Boat vacation rentals in Florida Keys

4.91 out of 5 average rating, 378 reviews

The two-story eco-friendly River Queen vessel is anchored on tranquil waters. Its modern design is complemented by expansive windows, and a spacious rooftop deck is visible. The 10-foot dinghy is secured alongside, providing easy access to the shore.

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.

The sailing catamaran Purpus is shown gliding over the water, featuring a sleek white hull and a large deck. A spacious area is visible at the bow with crew members actively adjusting the sail. The overall design emphasizes both function and elegance.

4.9 out of 5 average rating, 30 reviews

Amazing 4 Bdrm, 4 Bath Catamaran- Sleeps up to 8

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, ship store, pools, ice cream shop and laundry. Charter options available for additional fee.

4.87 out of 5 average rating, 104 reviews

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

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.

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.

4.91 out of 5 average rating, 204 reviews

Stay on Roxie - free transport, snacks & ice. 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. 🛥️🌴🎣

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.

4.82 out of 5 average rating, 22 reviews

Yacht Just Chillin': Anchored Out on the Ocean!

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 charter guests receive 2-for-1 water shuttles for their stay! Welcome Aboard!

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!

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.

4.8 out of 5 average rating, 139 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 30-foot boat is docked in the marina, displaying a clean white hull with the name 'Lady Christine' featured on the stern. A blue canopy provides shade over the cockpit area, which includes comfortable seating. The surrounding marina features additional boats in the background.

4.84 out of 5 average rating, 182 reviews

"Lady Christine" at Beautiful Resort/Marina

Experience the best that Key West has to offer while staying on a lovely Bayliner. Just 5 miles from downtown Key West. Waterfront living, wonderful amenities and access to an abundance of excursions that leave right from the marina. Parking space right in front of the boat slip and a free hourly shuttle to downtown Key West! Bicycle and Scooter rentals available on site, Waterfront Swimming pool, 2 restaurants, Complimentary WiFi access, 24hr fitness center and laundry facilities

Top guest favorite

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, 356 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.

4.83 out of 5 average rating, 251 reviews

A spacious bed is adorned with various decorative pillows and a cozy blanket. The wall surrounding the bed is filled with diverse framed artworks and photographs, contributing to an artistic environment. A secondary bed is partially visible in the background.

Condo in Miami

Hippie Haven 420 Friendly In South Beach Miami

This place is in South Beach Miami Beach. You'll meet me on the 14th and Euclid to check you in directly. For starters; this place is for the Hippie, relaxed, bohemian type. There are pictures on the wall for conversation starters and artistic expression. There are carpets on the floor to give a smooth, comfortable, soft feeling under your feet, as well as the carpets.are cleaned and/or upgraded periodically. NO CIGARETTES, BLACK & MILDS OR CIGARS SMOKED INSIDE. PERIOD.