Boat vacation rentals in Monroe County

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Top-rated boat rentals in Monroe County

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Guest favorite

Boat in Tavernier

4.92 out of 5 average rating, 345 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.

May 24 – 31

R5,725 ZAR per night

Guest favorite

Home in Miami

4.95 out of 5 average rating, 63 reviews

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.

Sep 19 – 26

R7,951 ZAR per night

Superhost

Boat in Key West

4.91 out of 5 average rating, 11 reviews

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.

Mar 3 – 10

R17,497 ZAR per night

Superhost

Houseboat in Key West

4.81 out of 5 average rating, 253 reviews

Key West Houseboat Paradise

56 foot houseboat (1987), Fully Rebuilt in 2022. On a old 15 slip dock on Stock Island, 15 min drive to Key West. Big living room, Full Kitchen, Queen Bdrm + sofa bed. The dock is very local, 'old Key West' sort of vibe with mostly older live-aboard boats. The property has an fairly industrial feel to it with a 2-bay local garage/taxi company on site so Shore Side is nuthin' fancy but the back deck looks out on mangrove islands dotting Boca Chica Channel with two 12' Sea Kayaks ready to go.

Aug 25 – Sep 1

R7,300 ZAR per night

Superhost

Boat in Key West

4.83 out of 5 average rating, 36 reviews

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

Jun 13 – 20

R3,882 ZAR per night

Superhost

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!

Jan 20 – 27

R15,500 ZAR per night

Guest favorite

Boat in Key West

4.93 out of 5 average rating, 43 reviews

Sailboat in Luxury Marina

You will have an unforgettable experience staying on Allora, a 41 ft. sailboat, docked at the Perry Hotel and Marine - a luxury marina. PLEASE VIEW VIDEO BEFORE BOOKING: search "Allora walk through" on youtube Wake up to a freshly brewed cup of coffee and sit in the cockpit watching the sun rise across the water. Swim in the 2 heated, salt water pools and try out one of the many first class restaurants on site. Be sure to take advantage of the free shuttle to old town Key West.

Jun 2 – 9

R2,704 ZAR per night

Guest favorite

Boat in Key West

4.86 out of 5 average rating, 150 reviews

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.**

Oct 8 – 15

R15,640 ZAR per night

Guest favorite

Boat in Islamorada

4.92 out of 5 average rating, 327 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.

Jan 28 – Feb 4

R3,515 ZAR per night

Guest favorite

Townhouse in Key Largo

4.91 out of 5 average rating, 33 reviews

Beautiful Oceanside Mariner's 3 Bedroom Townhome

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.

Mar 27 – Apr 3

R12,011 ZAR per night

Superhost

Boat in Key West

4.79 out of 5 average rating, 73 reviews

The Escape- Private 2 Bed Rm Boat Beautiful Marina

Our Marina has a pool and a small private beach overlooking the beautiful Keys water! 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 sport fisher 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.

Jan 8 – 15

R6,283 ZAR per night

Boat in Marathon

4.61 out of 5 average rating, 33 reviews

Viking Yacht Getaway in the Keys

Dive into the beautiful weather of the Florida keys. Whether you enjoy your time fishing, kayaking in the sun or simply just hanging out with friends & family our beautiful Viking Yacht will make your time here priceless! 1 Hours from Key West & Key West International Airport 2 Hours from Miami International Airport Docked Use of the Boat Can facilitate a captain and crew for inshore reef fishing for an extra price

Dec 7 – 14

R4,644 ZAR per night