Rockland Key Vacation Packages
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Top Rockland Key Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Ready to book your vacation to Rockland Key?
Rockland Key Hotel Deals
Southernmost Beach Resort and Guesthouses
1319 Duval Street Key West FL
Fully refundableReserve now, pay when you stay
CA $225
CA $356 total
Sep 30 - Oct 1
includes taxes & fees
8.6/10 Excellent! (3,614 reviews)
"Access to Duval st."
Reviewed on Sep 23, 2026
Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
CA $166
CA $266 total
Sep 24 - Sep 25
includes taxes & fees
8.6/10 Excellent! (2,681 reviews)
"Wish there were more options as far as eating, the staff was helpful in some ways, I think they were training a lot of them which is fine, I get it. Room was very clean. Would have been nice if there was an indoor eating area not just the outdoor bar areas but it was fine. Never were able to locate ..."
Reviewed on Sep 23, 2026
Margaritaville Beach House Key West
2001 South Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
CA $250
CA $370 total
Oct 6 - Oct 7
includes taxes & fees
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.
Frequently asked questions
How much does a Rockland Key vacation package cost?
Choose from any combination of flights, hotels and car rentals, and you can be vacationing in Rockland Key from just CA $1,802. And the more you bundle, the more you save. The vacation of your dreams has never been so affordable.
How do I get a cheap travel package to Rockland Key?
Creating your own Rockland Key vacation package with Expedia is a smart way to save. We have access to more than 550 air carriers and 1,000,000 properties all over the world. With such a fabulous range to choose from, you'll have no hassles creating your ideal escape.
Where should I stay in Rockland Key?
A getaway to Rockland Key isn't complete without paying a visit to Boca Chica Nude Beach, Key West Naval Station and Boca Chica Beach. Spend your nights near these popular sights and make sightseeing simple.
How far in advance should I book my Rockland Key vacation?
Savvy travelers will likely want to reserve their seats as early as possible. You can generally compare international airfares on Expedia up to 12 months before your intended flight. If you're booking at the last minute, there's no need to worry. Low prices sometimes appear in the last weeks before departure.
What does an Expedia Rockland Key travel package include?
Hotels, flights and rental cars — we have them covered. With Expedia, you can shape your Rockland Key travel package your way. All you have to do is figure out what you need. Once you've made your booking, you can add on fun things like activities and tours. The more you bundle, the more you save!
What should I know before booking a Rockland Key travel package?
You'll save big with an Expedia travel package. Combine your flights, rental cars and hotels and be rewarded with terrific discounts. Hotels aren't your only choice, however. Book with us and choose from island villas, cozy city apartments and even glamping tents!
Can I choose my airline with a Rockland Key Expedia vacation package?
Yes — and it's simple too. Expedia has access to more than 550 partner airlines throughout the world. Our vacation packages give you the freedom to take your pick of available flights, hotels and activities that fit your needs.
If I'm not able to travel, can I cancel my Rockland Key vacation package?
Certainly, and we'll help you every step of the way. You may be able to change or cancel your Rockland Key vacation package at no cost if you booked in the last 24 hours. But you may be charged a fee by your hotel, airline or car rental company if your booking is older than that. If life throws you a curveball, have a look at our Customer Service Portal for further information.
Explore a world of travel with Expedia
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- Flights from Daytona Beach (DAB) to Key West (EYW)
- Flights from Fort Myers (RSW) to Key West (EYW)
- Flights from Tampa (TPA) to Key West (EYW)
- Flights from Sarasota (SRQ) to Key West (EYW)
- Flights from New York (JFK) to Key West (EYW)
- Flights from Raleigh (RDU) to Key West (EYW)
- Flights from Ottawa (YOW) to Key West (EYW)
- Flights from Orlando (MCO) to Key West (EYW)
- Flights from St. Petersburg (PIE) to Key West (EYW)
- Flights from Kailua-Kona (KOA) to Key West (EYW)
- Flights from Detroit (DTW) to Key West (EYW)
- Flights from Key West Intl.
- Flights from Seattle (SEA) to Key West (EYW)
- Flights from Buffalo (BUF) to Key West (EYW)
- Flights from Hamilton (YHM) to Key West (EYW)
- Flights from Montreal (YUL) to Key West (EYW)
- Flights from Regina (YQR) to Key West (EYW)
- Flights from Jacksonville (JAX) to Key West (EYW)
- Flights to Raccoon Key
- Flights from West Palm Beach (PBI) to Key West (EYW)
- Flights from Vancouver (YVR) to Key West (EYW)
- Flights from Boston (BOS) to Key West (EYW)
- Flights from Miami (MIA) to Key West (EYW)
- Flights from San Francisco (SFO) to Key West (EYW)
- Flights from Fort Lauderdale (FLL) to Key West (EYW)
- Visit Cow Key
- Crane Point Museum and Nature Center
- Clarence S. Higgs Memorial Beach Park
- Calusa Beach
- Smathers Beach
- Mallory Square
- Fort East Martello Museum and Gallery
- Sunset Park Beach
- Visit Boca Chica Key
- Harry S. Truman Little White House
- Florida Keys Eco - Discovery Center
- Curry Hammock State Park
- Visit Key West
- Seven Mile Bridge
- Visit Downtown Key West
- Southernmost Point
- Veterans Memorial Park & Beach
- Sombrero Beach
- Mel Fisher Maritime Museum
- Marathon Vacations
- Key West Lighthouse and Keeper's Quarters Museum
- All inclusive Vacation Packages Lower Florida Keys
- South Beach
- Boca Chica Nude Beach
- Duval Street
- All inclusive Vacation Packages Key West
- Key West Vacations
- Key West Shipwreck Museum
- Fort Zachary Taylor Historic State Park
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
