stay on a sailboat in key west

• Key West Fishing Charters
• Key West Deep Sea Fishing
• Key West Flats Fishing
• Key West Boat Rentals
• Dry Tortugas Charter Trips
• Large Group Charters
• Custom Charters
• Key West Sunset Cruise
• Overnight Charters
• Key West Sailing
• Key West Yacht Rentals
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Stay On A Boat In Key West

Book key west overnight charters.

Many vacationers want to know how to stay on a boat in Key West. The answer depends on the size and type of boat you’re interested in chartering. There’s a wide range of choices, from a luxury yacht that sleeps eight or more on the high end to something more intimate, like a 30-foot sailing sloop for two.

Call Key West Charter Boat and we’ll be happy to answer all of your overnighting questions. Or fill out a quote form. We’ll quickly get back to you with prices and boat availabilities.

One of the most common questions is where to stay on a boat in Key West? Again, you have several options, from multiple marinas on Key West to locations on Stock Island or even anchored out in Key West Harbour.

Charter QUOTES

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Charter Type Charter Type Overnight Charter Yacht Charter Sailing Charter Deep Sea Fishing Charter Flats Fishing Charter Private Custom Charter Large Group Charter Sunset Charter Boat Rental Dry Tortugas Charter Cuba Charter Jet Ski Charter Spear Fishing Charter Snorkeling Scuba Diving Glass Bottom Boat Dolphin Watching Lobstering Charter Corporate Boat Party Wedding Charter Film Production Charter Other

Duration Duration Half Day (4hrs) 3/4 Day (6hrs) Full Day (8hrs) Multiple Day

Number Of Participants Number Of Participants 1 2 3 4 5 6 More Than 6

Location Location Key West (Lower Keys) Islamorada / Marathon (Middle Keys) Key Largo (Upper Keys) Dry Tortugas Cuba Other...

Date(s) Of Charter

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Key west liveaboard charters.

Stay on a boat in Key West and you always have the option to venture outward. Many boats cruise to Dry Tortugas, just 70 miles away. Explored by Ponce de Leon in 1513, the island group is famous for its abundance of sea turtles. In fact, the Spaniard named the islands Las Tortugas , The Turtles. Now one of America’s most beautiful national parks, Las Tortugas is a few hours boat ride from Key West. If you go, remember to bring snorkeling gear. The pristine island waters are teaming with marine wildlife. When you’ve finished exploring, either retrace your route back to Key West or drop anchor and spend the night aboard. With no competition from artificial light, the Milky Way feels close enough to reach out and touch. We recommend anchoring.

Call us or fill out a quote form and stay on a boat in Key West for your next holiday . Book a romantic night on a vintage wooden sailboat in Key West harbor. Plan a family getaway cruising aboard a 65-foot catamaran, spending each tropical evening at a different anchorage. Hire a private luxury yacht for a special weekend with close friends. There’s something indescribable about waking to the rhythm of waves rippling against the hull of a boat. It’s even better when you stay on a boat in Key West Florida.

We chartered a catamaran down to the Dry Tortugas for 3 nights.  I have never seen the stars so bright.  The experience of a lifetime.

Many vacationers want to know how to stay on a boat in Key West. The answer depends on the size and type of boat you’re interested in chartering. There’s a wide range of choices, from a luxury yacht that sleeps eight or more on the high end, to something more intimate, like a 30-foot sailing sloop for two.

CHARTER QUOTES

  book key west overnight charters .

Stay On A Boat In Key West – Fort Jefferson

Stay On A Boat In Key West – Dinner Cruise

Stay On A Boat In Key West – Yacht Salon

Stay On A Boat In Key West -Cabin Beds

Stay On A Boat In Key West – Bahamas

Stay On A Boat In Key West – Family Trip

Stay On A Boat in Key West – Night Lounge

Best Charters Best Prices

 Key West & Marathon, Florida

We specialize in private luxury yacht & sailing charters at affordable prices. we offer day charters as well as multi-day charters., why blue ocean yacht charters.

Blue Ocean Yacht Charters, located in Key West, Florida, makes yacht rentals affordable and life-changing.  We offer private multi-day bareboat charters to amazing destinations like The Dry Tortugas and the Florida Keys.  Just looking for a day charter?  Look no further.  We offer four hour, eight hour, and 24 hour charters as well multi-day charters.

All our yachts come fully equipped to make your private boat charter experience what you’re looking for. We offer motor and sailing yachts that provide the best boat rental experience.  

