Boat holiday rentals in Monroe County

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Top-rated boat rentals in Monroe County

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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

4.75 out of 5 average rating, 12 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

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

4.91 out of 5 average rating, 387 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.

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 Miami

4.86 out of 5 average rating, 118 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.

Boat in Key West

4.75 out of 5 average rating, 28 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!

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, 225 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. 🛥️🌴🎣

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

4.81 out of 5 average rating, 155 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.

Top guest favourite

The image features a distant houseboat silhouetted against a vibrant sunset, reflecting shades of orange and purple on the water's surface. The view is taken from a skiff, with gentle ripples seen in the foreground, creating a serene atmosphere.

Boat in Islamorada

4.93 out of 5 average rating, 371 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

4.85 out of 5 average rating, 33 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!

Guest favourite

A 2007 420 Lagoon Catamaran is anchored in clear turquoise waters, displaying its sleek white hull and tall masts against a backdrop of vibrant clouds and blue sky.

Boat in Key West

4.87 out of 5 average rating, 164 reviews

All Inclusive! Snorkel • Sail • Sun & Fun

Stay aboard our 42’ Lagoon 420 catamaran anchored off downtown Key West. Hosted by Captain Dan, a 10-year Superhost, your all-inclusive stay includes snorkeling, sailing, spear fishing, and fishing gear. Relax in the private queen cabin with ensuite bath, enjoy the fully equipped galley, and unwind in the air-conditioned salon. Quick dinghy rides bring you to Key West’s vibrant dining and nightlife. Your perfect floating island escape!

The airy salon features large windows that provide views of the marina. A cozy L-shaped sofa with blue accent pillows surrounds a spacious coffee table, and a patterned rug adds contrast to the wood flooring. A small dining table with two chairs is positioned near the galley.

Boat in Key West

4.5 out of 5 average rating, 10 reviews

The Sea Ray Experience

Welcome aboard the Luxurious Sea Ray Experience! This spacious yacht boasts a stylish interior with two staterooms, bathroom, a cozy galley, and a comfortable salon. Enjoy breathtaking views from the flybridge or unwind in the elegantly appointed living spaces. Equipped with modern amenities, this vessel offers a unique stay, perfect for entertaining guests. Experience the allure of life on the water with our Sea Ray Experience.

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 Miami

4.98 out of 5 average rating, 855 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.