Boat holiday rentals in Monroe County

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Top-rated Boat Accommodation in Monroe County

Guests agree: These boat accommodation options are highly rated for location, cleanliness and more.

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Top Guest favourite

The eco-friendly two-story River Queen vessel is anchored in a calm harbor, showcasing a modern design. The structure features large windows and a rooftop terrace, with a wind turbine on the left. The surrounding landscape includes lush greenery, complementing the serene water view.

Boat in Tavernier

4.92 out of 5 average rating, 401 reviews

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.

A classic Hans Christian sailboat is docked at a marina, featuring wooden accents and a blue canopy. The deck displays ample space with cushions and nautical equipment, while a scenic view of surrounding boats and palm trees is visible in the background under a partly cloudy sky.

Boat in Key West

4.8 out of 5 average rating, 15 reviews

Romantic Captain's Quarters

Create unforgettable memories and experience a one-of-a-kind getaway on this classic Hans Christian sailboat, a true Picasso on the water! Docked at the stunning Perry Marina and Resort, your stay promises adventure and romance. Unleash your creativity with provided art supplies and musical instruments. Take advantage of resort amenities: two swimming pools, three restaurants, shuttle service to downtown, parking, happy hour, and concierge services for outdoor activities. Book your escape today!

Guest favourite

A light-filled living area features a neutral-colored sofa and a round coffee table. Two elegant lamps provide soft illumination. A view of a green, tropical-themed outdoor area is visible through large glass doors, creating a seamless connection between indoor and outdoor spaces.

Home in Brickell

4.86 out of 5 average rating, 133 reviews

Home near 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.

Guest favourite

A motorboat is anchored on calm waters, featuring a spacious front deck. Two individuals are seated comfortably, enjoying the view. The boat's sleek design is complemented by a canopy overhead and small steps leading into the water, creating a relaxed atmosphere.

Boat in Key West

4.9 out of 5 average rating, 245 reviews

Stay on Roxie - free transport & snacks, BYOB.

Read our reviews and relax with last minute weather cancellation! 🌞 Shower, toilet and power to recharge phones, full cellular. Enjoy a peaceful night or two on the water! Free parking and one free round trip transport to/from Roxie per night stay! Roxie is anchored in ~3ft lagoon. We live on a boat a half-mile away if you need anything at all! Roxie has a Keurig, coffee pods, bread, peanut butter-jelly, and bottled waters. No cooking but you may bring to-go food, beer/booze/wine. 🛥️🌴🎣

Guest favourite

Boat in Key West

4.79 out of 5 average rating, 33 reviews

Beautiful 43 ' sportfish yacht

Come enjoy a yacht stay at Stock Island Yacht Club! Gorgeous facilities with Beach, pool, bar, and a gym!. The boat does not go out during the booking, but we can arrange a charter on it or other boats. We also rent street legal golf carts, outboard boats, and private backcountry sandbar charters. Come enjoy paradise on the Lisa Lynn! The marina has a small but gorgeous beach, amazing pool, and great tiki hut area. The tiki is at the end of a mangrove boardwalk, great place for a morning walk!

Superhost

A sailing catamaran is anchored in clear turquoise waters, showcasing its modern design and spacious deck area. The boat features a blue canopy protecting outdoor seating, with lush greenery in the background against a bright sky.

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!

Guest favourite

A serene waterfront view captures a light-colored building with turquoise accents, surrounded by lush palm trees. The calm water reflects the structure and sky, creating a tranquil atmosphere. Soft clouds float above, enhancing the peaceful setting of the marina.

Boat in Key West

4.83 out of 5 average rating, 184 reviews

A Great Escape! Private 2 Bed Rm Beautiful Marina

Our Marina has a pool and a small private beach overlooking the beautiful Keys water! More affordable than most places in Key West while able to reconnect with nature at this private getaway on the Great Escape. As you approach the boat, you feel your dream vacation has come true . One of a lifetime. Staying on a beautiful sportfisher yacht, laying in the waters of the calm keys and in the most beautiful peaceful marina, will definitely set you free from all your worries and stress.

