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 2 to Aug 3
$440 total
Aug 2 - Aug 3
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 ...
"A wonderful experience from start to finish! The space was exactly as pictured, very cozy, and well-stocked with everything we needed. Thanks for a flawless trip."
Reviewed on Jul 1, 2026
Pier House Resort & Spa
1 Duval St Key West FL
Fully refundableReserve now, pay when you stay
$376 nightly
The price is $423 total per night from Jul 8 to Jul 9
$423 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. ...
"Helpfull staff very clean room and beautiful ocean view"
Reviewed on Jul 1, 2026
Havana Cabana at Key West
3420 N. Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
$184 nightly
The price is $207 total per night from Jul 16 to Jul 17
$207 total
Jul 16 - Jul 17
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 ...
"I did not enjoy my stay here. I thought the hotel looked better in the pics and i could have booked at one of the local Marriott properties and used my points but i thought i was upgrading to a nicer stay. The rooms were small and uncomfortable. The beds were uncomfortable. The only positive i can ..."
Reviewed on Jul 1, 2026
Southernmost Beach Resort and Guesthouses
1319 Duval Street Key West FL
Fully refundableReserve now, pay when you stay
$239 nightly
The price is $269 total per night from Jul 14 to Jul 15
$269 total
Jul 14 - Jul 15
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 ...
"Beautiful resort ! Very clean ! The staff was amazing , everyone on the property was very friendly They always reached out from the front desk ( not a virtual assistant) to make sure you had all that you needed and to let you know about fun events they were having that day , thank you Frank ,Marilyn ..."
Reviewed on Jul 1, 2026
Margaritaville Beach House Key West
2001 South Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
$265 nightly
The price is $298 total per night from Jul 7 to Jul 8
$298 total
Jul 7 - Jul 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 ...
"Great overall experience! The ocean view suite was awesome! Highly recommend"
Reviewed on Jul 2, 2026
Beachside Resort & Residences
3841 N Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
$218 nightly
The price is $245 total per night from Jul 15 to Jul 16
$245 total
Jul 15 - Jul 16
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 ...
"The elevators were not working. But everything was else was good"
Reviewed on Jul 2, 2026
Casa Marina Key West, Curio Collection by Hilton
1500 Reynolds Street Key West FL
Fully refundableReserve now, pay when you stay
$252 nightly
The price is $283 total per night from Jul 12 to Jul 13
$283 total
Jul 12 - Jul 13
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 ...
"Very nice hotel, the room was excellent, The breakfast was very good, complimentary coffee was great. Whirlpool spa was underwhelming and the pool water was on the warm side, but the pool staff was very attentive."
Reviewed on Jul 1, 2026
Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
$184 nightly
The price is $207 total per night from Jul 5 to Jul 6
$207 total
Jul 5 - Jul 6
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 ...
"Did not like the rooms. They were like a motel set up"
Reviewed on Jul 1, 2026
Hilton Garden Inn Key West / The Keys Collection
3850 N Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
$149 nightly
The price is $168 total per night from Jul 14 to Jul 15
$168 total
Jul 14 - Jul 15
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 ...
"The hotel charges $15 per day for parking, $18/person per day for breakfast and $30 per day in resort fees. I thought the Expedia rate included everything when I booked it."
Reviewed on Jul 1, 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
Margaritaville Beach House Key West
5 out of 5
Posted 1 hour ago
Travelocity Verified Review
"Great overall experience! The ocean view suite was awesome! Highly recommend"
A verified traveler stayed at Margaritaville Beach House Key West
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