Rockland Key Vacation Packages
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Top Rockland Key Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Coconut Beach Resort
Old Town Key West
CA $1,687
per person
Sep 16 - Sep 20
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
8.8/10 Excellent! (212 reviews)
Había sargazo y no se podía usar la picina por qué el olor era demasiado fuerte, el aire acondicionado de la habitación estaba dañado y solo tenían una unidad portátil dentro de el cuarto que se notaba que llevaba algún tiempo puesta por el tape y todo, la ducha no funcionaba bien, no hay elevador y hay mil escaleras… No me fui porque era solo por una noche y pagué un precio alto por ser 4 de Julio pero para quedarse por varios días no hubiera podido con tantas cosas mal. El personal muy chevere, la localización muy buena, la picina muy linda.
Reviewed on Jul 26, 2026
The Marker Key West Harbor Resort
Key West Historic District
CA $3,437
per person
Oct 22 - Oct 28
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Key West (EYW)
9.2/10 Wonderful! (1,020 reviews)
Everything was excellent, the only thing was my Brother and I requested an 1 1/2 late checkout, he's handicapped and it would have helped not having to rush but were denied.
Reviewed on Aug 8, 2026
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 $192
CA $318 total
Sep 1 - Sep 2
includes taxes & fees
8.8/10 Excellent! (3,489 reviews)
"Disappointing Stay — Not What We Expected From a “Beach Resort” Unfortunately, our stay at Southernmost Beach Resort was very disappointing and did not live up to our expectations, particularly considering the price and how the property is marketed. The rooms were not up to the standard we expected ..."
Reviewed on Aug 8, 2026
Beachside Resort & Residences
3841 N Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
CA $144
CA $295 total
Aug 17 - Aug 18
includes taxes & fees
8.6/10 Excellent! (2,409 reviews)
"Specious rooms"
Reviewed on Aug 7, 2026
Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
CA $168
CA $268 total
Sep 7 - Sep 8
includes taxes & fees
8.6/10 Excellent! (2,608 reviews)
"The hotel was ok, nothing special to need to pay $50 a day resort fee. The rooms are your typical hotel room, nothing fancy. One hard chair to sit on, no couch or other seating besides bed. No clock or microwave in room. Bathroom has a standing glass shower with no privacy which is not convenient ..."
Reviewed on Aug 8, 2026
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 $1,144. 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 Raleigh (RDU) to Key West (EYW)
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- Flights from Orlando (MCO) to Key West (EYW)
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- Flights from Key West Intl.
- Flights from Seattle (SEA) to Key West (EYW)
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- Flights to Raccoon Key
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- 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.
