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, 119 reviews

4/3 Private Pool w Heater/Dock/Kayaks & more incl.

Our home is close to grocery stores, restaurants and dining, the beach, family-friendly activities, and public transport. You’ll love my place because of the high ceilings, the views, the location, the people, and the ambiance. Our place is good for couples, business travelers, and families (with kids). Included in the rental you'll have access to 4 bicycles for adults and 2 tandem kayaks and 2 paddle boards during your stay. We have a cooler, 2 beach umbrellas and 4 beach chairs for your use.

Jun 1 – 8

G$145,722 GYD per night

Guest favorite

Guest suite in Marathon

4.98 out of 5 average rating, 184 reviews

Casa Mariposa: Easy walk to Sombrero Beach

Book your relaxing getaway now at Casa Mariposa in the heart of the Florida Keys! See why we were rated a top 15 cozy retreat in the Keys, 1 0f 24 amazing AirBNB rentals in the Keys, and, in 2023, 1 of 23 Amazing Airbnbs In Florida Keys. Step out from your private suite to our 50' lap pool surrounded with tropical foliage, large patio, and tropical gardens. Avoid beach parking fees with a short walk from your suite at Casa Mariposa! Contact us if you are interested in other lengths of stay.

Jul 30 – Aug 6

G$45,270 GYD per night

Guest favorite

Home in Marathon

4.97 out of 5 average rating, 35 reviews

Waterfront Private Home w/Pool-Family&Pet Friendly

Welcome to Casa Pina! Located right in the heart of Marathon. Enjoy your trip to the keys in this stunning custom canal-front, 3 bed/3 bath private house comfortably accommodating 8 ppl, with soaring 25 ft wood ceilings, your own private pool, large yard, 40 ft dock, kayaks, paddle boards, grill. Plus a huge screened in Patio and game room with a pool table. Driveway with Ample parking, enough for four cars+ or three and a boat. This house has everything you need for your Florida Keys getaway!

Sep 29 – Oct 6

G$95,109 GYD per night

Guest favorite

Villa in Marathon

5.0 out of 5 average rating, 11 reviews

LUX 2-Bedroom. Waterfront. NEW POOL-FALL 2024

On a wide, deep-water canal, this Resort like home features over 1,700 sq. ft. with 2 bedrooms, 2 bath plus a sitting room. You'll be captivated by the view from the glass doors leading onto a sprawling deck overlooking the crystal-clear canal. Chef's kitchen w/granite countertops, professional gas range, all stainless appliances and an enormous island. Bright sitting room, perfect for appreciating the view. 60' seawall with plenty of depth for a deep draft boat and ample turn around space.

Aug 6 – 13

G$91,861 GYD per night

Superhost

Home in Marathon

4.87 out of 5 average rating, 15 reviews

Serenity at Sombrero | Private Pool, Spa & Dock

Stay in Luxury! Enjoy the new construction and décor of this sparkling clean waterfront home. Brand new dock and pool with built in hot tub! Your stay in Marathon will be perfect! Minutes from Sombrero Beach located on a beautiful canal minutes from everything including the Turtle Hospital, Aquarium Adventures, shopping, bait shops, restaurants, and fast food. The secluded location of this house will let you decompress in peace while still being close to everything Marathon has to offer.

Jan 25 – Feb 1

G$108,926 GYD per night

Guest favorite

Guest suite in Key Colony Beach

4.99 out of 5 average rating, 82 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.

May 25 – Jun 1

G$40,194 GYD per night

Superhost

Villa in Marathon

4.89 out of 5 average rating, 145 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!

Dec 16 – 23

G$86,231 GYD per night

Guest favorite

Home in Marathon

4.99 out of 5 average rating, 106 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.

Dec 2 – 9

G$156,154 GYD per night

Guest favorite

Villa in Marathon

5.0 out of 5 average rating, 18 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.

Sep 21 – 28

G$198,542 GYD per night

Guest favorite

Home in Marathon

4.9 out of 5 average rating, 21 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.

Mar 24 – 31

G$67,185 GYD per night

Guest favorite

Home in Marathon

4.9 out of 5 average rating, 136 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.

Mar 15 – 22

G$73,616 GYD per night

Guest favorite

Condo in Marathon

4.87 out of 5 average rating, 191 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 - PLR2020-00756

Nov 25 – Dec 2

G$48,677 GYD per night