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Dismal Key Vacation Packages

Dismal Key Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
La Quinta Inn & Suites by Wyndham Ft. Myers-Sanibel Gateway

La Quinta Inn & Suites by Wyndham Ft. Myers-Sanibel Gateway

2.5 out of 5
Save 100% on your flight
per person
Oct 29 - Nov 2
found 1 day ago
Roundtrip flight included
Cleveland (CLE) 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 breakfast and the pool in our reviews. Popular attractions Key West Express and Bunche Beach are located nearby.
Tween Waters Island Resort & Spa

Tween Waters Island Resort & Spa

3 out of 5
Save 100% on your flight
per person
Oct 29 - Nov 2
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Fort Myers (RSW)
Book a stay at this beach resort in Captiva. Enjoy 2 outdoor pools, a full-service spa, and 3 restaurants. Popular attractions Captiva Beach and Captiva Chapel By the Sea are located nearby.
Resort Harbour Properties

Resort Harbour Properties

3.5 out of 5
Save 100% on your flight
per person
Oct 29 - Nov 2
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Fort Myers (RSW)
Stay at this 3.5-star beach condo in Fort Myers. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions Key West Express and Sanibel Island Southern Beach are located nearby.
South Seas Resort

South Seas Resort

3.5 out of 5
Save 100% on your flight
per person
Oct 29 - Nov 2
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Fort Myers (RSW)
Book a stay at this beach resort in Captiva. Enjoy 2 outdoor pools, 2 restaurants, and a private beach. Popular attractions Jungle Drums and McCarthy's Marina are located nearby.
Embassy Suites by Hilton Fort Myers Estero

Embassy Suites by Hilton Fort Myers Estero

3.5 out of 5
Save 100% on your flight
per person
Oct 29 - Nov 2
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Fort Myers (RSW)
Stay at this 3.5-star business-friendly hotel in Estero. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions Hertz Arena and Coconut Point Mall are located nearby.
Doubletree by Hilton Fort Myers at Bell Tower Shops

Doubletree by Hilton Fort Myers at Bell Tower Shops

4 out of 5
Save 100% on your flight
per person
Oct 29 - Nov 2
found 1 day ago
Roundtrip flight included
Cleveland (CLE) 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 Bell Tower Shops and Barbara B Mann Hall are located nearby.
Hilton Garden Inn Ft Myers

Hilton Garden Inn Ft Myers

3 out of 5
Save 100% on your flight
per person
Oct 29 - Nov 2
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Fort Myers (RSW)
Stay at this 3-star business-friendly hotel in Fort Myers. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Barbara B Mann Hall and Bell Tower Shops are located nearby.
Hilton Garden Inn Fort Myers Airport/FGCU

Hilton Garden Inn Fort Myers Airport/FGCU

3 out of 5
Save 100% on your flight
per person
Oct 29 - Nov 2
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Fort Myers (RSW)
Stay at this 3-star business-friendly hotel in Fort Myers. Enjoy free parking, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff in our reviews. Popular attractions Hertz Arena and JetBlue Park at Fenway South are located nearby.
Edison Beach House

Edison Beach House

3.5 out of 5
Save 100% on your flight
per person
Oct 29 - Nov 2
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Fort Myers (RSW)
Stay at this 3.5-star beach aparthotel in Fort Myers Beach. Enjoy free parking, a beach locale, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Key West Express and Lynn Hall Memorial Park 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
per person
Oct 29 - Nov 2
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Fort Myers (RSW)
Stay at this 4-star golf aparthotel in Estero. Enjoy free WiFi, free parking, and 3 outdoor pools. Popular attractions Coconut Point Mall and Bonita Springs Public Beach are located nearby.
Courtyard by Marriott Fort Myers Cape Coral

Courtyard by Marriott Fort Myers Cape Coral

3 out of 5
Save 100% on your flight
per person
Oct 29 - Nov 2
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Fort Myers (RSW)
Stay at this 3-star 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 Edison Mall and Eagle Harbor Golf Club are located nearby.
Matanzas Inn Bayside Resort and Marina

Matanzas Inn Bayside Resort and Marina

3 out of 5
Save 100% on your flight
per person
Oct 29 - Nov 2
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Fort Myers (RSW)
Stay at this 3-star 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 Ostego Bay Marine Science Center are located nearby.

3-4 Night Vacations in Dismal Key

Price found within the past 48 hours. Click for updated prices.
La Quinta Inn & Suites by Wyndham Ft. Myers-Sanibel Gateway

La Quinta Inn & Suites by Wyndham Ft. Myers-Sanibel Gateway

2.5 out of 5
Save 100% on your flight
per person
Oct 29 - Nov 2
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Fort Myers (RSW)
Tween Waters Island Resort & Spa

Tween Waters Island Resort & Spa

3 out of 5
Save 100% on your flight
per person
Oct 29 - Nov 2
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Fort Myers (RSW)
Resort Harbour Properties

Resort Harbour Properties

3.5 out of 5
Punta Rassa
Save 100% on your flight
per person
Oct 29 - Nov 2
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Fort Myers (RSW)
South Seas Resort

South Seas Resort

3.5 out of 5
Save 100% on your flight
per person
Oct 29 - Nov 2
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Fort Myers (RSW)

5-7 Night Vacations in Dismal Key

Price found within the past 48 hours. Click for updated prices.
La Quinta Inn & Suites by Wyndham Ft. Myers-Sanibel Gateway

