Rockland Key Holidays

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Top Flight + Hotel Deals in Rockland Key

Price found within the past 48 hours. Click for updated prices.
Havana Cabana at Key West - Adults Only
Lighthouse Hotel - Key West Historic Inns
Douglas House
Almond Tree Inn Hotel - Adults Only
Paradise Inn Key West - Adults Only

Top hotels in Rockland Key

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 €336 per night from 9 Apr to 10 Apr
€336
includes taxes & fees
9 Apr - 10 Apr
8.2/10 Very Good! (1,017 reviews)
Nice quick trip
"We had a really great time for an unexpected trip to Key West. All the staff were nice and the whole facility was clean and comfortable. The heated pool felt great. We will definitely consider staying here again."

Reviewed on 22 Mar 2025

Beachside Resort & Residences
Southernmost Beach Resort
Southernmost Beach Resort
4 out of 5
1319 Duval Street, Key West, FL
Fully refundable
The price is €475 per night from 31 Mar to 1 Apr
€475
includes taxes & fees
31 Mar - 1 Apr
8.6/10 Excellent! (2,339 reviews)
"Loved the property! Like they have 3 pools and great access to the Beach! We would definitely stay again. Only negative thing I can say is the resort amenities are limited for the 60 daily reset fee. Bikes should be included."

Reviewed on 21 Mar 2025

Southernmost Beach Resort
Margaritaville Beach House Key West
Margaritaville Beach House Key West
4 out of 5
2001 South Roosevelt Boulevard, Key West, FL
Fully refundableReserve now, pay when you stay
The price is €454 per night from 7 Apr to 8 Apr
€454
includes taxes & fees
7 Apr - 8 Apr
8.6/10 Excellent! (1,711 reviews)
Margaritaville stay
"The rooms were VERY clean. Nice and bright with fridge and microwave. And complimentary water, which is so nice. The public areas are well kept and clean and pretty. Great music piped through!"

Reviewed on 21 Mar 2025

Margaritaville Beach House Key West
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 €1,363. 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.