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All listings in Florida

Incredible sailboat rentals in Florida, United States.

Page 2 of 5103 listings

Luxury Sailing Catamaran in Key West
Sailing in Key West · 10 guests

Luxury Sailing Catamaran in Key West

5.0
$250hour
Sailing From Pompano Beach, FL - $150/Hour - $30/Person
Sailing in Pompano Beach · 10 guests

Sailing From Pompano Beach, FL - $150/Hour - $30/Person

4.5
Superowner
Best of 2023
$30person
Relaxing Catamaran Adventure: Snorkel, Sail, Dolphins
Sailing in Fort Walton Beach · 6 guests

Relaxing Catamaran Adventure: Snorkel, Sail, Dolphins

5.0
$149hour
Catamaran Party Boat up to 49 people. Includes: 1-Captain, 2-Mates
Sailing in Miami Beach · 49 guests

Catamaran Party Boat up to 49 people. Includes: 1-Captain, 2-Mates

5.0
Superowner
$900hour
30 foot Jupiter Center Console Rental in Fort Lauderdale, Florida
Powerboats in Deerfield Beach · 10 guests

30 foot Jupiter Center Console Rental in Fort Lauderdale, Florida

5.0
$200hour
Got ASA Certification? Book this Jeanneau 389 Sailing Yacht
Sailing in West Palm Beach · 8 guests

Got ASA Certification? Book this Jeanneau 389 Sailing Yacht

5.0
$740day
64' Roberts Sailing Ketch for Charter in Jacksonville Area
Sailing in Green Cove Springs · 6 guests

64' Roberts Sailing Ketch for Charter in Jacksonville Area

5.0
$138-$217hour
Sailing  Miami and Key Biscayne on board Catamaran Lagoon 450F
Sailing in Miami · 13 guests

Sailing Miami and Key Biscayne on board Catamaran Lagoon 450F

5.0
$450hour
John’s Pass: Sailing, dolphins and sightseeing
Sailing in Treasure Island · 6 guests

John’s Pass: Sailing, dolphins and sightseeing

5.0
$200hour
41' Island Trader Ketch in Key West, Florida!
Sailing in Stock Island · 6 guests

41' Island Trader Ketch in Key West, Florida!

4.9
$162-$199hour
Catamaran Party Boat 42-people Includes: 1-Captain, 1-Mate and 1-Bartender
Sailing in Miami · 42 guests

Catamaran Party Boat 42-people Includes: 1-Captain, 1-Mate and 1-Bartender

3.0
Superowner
$800hour
Sailing From West Palm Beach, FL - $150/Hour - $30/Person
Sailing in West Palm Beach · 6 guests

Sailing From West Palm Beach, FL - $150/Hour - $30/Person

4.7
Superowner
Best of 2023
$150hour
Ultimate Intercoastal Cruiser and Sandbar party boat in Deerfield Beach, Florida
Powerboats in Deerfield Beach · 10 guests

Ultimate Intercoastal Cruiser and Sandbar party boat in Deerfield Beach, Florida

5.0
$125hour
Hunter 336 Sailboat! Relaxing Sailing Palm Beach
Sailing in North Palm Beach · 4 guests

Hunter 336 Sailboat! Relaxing Sailing Palm Beach

5.0
$120hour
Leopard 40 Cruising Catamaran for Up to 6 People in Stuart, FL with Captain Paul
Sailing in Stuart · 6 guests

Leopard 40 Cruising Catamaran for Up to 6 People in Stuart, FL with Captain Paul

5.0
$225hour
50' Party Boat Catamaran in Miami ($1,200  PER HOUR)
Sailing in Miami Beach · 42 guests

50' Party Boat Catamaran in Miami ($1,200 PER HOUR)

4.8
$1,100hour
Captained Charter On 33ft The Key West's Most Versatile Sailboat! (With Captain Only)
Sailing in Key West · 12 guests

