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
$219 nightly
The price is $246 total per night from Nov 1 to Nov 2
$246 total
Nov 1 - Nov 2
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 ...
"pool was the best with food and bar right next. shuttle service to town was excellent can't wait to go back!"
Reviewed on Oct 15, 2026
Margaritaville Beach House Key West
2001 South Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
$251 nightly
The price is $282 total per night from Oct 29 to Oct 30
$282 total
Oct 29 - Oct 30
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, ...
"It is such a convenient location and beautiful place to stay. Beds are comfy! Wish they had a little more to offer on their menu though."
Reviewed on Oct 15, 2026
Beachside Resort & Residences
3841 N Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
$202 nightly
The price is $227 total per night from Oct 27 to Oct 28
$227 total
Oct 27 - Oct 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 ...
"We were very happy with how nice, clean and comfortable our 1 bedroom was. The staff was very helpful via text messages for anything we needed like coffee. The pool was clean and well kept. The shuttle bus to Duval street was a very pleasant surprise and the drivers were really prompt."
Reviewed on Oct 15, 2026
Southernmost Beach Resort and Guesthouses
1319 Duval Street Key West FL
Fully refundableReserve now, pay when you stay
$225 nightly
The price is $253 total per night from Oct 25 to Oct 26
$253 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 ...
"This property is beautiful and in a great location.My husband and I were here for a ling weekend to celebrate his 60th birthday and had a wonderful time. It was awesome to wake up to the sound of ocean waves and tropical breezes. Oh and I can't forget the roosters.. We weren't sure if we needed a ..."
Reviewed on Oct 15, 2026
Casa Marina Key West, Curio Collection by Hilton
1500 Reynolds Street Key West FL
Fully refundableReserve now, pay when you stay
$276 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
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 ...
"Great property"
Reviewed on Oct 15, 2026
DoubleTree Resort by Hilton Grand Key - Key West
3990 S Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
$149 nightly
The price is $168 total per night from Oct 27 to Oct 28
$168 total
Oct 27 - Oct 28
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 ...
"Beautiful resort. Very good restaurant on site. Shuttle bus to and from Old Town Key West every hour. The staff was exceptional. Highly recommend this resort."
Reviewed on Oct 13, 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 Oct 25 to Oct 26
$197 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 ...
Ibis Bay Beach Resort
3101 N. Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
$220 nightly
The price is $248 total per night from Oct 18 to Oct 19
$248 total
Oct 18 - Oct 19
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 ...
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 28 to Oct 29
$147 total
Oct 28 - Oct 29
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 ...
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 less than an hour ago
Travelocity Verified Review
"We were very happy with how nice, clean and comfortable our 1 bedroom was. The staff was very helpful via text messages for anything we needed like coffee. The pool was clean and well kept. The shuttle bus to Duval street was a very pleasant surprise and the drivers were really prompt."
A verified traveler stayed at Beachside Resort & Residences
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