Holiday rentals in Boot Key

4.99 out of 5 average rating, 136 reviews

Cancellation Deal: 08/02 thru 08/09

2025 - New concrete dock, fenders & fish filet table. This ground level waterfront home has received a new face lift. Completely remodeled 3 bedroom with bonus room in the well known Sombrero Beach neighborhood. Just a short block walk to the sandy beach shore. Home has an open floor plan overlooking the in-ground pool deck and new tiki hut. Enjoy your morning coffee and happy hour in the screened-in porch with views of the wide lagoon. Come and create your family memories in the fabulous Keys.

4.96 out of 5 average rating, 105 reviews

Home in Key Colony Beach

Captain’s Quarters Ahoy Mateys! Florida, Keys

This is located at the Florida Keys in Key Colony, Marathon. It is a spacious two bedroom, two bathroom duplex surrounded by water. It is a renovated beauty and close to the best restaurants and the tranquility of this city. It is the perfect getaway where you can recharge your exhausted batteries. Captain’s Quarters is a clean and spacious base camp location for the many adventures that await you in this amazing location. Water views and the accessibility to the best fishing in the world.

Guest suite in Key Colony Beach

4.99 out of 5 average rating, 108 reviews

Turtle-By-The-Sea: the Best Deal in KCB!

A perfect get-away for couples or budget travelers, Turtle-by-the-Sea is the best priced vacation rental or hotel room in the middle-keys. Together with its prime location and amenities there simply isn’t a better deal to be had! Bursting with Keys charm, this cozy retreat is the perfect place to relax & escape. Owners Mallory & Steve infused their love of the Keys & its surrounding ocean into every aspect of their waterside home. Shoot us a message & start planning your dream Keyscation!

5 out of 5 average rating, 13 reviews

Luxury Paradise • Seagrass-Free. New 5BR Pool Home

Escape to this new stunning waterfront pool home. Enjoy panoramic ocean views, a private boat dock, with , fishing area, snorkeling, kayaks, paddle boards, bicycles and more.... The spacious, modern interior features a fully equipped kitchen, cozy bedrooms, and an open living area perfect for relaxation. Step outside to a beautiful patio or two balconies with seating to take in the views. Ideal for multiple couples, big families, or friends looking to explore the best of the Marathon key.

Apartment in Key Colony Beach

4.96 out of 5 average rating, 207 reviews

Oceanfront Sunrise Condo Private Beach Heated Pool

Impeccable condo directly on the ocean with water views from every window. Located in Key Colony Beach (middle Keys) with heated pool and private beach. Unit #20 is a studio condo with a classic Keys interior: newly renovated bathroom and crisp white kitchen stocked with everything needed to cook a complete meal (stove, oven, toaster, microwave, blender, fridge, etc). Enjoy the private back balcony and private beach with lounge chairs, patio tables, tiki's and BBQ grills for guest use.

Superhost

Boat in Marathon

4.8 out of 5 average rating, 270 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.

4.95 out of 5 average rating, 116 reviews

Home in Key Colony Beach

Waterfront Home 37.5-ft dock, Cabana Club Included

Bright, Open Floor Plan with new floors & kitchen. East facing for sunny mornings and shady afternoons on the great screened porch. Two roomy bedrooms and 2 full baths. Plenty of parking on the paved driveway. Perfectly located with the boater and angler in mind on a 37. 5 ft concrete dock, on deep & wide canal. Here on Key Colony Beach you can walk or bike the entire city to the marina, Sunset Park, 3 restaurants, play golf, tennis, pickle ball, bocce ball, horseshoes & basketball.

4.91 out of 5 average rating, 320 reviews

Villa in Marathon

New Aqua Lodge 2Beds 1 Bath with Full Kitchens

This hip spot is the new thing in lodging. Aqua Lodge is all the modern amenities while being on the water. Full kitchens, flat screen tv's, wi-fi , pool, bikes, sunset beach. We have it all right at your finger tips. You can sleep up to 5 people comfortably. We have great air conditioning and big showers. The deck is furnished with a dining table for those romantic outdoor dinners in the moonlight. We also have a sunset beach area for the best sunsets in the Florida keys!

4.96 out of 5 average rating, 114 reviews

Anglers Terrace, Condé Nast Traveler's Best Airbnb

As published in Condé Nast Traveler, this is one of the best Airbnb's in Florida. Newly Built two story Tropical Oasis with pool has been thought-out meticulously. An open, very light & spacious floor plan, carefully appointed furnishings, and great location provide the perfect surroundings. Decorated with a Zen sensibility, It’s outdoor Patio deck and Rooftop Terrace extends your living space into the private quiet ocean setting with panoramic views

4.89 out of 5 average rating, 120 reviews

Houseboat in Marathon

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.

