Rockland Key Vacations from $1,417
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The Latest Rockland Key vacation packages
Price found within the past 48 hours. Click for updated prices.
The Gardens Hotel
Old Town Key West
$1,417
per person
Dec 5 - Dec 9
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.8/10 Exceptional! (1,003 reviews)
This was our first time at the Garden House and we LOVED it! Everything about the place was outstanding. So much, that we booked again to stay there in October, 2026. The staff, drinks, food, grounds....Everything is just wonderful.l
Reviewed on Sep 8, 2026
Tropical Dreaming by Avantstay 4 Blks to Beach! Private Pool!
Old Town Key West
$2,146
per person
Oct 15 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
10/10 Exceptional! (1 review)
Loved the closeness to Duval st and the privacy
Reviewed on Oct 17, 2025
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Southernmost Beach Resort and Guesthouses
1319 Duval Street Key West FL
Fully refundableReserve now, pay when you stay
$209 nightly
$235 total
Sep 22 - Sep 23
Total with taxes and fees
Beachside Resort & Residences
3841 N Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
$188 nightly
$212 total
Sep 20 - Sep 21
Total with taxes and fees
8.6/10 Excellent! (2,503 reviews)
"Our stay was excellent! Everyone was super nice"
Reviewed on Sep 9, 2026
Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
$159 nightly
$178 total
Sep 22 - Sep 23
Total with taxes and fees
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.
Find the Best Rockland Key Vacation Packages
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
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- Visit Downtown Key West
- Robbie's
- Museum of Art & History at the Custom House
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- Key West Golf Club
- Key West Vacations
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.