Captained Charter On 33ft The Key West's Most Versatile Sailboat! (With Captain Only)

4.6
$175-$200hour
Stunning Luxe 60' White Princess Yacht
Events in Fort Lauderdale · 13 guests

Stunning Luxe 60' White Princess Yacht

New
$750hour
"Boldly Go" Yacht Charter in Tampa, FL
Sailing in Bay Pines · 6 guests

"Boldly Go" Yacht Charter in Tampa, FL

New
$202hour
Sunseeker Manhattan Motor Yacht in Miami
Powerboats in North Miami Beach · 12 guests

Sunseeker Manhattan Motor Yacht in Miami

5.0
$1,000hour
The Catamaran Party Boat, accommodating up to 49 guests crewed 1 Captain+ 2 crew
Events in Fort Lauderdale · 49 guests

The Catamaran Party Boat, accommodating up to 49 guests crewed 1 Captain+ 2 crew

New
Superowner
$900hour
Fort Lauderdale Bahamas Sailing Charters
Sailing in Fort Lauderdale · 6 guests

Fort Lauderdale Bahamas Sailing Charters

5.0
$119-$120hour
38 Foot Sailing Yacht for a Day of Fun in the Sun
Sailing in Miami · 10 guests

38 Foot Sailing Yacht for a Day of Fun in the Sun

New
$88-$117hour
Full or Half Day Private Charter Aboard 50' Ohana in Panama City, Florida
Sailing in Panama City · 12 guests

Full or Half Day Private Charter Aboard 50' Ohana in Panama City, Florida

5.0
$299-$320hour

Sailing Reviews in Florida

  1. LR

    Lori

    Luxury Sailing Catamaran in Key West

    Awesome boat!! Ashley was very helpful and easy to communicate with. Nils, the captain was very welcoming and informative as we cruised around looking for sea life. We saw turtles, dolphins and even a hammerhead shark. It was such a relaxing day. Thanks Ashley and Nils for making our day great.

  2. JA

    Jody

    Luxury Sailing Catamaran in Key West

    Five stars isn't enough! The catamaran is beautiful, and the crew was extremely accommodating. Captain Nils and First Mate Patrick are top notch seamen and gentlemen to boot. Took us to all the best spots to enjoy the beauty and majesty of Key West!!! We cant recommend them highly enough!

  3. PA

    Peggy

    30 foot Jupiter Center Console Rental in Fort Lauderdale, Florida

    Our party of six adults and three children had the best time with Mike and his beautiful Jupiter 30. The boat was in immaculate order, had plenty of seating for all of us, and was safe for the kids to roam around on. A great sound system kept both kids and adults entertained. Mike truly is the best captain one can ask for. Quick to respond to our requests before the trip, and attentive, safe and positive during it. 10/10 from our whole party of nine

  4. ES

    Emily

    Got ASA Certification? Book this Jeanneau 389 Sailing Yacht

    Captain Bill is professional, prompt, knowledgeable, and fun! Highly recommend booking with Captain Bill whether it’s a pleasure cruise or making your boyfriend’s dream come true by going ocean sailing. Captain Bill is amendable and very generous with letting us operate the boat. Thank you Captain Bill!

  5. CM

    Chris

    Got ASA Certification? Book this Jeanneau 389 Sailing Yacht

    Bill was great! There was regular, clear communication leading up to bareboat charter. He was also extremely accommodating as we made itinerary adjustment based on weather. He also provided helpful local knowledge during briefing to ensure safe and fun charter. Lorikeet is well maintained with up to date electronics and in excellent shape. I hope to return for future trips! Thanks Bill

  6. Anthony

    Anthony

    Got ASA Certification? Book this Jeanneau 389 Sailing Yacht

    Great overnight charter! Spent the day sailing the Atlantic followed by an evening of dining and nightlife in West Palm Beach. Bill was very thorough in making sure everything was prepared for an overnight charter. I will be doing another overnighter again!