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
$296 nightly
The price is $333 total per night from May 4 to May 5
$333 total
May 4 - May 5
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 property was friendly with pets. Staff very nice.
Reviewed on Apr 6, 2026

Oceans Edge Key West Resort, Hotel & Marina
5950 Peninsular Avenue Key West FL
Fully refundableReserve now, pay when you stay
$270 nightly
The price is $304 total per night from Apr 29 to Apr 30
$304 total
Apr 29 - Apr 30
Total with taxes and fees
A marina, 6 outdoor pools, and a 24-hour gym are all featured at this smoke-free hotel. Business travelers can take advantage of the free WiFi in public areas. ...
Yes
Reviewed on Apr 4, 2026

Parrot Key Hotel & Villas
2801 N Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
$271 nightly
The price is $305 total per night from Apr 13 to Apr 14
$305 total
Apr 13 - Apr 14
Total with taxes and fees
This smoke-free hotel features 4 outdoor pools, a gym, and a restaurant. Traveling on business? Take advantage of the business center, free WiFi in public areas, ...
Our stay was amazing ! friendly staff, beautiful pools, and the grove was a great food and drink option. When we checked in, they upgraded us to a room that opened right onto the beach (we booked the room with a balcony) and it was incredible for soaking up sun during the day and relaxing at ...
Reviewed on Apr 3, 2026

The Laureate Key West
3444 N Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
$250 nightly
The price is $281 total per night from Apr 20 to Apr 21
$281 total
Apr 20 - Apr 21
Total with taxes and fees
This hotel features an outdoor pool and an indoor pool. If you want to take your pet along, this pet-friendly property offers everything you'll need for your ...
Everything was amazing! The laundry facilities on point!
Reviewed on Apr 5, 2026

Southernmost Beach Resort and Guesthouses
1319 Duval Street Key West FL
Fully refundableReserve now, pay when you stay
$393 nightly
The price is $442 total per night from May 6 to May 7
$442 total
May 6 - May 7
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 ...
Great location to walk around to great shopping and restaurants. We enjoyed time by the pool and enjoyed the variety of pool options! The beach was fantastic and the cafe was a great spot for breakfast. Would definitely return!!
Reviewed on Apr 6, 2026

Margaritaville Beach House Key West
2001 South Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
$299 nightly
The price is $337 total per night from May 6 to May 7
$337 total
May 6 - May 7
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 ...
Nice place that offered great accommodations!
Reviewed on Apr 5, 2026

Beachside Resort & Residences
3841 N Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
$240 nightly
The price is $270 total per night from Apr 7 to Apr 8
$270 total
Apr 7 - Apr 8
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 ...
Check-in wasn’t the best. The guy at the desk said they would text when the room was ready. I never got a text, ended up going back to a different employee and apparently my room had been ready. Elevators out of order, of course, so had to drag bags up 3 flights of stairs. No daily housekeeping. ...
Reviewed on Apr 6, 2026

Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
$283 nightly
The price is $318 total per night from Apr 20 to Apr 21
$318 total
Apr 20 - Apr 21
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 an arcade/game room, and families will appreciate ...
Beautiful and clean
Reviewed on Apr 6, 2026

Ibis Bay Beach Resort
3101 N. Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
$261 nightly
The price is $294 total per night from May 5 to May 6
$294 total
May 5 - May 6
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 ...
Clean quirky rooms. Comfy beds. Restaurant, bar, pool. Lots of activities. Just ok beach. We rented a golf cart & cruised around town. And a great time was had by all!
Reviewed on Apr 6, 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
28 properties
Recent Rockland Key hotel reviews by fellow wanderers

Southernmost Beach Resort and Guesthouses
5 out of 5
Posted 1 hour ago
Travelocity Verified Review
"Great location to walk around to great shopping and restaurants. We enjoyed time by the pool and enjoyed the variety of pool options! The beach was fantastic and the cafe was a great spot for breakfast. Would definitely return!! "
A verified traveler stayed at Southernmost Beach Resort and Guesthouses
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