Book Hotels in Rockland Key, FL
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Top Rockland Key hotels
Hyatt Vacation Club at Windward Pointe, Key West
3675 South Roosevelt Boulevard Key West FL
Fully refundable
$391 nightly
The price is $440 total per night from Aug 9 to Aug 10
$440 total
Aug 9 - Aug 10
Total with taxes and fees
This hotel features an outdoor pool, a hot tub, and a restaurant. Guests will appreciate free perks like free self parking and WiFi in public areas. A snack ...
"I highly recommend this property! The place was beautiful and the pool and grounds really lovely. Can't wait to go back."
Reviewed on Jul 8, 2026
Pier House Resort & Spa
1 Duval St Key West FL
$376 nightly
The price is $423 total per night from Jul 15 to Jul 16
$423 total
Jul 15 - Jul 16
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. ...
"From check in to check out very accommodating and friendly. The grounds were beautiful! Beach front was great for being in Key West! Room was comfortable and clean. Restaurants were great. Best side of the Island to be on. Everything was walkable. Right at the end of Duval. So many options around. ..."
Reviewed on Jul 8, 2026
La Concha Key West, Autograph Collection
430 Duval St Key West FL
Fully refundableReserve now, pay when you stay
$225 nightly
The price is $253 total per night from Aug 2 to Aug 3
$253 total
Aug 2 - Aug 3
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 ...
"Great location"
Reviewed on Jul 6, 2026
Southernmost Beach Resort and Guesthouses
1319 Duval Street Key West FL
Fully refundableReserve now, pay when you stay
$232 nightly
The price is $261 total per night from Jul 15 to Jul 16
$261 total
Jul 15 - Jul 16
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 ...
"3 pools to choose from."
Reviewed on Jul 9, 2026
Margaritaville Beach House Key West
2001 South Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
$246 nightly
The price is $277 total per night from Aug 9 to Aug 10
$277 total
Aug 9 - Aug 10
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 room had a terrible order to it and the furniture looked very worn out. We didn't even unpacked, and went down and checked out"
Reviewed on Jul 8, 2026
Beachside Resort & Residences
3841 N Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
$212 nightly
The price is $239 total per night from Jul 12 to Jul 13
$239 total
Jul 12 - Jul 13
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 ...
"Our stay was truly memorable and I would recommend to everyone!!!"
Reviewed on Jul 8, 2026
Casa Marina Key West, Curio Collection by Hilton
1500 Reynolds Street Key West FL
Fully refundableReserve now, pay when you stay
$223 nightly
The price is $251 total per night from Jul 16 to Jul 17
$251 total
Jul 16 - Jul 17
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 is inaccessible. The sargassam (seaweed) makes it unusable, even if it were to be cleaned it’s lined with rocks. You must leave the hotel to use the beach. The smell is unbearable."
Reviewed on Jul 8, 2026
Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
$175 nightly
The price is $197 total per night from Jul 12 to Jul 13
$197 total
Jul 12 - Jul 13
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 ...
"My favorite place I’ve stayed ever. My wife and I spent the first 3 nights of our honeymoon at the Blue Flamingo Resort. We spent most of one our days at the resort. Honestly, we could have stayed there the whole time but we booked a lot. We had the Oceanview King room. We loved the pool. We enjoyed ..."
Reviewed on Jul 8, 2026
Hilton Garden Inn Key West / The Keys Collection
3850 N Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
$156 nightly
The price is $176 total per night from Jul 12 to Jul 13
$176 total
Jul 12 - Jul 13
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 ...
"Staff super friendly, and overall it’s a nice hotel. The traffic was loud if you stayed in the front building. It was also difficult to make a left turn out of the parking lot onto Rosevelt Dr."
Reviewed on Jul 8, 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
Havana Cabana at Key West
5 out of 5
Posted 1 hour ago
Travelocity Verified Review
"What an amazing experience. Can't wait to visit again soon."
A verified traveler stayed at Havana Cabana at Key West
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