Vacation rentals in Boot Key Harbor

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Top-rated vacation rentals in Boot Key Harbor

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Guest favorite

Villa in Marathon

4.95 out of 5 average rating, 123 reviews

Private 4/3 Pool Heater/Dock/Kayaks/Bikes,etc

Wake up to breathtaking water views at our 4-bedroom, 3-bathroom villa. Enjoy the 1800 sq ft layout, fully equipped kitchen w/stainless steel appliances, and granite countertops. Sleeps 10 with memory foam beds. Outside, relax by your private heated pool (winter) and tiki-shaded area. Fish from the 32' dock or use the BBQ gas grill. Includes 2 kayaks, 2 paddleboards, and 4 adult bikes for a 5-minute ride to Sombrero Beach. Exterior cameras for security. Vacation License #VACA-22-40. Book now!

Guest favorite

Guest suite in Marathon

4.98 out of 5 average rating, 193 reviews

Casa Mariposa: Easy walk to Sombrero Beach

***SUMMER SALE*** Book your relaxing getaway now at Casa Mariposa in the heart of the Florida Keys! See why we were rated by Forbes the #1 Airbnb for couples south of Orlando for 2024 and a top 10 Airbnb in Florida. Step from your private suite to our 50' chilled lap pool surrounded with swaying palm trees and tropical foliage, large coral stone patio, and extensive tropical gardens. Avoid beach parking fees at beautiful Sombrero Beach with a short stroll from your suite at Casa Mariposa!

Guest favorite

Home in Marathon

4.94 out of 5 average rating, 35 reviews

Tropical Dream Vacation - 3bdrm/2bath CANAL FRONT!

Family friendly, newly renovated, modern beach home located in Marathon, the heart of the Florida Keys - CANAL FRONT! This property contains a spacious environment, with 3 bedrooms, 2 bathrooms, an open concept living room that has a queen size sofa bed, a private pool, and a 50 ft private dock. It is located less than one mile (0.8 miles) from the beautiful Sombrero Beach! Ample parking space for cars and a boat trailer. We hope you enjoy our Tropical Dream Vacation Home! #VACA-22-149

Superhost

Home in Marathon

4.91 out of 5 average rating, 11 reviews

Sombrero Beach Getaway

Spend your days boating, fishing, and swimming in the South Florida sunshine when you escape to this waterfront home in Marathon! Scenically, this home features a 90 -foot dock (with a filet cleaning table and water), a private heated outdoor pool, and a patio where you can grill your fresh catch each evening. We are located just minutes away from restaurants, bars and entertainment. Key West is less than an hour from the property. We can provide help with Golf Cart and Boat rentals.

Guest favorite

Guest suite in Key Colony Beach

4.99 out of 5 average rating, 93 reviews

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

A perfect get-away for couples or budget travelers, the Turtle-by-the-Sea Guest Suite 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. Newly rebuilt & reimagined, owners Mallory & Steve infused their love of the Keys & its surrounding ocean into every aspect of their waterside home.

Superhost

Villa in Marathon

4.91 out of 5 average rating, 229 reviews

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!

Guest favorite

Home in Marathon

4.99 out of 5 average rating, 121 reviews

Sea Ray Cove , 75’ boat dock, 1 block from beach!

2024 - New Weber grill 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.

Guest favorite

Condo in Marathon

4.9 out of 5 average rating, 112 reviews

Christmas Getaway – Pool, Balcony & Marina Access!

Welcome to THE MAD MAHI – your ultimate waterfront getaway! This stunning 1-bedroom condo (sleeps 4) in Marathon features a full kitchen, private balcony, resort pool, Tiki Bar, restaurant, and full-service Marina with boat ramp, trailer parking, and boat slips available. Enjoy exclusive access to the CABANA CLUB with its private beach, pool, and bar & grill. Perfectly located between Key Largo and Key West, with shops and dining just a walk or bike ride away.

Guest favorite

Villa in Marathon

5 out of 5 average rating, 25 reviews

Sombrero Beach house with dock and tropical pool

Casa MarBella @ Sombrero Beach offers plenty of indoor and outdoor space. Enjoy our beautiful pool with flowing waterfall which can be heated for an additional fee. Please inquire before booking. Dock on deep water canal with shore power and commercial ice maker in the garage. Weber gas grill, convenient outdoor counter with built-in ice chest and sink. Large yeti cooler with wheels, paddle board, 12ft fishing kayak, beach tricycle, pedal boat and 4 bikes.

Guest favorite

Home in Marathon

4.88 out of 5 average rating, 33 reviews

Luxe Waterfront Keys Cottage- with Jacuzzi

Meet Casa Kokomo, a laid-back luxe retreat in the Florida Keys. This home offers the perfect blend of salt life and relaxation. Plenty of natural light enters through the large windows in the sunroom, creating a warm ambiance. For those who enjoy the outdoors, step out to the backyard for fresh ocean air, unwind in your private hot tub or visit nearby sand-bars. Property includes a 32-foot private dock, with direct ocean access. Max boat size 30Ft.

Guest favorite

Home in Marathon

4.9 out of 5 average rating, 146 reviews

Waterfront Cozy Modern Retreat w/Deep Canal

Welcome to our beautiful waterfront home in Marathon! Our smoke-free property is modern, clean and features a 37ft long concrete dock, perfect for boating and fishing enthusiasts. With easy access to the movie theater, Sombrero Beach, Turtle Hospital, Publix, Walgreens, and delicious restaurants, you'll have everything you need right at your fingertips. We can't wait for you to experience the peacefulness and convenience of our lovely home.

Superhost

Condo in Marathon

4.88 out of 5 average rating, 214 reviews

Sombrero Beach Tropical Getaway

Find an ideal home base for exploring the Florida Keys at our canal-front condo in Marathon, a cozy escape with a private balcony and easy access to the open ocean. You can spend your days boating, fishing, snorkeling, and lounging at Sombrero Beach, and return home each evening to a comfortable living space, a flatscreen cable TV, and an on-site Pool, tiki bar and restaurant! Vacation Rental Number - VACA-21-19