Private & Shared Sailing Charters

Sunset sail key west.

Have the sea to yourself with Sunset Sail Key West—chartered sailing trips led by us, tailored to you.

Get inspired with our most popular trips!

Private sunset sail.

Chillout Lilypad Sail

Key West Daysail

Sunset Sail on When & If

Privates Charters

Discover your perfect private charter.

Set out on a snorkeling, stargazing, or sunset sail, or build your own custom trip. Romance, relax or unwind from the privacy of your own chartered sailboat.

Shared Trips

Come together on a shared charter.

Rise above the crush of the crowds and set sail on a unique shared sunset charter, with a few friends you haven’t met yet. A personable local crew and captain will treat you to a stunning sunset view from the deck of an unforgettable vessel– General Patton’s elegant, private schooner When and If.

Three Classic Boats

View our fleet.

We sail a fleet of three vintage sailboats, each with their own unique charm and appeal. A custom sloop, a classic ketch, and a historic schooner are waiting to make memories with you on the crystal clear waters of Key West. Each boat is suited to different types of outings, so take a moment to get acquainted with our vessels.

Real. Fun. Sailing.

When And If is back at beautiful Stock Island Marina!

Check Out Our Ship's Store!

Wreckers' Race Season Is Back!

Hello, Sailor! Don’t miss out on the latest Sunset Sail news & offers.

Friends of SSKW

Legal & safety.

Boat vacation rentals in Florida Keys

Find and book unique boat rentals on Airbnb

Top-rated boat rentals in Florida Keys

Guests agree: these boat rentals are highly rated for location, cleanliness, and more.

Boat in Tavernier

Island Sanctuary Islamorada

Stay aboard the eco-friendly two-story 63 ft River Queen with a 360 degree view with beautiful sunrises and sets, mored 1/8 mi offshore in a quite harbor close to shopping center, movie theater, hospital, bars & restaurants. A 10-foot dinghy with small outboard to come & go from shore "ONLY", nowhere else. I also offer Personal Training, deep tissue work & Life Coach sessions. I live on the vessel about a hundred yards from you so if there are any questions, etc. I will be there to assist you.

Boat in Fort Lauderdale

Graceland Fort Lauderdale Tiny House Treehouse

A short walk to the beach and downtown, Graceland is where your boat house becomes a tree house on a high tide. This 1979 remodeled vintage double cabin is a hidden gem, an exotic experience for the most sophisticated travelers. Situated conveniently on Las Olas, Grace is a short walking distance to the bustling downtown & the sunny beaches of Fort Lauderdale. The boat has 2.5 cabins & 2 full en-suite bathrooms. Host lives onsite and available when needed. Graceland was founded by Rose in 2022.

Home in Miami

Luxury Home in Brickell Miami, 5 min to the Beach!

This amazing home situated in a convenient location of Miami, was professionally designed and accommodated to suit your vacation needs. Enjoy our chef inspired large fully equipped kitchen, our ample sophisticated and modern bathrooms, as well as our comfortable bedrooms, upgraded with fine linens and hotel quality mattresses. The Roads is an incredible neighborhood in the limits of Brickell, filled with sidewalks, roundabouts, wide tree lined streets surrounded by tropical native Miami plants.

Boat in Naples

"Comfort Zone" Private Yacht-Charter

2-BR, 2-Bath at Port of the Isles, Fl. 30 minutes from Naples, Marco Island, Everglades & more. Large salon & tall windows for great views, dine seating & full sz. frig. Kureg, convection oven, stove, pots/pans, dishes, everything you could need to cook. Forward stateroom w double berth w private access to head w shower, large closets and storage. AFT cabin master has queen size island bed, huge closets, plenty of built in storage private head with shower/tub. Cruise options available!

Condo in Miami

Miami Beach 420 Friendly 10 mins from Cruise Port

READ THE REVIEWS to see how much of an effort we make to ensure you have the BEST TIME while here. This place is in SOUTH BEACH MIAMI not the venetian causeway. The place has 2 TVs, 2 Queen beds. Prime Location 💯. NO CIGARETTE SMOKING, NO ANIMALS ALLOWED & NO SHOES INSIDE. Keep in mind that other people live within the building, so be aware of the noise but HAVE FUN. This is not a hotel; this is an Air bnb. You will NOT find a better deal on MIAMI BEACH in this area with a host like Vincent.

