Rockland Key Vacations

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Find the Best Rockland Key Vacation Packages

Rockland Key Hotel Deals

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

1319 Duval Street Key West FL
Fully refundableReserve now, pay when you stay
￥23,256
￥37,870 total
Sep 8 - Sep 9
includes taxes & fees
8.6/10 Excellent! (3,548 reviews)
"Everything was wonderful except the private beer area. We could not use it because of the sargassum and I wish they would have sent a message so we could have planned better. It was one of the reasons I booked there. If we could have used the beach it would have been a 10/10. Cleaning took a while ..."

Reviewed on Aug 30, 2026

Southernmost Beach Resort and Guesthouses
Ibis Bay Beach Resort

Ibis Bay Beach Resort

3101 N. Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
￥16,764
￥24,025 total
Sep 13 - Sep 14
includes taxes & fees
8.2/10 Very Good! (2,362 reviews)
"Todo Super bien; el personal que trabaja en la instalación te hacen sentir como en casa muy acogedor; tranquilo y un servicio increíble"

Reviewed on Aug 30, 2026

Ibis Bay Beach Resort
Havana Cabana at Key West

Havana Cabana at Key West

3420 N. Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
￥22,253
￥35,191 total
Aug 31 - Sep 1
includes taxes & fees
Havana Cabana at Key West
See all 3,259 properties in Rockland 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.

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 . 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.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.