La Quinta Inn & Suites by Wyndham Ft. Myers-Sanibel Gateway

2.5 out of 5
per person
Oct 22 - Oct 28
found 1 day ago
Roundtrip non-stop flight included
New Orleans (MSY) to Fort Myers (RSW)
Sanibel Island Beach Resort

Sanibel Island Beach Resort

3 out of 5
Save 100% on your flight
per person
Oct 22 - Oct 28
found 1 day ago
Roundtrip non-stop flight included
New Orleans (MSY) to Fort Myers (RSW)
Hilton Garden Inn Fort Myers Airport/FGCU

Hilton Garden Inn Fort Myers Airport/FGCU

3 out of 5
Miromar Lakes
Save 100% on your flight
per person
Oct 22 - Oct 28
found 1 day ago
Roundtrip non-stop flight included
New Orleans (MSY) to Fort Myers (RSW)
Embassy Suites by Hilton Fort Myers Estero

Embassy Suites by Hilton Fort Myers Estero

3.5 out of 5
Save 100% on your flight
per person
Oct 22 - Oct 28
found 1 day ago
Roundtrip non-stop flight included
New Orleans (MSY) 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
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 hotel 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
JW Marriott Marco Island Beach Resort
JW Marriott Marco Island Beach Resort
4 out of 5
400 S Collier Blvd, Marco Island, FL
Book a stay at this beach resort in Marco Island. Enjoy 3 outdoor pools, a full-service spa, and 5 restaurants. Our guests praise the helpful staff and the property ...
JW Marriott Marco Island Beach Resort
See all 3,665 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.

Top Flight Deals

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

Spirit Airlines
Tue, Dec 10 - Tue, Dec 17
DTW
Detroit Metropolitan Wayne County
RSW
Southwest Florida Intl.
$78 Roundtrip, just found
$78
Roundtrip
just found
Select Spirit Airlines flight, departing Tue, Dec 10 from Detroit Metropolitan Wayne County to Southwest Florida Intl., returning Tue, Dec 17, priced at $78 just found
Spirit Airlines
Mon, Nov 11 - Mon, Nov 18
BOS
Logan Intl.
RSW
Southwest Florida Intl.
$78 Roundtrip, found 9 hours ago
$78
Roundtrip
found 9 hours ago
Select Spirit Airlines flight, departing Mon, Nov 11 from Logan Intl. to Southwest Florida Intl., returning Mon, Nov 18, priced at $78 found 9 hours ago
Frontier Airlines
Sat, Oct 26 - Wed, Nov 6
CLE
Hopkins Intl.
RSW
Southwest Florida Intl.
$88 Roundtrip, found 3 days ago
$88
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Sat, Oct 26 from Hopkins Intl. to Southwest Florida Intl., returning Wed, Nov 6, priced at $88 found 3 days ago
Spirit Airlines
Tue, Feb 11 - Wed, Feb 19
IND
Indianapolis Intl.
RSW
Southwest Florida Intl.
$98 Roundtrip, found 3 days ago
$98
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Tue, Feb 11 from Indianapolis Intl. to Southwest Florida Intl., returning Wed, Feb 19, priced at $98 found 3 days ago

Book the perfect getaway to Dismal Key

With Hotwire, booking your next trip to Naples is a breeze. When it comes to planning a show-stopping vacay, you’re the reigning champion of doing it on a dime. You love to plan exciting destination adventures while saving money on a budget.

Hotwire is here to help you plan a smooth sailing trip to Dismal Key while saving some major cash. Doubling up on vacation expenses like hotel and car rentals and fun-filled excursions can save you money—especially when you book one of Hotwire’s vacation packages.

If your trip to is spur-of-the-moment and you’re leaving soon, Hotwire can save you up to 60% off your rentals with Hotwire Hot Rate deals. Book with Hotwire to grab a stellar Dismal Key flight and hotel package for as low as $200.

Living it up in Naples means getting there in style and staying in a hotel that matches your mood. Book one of Hotwire’s Dismal Key, Naples vacation packages to enjoy the best of both worlds. Flight and hotel packages typically include roundtrip non-stop flights and multi-day hotel stays. Packages are priced per person and are perfect for flying solo or traveling with a group of friends or family. Conveniently choose from Hotwire’s inventory of hotels in Dismal Key for some of the best accommodations and flight deals.

FAQs about cheap Dismal Key packages:

How to get cheap vacation deals to Dismal Key?

Save up to 60% off vacation deals with Hotwire Hot Rates. Just plug in your general preferences and let Hotwire choose matching hotels for as low as $108.

How much are Dismal Key packages?

Vacation packages to Dismal Key vary in price. They are priced per person and include discounted hotel and flight costs. With Hotwire, you can score a vacation package for as low as $200.

How to find cheap car rentals near Dismal Key?

Hotwire partners with some of the most reliable car rental companies in Naples to bring you the best car rental deals in Dismal Key for as low as . Select a rental from Hotwire’s extensive inventory of cars for every travel style. If you plan on bringing friends or family along, opt for a spacious SUV. If you’re visiting on business but still plan to make time for off-the-clock adventures, Hotwire offers sleek luxury and convertible rentals.

Is it safe to travel to Dismal Key now?

With recent COVID-19 closures and reopenings, many people are wondering, “Is it safe to travel to Dismal Key right now?” When it’s time to book your vacation, check out the most up-to-date information on all safety measures, any restrictions, and guidance on traveling during the coronavirus pandemic.

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