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Summerland Key, Florida Boat Rentals & Yacht Charters

Chaparral 23ft Powerboat with Bimini Cover for Daily Rental
Fishing in Cudjoe Key · 8 guests

Chaparral 23ft Powerboat with Bimini Cover for Daily Rental

New
$700/day
24ft Cobia 237 Center Console for rent in Big Pine RV park
Fishing in Big Pine Key · 8 guests

24ft Cobia 237 Center Console for rent in Big Pine RV park

5.0
$75+/hour
Perfect Sandbar Rental! 2024 Hurricane 205-SS Deck Boat
Powerboats in Big Pine Key · 10 guests

Perfect Sandbar Rental! 2024 Hurricane 205-SS Deck Boat

New
$70/hour
25ft Premier Pontoon Experience Big Pine Key Verado 250HP
Powerboats in Big Pine Key · 16 guests

25ft Premier Pontoon Experience Big Pine Key Verado 250HP

5.0
$65/hour
26ft Twin Vee PowerCat Experience Big Pine Key for 6 Guests
Powerboats in Big Pine Key · 6 guests

26ft Twin Vee PowerCat Experience Big Pine Key for 6 Guests

New
$100+/hour
Private sandbar trip
Powerboats in Key West · 6 guests

Private sandbar trip

5.0
$85+/hour
Ultimate speed, spacious comfort and elegant style ... Best Time Ever!
Events in Key West · 12 guests

Ultimate speed, spacious comfort and elegant style ... Best Time Ever!

5.0
$200/hour
SUV of the Seas - Top Luxury Adventure Boat in Key West, FL
Events in Stock Island · 13 guests

SUV of the Seas - Top Luxury Adventure Boat in Key West, FL

5.0
Superowner
$238+/hour
Instant Book
37ft Midnight Express Open Luxury Yacht on The Waters of Key West!
Events in Key West · 12 guests

37ft Midnight Express Open Luxury Yacht on The Waters of Key West!

New
$175+/hour
"Satisfaction" Morgan 41 Classic Sailboat for Charter in Key West
Sailing in Key West · 6 guests

"Satisfaction" Morgan 41 Classic Sailboat for Charter in Key West

New
$351/hour
Passport 40 Sailboat in Key West - Comfortable Sailing for Up to 6 Guests
Sailing in Key West · 6 guests

Passport 40 Sailboat in Key West - Comfortable Sailing for Up to 6 Guests

New
$150/hour
Dry Tortugas National Park Trip — Private Charter from Key West
Events in Key West · 12 guests

Dry Tortugas National Park Trip — Private Charter from Key West

New
$250/hour
Instant Book
37’ Luxury Freeman with Bathroom, Shade & Key West Charters
Powerboats in Key West · 12 guests

37’ Luxury Freeman with Bathroom, Shade & Key West Charters

New
$250+/hour
Reel Paradise Key West Sandbar + Snorkel + Private Charter + Light Tackle Fishin
Events in Key West · 12 guests

Reel Paradise Key West Sandbar + Snorkel + Private Charter + Light Tackle Fishin

5.0
$200+/hour
Instant Book
 Belzona 32 Walkaround - Luxury Custom Sports Activity Comfort Charter
Powerboats in Key West · 10 guests

Belzona 32 Walkaround - Luxury Custom Sports Activity Comfort Charter

5.0
$130+/hour
Sea Ray 270 Key West Experience
Tours in Key West · 6 guests

Sea Ray 270 Key West Experience

5.0
$165/hour
Luxury 46' Lagoon Catamaran in Key West and Dry Tortugas
Sailing in Key West · 12 guests

Luxury 46' Lagoon Catamaran in Key West and Dry Tortugas

New
$560+/hour
45' Sea Ray Luxury Yacht | Direct Owner | Key West, Dry Tortugas
Events in Key West · 12 guests

45' Sea Ray Luxury Yacht | Direct Owner | Key West, Dry Tortugas

New
$500/hour
67’ Luxury Power Catamaran – 6 Cabins, Jet Ski, Book Direct with the Owner
Events in Key West · 12 guests

67’ Luxury Power Catamaran – 6 Cabins, Jet Ski, Book Direct with the Owner

5.0
$750+/hour
Best Ocean Adventure in Key West – GetMyBoat Superowner and Best of 2025.
Powerboats in Key West · 8 guests

Best Ocean Adventure in Key West – GetMyBoat Superowner and Best of 2025.

