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All listings in Florida

Incredible sailboat rentals in Florida, United States.

Page 2 of 5104 listings

Marlowe Hunter 33’ Sailing In Fort Lauderdale
Sailing in Fort Lauderdale · 6 guests

Marlowe Hunter 33’ Sailing In Fort Lauderdale

5.0
$90+/hour
Sunset, Hour and Day Sailing Tours in St. Pete Beach - 30ft Dufour Sailboat
Sailing in Saint Pete Beach · 6 guests

Sunset, Hour and Day Sailing Tours in St. Pete Beach - 30ft Dufour Sailboat

5.0
$110/hour
Sea Ray Sundancer 38ft – Classic Luxury Cruise in Miami!
Events in Miami · 13 guests

Sea Ray Sundancer 38ft – Classic Luxury Cruise in Miami!

5.0
$100/hour
Lagoon 42 Sailing Catamaran for Up to 13 (12 + Charterer) Guests Near Stuart, FL
Sailing in Stuart · 13 guests

Lagoon 42 Sailing Catamaran for Up to 13 (12 + Charterer) Guests Near Stuart, FL

5.0
$354/hour
Luxury Sailing Experience on Robertson & Caine Leopard 40
Sailing in Saint Petersburg · 12 guests

Luxury Sailing Experience on Robertson & Caine Leopard 40

5.0
Superowner
$799+/hour
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
$1,100/hour
Hunter 336 Sailboat! Relaxing Sailing Palm Beach
Sailing in North Palm Beach · 4 guests

Hunter 336 Sailboat! Relaxing Sailing Palm Beach

5.0
$120/hour
⛵️ Catamaran Party Boat 42-people Includes: 1-Captain, 1-Mate and 1-Bartender
Sailing in Miami Beach · 42 guests

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

3.0
Superowner
$700+/hour
48 Ft Catamaran sailing on the Biscayne Bay . Party, Sound healing, Wingfoil
Sailing in Miami · 13 guests

48 Ft Catamaran sailing on the Biscayne Bay . Party, Sound healing, Wingfoil

5.0
$187+/hour
33ft The Key West's Most Versatile Sailboat! (With Captain Only)
Sailing in Key West · 12 guests

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

4.6
$199+/hour
Fort Lauderdale - Bahamas Sailing Charters
Sailing in Fort Lauderdale · 6 guests

Fort Lauderdale - Bahamas Sailing Charters

5.0
$130+/hour
Beautiful 36' Sea Ray Motor Yacht up to 12 guests and floating mat in Miami!!
Powerboats in Miami · 10 guests

Beautiful 36' Sea Ray Motor Yacht up to 12 guests and floating mat in Miami!!

4.3
$100+/hour
60' Sailing Party Catamaran in Miami Florida
Sailing in Miami Beach · 49 guests

60' Sailing Party Catamaran in Miami Florida

4.6
$1,300/hour
Luxurious 40ft Leopard Catamaran - Captain Included
Sailing in Saint Petersburg · 6 guests

Luxurious 40ft Leopard Catamaran - Captain Included

5.0
Superowner
$315+/hour
42' Wanderlust - The Best Sailing Cat in the Market - Sarasota
Sailing in Sarasota · 12 guests

42' Wanderlust - The Best Sailing Cat in the Market - Sarasota

5.0
$499+/hour
COME AND ENJOY THE C'YA WITH US AND FAMILY
Events in Miami · 13 guests

COME AND ENJOY THE C'YA WITH US AND FAMILY

New
Superowner
$365+/hour
2 Hour Sunset River Cruise for up to 6 people in Fort Lauderdale
Sailing in Fort Lauderdale · 6 guests

2 Hour Sunset River Cruise for up to 6 people in Fort Lauderdale

5.0
$150/hour
Lagoon 42' Private Sailing Adventure in Florida with Captain Eric
Sailing in Deerfield Beach · 8 guests

Lagoon 42' Private Sailing Adventure in Florida with Captain Eric

5.0
$300/hour
40 ft Jeanneau Sloop Charter in Fort Lauderdale
Sailing in Fort Lauderdale · 6 guests

40 ft Jeanneau Sloop Charter in Fort Lauderdale

5.0
$109+/hour
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
$200/hour
21ft Sun Tracker 20 Party Barge {Catch a Vibe}
Powerboats in Fort Lauderdale · 6 guests

21ft Sun Tracker 20 Party Barge {Catch a Vibe}

5.0
$100/hour
45' Luxury Sailing Catamaran Charter
Sailing in Saint Petersburg · 6 guests

45' Luxury Sailing Catamaran Charter

5.0
$300+/hour
Aicon 67 Fly  – Elite Luxury Yacht Experience
Events in Miami · 13 guests

Aicon 67 Fly – Elite Luxury Yacht Experience

New
$350/hour
Instant Book
Leopard 53 Power Catamaran (25-ft wide deck space)
Powerboats in Fort Lauderdale · 12 guests

Leopard 53 Power Catamaran (25-ft wide deck space)

New
$340+/hour

Sailing Reviews in Florida

  1. MT

    Michelle

    Hunter 336 Sailboat! Relaxing Sailing Palm Beach

    We had the absolute best time with Gerald. From the moment we stepped on the boat, we were treated like family. His kindness, generosity, and genuine spirit made the entire experience feel so special. What stood out most was not only how much fun we had, but how it truly felt like we made a new friend. Gerald’s knowledge of the area is expert level, and he shared so many great insights that made the day even more enjoyable. This was such a memorable experience for our group, and we cannot recommend him enough. We will absolutely be back.

  2. SS

    Stephanie

    Luxurious 40ft Leopard Catamaran - Captain Included

    Best boat rental experience I've ever had!

  3. PC

    Paul

    Marlowe Hunter 33’ Sailing In Fort Lauderdale

    Captain Thomas was great and made the experience a real pleasure. He did an excellent job explaining some basics of sailing and allowed me to captain the boat with his guidance. Great value was icing on the cake. Don’t hesitate to book with Captain Thomas.

  4. AC

    Allison

    Marlowe Hunter 33’ Sailing In Fort Lauderdale

    We had an amazing time out with Thomas and Steve. The weather turned out to be perfect for sailing and we really enjoyed being able to anchor and enjoy the lake on the intercoastal. They both were committed to making sure you had a very relaxing ride and had all the drinks you needed. When we visit Ft. Lauderdale again, we will book again!

  5. BL

    Bridgette

    Lagoon 42 Sailing Catamaran for Up to 13 (12 + Charterer) Guests Near Stuart, FL

    We truly can't say enough great things about this boat, this crew or the entire experience. From the moment we stepped aboard, it was 1st Rate. The crew was both Professional and Charming. Smooth sailing, engaging conversation and incredible scenery. Book this luxury liner for yourself. You'll throughly enjoy yourself.

  6. JP

    Jeff

    Lagoon 42 Sailing Catamaran for Up to 13 (12 + Charterer) Guests Near Stuart, FL

    We spent an afternoon with Paul on his boat with 6 adults and 2 infants. Paul is a great Captain and host and the boat is very roomy and stable. Even under full sail we felt very comfortable with the 2 grand-kids on board. Would highly recommend Captain Paul as a first rate skipper and an excellent boat to spend time on.