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Dismal Key Vacation Packages

Dismal Key Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Courtyard by Marriott Fort Myers Cape Coral

Courtyard by Marriott Fort Myers Cape Coral

3 out of 5
Price was $734, price is now $527 per person
$527
per person
May 27 - Jun 3
found 1 day ago
Roundtrip flight included
Hartford (BDL) to Fort Myers (RSW)
Book a stay at this business-friendly hotel in Fort Myers. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Lee Health Sports Complex and Edison Mall are located nearby.
Chadwick Cove Resort & Marina

Chadwick Cove Resort & Marina

4 out of 5
Price was $927, price is now $687 per person
$687
per person
May 27 - May 31
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
Book a stay at this beach condo in Englewood. Enjoy free WiFi, free parking, and 7 restaurants. Popular attractions Englewood Beach and Lemon Bay 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 $2,406, price is now $1,261 per person
$1,261
per person
Jun 5 - Jun 11
found 1 day ago
Roundtrip flight included
Hartford (BDL) 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 Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Save 100% on your flight
Price was $1,105, price is now $652 per person
$652
per person
Jun 5 - Jun 11
found 1 day ago
Roundtrip 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 Barefoot Beach are located nearby.
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 $946, price is now $626 per person
$626
per person
May 29 - Jun 3
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.
Matanzas Inn Bayside Resort and Marina

Matanzas Inn Bayside Resort and Marina

3 out of 5
Save 100% on your flight
Price was $954, price is now $644 per person
$644
per person
May 29 - Jun 3
found 1 day ago
Roundtrip flight included
Boston (BOS) 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.
Hyatt Vacation Club at Coconut Cove, Bonita Springs

Hyatt Vacation Club at Coconut Cove, Bonita Springs

4 out of 5
Save 100% on your flight
Price was $1,382, price is now $962 per person
$962
per person
Jun 5 - Jun 11
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 Coconut Point Mall and Bonita Springs Public Beach are located nearby.
The Lighthouse Resort Inn & Suites

The Lighthouse Resort Inn & Suites

3 out of 5
Save 100% on your flight
Price was $900, price is now $636 per person
$636
per person
May 29 - Jun 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Stay at this hotel in Fort Myers Beach. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Key West Express and Estero Boulevard Beach are located nearby.
Mariners Boathouse by Coolvacay

Mariners Boathouse by Coolvacay

3 out of 5
Save 100% on your flight
Price was $994, price is now $705 per person
$705
per person
Jun 3 - Jun 8
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 Estero Boulevard Beach are located nearby.
THE Palmview AND Sandpiper Inns

THE Palmview AND Sandpiper Inns

3.5 out of 5
Save 100% on your flight
Price was $1,014, price is now $728 per person
$728
per person
Jun 3 - Jun 8
found 1 day ago
Roundtrip flight included
Boston (BOS) 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.
Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

4 out of 5
Price was $762, price is now $548 per person
$548
per person
Jun 11 - Jun 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Book a stay at this spa resort in Punta Gorda. Enjoy 2 outdoor pools, a full-service spa, and 7 restaurants. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Peace River and Bayshore Live Oak Park are located nearby.
Tween Waters Island Resort & Spa

Tween Waters Island Resort & Spa

3 out of 5
Save 100% on your flight
Price was $1,323, price is now $959 per person
$959
per person
Jun 3 - Jun 8
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 North Captiva Island Beach and Captiva Beach are located nearby.

3-4 Night Vacations in Dismal Key

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 $617, price is now $400 per person
$400
per person
Jun 3 - Jun 6
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Chadwick Cove Resort & Marina

Chadwick Cove Resort & Marina

4 out of 5
Price was $927, price is now $687 per person
$687
per person
May 27 - May 31
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 $1,931, price is now $1,112 per person
$1,112
per person
Jun 18 - Jun 22
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
The Suites at Fishermen’s Village- 2 Bedroom Suites

The Suites at Fishermen’s Village- 2 Bedroom Suites

3 out of 5
Punta Gorda Isles
Price was $861, price is now $605 per person
$605
per person
Jun 11 - Jun 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)

5-7 Night Vacations in Dismal Key

Price found within the past 48 hours. Click for updated prices.
The Suites at Fishermen’s Village- 2 Bedroom Suites

The Suites at Fishermen’s Village- 2 Bedroom Suites

3 out of 5
Punta Gorda Isles
Save 100% on your flight
Price was $946, price is now $626 per person
$626
per person
May 29 - Jun 3
found 1 day 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
Save 100% on your flight
Price was $2,406, price is now $1,261 per person
$1,261
per person
Jun 5 - Jun 11
found 1 day ago
Roundtrip 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 $1,105, price is now $652 per person
$652
per person
Jun 5 - Jun 11
found 1 day ago
Roundtrip flight included
Hartford (BDL) to Fort Myers (RSW)
Matanzas Inn Bayside Resort and Marina

Matanzas Inn Bayside Resort and Marina

3 out of 5
Save 100% on your flight
Price was $954, price is now $644 per person
$644
per person
May 29 - Jun 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)

Dismal Key Last Minute Hotel Deals

Port of the Islands Everglades Adventure Resort

Port of the Islands Everglades Adventure Resort

2.5 out of 5
Naples FL
Book a stay at this business-friendly hotel in Naples. Enjoy free WiFi, free parking, and a marina. Our guests praise the helpful staff in our reviews. Popular ...
Port of the Islands Everglades Adventure Resort
Hilton Marco Island Beach Resort and Spa

Hilton Marco Island Beach Resort and Spa

4 out of 5
560 S Collier Blvd Marco Island FL
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 ...
Hilton Marco Island Beach Resort and Spa
Villa Marco Island

Villa Marco Island

3.5 out of 5
192 Gulfport Court Marco Island FL
Book a stay at this beach villa in Marco Island. Enjoy free WiFi, free parking, and private pools. Popular attractions South Marco Beach and City of Marco Island ...
Villa Marco Island
See all 4,004 properties in Dismal Key
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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