Book Hotels in Rockland Key, FL
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Top Rockland Key hotels
The Laureate Key West
3444 N Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
$184 nightly
The price is $207 total per night from May 25 to May 26
$207 total
May 25 - May 26
Total with taxes and fees
This hotel features an outdoor pool and an indoor pool. If you want to take your pet along, this pet-friendly property offers everything you'll need for your ...
"Excellent"
Reviewed on May 19, 2026
Havana Cabana at Key West
3420 N. Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
$212 nightly
The price is $238 total per night from Jun 11 to Jun 12
$238 total
Jun 11 - Jun 12
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 ...
"Havana Cabana could be a 4 or 5 star except for a couple of things. First is there late check out - $75 for an extra two hours. I was able get the concierge to allow it gratis but I had to work for it. Another item was on the last night we found a cockroach and a worm type insect. Nasty. However ..."
Reviewed on May 19, 2026
La Concha Key West, Autograph Collection
430 Duval St Key West FL
Fully refundableReserve now, pay when you stay
$239 nightly
The price is $269 total per night from May 25 to May 26
$269 total
May 25 - May 26
Total with taxes and fees
This smoke-free hotel includes 3 restaurants, an outdoor pool, and a 24-hour gym. Traveling on business? Take advantage of the free WiFi in public areas, express ...
"I've been going down to Key West for my birthday for close to a decade. I've stayed at a lot of different hotels. They're all generally pretty great. They excel in some things but lack in other things. I think I finally found the PERFECT hotel in Key West! La Concha turned 100 years this year!! But ..."
Reviewed on May 19, 2026
Margaritaville Beach House Key West
2001 South Roosevelt Boulevard Key West FL
$295 nightly
The price is $332 total per night from Jun 7 to Jun 8
$332 total
Jun 7 - Jun 8
Total with taxes and fees
This hotel features a restaurant, an outdoor pool, and a bar/lounge. If you want to take your pet along, this pet-friendly property offers everything you'll ...
"Excellent service, highly recommended"
Reviewed on May 19, 2026
Southernmost Beach Resort and Guesthouses
1319 Duval Street Key West FL
Fully refundable
$261 nightly
The price is $294 total per night from Jun 8 to Jun 9
$294 total
Jun 8 - Jun 9
Total with taxes and fees
This hotel features a full-service spa, 3 outdoor pools, and a restaurant. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Traveling ...
"Our shower leaked all over the bathroom. Front desk staff was rude everyday. Very limited pool chairs. Pools were cloudy and could have used a good cleaning."
Reviewed on May 20, 2026
Beachside Resort & Residences
3841 N Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
$227 nightly
The price is $255 total per night from May 27 to May 28
$255 total
May 27 - May 28
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 ...
"Amazing staff, kind and friendly"
Reviewed on May 19, 2026
Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
$193 nightly
The price is $217 total per night from Jun 1 to Jun 2
$217 total
Jun 1 - Jun 2
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 ...
"Great room, great amenities and nice staff! If you play cornhole after it rains the wet bean bags will turn your fingers blue 😂"
Reviewed on May 19, 2026
Casa Marina Key West, Curio Collection by Hilton
1500 Reynolds Street Key West FL
Fully refundableReserve now, pay when you stay
$293 nightly
The price is $330 total per night from Jun 14 to Jun 15
$330 total
Jun 14 - Jun 15
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 ...
"The beach and pool area were very nice. Service was also great on the beach. Rooms were very clean. The only thing negative about the property is they charge you for parking. So on top of the 60 dollar resort fee parking is an additional 40 to 50 dollars a day. Complementary parking should be available ..."
Reviewed on May 20, 2026
Hilton Garden Inn Key West / The Keys Collection
3850 N Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
$160 nightly
The price is $180 total per night from May 26 to May 27
$180 total
May 26 - May 27
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 ...
"Property was clean"
Reviewed on May 20, 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.
Hotels in Rockland Key with star-rating
Check Rockland Key Hotels by Star Rating
4 Star Hotels
31 properties
Recent Rockland Key hotel reviews by fellow wanderers
Southernmost Beach Resort and Guesthouses
3 out of 5
Posted 2 hours ago
Travelocity Verified Review
"Our shower leaked all over the bathroom. Front desk staff was rude everyday. Very limited pool chairs. Pools were cloudy and could have used a good cleaning."
A verified traveler stayed at Southernmost Beach Resort and Guesthouses
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