hyatt Vacation Club at Coconut Cove, Bonita Springs

4 out of 5

Save 100% on your flight

Price was $1,154, price is now $751 per person

$751

per person

Dec 9 - Dec 15

found 1 day ago

Roundtrip flight included

Hartford (BDL) to Fort Myers (RSW)

Book a stay at this golf hotel in Bonita Springs. Enjoy free WiFi, free parking, and 3 outdoor pools. Popular attractions Bonita Springs Public Beach and Hertz Arena are located nearby.

Best resort/vacation I’ve ever had in Florida. Four pools a lazy river two hot tubs two bars and a restaurant. And the private island! We will definitely be back. The staff was beyond nice and courteous. Do not hesitate to book a stay here.

Reviewed on Sep 28, 2026

Mariners Boathouse by Coolvacay

3 out of 5

Save 100% on your flight

Price was $1,366, price is now $908 per person

$908

per person

Dec 17 - Dec 22

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

Tween Waters Island Resort & Spa

3 out of 5

Save 100% on your flight

Price was $1,363, price is now $915 per person

$915

per person

Dec 17 - Dec 22

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.

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 16 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.