Houseboat vacation rentals in Monroe County

Find and book unique houseboat rentals on Airbnb

Top-rated houseboat rentals in Monroe County

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

0 of 0 items showing

1 of 3 pages

Guest favorite

Boat in Tavernier

4.92 out of 5 average rating, 351 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.

Superhost

Boat in Key West

4.91 out of 5 average rating, 22 reviews

The Salty Sunshine of Key West

Anchored in one of Key West's most serene and protected bays, the Salty Sunshine invites you to embark on a romantic getaway or gather with friends for unforgettable memories in this vibrant island paradise. Experience the magic of Key West as the sun rises and sets uniquely over the shimmering waters of the Southernmost City. Enjoy unobstructed 360-degree views from the comfort of our top deck, coffee, sunrise, wine, sunset. Cherished memories that last a lifetime. Water transportation needed.

Guest favorite

Houseboat in Key West

5 out of 5 average rating, 50 reviews

Key West Outpost: eco-vacation

The Outpost is a unique experience. This is a place where you can be completely off the grid, but still have all of the amenities. Private conch cottage on the backcountry waters surrounding Key West. Enjoy watching the amazing wildlife from your private deck. You can paddle board, kayak or do some light tackle fishing right off the boat. You can even add eco-tours to enhance the adventure. We will take you out for arrival and bring you back on your departure day, via one of our other boats.

Superhost

Houseboat in Key West

4.83 out of 5 average rating, 283 reviews

Key West Houseboat Paradise

282 reviews over 5 years! SuperHost Rated! Queen Bed, Full Kitchen, Big Living Rm, Full Bath & 3 Sun Decks. Completely rebuilt in 2022. 15 min from downtown, tucked away on a wooden dock. The vibe is 'Old-School Key West'. The property has a light-industrial feel with a 2-bay auto garage & a warehhouse, so the shore side isn't fancy but the Back Deck View is a mile-wide ocean channel with dozens of bright green mangrove islands and a pair of Sea Kayaks just waiting for you to go exploring.

Superhost

Houseboat in Stock Island

4.75 out of 5 average rating, 4 reviews

Stella on Stock Island

Perched on the shimmering waters, this 1 bedroom, 1 bath houseboat epitomizes cozy waterfront living. Step inside and you'll find yourself welcomed into an inviting living space. The living area transitions into a kitchen complete with essential appliances. Down the hall from the living area lies the bedroom offering a peaceful haven for rest and relaxation after a day spent exploring. An elegantly appointed bathroom awaits, featuring modern fixtures and amenities. Queen Bed & Sofa Bed

Superhost

Boat in Marathon

4.77 out of 5 average rating, 214 reviews

Paradise awaits on this cozy houseboat!

Our vision is for you to kick back, relax, and find your home away from home! Wether you want to celebrate with your loved one or retreat by yourself this floating home offers comfortable space for 2 adults. Located near the 7 mile bridge in Marathon Florida on the Atlantic Ocean nestled in a quiet, reserved mangrove area. This spot is fantastic because you have unparalleled access to out of this world sunset/sunrise views. Kayak through the mangrove and explore the surrounding areas.

Guest favorite

Houseboat in Key Largo

5 out of 5 average rating, 10 reviews

Floating Oasis: Elegant Overwater Bungalow Escape

When you book with Ombi, your journey to tranquility begins. You'll be assigned a captain who will ensure every detail of your stay is perfect. Upon arrival, you’ll meet your captain, who will escort you to your floating retreat and make sure you know how to get the most out of your stay. Savor your complimentary morning coffee, tea, and delightful desserts. Perfect for couples or solo travelers seeking a serene escape to reconnect with nature. *Boat transfer not included in price.

Guest favorite

Boat in Islamorada

4.88 out of 5 average rating, 209 reviews

HOUSEBOAT 2BD, PRIVATE KEYS COTTAGE LOGGERHEAD

Tucked away in the vibrant Florida Keys, is our pristine paradise. We are located in the heart of Islamorada, where the weather is always gorgeous, the fishing never disappoints, and the sunsets are mesmerizing. If you are seeking a relaxing get away, look no further. On site, you will have the luxury of renting your own private boat. Boat rentals are 20% off for guests! Unfortunately, we do not have spare slips for private boats at this time. A 5% lodging tax will be charged on arrival.

Superhost

Houseboat in Key West

4.83 out of 5 average rating, 198 reviews

Happys Houseboat

Looking for a unique and unforgettable vacation experience in Key West? Look no further than this charming houseboat listed on Airbnb! Escape the ordinary and indulge in the tranquility of living on the water. Our houseboat offers all the comforts of a cozy home, with the added bonus of breathtaking views and a prime location. Included in the rental is use of a skiff to get to and from land and a seventh generation local captain to assist in check in and give a tour of the Houseboat.

Guest favorite

Boat in Islamorada

4.92 out of 5 average rating, 331 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

Houseboat in Big Pine Key

4.74 out of 5 average rating, 141 reviews

2 Bedroom Aqualodge # 11 Grouper

This 2 Bedroom Aqualodge is an adorable accommodation in the Old Wooden Bridge Resort and Marina. You are able to enjoy the resort amenities during your stay. Beautiful Salt Water pool, Fish Cleaning Stations. Renters can also bring their boat or rent a boat from OWB at an additional fee. There is NO Swimming in the Marina Boat Basin. There is a beautiful salt water pool to use for your swimming pleasure. This is a marina with houseboats and rental boats in the slips.

Guest favorite

Houseboat in Marathon

4.89 out of 5 average rating, 97 reviews

Houseboat Getaway In Marathon

Get ready to indulge in a relaxing and unforgettable experience at the first overwater houseboat getaway in Marathon, Florida! 🌴🌊 What awaits you is - fun filled days living and exploring out on the fabulous florida keys waters in your own private aqualodge, breathtaking sunsets, and a private sanctuary perched above the sea. 😍 Don't miss out on this one-of-a-kind experience! Book your stay now and create memories that will last a lifetime.