A vibrant sailing vessel is anchored in clear turquoise waters, with a tall mast and vibrant blue sails. The sunlight reflects off the water, creating a serene atmosphere. A sandy beach is visible in the distance, framed by a clear blue sky with scattered clouds.

Boat in Key West

4.84 out of 5 average rating, 81 reviews

Beautiful sailing yacht on the water in Key West!

Sailing Vessel Maruquis is one of the cleanest and most beautiful rentable sailing yachts in Key West. Meticulously maintained, this top-notch yacht is MOORED just offshore Key West, and she is ready to provide the "live-aboard experience" with unbeatable ocean views! Guest transportation to/from vessel via local Ship2Shore shuttle service (additional fee). Find your peace and serenity onboard as you watch the sun rise and set from the water. Plan your escape to sunny Key West today!

Top Guest favourite

A solar and wind powered houseboat is moored on calm waters, featuring bright yellow shutters and a roof deck. Wind turbines and an American flag adorn the top, contrasting with the soothing blue sky and fluffy clouds in the background.

Boat in Islamorada

4.93 out of 5 average rating, 391 reviews

360 DEGREE WATERVIEW HOUSEBOAT

IMPORTANT Enjoy your own private retreat aboard a solar and wind powered houseboat moored 1/2 mile from land in the beautiful Islamorada Please do not arrive after dark and NO night riding. Need experience with hand pull outboard motors a 12 foot skiff with a 6hp outboard motor is provided reliable to go back and forth from shore NOT reliable for exploring No hot water on shower, heat water in Tpots or Solar bags. Please shave before arriving No suitcases, least amount of cloths.

Superhost

The yacht 'Just Chillin' is illuminated at night, showcasing its sleek design and multiple levels. Soft light emanates from the upper deck, highlighting the covered patio. Reflections of the boat shimmer on the water, creating a serene nighttime setting.

Boat in Key West

4.82 out of 5 average rating, 49 reviews

Just Chillin' Out on the Ocean: 1/2 Off Charters!

Live your dream of sleeping out on on the ocean in a deluxe cabin cruiser yacht. Yacht "Just Chillin" features two state rooms each with comfy queen beds, two full bathrooms, A/C, hot water, high speed internet, covered patio, full dining , kitchen, living rooms and more! The yacht is anchored out on the ocean: see unbelievable waterfront sunsets and wildlife right from the boat! Enjoy this unique experience! All guests receive HALF OFF excursions! Welcome Aboard!

Superhost

Boat in Key West

4.84 out of 5 average rating, 37 reviews

Beautiful 42ft Catamaran 1 mile from Duval St.

Escape to paradise aboard our 420 Lagoon, 42' catamaran anchored in turquoise waters off Key West. Recently refit, she offers 3 cozy cabins, 3 baths (two full shower), a well-equipped galley, and full A/C. Sleeps 6 with space to relax inside or on deck under the stars. Sway with gentle waves, watch dolphins swim by, and let island breezes and sunsets make this your private floating getaway in the Keys.

Top Guest favourite

A sailboat is anchored in calm waters during sunset, with vibrant orange and purple hues reflected on the surface. The silhouette of the boat, featuring a tall mast and a shaded cockpit area, contrasts against the colorful sky. Nearby boats are visible in the distance.

Boat in Coconut Grove

4.98 out of 5 average rating, 911 reviews

Hunter 26 Sailboat

A one-of-a-kind experience for those who want to enjoy Miami from a different perspective. Can accommodate up to two people, includes a basic toilet and freshwater. The boat is anchored in Biscayne Bay, which allows you to view the Miami skyline from a distance. You'll be in the famous Coconut Grove area. I will be taking you from the dinghy dock to the boat. Two kayaks are included for guests.