4.92 out of 5 average rating, 12 reviews

NEW! Private Pool, 50’ Dock, Kayaks, Waterfront

Slack Tide Cove Welcome to Slack Tide Cove, a stunning 3-bedroom, 2-bathroom waterfront retreat in the heart of Marathon, FL. This brand-new construction is chicly decorated with a coastal theme, offering the perfect blend of luxury and relaxation. Take in breathtaking views of Boot Key Harbor from the pool or balcony, and enjoy 50 feet of deep-water dockage with a fish cleaning station for your day’s catch.

Superhost

Serviced apartment in Marathon

4.84 out of 5 average rating, 126 reviews

Knight's Key Suites Deluxe King Room w/ Kitchen

One-of-a-kind place accommodations located next to the 7-Mile Bridge. These rooms feature one king bed that can accommodate up to two people. The room comes equipped with a kitchen. Perfect for long or short-term stays! Knights Key Suites will be performing some concrete work to the exterior facade and adding new railings, the work will be done September 3, 2024- October 10, 2024 Monday-Friday 9:00am- 5:00pm

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Other great holiday rentals in Boot Key

5 out of 5 average rating, 12 reviews

Luxury 5Bdrm/6bath New in 2024

CatherineRating, 5 stars1 week ago

Timothy’s house was spacious, comfortable, and clean. The pool was a great way to beat the Florida Keys heat and the sunset views from the 3rd floor were awesome! Boaters will love the boat ramp next door. The fish cleaning table and outdoor freezer were a huge plus.

Houseboat in Marathon

4.82 out of 5 average rating, 11 reviews

Tiny Home Aqua Lodges 2/1

JasonRating, 5 stars2 weeks ago

Great spot. Would stay again

5 out of 5 average rating, 40 reviews

Movie Theater | HotTub | Pool | Boat/RV/EV Parking

AnneRating, 5 stars1 week ago

We almost stayed at a hotel, but I saw Christian’s place pop up and it looked like a fun place for the family. It is so awesome! It is exactly as described.and more . He uses every inch of that awesome property for something fun. It’s also a close drive or bike ride to so many things. We took almost all of his suggestions on places to eat and things to do and they were right on. The last night we all chilled outside and projected the Goonies on the outdoor screen and had some good relaxing family time. He is an excellent host and is so helpful. We are all so happy we chose his Airbnb.. Thank you so much, Christian! You are one of a kind and your place is so cool.

5 out of 5 average rating, 37 reviews

Viva La Playa: Oceanview 3BR Retreat

BrigidRating, 5 stars1 month ago

We had a fantastic stay at Karen's place in the Keys! It perfectly suited the needs of our family of 5- 3 cute and cozy bedrooms, 2 full bathrooms, Beautiful and fully stocked kitchen, Washer/dryer to take care of beach towels and swim suits, Deck that overlooks the ocean that was perfect for morning coffee with the sunrise, and many more amenities. It was centrally located in the Keys to allow for travel from Key Largo to Key West in a little over an hour to each end. All in all, one of our favorite family spots, and we hope to one day visit again soon! Thank you so much!

5 out of 5 average rating, 11 reviews

Marathon Paradise

DanielRating, 5 stars1 month ago

A great place to stay for our family. Juan was an excellent communicator. Will definitely be back to stay again!

5 out of 5 average rating, 51 reviews

Luxury Boating Paradise+Pool+Sailing Kayaks

RickRating, 5 stars1 week ago

We had an amazing family weekend here! The home was spotlessly clean, beautifully maintained, and incredibly well equipped with everything we needed. The ping pong table, video games, and sail kayaks were huge hits with the whole family. We also rented a boat, and having a private dock made that experience seamless and unforgettable. The location was quiet, safe, and perfect for quality time—cozy enough to relax, yet close to everything we needed. It truly felt like a home away from home. For all the amenities and the exceptional condition of the property, the price was a fantastic value. We’ve stayed in many vacation rentals, but this one stands out as one of the best. We’re already looking forward to coming back. Highly recommended!

Superhost

Boat in Marathon

4.73 out of 5 average rating, 71 reviews

Private 45’ Luxury Yacht

Janice Rating, 5 stars1 month ago

A wonderful experience! We enjoyed our week on the Yacht, "Comfortably Numb". The Host was exceptional. Keliy, was very clear and attentive. She recommended bike rentals, local attractions, beach location, and views from the deck. The place smelled fresh and clean. The indoor temperature was cool. The humidity was controlled. We loved the bean bag seats to watch the sunrise and sunsets from the deck. The indoor accommodations was very large, roomy, and comfortable. We plan to reserve this place again in the future. We learned alot since we are are planning to purchase a yacht for full time living and charter boat fishing. Keliy was a sweetheart with engaging communication as we asked lots about boating questions. Our first visit to The Keys was amazing. Thank you! Janice Correa & Captain Bernie Kohler