Rockland Key Vacations from $670
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The Latest Rockland Key vacation packages
Price found within the past 48 hours. Click for updated prices.
Winslow's Bungalows - Key West Historic Inns
Old Town Key West
$670
per person
Nov 9 - Nov 12
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (1,397 reviews)
Two concerns:
1) TV issue was not addressed by staff in a timely fashion. Note; the amenity fee was reduced as a result.
2) concern may be equal parts
Winslow’s Bungalows and Expedia. There should be transparent pricing that includes the TOTAL AMOUNT. It’s distasteful to a customer amenity fees, etc. show up at check-in/out. Just quote the customer the true cost of their stay and avoid creating a frustration on behalf of the consumer.
Reviewed on Sep 1, 2026
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Southernmost Beach Resort and Guesthouses
1319 Duval Street Key West FL
Fully refundableReserve now, pay when you stay
$210 nightly
$237 total
Sep 9 - Sep 10
Total with taxes and fees
8.6/10 Excellent! (3,562 reviews)
"From check in and check out everything in between this Hotel was everything and more during our weekend girls trip get away!! We will not hesitate to book again in a few months!!"
Reviewed on Sep 2, 2026
Beachside Resort & Residences
3841 N Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
$185 nightly
$208 total
Sep 3 - Sep 4
Total with taxes and fees
8.6/10 Excellent! (2,483 reviews)
"Hot tub wasn’t working. It was just warm water. Gym was very hot. Beach wasn’t great. Elevator in my building wasn’t working g but you can use the one from the building next to it and walk over. So not that bad. Pool was great. Never crowded. Room was excellent. We had a suite with pool access. There ..."
Reviewed on Sep 1, 2026
Margaritaville Beach House Key West
2001 South Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
$234 nightly
$263 total
Sep 16 - Sep 17
Total with taxes and fees
8.8/10 Excellent! (1,799 reviews)
"Staff was excellent and very accommodating. Room was clean and plenty of room. The pool view was great. Shuttle service to old town is extremely helpful. The ice pops by the pool and the afternoon cookies were a welcome perk. The food was very good and plentiful at the restaurant. But they can use ..."
Reviewed on Sep 2, 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.
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Rockland Key Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
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- Key West Shipwreck Museum
- Duval Street
- Key West National Wildlife Refuge
- Bahama Village Vacations
- Key West Firehouse Museum
- Smathers Beach
- Sombrero Beach
- The Kite House
- Fort Zachary Taylor Historic State Park
- Saint Mary Star of the Sea
- Key West Butterfly and Nature Conservatory
- Key West Historic District Vacations
- Schooner Western Union
- Visit Big Pine Key
- Cow Key Vacations
- Southernmost Point
- Mallory Dock
- Boca Chica Nude Beach
- Sails To Rails Museum at Flagler Station
- Key West Lighthouse and Keeper's Quarters Museum
- Key West Tropical Forest and Botanical Garden
- Jackson Square
- Ernest Hemingway Home and Museum
- San Carlos Institute - Casa Cuba
- Fort East Martello Museum and Gallery
- South Beach
- Waterfront Playhouse
- Tennessee Williams Key West Exhibit
- Stock Island Yacht Club & Marina
- Key West Burlesque Theater
- All inclusive Vacation Packages Key West
- Visit Downtown Key West
- Robbie's
- Museum of Art & History at the Custom House
- Old Town Key West Vacations
- Clarence S. Higgs Memorial Beach Park
- Mallory Square
- Key West Golf Club
- Key West Vacations
- Harry S. Truman Little White House
- Sunset Key Vacations
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.