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Captiva Vacation Packages

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Captiva Flight + Hotel Packages

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

Manasota Key Resort

2.5 out of 5
Price was $742, price is now $396 per person
$396
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Fort Myers (RSW)
Book a stay at this beach hotel in Englewood. Enjoy free WiFi, free parking, and a private beach. Our guests praise the helpful staff in our reviews. Popular attractions Englewood Beach and Manasota Beach are located nearby.

LaPlaya Beach & Golf Resort - A Noble House Resort

LaPlaya Beach & Golf Resort - A Noble House Resort

4.5 out of 5
Save 100% on your flight
Price was $1,771, price is now $978 per person
$978
per person
Oct 10 - Oct 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 Delnor-Wiggins Pass State Park are located nearby.
We love laplaya and go there 1-2 x a year. Beach is always amazing w great beach and wait staff! Food at bakery is delicious!

Reviewed on Jul 29, 2026

The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Save 100% on your flight
Price was $1,352, price is now $772 per person
$772
per person
Oct 15 - Oct 22
found 19 hours ago
Roundtrip non-stop flight included
Hartford (BDL) 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 Delnor-Wiggins Pass State Park are located nearby.

Casa Ybel Resort

Casa Ybel Resort

2.5 out of 5
Save 100% on your flight
Price was $623, price is now $402 per person
$402
per person
Oct 12 - Oct 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 Sanibel Island Lighthouse are located nearby.

Landing Furnished Apartments - Naples, FL

Landing Furnished Apartments - Naples, FL

4 out of 5
Save 100% on your flight
Price was $1,189, price is now $808 per person
$808
per person
Oct 15 - Oct 22
found 19 hours ago
Roundtrip non-stop flight included
Hartford (BDL) to Fort Myers (RSW)
Book a stay at this business-friendly apartment in Naples. Enjoy free WiFi, a rooftop terrace, and a fitness center. Popular attractions Fifth Avenue South and Naples Beach are located nearby.
Close by beach and 5th avenue

Reviewed on Jul 10, 2026

The Suites at Fishermen’s Village- 2 Bedroom Suites

The Suites at Fishermen’s Village- 2 Bedroom Suites

3 out of 5
Save 100% on your flight
Price was $1,073, price is now $731 per person
$731
per person
Sep 3 - Sep 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Stay at this aparthotel in Punta Gorda. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Fishermen's Village and Military Heritage Museum are located nearby.
The property was very clean. Kitchen was stocked with dishes, pots and pans, utensils and everything we could want. The beds and pillows were comfortable. Ceiling fans were in every room. Couch and chair was clean and comfortable. TVs in every room. Centrally located. Easy to access.

Reviewed on Jul 30, 2026

Inn on Fifth

Inn on Fifth

4 out of 5
Save 100% on your flight
Price was $1,515, price is now $1,033 per person
$1,033
per person
Oct 15 - Oct 22
found 19 hours ago
Roundtrip non-stop flight included
Hartford (BDL) to Fort Myers (RSW)
Book a stay at this spa hotel in Naples. Enjoy a full-service spa, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Fifth Avenue South and Naples Beach are located nearby.

Casa Tiki

Casa Tiki

3 out of 5
Price was $1,195, price is now $836 per person
$836
per person
Oct 17 - Oct 24
found 9 hours ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Stay at this vacation home in Cape Coral. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Edison and Ford Winter Estates and Four Mile Cove Ecological Preserve are located nearby.

Captiva Vacation Packages 3-4 Night Stays

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

Manasota Key Resort

2.5 out of 5
Price was $742, price is now $396 per person
$396
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Fort Myers (RSW)
LaPlaya Beach & Golf Resort - A Noble House Resort

LaPlaya Beach & Golf Resort - A Noble House Resort

4.5 out of 5
Vanderbilt Beach
Save 100% on your flight
Price was $1,771, price is now $978 per person
$978
per person
Oct 10 - Oct 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Fort Myers (RSW)
Casa Ybel Resort

Casa Ybel Resort

2.5 out of 5
Mid Island
Save 100% on your flight
Price was $623, price is now $402 per person
$402
per person
Oct 12 - Oct 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Fort Myers (RSW)
The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Price was $1,155, price is now $781 per person
$781
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)

Captiva Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Stay Inn & Suites

Stay Inn & Suites

2.5 out of 5
Winkler
Save 100% on your flight
Price was $581, price is now $386 per person
$386
per person
Aug 29 - Sep 5
found 23 hours ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
LaPlaya Beach & Golf Resort - A Noble House Resort

LaPlaya Beach & Golf Resort - A Noble House Resort

4.5 out of 5
Vanderbilt Beach
Price was $2,915, price is now $1,475 per person
$1,475
per person
Oct 15 - Oct 22
found 19 hours ago
Roundtrip non-stop flight included
Hartford (BDL) to Fort Myers (RSW)
The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Save 100% on your flight
Price was $1,352, price is now $772 per person
$772
per person
Oct 15 - Oct 22
found 19 hours ago
Roundtrip non-stop flight included
Hartford (BDL) to Fort Myers (RSW)
Casa Ybel Resort

Casa Ybel Resort

2.5 out of 5
Mid Island
Save 100% on your flight
Price was $1,110, price is now $677 per person
$677
per person
Oct 1 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Frontier Airlines
Mon, Sep 21 - Tue, Oct 13
CLE
Hopkins Intl.
RSW
Southwest Florida Intl.
$100 Roundtrip, found 11 hours ago
$100
Roundtrip
found 11 hours ago
Select Frontier Airlines flight, departing Mon, Sep 21 from Hopkins Intl. to Southwest Florida Intl., returning Tue, Oct 13, priced at $100 found 11 hours ago
Frontier Airlines
Sun, Aug 30 - Thu, Sep 17
PHL
Philadelphia Intl.
RSW
Southwest Florida Intl.
$111 Roundtrip, found 11 hours ago
$111
Roundtrip
found 11 hours ago
Select Frontier Airlines flight, departing Sun, Aug 30 from Philadelphia Intl. to Southwest Florida Intl., returning Thu, Sep 17, priced at $111 found 11 hours ago
Allegiant Air
Thu, Aug 27 - Sun, Aug 30
PSM
Portsmouth Intl.
PGD
Punta Gorda Airport
$122 Roundtrip, found 2 hours ago
$122
Roundtrip
found 2 hours ago
Select Allegiant Air flight, departing Thu, Aug 27 from Portsmouth Intl. to Punta Gorda Airport, returning Sun, Aug 30, priced at $122 found 2 hours ago
Breeze Airways
Wed, Jan 13 - Sat, Jan 16
PSM
Portsmouth Intl.
RSW
Southwest Florida Intl.
$163 Roundtrip, found 1 day ago
$163
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Wed, Jan 13 from Portsmouth Intl. to Southwest Florida Intl., returning Sat, Jan 16, priced at $163 found 1 day ago