Search Deals onCaptiva Vacation Packages
Captiva Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Wiggins Pass Chalet
Price was $924, price is now $667 per person
$667
per person
Jan 23 - Jan 27
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Book a stay at this business-friendly aparthotel in Naples. Enjoy free WiFi, free parking, and free bicycles on site. Our guests praise the helpful staff in our reviews. Popular attractions Barefoot Beach and Vanderbilt Beach are located nearby.
Facile d accès, accueil chaleureux, disponibilité de chaises parasol et serviettes de plage
Lieux propres, disponibilité des produits d hygiène et serviettes en libre service
Cuisinette et electros neuve neufs
Bémol proximité d un garage qui lave les véhicules à pression limitant le souhait d être sur le balcon
Reviewed on Nov 12, 2026
LaPlaya Beach & Golf Resort - A Noble House Resort
Price was $4,142, price is now $2,526 per person
$2,526
per person
Jan 21 - Jan 26
found 13 hours ago
Roundtrip flight included
Cleveland (CLE) to Fort Myers (RSW)
Book a stay at this luxury resort in Naples. Enjoy a full-service spa, 2 restaurants, and a private beach. Our guests praise the helpful staff in our reviews. Popular attractions Vanderbilt Beach and Barefoot Beach are located nearby.
The property is beautiful!!!!! Staff always attentive and polite but never intrusive
Food is good but drinks are weak and expensive…just get beer to get your $ worth
Reviewed on Nov 13, 2026
The Perry Hotel Naples
Price was $1,105, price is now $716 per person
$716
per person
Jan 23 - Jan 27
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.
If you are looking for a fantastic resort that’s nearby everything SWFL has to offer. This is the resort for you! I wasn’t sure what to expect booking but it was great. From the staff, to the room, the food and private boat to the beach. Every detail was noted and appreciated. I cannot wait to return! Thank you for making a tough trip into a wonderful one!
Reviewed on Nov 13, 2026
Hyatt Vacation Club at Coconut Cove, Bonita Springs
Price was $1,510, price is now $1,033 per person
$1,033
per person
Feb 5 - Feb 8
found 6 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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 Coconut Point Mall and Bonita Springs Public Beach are located nearby.
Windward Passage Resort
Price was $1,993, price is now $1,394 per person
$1,394
per person
Jan 24 - Jan 30
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.
Blue Sunset by Avantstay Pool + Spa + Fire Table Near Beaches + Naples
Price was $3,240, price is now $2,307 per person
$2,307
per person
Jan 24 - Jan 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Stay at this cottage in Bonita Springs. Enjoy free parking, patios, and in-room washers/dryers. Popular attractions Barefoot Beach and Bonita Springs Public Beach are located nearby.
Landing Incredible 1bd, Gym, Clubhouse
Price was $1,917, price is now $1,393 per person
$1,393
per person
Feb 4 - Feb 11
found 8 hours ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Stay at this apartment in North Fort Myers. Enjoy free parking, an outdoor pool, and a fitness center. Popular attractions Pine Island Shopping Center and Fort Myers Shopping Center are located nearby.
Captiva Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Captiva Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Mon, Jan 11 - Fri, Jan 22
PHL
Philadelphia Intl.
RSW
Southwest Florida Intl.
$80 Roundtrip, found 1 hour ago
$80
Roundtrip
found 1 hour ago
Tue, Jan 26 - Fri, Feb 26
DTW
Detroit Metropolitan Wayne County
RSW
Southwest Florida Intl.
$88 Roundtrip, found 11 hours ago
$88
Roundtrip
found 11 hours ago
Thu, Jan 7 - Fri, Jan 8
CLE
Hopkins Intl.
RSW
Southwest Florida Intl.
$141 Roundtrip, just found
$141
Roundtrip
just found
Mon, Jan 11 - Fri, Jan 22
TTN
Mercer
RSW
Southwest Florida Intl.
$142 Roundtrip, found 1 hour ago
$142
Roundtrip
found 1 hour ago
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