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Summerland Key, Florida Boat Rentals & Yacht Charters

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
$100/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

5.0
$100+/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
$80/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
$75/hour
Private sandbar trips🌞No Fishing
Powerboats in Key West · 6 guests

Private sandbar trips🌞No Fishing

5.0
$125+/hour
Cruise Key West on a 38ft Tiara 38LS Yacht, Bareboat Charter for Up to 12 Guests
Powerboats in Key West · 12 guests

Cruise Key West on a 38ft Tiara 38LS Yacht, Bareboat Charter for Up to 12 Guests

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!

5.0
$175+/hour
Morgan 41 Classic Sailboat for Charter in Key West
Sailing in Key West · 6 guests

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
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
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
 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
$135+/hour
Sea Ray 270 Key West Experience
Tours in Key West · 6 guests

Sea Ray 270 Key West Experience

5.0
$165/hour
Unwind in Sunlit Luxury: Experience 360° Views Aboard This One-of-a-Kind Yacht!
Sailing in Stock Island · 12 guests

Unwind in Sunlit Luxury: Experience 360° Views Aboard This One-of-a-Kind Yacht!

New
$325+/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
Private Key West Charter: Sandbar, Snorkel, Sunset & Reef
Powerboats in Key West · 8 guests

Private Key West Charter: Sandbar, Snorkel, Sunset & Reef

5.0
$142+/hour
67’ Luxury Power Catamaran – 6 Cabins, Jet Ski, Celebrations and Getaways
Events in Key West · 12 guests

67’ Luxury Power Catamaran – 6 Cabins, Jet Ski, Celebrations and Getaways

5.0
$750+/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 Yacht with lots of Outdoor Spaces and Water Toys serving Key West
Events in Stock Island · 12 guests

88ft Lazzara Yacht 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
Sail in Luxury: Smack Offers Space, Style, and Seamless Comfort
Sailing in Stock Island · 12 guests

Sail in Luxury: Smack Offers Space, Style, and Seamless Comfort

New
$260+/hour

Summerland Key Reviews

  1. Jaelyn

    Jaelyn

    Private sandbar trips🌞No Fishing

    We had such a great experience! Captain Eric was awesome, super friendly, professional, and made sure we had a good time the entire trip. Everything was easy and stress free, and we felt comfortable and taken care of the whole time. We had so much fun out on the water and would definitely book with him again. Highly recommend Captain Eric if you’re looking for a great boat day!

  2. JL

    John

    Sea Ray 270 Key West Experience

    We had an absolutely amazing experience with Captain Serghei! Our whole family truly enjoyed every moment on the water. We visited four beautiful sandbars and ice and bottled water were included, which was a great touch. What really made this trip special was the personal attention from Captain Serghei. He didn’t just stay on the boat, he got in the water with us, showed us around and explained all the different areas along the way. He even took our phones and captured pictures of the entire group, so we could enjoy the experience without worrying about getting photos ourselves. Those little personal touches made us feel so welcome and created memories we’ll treasure. Captain Serghei was friendly, knowledgeable, and genuinely cared about making sure our family had a fantastic time. We highly recommend this experience to anyone looking for a fun, relaxing, and memorable day on the water. We would absolutely do it again!

  3. Carly

    Carly

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

    Captain Jack is great . He is very accommodating knowledgeable and great with the kids . Trip was made easy and we did everything we wanted .

  4. DO

    Deniz

    Private sandbar trips🌞No Fishing

    It was my first time using getmyboat and I am glad it connected us with Eric. Such a caring and fun captain. Definitely recommend him and I will be booking another trip with him when I am back here. Thank you so much for everything!

  5. Chasen

    Chasen

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

    My and girlfriends first time In the keys and we did it the right way. This boat was so fun and fast and very Clean. Our captain was absolutely the best. He was a vibe the whole time and took us to the most beautiful spots

  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!