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
$206 nightly
The price is $232 total per night from Sep 22 to Sep 23
$232 total
Sep 22 - Sep 23
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 ...
"The room was spacious and clean"
Reviewed on Sep 10, 2026
Havana Cabana at Key West
3420 N. Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
$166 nightly
The price is $187 total per night from Sep 27 to Sep 28
$187 total
Sep 27 - Sep 28
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 ...
"The pool is super but the prices of the food and breakfast are a little high"
Reviewed on Sep 11, 2026
Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
$160 nightly
The price is $180 total per night from Sep 13 to Sep 14
$180 total
Sep 13 - Sep 14
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 ...
"Muy limpio y bonito, un servicio especial"
Reviewed on Sep 10, 2026
Casa Marina Key West, Curio Collection by Hilton
1500 Reynolds Street Key West FL
Fully refundableReserve now, pay when you stay
$296 nightly
The price is $333 total per night from Sep 29 to Sep 30
$333 total
Sep 29 - Sep 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 ...
"The location is fantastic, and the staff is wonderful. I’m already planning to return!"
Reviewed on Sep 10, 2026
Southernmost Beach Resort and Guesthouses
1319 Duval Street Key West FL
Fully refundableReserve now, pay when you stay
$210 nightly
The price is $237 total per night from Sep 20 to Sep 21
$237 total
Sep 20 - Sep 21
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, along ...
Beachside Resort & Residences
3841 N Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
$188 nightly
The price is $212 total per night from Sep 13 to Sep 14
$212 total
Sep 13 - Sep 14
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 ...
Margaritaville Beach House Key West
2001 South Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
$234 nightly
The price is $263 total per night from Sep 24 to Sep 25
$263 total
Sep 24 - Sep 25
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, ...
DoubleTree Resort by Hilton Grand Key - Key West
3990 S Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
$133 nightly
The price is $150 total per night from Sep 27 to Sep 28
$150 total
Sep 27 - Sep 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 ...
Ibis Bay Beach Resort
3101 N. Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
$130 nightly
The price is $146 total per night from Sep 13 to Sep 14
$146 total
Sep 13 - Sep 14
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 ...
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 12 hours ago
Travelocity Verified Review
"The pool is super but the prices of the food and breakfast are a little high"
A verified traveler stayed at Havana Cabana at Key West
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