Upper Matecumbe Key Pet-friendly Vacations

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Top Pet-friendly vacation packages in Upper Matecumbe Key

Price found within the past 48 hours. Click for updated prices.
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

New Town
¥169,230
per person
Nov 7 - Nov 12
found 4 hours ago
Roundtrip non-stop flight included
Indianapolis (IND) to Key West (EYW)
8.6/10 Excellent! (2,652 reviews)
Friendly and helpful staff. Love the 2 pools. It's great that they have a complimentary shuttle to take you downtown.

Reviewed on Sep 22, 2026

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

Old Town Key West
Save 100% on your flight
¥287,588
per person
Nov 7 - Nov 12
found 4 hours ago
Roundtrip non-stop flight included
Indianapolis (IND) to Key West (EYW)
8.6/10 Excellent! (3,560 reviews)
The staff was personable and pleasant. My room was great and facility maintained well. There was one pool down for service. My beach access due to seaweed/seagrass. The smell was terrible several times a day. Was hard to enjoy the beautiful outdoor restaurant. We were able to get a few times in. Food was great! I feel those things should have been advised to customers prior to booking.

Reviewed on Sep 23, 2026

Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive

Old Town Key West
Save 100% on your flight
¥312,050
per person
Nov 7 - Nov 12
found 4 hours ago
Roundtrip non-stop flight included
Indianapolis (IND) to Key West (EYW)
9.4/10 Exceptional! (1,001 reviews)
Hilton Key West Resort & Marina

Hilton Key West Resort & Marina

¥193,306
per person
Nov 7 - Nov 12
found 4 hours ago
Roundtrip non-stop flight included
Indianapolis (IND) to Key West (EYW)
9/10 Wonderful! (1,831 reviews)
Nice and comfortable

Reviewed on Sep 20, 2026

La Concha Key West, Autograph Collection

La Concha Key West, Autograph Collection

Key West Historic District
¥271,828
per person
Nov 7 - Nov 12
found 4 hours ago
Roundtrip non-stop flight included
Indianapolis (IND) to Key West (EYW)
9/10 Wonderful! (476 reviews)
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