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Jun 19 - Jun 21
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Top Rockland Key hotels

Havana Cabana at Key West

Havana Cabana at Key West

4 out of 5
3420 N. Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
$214 nightly
The price is $241 total per night from Jul 7 to Jul 8
$241 total
Jul 7 - Jul 8
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 was a wonderful place to stay, staff is very helpful and friendly"

Reviewed on Jun 18, 2026

Opens in a new windowHavana Cabana at Key West
Hyatt Centric Key West Resort and Spa

Hyatt Centric Key West Resort and Spa

4 out of 5
601 Front St Key West FL
Fully refundableReserve now, pay when you stay
$261 nightly
The price is $294 total per night from Jun 21 to Jun 22
$294 total
Jun 21 - Jun 22
Total with taxes and fees
This smoke-free resort features a full-service spa, a marina, and a restaurant. Enjoy the outdoor pool and perks like free WiFi. Enjoy the 24-hour gym and unwind ...
"We had the most amazing experience specially at the bar with Amber was amazing. She knew exactly what my pup wanted shaking but not stir."

Reviewed on Jun 16, 2026

Opens in a new windowHyatt Centric Key West Resort and Spa
Pier House Resort & Spa

Pier House Resort & Spa

4 out of 5
1 Duval St Key West FL
Fully refundableReserve now, pay when you stay
$325 nightly
The price is $366 total per night from Jul 8 to Jul 9
$366 total
Jul 8 - Jul 9
Total with taxes and fees
This smoke-free resort features a private beach, a full-service spa, and a restaurant. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. ...
"Great location"

Reviewed on Jun 17, 2026

Opens in a new windowPier House Resort & Spa
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
$266 nightly
The price is $299 total per night from Jun 29 to Jun 30
$299 total
Jun 29 - Jun 30
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 ...
"Overall our stay was nice. We loved the shores pool, and paid extra for ocean view and balcony, which was ruined by the sargassum(out of resorts control of course). Also the balcony was not a private balcony attached to our room, it was just an extension off the walk way open to anyone really, so ..."

Reviewed on Jun 17, 2026

Opens in a new windowSouthernmost Beach Resort and Guesthouses
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
$264 nightly
The price is $297 total per night from Jun 21 to Jun 22
$297 total
Jun 21 - Jun 22
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 ...
"The hotel was nice, but not as nice as some of the other Margaritaville resorts we’ve stayed at. The pool area is small and unfortunately the beach across the street was unusable. That’s not the hotel’s fault, but part of the reason I chose to stay there was the proximity to the beach. The rooms ..."

Reviewed on Jun 16, 2026

Opens in a new windowMargaritaville Beach House Key West
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
$175 nightly
The price is $197 total per night from Jun 21 to Jun 22
$197 total
Jun 21 - Jun 22
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 ...
"Blue Flamingo was a wonderful hotel and I will go back. The pools were lovely, but it would have been nice if one pool was designated to children and the other for adults. The room was lovely as well. Our only problem was with housekeeping. Upon cleaning our room, they took all the dirty towels but ..."

Reviewed on Jun 17, 2026

Opens in a new windowBlue Flamingo Resort Key West
Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton

4 out of 5
1500 Reynolds Street Key West FL
Fully refundableReserve now, pay when you stay
$317 nightly
The price is $356 total per night from Jun 29 to Jun 30
$356 total
Jun 29 - Jun 30
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 ...
"Although i can appreciate the historic nature of the property, roaches are unacceptable. There is also no beach as sold by the pictures on all hotel platforms."

Reviewed on Jun 17, 2026

Opens in a new windowCasa Marina Key West, Curio Collection by Hilton
DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West

4 out of 5
3990 S Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
$169 nightly
The price is $190 total per night from Jun 28 to Jun 29
$190 total
Jun 28 - Jun 29
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 ...
"Overall was a nice stay!"

Reviewed on Jun 18, 2026

Opens in a new windowDoubleTree Resort by Hilton Grand Key - Key West
Hilton Garden Inn Key West / The Keys Collection

Hilton Garden Inn Key West / The Keys Collection

3.5 out of 5
3850 N Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
$140 nightly
The price is $157 total per night from Jun 29 to Jun 30
$157 total
Jun 29 - Jun 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 ...
"We had a great time. No complimentary breakfast as advertised but the shuttle to downtown was great"

Reviewed on Jun 17, 2026

Opens in a new windowHilton Garden Inn Key West / The Keys Collection
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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.

Recent Rockland Key hotel reviews by fellow wanderers

Havana Cabana at Key West

Havana Cabana at Key West

5 out of 5
Posted 2 hours ago
Travelocity Verified Review
"It was a wonderful place to stay, staff is very helpful and friendly"
A verified traveler stayed at Havana Cabana at Key West
Havana Cabana at Key West

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