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The Best Sailboat Rentals Near Winter Haven
Browse, book, and get out onto the water with local captains and boat owners.
Suggested Searches
Types of Boats Popular in Winter Haven
Jet Skis
Fast, fun, and easy to operate, these are a guaranteed good time on the water
$50-$130
Fishing Charters
Let a captain do the driving while you do the fishing
$50-$75
Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$100-$175
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$50-$75
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$55-$150
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$75
Rafting
A high-energy adventure for the whole family
$75
Top Sailboat Rental Locations Near Winter Haven
Kissimmee, Florida
21 boats to rent
Saint Cloud, Florida
9 boats to rent
Orlando, Florida
34 boats to rent
Tampa, Florida
422 boats to rent
Ruskin, Florida
7 boats to rent
Tampa Bay, Florida
234 boats to rent
Saint Petersburg, Florida
262 boats to rent
Lake Tarpon, Florida
12 boats to rent
Gulfport, Florida
18 boats to rent
Holiday, Florida
16 boats to rent
Bradenton, Florida
20 boats to rent
Tarpon Springs, Florida
22 boats to rent
Dunedin, Florida
16 boats to rent
Tierra Verde, Florida
80 boats to rent
Largo, Florida
37 boats to rent
Saint Pete Beach, Florida
40 boats to rent
Clearwater, Florida
236 boats to rent
Bay Pines, Florida
14 boats to rent
Recent Reviews in Winter Haven
FG
Frank
42' Wanderlust - The Best Sailing Cat in the Market - Sarasota
Thank you for such an amazing and memorable time. Our family had a blast. It was exactly what we were looking for! Boat was gorgeous and the staff was attentive, friendly and knowledgeable ! Anyone looking to charter, you guys will be our go to recommendation for sure!
KC
Krysten
2017 Robertson and Caine Leopard 40 - Luxury Catamaran
Our party had a wonderful time. It was a very pleasant sail and we pulled up to a near by beach where we could swim. The vessel is very spacious and clean. We felt safe as well. We would definitely sail again!
CW
Carly
Hunter 336 Sailboat! Relaxing Sailing Palm Beach
I rented the boat for and engagement photo shoot. The weather this time of year was very unpredictable and rainy, but Captain Gerald was great to work with and so funny. He made the day really enjoyable. Lovely boat and nice time, highly recommend!
Zach
2017 Robertson and Caine Leopard 40 - Luxury Catamaran
Could not recommend this vessel and crew more. We rented it for the 4th of July and it was an unforgettable experience for our group. Despite some shaky weather we still had a blast. The boat is incredible and such a fair rate compared to other similar listings. Captain Dave and Joe were AWESOME. Would book again in a heartbeat!
Leah
Sunset Sails: Explore the Open Waters of Tampa, Florida
Such an amazing experience! From the day I inquired to the moment we got off the boat , Arlo was a great person and made the experience unforgettable! Highly recommend, you won’t regret it and you’ll have the best memories to hold on to. Thank you again!
JR
Jeremy
Sunset Sails: Explore the Open Waters of Tampa, Florida
Whether you’re considering your first adventure out at sea or perhaps taken a few adventures, Arlo is your guy for a great sailing experience, kind heartedness, and very experienced in boats and adventures out at sea. He ensured that we were taken care of, well attended, and was an excellent host. I highly recommend Arlo. He gave a great experience.
Top Sailboat Rental Locations in the United States
Los Angeles, California
377 boats to rent
Miami, Florida
916 boats to rent
Marina del Rey, California
136 boats to rent
San Francisco, California
71 boats to rent
Honolulu, Hawaii
58 boats to rent
New York, New York
90 boats to rent
Oakland, California
39 boats to rent
Annapolis, Maryland
50 boats to rent
San Diego, California
101 boats to rent
Newport Beach, California
134 boats to rent
Charleston, South Carolina
118 boats to rent
Chicago, Illinois
281 boats to rent
Baltimore, Maryland
43 boats to rent
Dania Beach, Florida
247 boats to rent
Southampton, New York
67 boats to rent
Hitchcock, Texas
55 boats to rent
Noyack, New York
46 boats to rent
Texas City, Texas
37 boats to rent
How To Book on Getmyboat
Browse
Find the right listing for you and your crew, with options for boat types, group size, captained or self-charter, and lots more.
Inquire & Book
Found one you like? Send a rental inquiry with your preferred trip details, and you’ll receive an offer from your captain to book.
Enjoy
Coordinate a pick-up place and time, meet your boat captain, and get out onto the water!
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Real reviews from happy Getmyboaters.
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