Find deals on over 110 top-rated, price matched, things to do close to $500+ around Key West and beyond. Explore, compare, and book inspirational adventures for every type of trip and every type of traveler.

Sailfish
Likely to sell out
Much loved
Key West Deep Sea Fishing: Big Fish
Key West, Florida, United States
4.9 (110)
from $950
Much loved
Bimini Charters - Private 3hr Catamaran Charters, Sail & Snorkel
Key West, Florida, United States
5.0 (26)
from $750
Likely to sell out
Much loved
Private Sunset Cruise Around Key West
Key West, Florida, United States
4.9 (45)
from $350
Likely to sell out
Much loved
Key West Private Charter Rental: Luxury Boat With Captain
Key West, Florida, United States
4.8 (18)
from $899
Custom Lighting
Much loved
2-hour Private Sunset Cruise On A Tiki Bar Boat In Key West
Key West, Florida, United States
4.7 (64)
from $457
Keywest Half-day Inshore Fishing Private Charter
Key West, Florida, United States
4.9 (44)
from $750
Key West Sandbar Fishing Snorkel Catch And Cook Excursions
Key West, Florida, United States
5.0 (9)
from $750
Coolcast
Fishing Charters In Key West Florida
Key West, Florida, United States
4.8 (30)
from $900
always a beautiful day!
Much loved
Private Key West Sandbar And Paddle By Boat
Key West, Florida, United States
4.9 (31)
from $600
Much loved
Key West: Private Fishing Charter With Experienced Captain
Key West, Florida, United States
5.0 (16)
from $900
Deep Sea Fishing-key West Since 1965-45 Ft Cowgirl-cold Ac-4 Hrs
Key West, Florida, United States
4.6 (9)
from $1,050
Private Looe Key Snorkel From Big Pine Key
Key West, Florida, United States
5.0 (420)
from $575
Key West: Water Sports Adventure Includes Jetski, Parasail, Snorkel & Waterpark
Key West, Florida, United States
3.0 (2)
from $300
Sandbar Snorkel In The Backcountry Of Key West
Key West, Florida, United States
4.8 (41)
from $600
Key West Sandbar Charter
Key West, Florida, United States
5.0 (1)
from $800
Likely to sell out
Dry Tortugas National Park Day Trip By Luxury Boat: Axopar 37 Xc
Key West, Florida, United States
5.0 (1)
from $1,500
Much loved
Private 6-person Sandbar & Snorkeling Charter
Key West, Florida, United States
5.0 (17)
from $749
Private Boat Tour To Sand Bar Snorkel Dolphins And Sunset
Key West, Florida, United States
5.0 (12)
from $550
Much loved
Key West Photo Shoot At Your Resort Or The Beach
Key West, Florida, United States
4.9 (26)
from $350
Key West Private Romantic Sunset Sail For Couples
Key West, Florida, United States
1.0 (2)
from $999
Sandbar Excursion In Key West
Key West, Florida, United States
5.0 (29)
from $800
Key West Center Console Boat Rental With Sound And Seat Upgrade
Key West, Florida, United States
5.0 (3)
from $475
Much loved
Private Sandbar Adventure In Key West Backcountry
Key West, Florida, United States
5.0 (28)
from $500
Likely to sell out
37' Private Luxury Sunset Charter W. Music & Drinks, Up To 13 Ppl
Key West, Florida, United States
5.0 (2)
from $899
Full Day Premium 24ft Pontoon Boat With Cozy Lounge Upgrades
Key West, Florida, United States
5.0 (1)
from $550
Florida Keys Backcountry Eco Tour From Big Pine Key
Key West, Florida, United States
5.0 (11)
from $425
4 Hours Private Fishing Charters In Key West 40 Ft Irish Cowboy
Key West, Florida, United States
5.0 (8)
from $950
Full Day Charter Snorkeling Sandbar And Eco Safari Adventure
Key West, Florida, United States
5.0 (4)
from $900
Much loved
2 Hour Key West Mini Catamaran Eco Tour
Key West, Florida, United States
4.6 (17)
from $285
Likely to sell out
Much loved
Key West Tiki Bar Boat Cruise To A Popular Sand Bar
Key West, Florida, United States
4.9 (120)
from $565
Fishing on a shared charter catching Mahi on cowboy cowgirl sportfishing
6 Hour Shared Deep Sea Fishing In Key West
Key West, Florida, United States
New
from $250
Marathon Inshore Fishing Charter
Key West, Florida, United States
New
from $725
Bimini Charters - Private 6 Hour Catamaran Sail & Snorkel
Key West, Florida, United States
New
from $1,400
Private Romantic Sunset Cruise
Key West, Florida, United States
New
from $795
Bimini Charters - Private 2 Hour Catamaran Sail And Snorkel
Key West, Florida, United States
New
from $525
Marathon Florida Keys Fishing Experience Big Game
Key West, Florida, United States
New
from $1,495