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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.
Quality Inn Fort Myers Cape Coral

Quality Inn Fort Myers Cape Coral

2 out of 5
Price was $477, price is now $308 per person
$308
per person
Sep 15 - Sep 21
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
Book a stay at this business-friendly hotel in Fort Myers. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the clean rooms in our reviews. Popular attractions Edison and Ford Winter Estates and Edison Mall 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 $2,088, price is now $1,236 per person
$1,236
per person
Aug 29 - Sep 5
found 1 day ago
Roundtrip flight included
Boston (BOS) 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.

The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Save 100% on your flight
Price was $1,434, price is now $884 per person
$884
per person
Oct 8 - Oct 14
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 Delnor-Wiggins Pass State Park and Vanderbilt Beach are located nearby.
All great 👍.

Reviewed on Jul 16, 2026

A Wave From it All

A Wave From it All

2 out of 5
Save 100% on your flight
Price was $2,158, price is now $1,345 per person
$1,345
per person
Aug 25 - Aug 30
found 1 day ago
Roundtrip flight included
Cincinnati (CVG) to Fort Myers (RSW)
Stay at this vacation home in Fort Myers Beach. Enjoy free WiFi, free parking, and 6 beach bars. Popular attractions Key West Express and Estero Boulevard Beach are located nearby.

Manasota Key Resort

Manasota Key Resort

2.5 out of 5
Save 100% on your flight
Price was $1,180, price is now $785 per person
$785
per person
Sep 7 - Sep 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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.
We were only on property for 10 minutes before agreeing that we needed to come back every year. It is a little piece of paradise. We used all the things, from lawn chairs to shuffle boards, paddle boards, bikes, and pool. It is a short drive to restaurants and stores, but the kitchenette was perfect for cooking a quick meal. The rooms are spacious and comfortable.

Reviewed on Jul 16, 2026

Windward Passage Resort

Windward Passage Resort

2 out of 5
Save 100% on your flight
Price was $1,039, price is now $712 per person
$712
per person
Aug 25 - Aug 30
found 1 day ago
Roundtrip flight included
Cincinnati (CVG) 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 Estero Boulevard Beach are located nearby.
It was fabulous

Reviewed on Jun 30, 2026

Shell Island Beach Club

Shell Island Beach Club

4 out of 5
Save 100% on your flight
Price was $1,483, price is now $1,027 per person
$1,027
per person
Oct 3 - Oct 10
found 1 day ago
Roundtrip flight included
New York (JFK) to Fort Myers (RSW)
Book a stay at this beach aparthotel in Sanibel. Enjoy free WiFi, free parking, and 2 outdoor pools. Popular attractions Sanibel Island Southern Beach and Key West Express are located nearby.
Great place to stay on the beach! Woman at the front desk was rude!

Reviewed on Jun 7, 2026

Bellasera Resort

Bellasera Resort

4 out of 5
Save 100% on your flight
Price was $1,885, price is now $1,321 per person
$1,321
per person
Oct 8 - Oct 14
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 breakfast (surcharge). Our guests praise the pool and the bar in our reviews. Popular attractions Fifth Avenue South and Naples Beach are located nearby.

Captiva Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Price was $542, price is now $383 per person
$383
per person
Sep 11 - Sep 14
found 1 day ago
Roundtrip non-stop 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
Save 100% on your flight
Price was $983, price is now $605 per person
$605
per person
Sep 11 - Sep 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
Manasota Key Resort

Manasota Key Resort

2.5 out of 5
Save 100% on your flight
Price was $1,180, price is now $785 per person
$785
per person
Sep 7 - Sep 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
Windward Passage Resort

Windward Passage Resort

2 out of 5
Save 100% on your flight
Price was $901, price is now $635 per person
$635
per person
Aug 26 - Aug 30
found 1 day ago
Roundtrip non-stop flight included
Cincinnati (CVG) to Fort Myers (RSW)

Captiva Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Save 100% on your flight
Price was $1,434, price is now $884 per person
$884
per person
Oct 8 - Oct 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Tween Waters Island Resort & Spa

Tween Waters Island Resort & Spa

3 out of 5
Save 100% on your flight
Price was $1,747, price is now $973 per person
$973
per person
Sep 15 - Sep 21
found 1 day ago
Roundtrip non-stop 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
Save 100% on your flight
Price was $2,491, price is now $1,429 per person
$1,429
per person
Oct 8 - Oct 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
A Wave From it All

A Wave From it All

2 out of 5
Siesta Isle
Save 100% on your flight
Price was $2,158, price is now $1,345 per person
$1,345
per person
Aug 25 - Aug 30
found 1 day ago
Roundtrip flight included
Cincinnati (CVG) 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
Sun, Aug 30 - Mon, Sep 14
CLE
Hopkins Intl.
RSW
Southwest Florida Intl.
$126 Roundtrip, found 4 days ago
$126
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Sun, Aug 30 from Hopkins Intl. to Southwest Florida Intl., returning Mon, Sep 14, priced at $126 found 4 days ago
Delta
Tue, Sep 15 - Tue, Oct 6
BOS
Logan Intl.
RSW
Southwest Florida Intl.
$189 Roundtrip, found 7 hours ago
$189
Roundtrip
found 7 hours ago
Select Delta flight, departing Tue, Sep 15 from Logan Intl. to Southwest Florida Intl., returning Tue, Oct 6, priced at $189 found 7 hours ago
Delta
Tue, Dec 1 - Tue, Dec 15
MSP
Minneapolis - St. Paul Intl.
RSW
Southwest Florida Intl.
$199 Roundtrip, found 5 hours ago
$199
Roundtrip
found 5 hours ago
Select Delta flight, departing Tue, Dec 1 from Minneapolis - St. Paul Intl. to Southwest Florida Intl., returning Tue, Dec 15, priced at $199 found 5 hours ago
United
Tue, Sep 1 - Sat, Sep 12
EWR
Newark Liberty Intl. Airport
RSW
Southwest Florida Intl.
$202 Roundtrip, found 7 hours ago
$202
Roundtrip
found 7 hours ago
Select United flight, departing Tue, Sep 1 from Newark Liberty Intl. Airport to Southwest Florida Intl., returning Sat, Sep 12, priced at $202 found 7 hours ago