Book Hotels in Rockland Key, FL
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Top Rockland Key hotels
Havana Cabana at Key West
3420 N. Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
$236 nightly
The price is $265 total per night from Oct 30 to Oct 31
$265 total
Oct 30 - Oct 31
Total with taxes and fees
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Business travelers can take advantage of the free WiFi in public areas. Enjoy the hot tub ...
"It's was a great place to stay at!!!"
Reviewed on Oct 22, 2026
Margaritaville Beach House Key West
2001 South Roosevelt Blvd Key West FL
$275 nightly
The price is $310 total per night from Oct 25 to Oct 26
$310 total
Oct 25 - Oct 26
Total with taxes and fees
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the 24-hour gym and perks like a free airport shuttle. You'll appreciate the hot tub, ...
"The resort overall was great! Everyone friendly. Very clean. Food was good. Although staying all week, it would be nice if they had a few daily specials so you don’t have the same menu everyday. Well organized. A few things I would like to suggest or point out. The rooms did not get cool enough to ..."
Reviewed on Oct 21, 2026
Beachside Resort & Residences
3841 N Roosevelt Blvd Key West FL
$202 nightly
The price is $227 total per night from Oct 25 to Oct 26
$227 total
Oct 25 - Oct 26
Total with taxes and fees
This smoke-free hotel features a private beach, a marina, and 2 restaurants. Enjoy a day at the beach kayaking, or relax with sun loungers. Unwind with a drink ...
"We’ve stayed at this resort 3 times over the last few years and the room, staff, and concierge were great every time. We will be booking at this location again."
Reviewed on Oct 22, 2026
Casa Marina Key West, Curio Collection by Hilton
1500 Reynolds Street Key West FL
Fully refundableReserve now, pay when you stay
$295 nightly
The price is $332 total per night from Oct 30 to Oct 31
$332 total
Oct 30 - Oct 31
Total with taxes and fees
A private beach, a full-service spa, and 2 outdoor pools are all featured at this smoke-free resort. Relax with sun loungers and beach umbrellas, and cool off ...
"All I can say is all aspects were fantastic"
Reviewed on Oct 21, 2026
DoubleTree Resort by Hilton Grand Key - Key West
3990 S Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
$137 nightly
The price is $154 total per night from Oct 29 to Oct 30
$154 total
Oct 29 - Oct 30
Total with taxes and fees
This resort features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public ...
"Not our first stay but it’s always a pleasure staying there. We have nothing bad to say after 4 stays over the years"
Reviewed on Oct 21, 2026
Ibis Bay Beach Resort
3101 N. Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
$193 nightly
The price is $218 total per night from Oct 25 to Oct 26
$218 total
Oct 25 - Oct 26
Total with taxes and fees
This Art Deco hotel features a private beach, a marina, and a restaurant. Enjoy a day at the beach kayaking, or relax with sun loungers. Enjoy the outdoor pool ...
"Quiet property and restaurant on premises"
Reviewed on Oct 22, 2026
Hilton Garden Inn Key West / The Keys Collection
3850 N Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
$131 nightly
The price is $147 total per night from Oct 29 to Oct 30
$147 total
Oct 29 - Oct 30
Total with taxes and fees
This smoke-free hotel includes 2 restaurants, an outdoor pool, and a hot tub. Traveling on business? Take advantage of the business center and free WiFi in public ...
"Pros: great location, nice pool area, clean room, price good for the area, friendly staff. Cons: ice machine near our room broken, one of the elevators was out of order, bed uncomfortably firm, despite the website saying they had dinner inside the only food choices were from the poolside bar. Still ..."
Reviewed on Oct 19, 2026
Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
$166 nightly
The price is $187 total per night from Oct 25 to Oct 26
$187 total
Oct 25 - Oct 26
Total with taxes and fees
This hotel features 2 restaurants, 2 outdoor pools, and a 24-hour gym. There's fun for all ages with mini golf and a playground, and families will appreciate ...
Southernmost Beach Resort and Guesthouses
1319 Duval Street Key West FL
Fully refundableReserve now, pay when you stay
$235 nightly
The price is $265 total per night from Oct 25 to Oct 26
$265 total
Oct 25 - Oct 26
Total with taxes and fees
A full-service spa, 3 outdoor pools, and a restaurant are all featured at this hotel. Traveling on business? Take advantage of the 2 conference rooms, free WiFi ...
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.
Hotels in Rockland Key with star-rating
Check Rockland Key Hotels by Star Rating
4 Star Hotels
30 properties
Recent Rockland Key hotel reviews by fellow wanderers
Beachside Resort & Residences
5 out of 5
Posted 1 hour ago
Travelocity Verified Review
"We’ve stayed at this resort 3 times over the last few years and the room, staff, and concierge were great every time. We will be booking at this location again."
A verified traveler stayed at Beachside Resort & Residences
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