5.0
$175+/hour
37' Freedom Yacht With 1400 Horse Power In Key West, Florida
Powerboats in Stock Island · 13 guests

37' Freedom Yacht With 1400 Horse Power In Key West, Florida

New
$359/hour
88ft Lazzara with lots of Outdoor Spaces and Water Toys serving Key West
Powerboats in Stock Island · 12 guests

88ft Lazzara with lots of Outdoor Spaces and Water Toys serving Key West

5.0
$850+/hour
Captained 42' Sailing Catamaran with 3 cabins and all the toys
Sailing in Key West · 6 guests

Captained 42' Sailing Catamaran with 3 cabins and all the toys

5.0
$320/hour
Captained 80' Sailing Schooner Charter In Key West, Florida
Sailing in Key West · 32 guests

Captained 80' Sailing Schooner Charter In Key West, Florida

5.0
$475+/hour

Summerland Key Reviews

  1. CZ

    Chris

    Belzona 32 Walkaround - Luxury Custom Sports Activity Comfort Charter

    Captain Paul gave our family one of the most memorable experiences of our entire Florida Keys trip. From the moment we stepped on the boat, he was friendly, knowledgeable, and focused on making sure everyone had a great time. The day was the perfect mix of sightseeing, exploring, relaxing, and even a little fishing. We caught several mangrove snapper, and Liam even landed a barracuda, which was the highlight of his vacation. Along the way, we encountered a few unexpected challenges, but Paul stayed calm, positive, and professional, making sure our family was taken care of and still having fun. To top it all off, he filleted our catch and prepared fresh sashimi right on the boat. It doesn’t get much fresher than that. What could have been just another day on the water turned into an adventure our family will be talking about for years. If you’re looking for a captain who genuinely cares about his guests and goes above and beyond to create an unforgettable experience, Captain Paul is your guy.

  2. TP

    Taranjeet

    Sea Ray 270 Key West Experience

    He was simply fantastic! He made our experience even better by being his awesome self in addition to the most beautiful boat on the entire dock! He had prices it perfectly! We were a party of 5, with my best friends for over 25 years, and he also took phenomenal photos for us. We are coming again in June and will definitely go to him again!

  3. BC

    Bryan

    Captained 42' Sailing Catamaran with 3 cabins and all the toys

    Aaron was super fun and extremely knowledgeable. Our group of five has so much fun sailing the rougher, windier seas. We then made for a secluded spot to fish and swim while we waited for sunset. It was a glorious view and truly checked off a bucket list item for me. Bryan - Oregon

  4. BL

    Bill

    Reel Paradise Key West Sandbar + Snorkel + Private Charter + Light Tackle Fishin

    We booked a charter with Carlos. He responded quickly and with a great price. Captain Mikey picked us up on time and the boat was so clean and nice. He took us to three old lighthouses off the coast where we enjoyed the clear water and sunshine. We enjoyed the entire trip and got some great photos. Thanks guys for a wonderful day out in the Keys. Bill n Vicki.

  5. David

    David

    25ft Premier Pontoon Experience Big Pine Key Verado 250HP

    Very fast, well equipped and comfortable Pontoon Boat to experience the Florida Keys

  6. KR

    Kellianne

    SUV of the Seas - Top Luxury Adventure Boat in Key West, FL

    JP made booking our private charter seamless! He was very responsive and accommodating. Our bachelorette party of 9 had the most fantastic afternoon swimming, sunbathing and listening to music. Captain Robert gave us some options and we chose the sandbar. This was the highlight of our weekend- I recommend JP and his boat cruises to anyone!