Boat in Key West

Amazing 4 Bdrm, 4 Bath Catamaran - Purpus

Enjoy all the comforts of home including 4 luxurious staterooms with queen sized beds each with its own private bathroom, a full kitchen with everything needed for on board meal prep, spacious living areas down below and above on the decks. The boat is in great condition and has been well maintained inside and out. Purpus is docked in a first class marina with access to free parking, restaurants, bars, ships store, pools, coffee shop and laundry. Charter options available for additional fee.

Make Memories and Enjoy Sunsets on Euphoria

PLEASE READ ALL THE SECTIONS IN THE LISTING. 31ft BOAT ANCHORED at 1.5 mile off Key West NOT IN A MARINA. Transportation to the boat by water shuttle, fee not included in stay. REMEMBER ITS A BOAT, FUN EXCITING, ACCEPTANCE OF TRANSIENCE AND IMPERFECTIONS. THE AESTHETIC IS SOMETIMES DESCRIBED AS ONE OF APPRECIATING BEAUTY THAT IS IMPERFECT, IMPERMANENT AND INCOMPLETE IN NATURE. Embracing simplicity, nature imperfection and find joy, peace that nothing is perfect in this world. Enjoy Life

Boat in Key Largo

Yacht/Catamaran ON THE WATER in a Key Largo marina

You Must contact us before booking, the boat is often booked far in advance with multi-day sailing trips which do not reflect on this calendar. Enjoy a unique vacation experience on our comfy sailing catamaran, docked, inside a small Key Largo marina. 3 full suites with bathrooms means 6 people comfortably sleep. This listing is for the catamaran INSIDE the marina, for sail trips, message us! Ask us about our TripAd\/is0r reviews too! Our guests always love their sailing adventures!

ALL INCLUSIVE! Snorkel/Sail/Spear Fish/Fishing/Fun

You will love staying on this 45' GulfStar Sloop. The boat boasts 2 BR, 1.5 bath with shower, full working galley, A/C throughout and plenty of room to relax down below. Every reservation comes with a sunset sail along with day sailing, snorkeling or fishing. Layout and be lazy on the spacious deck or whatever you would like to do! Visit SailAway GetAways on FB for more detailed view. **Unfortunately one night reservations do not allow time for excursions. Except a sunset sail.**

Stay on the Roxie!

Enjoy ocean-breezy, star filled nights, in a relaxed setting on water, Key West style! Free, early bag storage! 🛥🌴 Free daily transport to and from Roxie anchored in protected, shallow bay as late as 11PM. You’ll have Roxie all to yourself. We live on a boat a half-mile away if you need anything. 😊 Roxie has electricity, a Keurig, snacks like chips, breakfast muffins or donuts , Keurig pods, bread, peanut butter and jelly, and bottled waters on ice! 🧊 🧊🧊

Boat in Miami

Sailboat with a view

EnjoyScenics views of downtown Miami and the entry port.On the other side the islands that connect it to Miami beach. The boat is on a mooring, with unique 360 degrees view. At same time require to go from shore with a dinghy .we provide the service. We include 1 roundtrip per day then it's $10 per roundtrip . Regular hours it's from 730 am till midnight. We have some exceptions for after hours with previous arrangements and during the ultra festival till 3am.

Townhouse in Key Largo

Mariners 210 Great Location with Marina Views

This marina facing 3 bedroom townhome is spacious and beautifully decorated. Relax with the whole family at this peaceful place to stay. The Oasis pool is probably the nicest pool in Key Largo with Ocean views and beach entrance it is a great spot for any age. Boater's would love this very well maintained Marina. Tennis and Pickle ball on site. Game room for kids and adults to enjoy. Many restaurants, watersports, and excursions nearby.

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Florida Keys boat rentals

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Last Minute Discount! 48' Yacht & Beautiful Resort

Private room in Marathon

Island Yacht Adventures

Hunter 26 Sailboat

Aqua Lodge Houseboat "Starfish"

Y Knot Charters - a superb charter

Boat in Miami Beach

Luxury 75’ Ferretti Yacht Stay in Miami Beach

Key West Cozy Private Boat

Boat in Marathon

Viking Yacht Getaway

Gonagain! Experience living on the water!

Boat in St Key West

Today Is The O'Day!

Luxury 40 ft yacht in paradise awaits you!

