Package deals near Key West Express

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Top Key West Express vacation deals

Price found within the past 48 hours. Click for updated prices.
Wiggins Pass Chalet
4.0-star property

Wiggins Pass Chalet

9.6/10 Exceptional! (233 reviews)

Jan 12 - Jan 19

7 night stay

Boston (BOS) to Fort Myers (RSW)

JetBlue Airways • Roundtrip • Coach
Save 100% on your flight
Price was $1,340, price is now $838 per person
$838
per person
found 1 day ago
Super clean, spacious and quiet.

Reviewed on Aug 31, 2025

LaPlaya Beach & Golf Resort - A Noble House Resort
4.5-star property

LaPlaya Beach & Golf Resort - A Noble House Resort

Vanderbilt Beach
8.8/10 Excellent! (1,003 reviews)

Jan 12 - Jan 19

7 night stay

Boston (BOS) to Fort Myers (RSW)

JetBlue Airways • Roundtrip • Coach
Save 100% on your flight
Price was $4,278, price is now $2,384 per person
$2,384
per person
found 1 day ago
Great customer service and guest services. Nice resort and good food.....we will definitely be back again.....

Reviewed on Jul 1, 2025

The Perry Hotel Naples
4.5-star property

The Perry Hotel Naples

9.6/10 Exceptional! (443 reviews)

Jan 12 - Jan 19

7 night stay

Boston (BOS) to Fort Myers (RSW)

JetBlue Airways • Roundtrip • Coach
Save 100% on your flight
Price was $1,787, price is now $1,035 per person
$1,035
per person
found 1 day ago
The AC in our room was not working, but the hotel was gorgeous with a very friendly staff.

Reviewed on Jul 29, 2025

GreenLinks Golf Villas at Lely Resort
3.0-star property

GreenLinks Golf Villas at Lely Resort

9.4/10 Exceptional! (532 reviews)

Feb 1 - Feb 5

4 night stay

Boston (BOS) to Fort Myers (RSW)

JetBlue Airways • Roundtrip • Coach
Save 100% on your flight
Price was $1,386, price is now $851 per person
$851
per person
found 1 day ago
This was an adequate accommodation for us for our stay. About equidistant from Naples and Marco Island, it provided good access to both. The decoration was IKEA-vintage in my view. Two complaints - although there were three tv’s in the unit, the one in the main bedroom was not functional. Also, on the morning after check in we were awakened early by a workman who told us to move our car from the parking lot for a resurfacing project. The parking was not available to us. We expressed annoyance at being placed in this unit at the front desk and were told that this project was planned and that it was the owner’s responsibility to inform us of this. We were told to park in the lot of a restaurant nearby. The early morning noise of heavy equipment was also noteworthy.

Reviewed on May 15, 2024

Inn on Fifth
4.0-star property

Inn on Fifth

Old Naples
9.4/10 Exceptional! (1,005 reviews)

Feb 1 - Feb 5

4 night stay

Boston (BOS) to Fort Myers (RSW)

JetBlue Airways • Roundtrip • Coach
Save 100% on your flight
Price was $2,489, price is now $1,567 per person
$1,567
per person
found 1 day ago
The location is a 10 but this isn’t a 5-star property. I’ve stayed at this hotel the past 5 years, always for 5 nights between Christmas and New Years. The value for the price is terrible. The hair dryers in the room are trash, the TV in our room flickered on and off during our entire stay in 2024, the rooms are clean but not immaculate, the elevator takes forever to move between floors. Overall this hotel could use a major refresh and I will be finding a different hotel to stay at in Dec 2025.

Reviewed on Jan 2, 2025

Southseas
3.0-star property

Southseas

No reviews

Dec 23 - Dec 30

7 night stay

Boston (BOS) to Fort Myers (RSW)

JetBlue Airways • Coach

Fort Myers (RSW) to Boston (BOS)

Delta • Coach
Save 100% on your flight
Price was $4,108, price is now $2,650 per person
$2,650
per person
found 1 day ago

Hotel deals near Key West Express

Margaritaville Beach Resort Fort Myers

Margaritaville Beach Resort Fort Myers

4 out of 5
251 Crescent Street, Fort Myers Beach, FL
0.61 mi from Key West Express
$204 nightly
The price is $228 total per night
$228 total
Nov 17 - Nov 18
Total with taxes and fees
At Margaritaville Beach Resort Fort Myers , guests enjoy a full-service spa, an outdoor pool, and a 24-hour gym. Valet parking is available for USD 35 per day. The front desk is staffed 24 hours a day to help with dry cleaning/laundry and concierge services. This beach hotel also has free WiFi in public areas.
Pool
Spa
Lani Kai Beachfront Resort

Lani Kai Beachfront Resort

3.5 out of 5
1400 Estero Blvd, Fort Myers Beach, FL
Free Cancellation
Reserve now, pay when you stay
0.58 mi from Key West Express
$176 nightly
The price is $197 total per night
$197 total
Nov 12 - Nov 13
Total with taxes and fees
Renovated in 2024, Lani Kai Beachfront Resort offers an outdoor pool, free WiFi in public areas, and conference space. Self parking is offered for USD 20.00 per night. The front desk is staffed 24 hours a day to help with securing valuables and luggage storage. Other amenities at this beach hotel include a seasonal outdoor pool, a terrace, and laundry facilities.
Pool
Free WiFi
DiamondHead Beach Resort

DiamondHead Beach Resort

3.5 out of 5
2000 Estero Blvd, Fort Myers Beach, FL
Free Cancellation
Reserve now, pay when you stay
0.57 mi from Key West Express
$215 nightly
The price is $240 total per night
$240 total
Nov 24 - Nov 25
Total with taxes and fees
At DiamondHead Beach Resort, guests enjoy an outdoor pool, a gym, and 2 hot tubs. If you decide to drive, there's free parking. The 24-hour front desk has multilingual staff ready to assist with concierge services and dry cleaning/laundry. Other amenities at this beach resort include free WiFi in public areas, meeting rooms, and conference space.
Pool
Hot Tub
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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.

Book a Key West Express vacation package

Stop dreaming and start traveling. If you’ve always wanted to see Key West Express, now is the perfect time. Book your getaway to Fort Myers Beach with Orbitz and get ready to tick this attraction off your bucket list. Plus when you lock in your package with us, you’ll have plenty of cash leftover to splash out on other amazing Fort Myers Beach sights. Because travel is all about investing in experiences, not things!

If you’re hoping to stay close to Key West Express, we’ve got you covered. Choose from a great range of hotels not far from this attraction. Roll out of bed, slip on your walking shoes and you’ll be there within moments. What could be more convenient than that? You won’t just be close to all the action — you’ll save money on transportation, and a hot shower and cozy bed will be within reach after a big day of exploring. Now that’s what we call a stress- free, full-of-fun getaway.

Orbitz has your ticket to a rewarding Key West Express vacation. Book your Fort Myers Beach package with us and you’ll be able to access Orbitz Rewards. Earn Orbucks when you reserve your flights, hotels and activities with Orbitz and redeem them at over 385,000 hotels worldwide. $1 Orbuck = $1 off your next hotel. Join, earn, redeem — just like that! When you join Orbitz Rewards, you’ll also instantly unlock exclusive deals and save on thousands of properties with Insider Pricing.

We believe the best reward that you can give to yourself or others is the gift of travel. So, don’t put off exploring Key West Express any longer. Save a bundle and book your Fort Myers Beach escape with Orbitz today.

^Savings based on all package bookings with Flight + Hotel made on Orbitz.com from 2019-04-01 - 2020-03-31 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.