Rockland Key Holidays

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Rockland Key Holiday

Our pick of the best Rockland Key Hotel Deals

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street Key West FL
Fully refundableReserve now, pay when you stay
The price is NZ$437 per night from 10 Aug to 11 Aug
NZ$437
10 Aug - 11 Aug
includes taxes & fees
8.8/10 Excellent! (3,481 reviews)
"There were ants all over the room. When I notified the front desk, she said she would have housekeeping come right away. They never showed up, ever. Beware of the multiple hidden fees including the $65 daily "amenity" fee which included use of the private beach (that you really couldn't use because ..."

Reviewed on 26 July 2026

Southernmost Beach Resort and Guesthouses
Beachside Resort & Residences

Beachside Resort & Residences

3.5 out of 5
3841 N Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
The price is NZ$392 per night from 17 Aug to 18 Aug
NZ$392
17 Aug - 18 Aug
includes taxes & fees
8.6/10 Excellent! (2,380 reviews)
"Our stay was perfectly pleasant. The hotel was clean, comfortable, and exactly as expected. We didn’t encounter any concerns or issues during our visit, and everything operated smoothly. Overall, it was a fine stay and met our needs without any problems."

Reviewed on 26 July 2026

Beachside Resort & Residences
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4 out of 5
3820 North Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
The price is NZ$331 per night from 25 Aug to 26 Aug
NZ$331
25 Aug - 26 Aug
includes taxes & fees
Blue Flamingo Resort Key West
See all 3,261 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 holiday package cost?
Choose from any combination of flights, hotels and car rentals, and you can be holidaying in Rockland Key from just . And the more you bundle, the more you save. The holiday of your dreams has never been so affordable.
How do I get a cheap travel package to Rockland Key?
Creating your own Rockland Key holiday 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 holiday?
Savvy travellers 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, cosy city apartments and even glamping tents!
Can I choose my airline with a Rockland Key Expedia holiday package?
Yes — and it's simple too. Expedia has access to more than 550 partner airlines throughout the world. Our holiday 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 holiday package?
Certainly, and we'll help you every step of the way. You may be able to change or cancel your Rockland Key holiday 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.