Boat in Naval Air Station Key West

Key west clean, comfy sailboat

Home in Fort Lauderdale

Entire Teak Yacht Ft. Lauderdale / Miami / Keys

Overnight Adventures aboard Miss Carolina

Luxury Living on the Water

Cozy Sailboat + Dinghy For Nature Lovers

Motor Boat and Overnight Stay on Sailboat

Dream Of A Yacht Like No Other

Private room in Key West

Yacht Your Ordinary Airbnb

57ft DeFever in Islamorada Marina

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Trip duration, multiple days (less than 1 week), weekly trip show boats that have weekly prices. most weekly boats outside of the us are available only saturday to saturday., boat length: 5ft -, manufacturer, boat build year: -, weekly trip, price: $ - $.

Key West, FL

boating guide

In addition to the best offers we have for boat and yacht charters in Key West, FL, see also options available for rent in these nearby locations:

• 12 boat rentals in Key West, FL
• 12 boat rentals in Stock Island, FL
• 12 boat rentals in Key Haven, FL
• 12 boat rentals in East Rockland Key, FL
• 12 boat rentals in Cudjoe Key, FL
• 12 boat rentals in Summerland Key, FL
• 12 boat rentals in Little Torch Key, FL
• 12 boat rentals in Big Pine Key, FL
• 9 boat rentals in Marathon, FL
• 9 boat rentals in Key Colony Beach, FL

Discover Key West, FL with Sailo - a gorgeous boating playground for you to enjoy!

Ready to see your options for renting a sailboat in key west, fl, learn how to find the perfect yacht for you, how much is it to charter a key west, fl yacht for a day, what is sailo’s cancellation policy, sustainable yachting tips.

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Boat Excursions

Let Captain Nikki help book the best Key West charter for you.

Boat charters boat charters, non-crowded        |        choose your captain        |        no hidden fees       .

PRIVATE CHARTER

Private Boat Charter Key West | Florida   Family vacay? Bachelorette party? Girls' weekend? Micro wedding? Customizable private trip! Captain Fuel Paddle board, floats Snorkel Equipment Sodas & Water Light snacks BYOB

(customizable private boat charter )  , all included, no hidden fees.

SUNSET SAIL

Public Sunset Sail Key West | Florida   2 hour sunset cruise Premier sailing vessel Champagne, beer, & wine Hors d'oeurves  

(public cruise w/ larger capacity but premier sailing experience)  .

DOLPHIN & SNORKEL TOUR

Dolphin / Snorkel Boat Charter Key West | Florida Swim noodles, floats Snorkel Equipment Sodas & Water Light snacks BYOB

(Non-crowded public trip, 6 passenger max !)  

SANDBAR EXCURSION

Sandbar Boat Charter Key West | Florida Paddle board, floats Snorkel Equipment Sodas & Water Light snacks BYOB

WHY CHOOSE SO KEY WEST

Bookings by an actual Captain

Owned & operated by Key West local, Captain Nikki

Non-crowded charters

Both private and public small group charters offering a more quality, intimate boating experience

Choose your Captain

Private charters can request to have Captain Nikki

No hidden fees

No gimmicky marketing spiels; just upfront details and pricing

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See fun footage from captain nikki's charters.

Book your dream boat charter with So Key West today! Offering both private charters & public charters - all small group, non-crowded for a better boating experience.

Don't miss out on the amazing sandbar excursions, snorkeling opportunities, dolphin watching charters, and private boating experiences in Key West.

Let So Key West simplify the booking process and help make your vacation beautiful.

What people are saying about Captain Nikki

Teresa   |   Florida

“We have been booking with Nikki for over 7 years. She has always been professional and competent as well attentive and personable. Nikki never hesitates to go the extra mile to make sure we have an excellent charter, snorkeling or sunset cruise... it's always an exceptional trip."

Tyrel   |   Oklahoma

"We booked a sandbar charter with Captain Nikki in May 2023. Luckily, we were the only guests on the charter so it was very private. Captain Nikki took us to some beautiful sandbars where we were able to swim around, see wildlife, etc. She was incredibly accomodating and kind to us. We have kept in touch since and plan on booking with her again when we visit Key West. 100% recommend Captain Nikki and That's So Key West Charters!!!"

Stephanie   |   Nebraska

“I jumped on a boat solo and almost moved to Key West because of it. My Aunt had to leave town last minute, but I decided to go alone anyway. I jumped on the boat and immediately felt welcomed by Captain Nikki, and at the time all women crew. I almost canceled and I'm so happy I didn't. The food, drinks, and vibe of the boat was amazing. So much so, am I moving to Key West? I would recommend 100%.”

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Dolphin & snorkel trip, sandbar excursion, private charter, sunset cruise, so key west, captain nikki, let captain nikki help., text or call (305) 209-5504, email [email protected].

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