Dismal Key Flight + Hotel Packages

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

Sleep Inn & Suites Port Charlotte - Punta Gorda

$518

per person

Mar 1 - Mar 7

found 16 hours ago

Roundtrip flight included

Chicago (ORD) to Fort Myers (RSW)

Book a stay at this business-friendly hotel in Port Charlotte. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Deep Creek Golf Club and Lake Betty Park are located nearby.

The Suites at Fishermen’s Village- 2 Bedroom Suites

Save 100% on your flight

$1,173

per person

Mar 5 - Mar 13

found 15 hours ago

Roundtrip flight included

Dallas (DFW) to Fort Myers (RSW)

Stay at this condo in Punta Gorda. Enjoy free WiFi, free parking, and a marina. 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.

South Seas Resort

Save 100% on your flight

$2,035

per person

Mar 7 - Mar 15

found 8 hours ago

Roundtrip flight included

Charlotte (CLT) to Fort Myers (RSW)

Book a stay at this beach resort in Captiva. Enjoy 3 outdoor pools, 7 restaurants, and a private beach. Popular attractions Jungle Drums and McCarthy's Marina are located nearby.

Tween Waters Island Resort & Spa

Save 100% on your flight

$660

per person

Mar 10 - Mar 14

found 1 day ago

Roundtrip flight included

Chicago (ORD) 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 Captiva Beach and Captiva Chapel By the Sea are located nearby.

LaPlaya Beach & Golf Resort - A Noble House Resort

Save 100% on your flight

$2,028

per person

Feb 26 - Mar 2

found 1 day ago

Roundtrip flight included

Charlotte (CLT) 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.

Marriott Sanibel Harbour Resort & Spa

$1,172

per person

Mar 8 - Mar 14

found 13 hours ago

Roundtrip flight included

Charlotte (CLT) to Fort Myers (RSW)

Book a stay at this spa resort in Fort Myers. Enjoy 3 outdoor pools, a full-service spa, and 4 restaurants. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Key West Express and Sanibel Island Southern Beach are located nearby.

Comfort Inn & Suites

$621

per person

Mar 1 - Mar 7

found 16 hours ago

Roundtrip flight included

Chicago (ORD) to Fort Myers (RSW)

Book a stay at this business-friendly hotel in Port Charlotte. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Deep Creek Golf Club and Lake Betty Park are located nearby.

THE Palmview AND Sandpiper Inns

Save 100% on your flight

$674

per person

Mar 7 - Mar 11

found 16 hours ago

Roundtrip flight included

Chicago (ORD) to Fort Myers (RSW)

Stay at this motel in Sanibel. Enjoy free WiFi, free parking, and in-room massages. Popular attractions Sanibel Island Southern Beach and Sanibel Island Golf Club are located nearby.

Casa Ybel Resort

Save 100% on your flight

$2,495

per person

Mar 7 - Mar 15

found 8 hours ago

Roundtrip flight included

Charlotte (CLT) 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 Gulfside City Park are located nearby.

Wyvern Hotel, an Ascend Collection Hotel

Save 100% on your flight

$668

per person

Mar 16 - Mar 20

found 8 hours ago

Roundtrip flight included

Detroit (DTW) to Fort Myers (RSW)

Book a stay at this luxury hotel 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 A. C. Freeman House and Gilchrist Park are located nearby.

Hilton Marco Island Beach Resort and Spa

Save 100% on your flight

$1,943

per person

Mar 13 - Mar 17

found 16 hours ago

Roundtrip non-stop flight included

Charlotte (CLT) to Fort Myers (RSW)

Book a stay at this beach resort in Marco Island. Enjoy a full-service spa, a beach locale, and room service. Our guests praise the pool and the restaurant in our reviews. Popular attractions Winterberry Beach and South Marco Beach are located nearby.

Compass by Margaritaville Hotel Naples

$927

per person

Feb 26 - Mar 2

found 1 day ago

Roundtrip flight included

Chicago (ORD) to Fort Myers (RSW)

Book a stay at this business-friendly hotel in Naples. Enjoy free breakfast, free parking, and a 24-hour fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Naples Zoo at Caribbean Gardens and Vanderbilt Beach are located nearby.

3-4 Night Vacations in Dismal Key

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

Hilton Garden Inn Ft Myers

Villas

$400

per person

Mar 9 - Mar 13

found 13 hours ago

Roundtrip flight included

Charlotte (CLT) to Fort Myers (RSW)

The Suites at Fishermen’s Village- 2 Bedroom Suites

Punta Gorda Isles

Save 100% on your flight

$710

per person

Mar 16 - Mar 20

found 8 hours ago

Roundtrip flight included

Detroit (DTW) to Fort Myers (RSW)

LaPlaya Beach & Golf Resort - A Noble House Resort

Vanderbilt Beach

Save 100% on your flight

$2,028

per person

Feb 26 - Mar 2

found 1 day ago

Roundtrip flight included

Charlotte (CLT) to Fort Myers (RSW)

Tween Waters Island Resort & Spa

$567

per person

Mar 4 - Mar 7

found 8 hours ago

Roundtrip flight included

Detroit (DTW) to Fort Myers (RSW)

5-7 Night Vacations in Dismal Key

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