Lower Matecumbe Key Luxury Vacations

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Top Luxury vacation packages in Lower Matecumbe Key

Price found within the past 48 hours. Click for updated prices.
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

Old Town Key West
¥119,618
per person
Nov 26 - Nov 28
found 1 day ago
Roundtrip flight included
Raleigh (RDU) to Key West (EYW)
8.6/10 Excellent! (3,636 reviews)
When I checked in at the property, they offer me a upgrade for $75 for a ocean view that really lured me in because I wanted the best of the best I was spending time with a special person, but they didn’t tell me that it wasn’t a flat $75 upgrade which I found out later. It was $75 a night and they told me that utilities was $1000 which one their website said there was $300 paid at the hotel so they use my thousand dollars to pay for the $75 a night upgrade was wasn’t explained to me they made it seem like I was gonna get the thousand dollars back -$75 for the upgrade so they pretty much suckered me in to a upgrade deal that didn’t benefit me, but benefited the resort and when I made phone calls to acquired about it, I was told that it is what it is and if I reached out to management, they were gonna tell me the exact same thing was I didn’t appreciate it so I’m still trying to contact management, which is no contact number available and if you ask me personally, and I travel a lot, I would never recommend this hotel to anyone honestly goes a long way

Reviewed on Oct 8, 2026

The Marker Key West Harbor Resort

The Marker Key West Harbor Resort

Key West Historic District
¥130,230
per person
Nov 26 - Nov 28
found 1 day ago
Roundtrip flight included
Raleigh (RDU) to Key West (EYW)
9.2/10 Wonderful! (1,024 reviews)
Very nice room with lots of space. Comfortable bed. Nice pool area with an outdoor bar and live music/entertainment. Good food. Friendly, helpful staff. Great location next to the historic seaport and 3 blocks from Duval Street. Lots of shops, restaurants, and bars within easy walking distance. Would definitely stay here again.

Reviewed on Oct 6, 2026

The Gardens Hotel

The Gardens Hotel

Old Town Key West
¥154,748
per person
Nov 26 - Nov 28
found 1 day ago
Roundtrip flight included
Raleigh (RDU) to Key West (EYW)
9.8/10 Exceptional! (1,005 reviews)
Absolutely love this place. Visited here last year and will plan again to be back soon. Very welcoming and is just beautiful. I can’t say enough about everyone that works there. Always a fantastic time,

Reviewed on Oct 8, 2026

Fontainebleau Miami Beach

Fontainebleau Miami Beach

Mid Beach
¥123,736
per person
Nov 26 - Nov 28
found 1 day ago
Roundtrip flight included
Louisville (SDF) to Miami (MIA)
8.4/10 Very Good! (9,051 reviews)
Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns

Old Town Key West
¥126,914
per person
Nov 26 - Nov 28
found 1 day ago
Roundtrip flight included
Raleigh (RDU) to Key West (EYW)
9.2/10 Wonderful! (1,432 reviews)
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5* Luxury vacations in Lower Matecumbe Key

Price found within the past 48 hours. Click for updated prices.
RS Suites - District 225 Miami

RS Suites - District 225 Miami

Downtown Miami
¥217,059
per person
Nov 22 - Nov 27
found 12 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Miami (MIA)
8.8/10 Excellent! (59 reviews)
5 out of 5

Reviewed on Oct 6, 2026

EAST Miami

EAST Miami

Brickell
¥275,650
per person
Nov 22 - Nov 27
found 12 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Miami (MIA)
9.2/10 Wonderful! (4,177 reviews)
Nobu Hotel Miami Beach

Nobu Hotel Miami Beach

Mid Beach
¥280,258
per person
Nov 22 - Nov 27
found 12 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Miami (MIA)
8.6/10 Excellent! (1,497 reviews)
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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.