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
$194 nightly
The price is $219 total per night from Oct 4 to Oct 5
$219 total
Oct 4 - Oct 5
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 ...
"This is the second year we have stayed here for our annual girl's trip. Everything was as great as it was last year. We plan on staying again next year."
Reviewed on Sep 17, 2026
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 Oct 1 to Oct 2
$263 total
Oct 1 - Oct 2
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, ...
"Loved this property. The pool area is very nice. You can order drinks and food at the pool. The staff is great and very friendly. They have a shuttle that takes you right down to Mallory Square and Duvall street. Definitely staying here again."
Reviewed on Sep 17, 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 Sep 28 to Sep 29
$269 total
Sep 28 - Sep 29
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 ...
"A wonderful stay! Conveniently located. Fios was delicious. Staff was great. Room was comfortable"
Reviewed on Sep 17, 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 20 to Sep 21
$180 total
Sep 20 - Sep 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 a playground, and families will appreciate ...
"Excellent relaxing destination"
Reviewed on Sep 17, 2026
Beachside Resort & Residences
3841 N Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
$185 nightly
The price is $208 total per night from Sep 20 to Sep 21
$208 total
Sep 20 - Sep 21
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 ...
"Front desk was indifferent and hard to communicate with possible language barrier"
Reviewed on Sep 17, 2026
Casa Marina Key West, Curio Collection by Hilton
1500 Reynolds Street Key West FL
Fully refundableReserve now, pay when you stay
$280 nightly
The price is $315 total per night from Sep 27 to Sep 28
$315 total
Sep 27 - Sep 28
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 ...
"We booked an oceanfront balcony room, but ended up on the first floor. We asked to be put on an upper floor or for a partial refund and the staff refused both."
Reviewed on Sep 17, 2026
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 20 to Sep 21
$146 total
Sep 20 - Sep 21
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 ...
"Had a great time here."
Reviewed on Sep 16, 2026
Havana Cabana at Key West
3420 N. Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
$175 nightly
The price is $197 total per night from Oct 4 to Oct 5
$197 total
Oct 4 - Oct 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 ...
Pier House Resort & Spa
1 Duval St Key West FL
Fully refundableReserve now, pay when you stay
$286 nightly
The price is $321 total per night from Oct 7 to Oct 8
$321 total
Oct 7 - Oct 8
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. ...
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
Blue Flamingo Resort Key West
5 out of 5
Posted less than an hour ago
Travelocity Verified Review
"Excellent relaxing destination"
A verified traveler stayed at Blue Flamingo Resort Key West
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