FLORIDA KEYS VACATION RENTALS
Finest Luxury Vacations offers you a variety of hand selected Florida Keys vacation rentals. Choose beach houses, condos and cottages in Key Largo, Key West, Marathon, Islamorada, and more. Florida Luxury Vacation Rentals offers you the opportunity to explore the wonderful keys, a tropical beach paradise from coast to coast.
BOOK YOUR FLORIDA KEYS VACATION RENTALS DIRECT & SAVE!
Direct information is provided to you as a directory. Enjoy browsing through all our wonderful luxury vacation rentals for tropical villas, beach condos, secluded cabins. Don’t forget about our exciting All Inclusive Packages, Wedding Destinations, Resort Vacation Packages, Family Vacations and so much more! You have the opportunity to see all we have to offer, so you can contact the provider directly for information, availability, reservations, special deals.
FLORIDA KEYS VACATIONS
MARATHON PROPERTIES...
El Tesoro
8 Guests | 3 Bedrooms | 2 Bathrooms | Canal Front Pool Home
Starting at $265 per Night
This home is the perfect Florida Keys get-away; it truly lives up to its name EL Tesoro! A 3 Bedroom, 2 Bath, Waterfront Home with in-ground heated pool, 40 ft of dockage, a ladder, a fish cleaning table, outdoor kitchen, and propane grill, yard games, bait freezer…
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Starfish Retreat
6 Guests | 2 Bedrooms | 2 Bathrooms | Waterfront Townhome
Starting at $215 per Night
Beautiful and spacious brand new vacation home with a boat slip #2 is included which will accommodate up to a 25 ft boat. This modern home is perfect for relaxing and getting away from it all. Upstairs deck faces the picturesque Gulf of Mexico…
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Dolfan Oceanfront Cottage
8 Guests | 4 Bedrooms | 2 Bathrooms | Oceanfront Pool Home
Starting at $462 per Night
This beautiful and spacious home has Direct Oceanfront Living. Ocean views and deep water dockage with boating access to the Atlantic Ocean. The hot tub, lounge chairs, room for outdoor seating, and beautiful landscaping make entertaining by the ocean easy…
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Tropical Seahorse at Coral Lagoon
8 Guests | 3 Bedrooms | 2.5 Bathrooms | Waterfront Luxury Villa
Starting at $250 per Night
Tropical Seahorse at Coral Lagoon – A 3 bedroom, 2.5 bathroom villa with resort pool at Coral Lagoon. The Tropical Seahorse features an airy layout and alluring nautical themed décor throughout the entire home…
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Flip Flop Inn
8 Guests | 3 Bedrooms | 3 Bathrooms | Waterfront Townhome
Starting at $200 per Night
~ Flip Flop Inn at Bonefish Yacht Club ~ Spacious with tons of natural light 3 BR 3 BA at one of Marathon, Florida Keys most beautiful communities, Bonefish Yacht Club ~ Magnificent views from this home…
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Captain's Cure at Indigo Reef
8 Guests | 3 Bedrooms | 2.5 Bathrooms | Pet Friendly Waterfront Villa
Starting at $398 per Night
Escape to a tropical haven in the heart of the Florida Keys with our charming 3-bedroom, 2-bathroom townhome at Indigo Reef Resort. Nestled along the stunning Gulf of Mexico, this vacation rental promises breathtaking views, top-notch amenities…
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Vaca Cut Sunset
12 Guests | 5 Bedrooms | 4 Bathrooms | Waterfront Pool Home
Starting at $857 per Night
Location Location Location! Located on the Vaca Cut Channel in Marathon, with immediate boating access to the Atlantic Ocean and the Gulf of Mexico. Spoil yourself at this gorgeous property with open water and Sunset views…
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The Lazy Lime
10 Guests | 5 Bedrooms | 2 Bathrooms | Oceanfront Pool Home
Starting at $1000 per Night
The Lazy Lime is a stunning gulf front newly updated 5 bedroom 3 bathroom single family home. Ask about adding the garden villa to add another 1/1 with a second pool! Looking for the perfect vacation retreat? Look no further! This stunning 5 bedroom home has it all!…
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Coastal Key
6 Guests | 3 Bedrooms | 2 Bathrooms | Canal Front Pool Home
Starting at $315 per Night
Sombrero Beach area of Marathon. Beautifully decorated brand new home, located down the street from Sombrero Beach. This home has a private pool, private dock, fish cleaning station, bait freezer, outdoor TV in covered patio, gas grill, 4 bikes, 2 kayaks, 2 paddle board!…
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Angler's Retreat
8 Guests | 3 Bedrooms | 2 Bathrooms | Canal Front Vacation Home
Starting at $225 per Night
Enjoy the Florida Keys in this stunning 3 bedroom / 2 bath updated single family located minutes away from Sombrero Beach! This updated home comes with a fully equipped kitchen, large flat screen tv in the living room and gorgeous water views…
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PELAGIC RETREAT
6 Guests | 2 Bedrooms | 2 Bathrooms | Waterfront Family Vacation Home
Starting at $1800 per Week
Perfectly updated and appointed canal-front home on the Gulf side. This location is great for diving, boaters, lobstering, and just relaxing! Two bedroom, two and a half bathroom stilted half-duplex with upgraded furnishings…
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“FLORIDA KEYS VACATION RENTALS “
SOMBRERO BEACH BUMMIN’
8 Guests | 3 Bedrooms | 2 Bathrooms | Canal Front Family Vacation Home
Starting at $2300 per Week
Privacy galore at this great location on Sombrero Beach Rd! Famous Sombrero Beach is approximately half mile down the dedicated bike path from this stilted 3 bedroom single family home!…
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“FLORIDA KEYS VACATION RENTALS “
IT’S ABOUT KEYS TIME
8 Guests | 4 Bedrooms | 3 Bathrooms | Waterfront Vacation Home
Starting at $2000 per Week
Well appointed, spacious half duplex with 37.5 ft of deep water dockage on a wide canal in the heart of Key Colony Beach. This well-kept, updated home has living space on 3 levels!…
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OCEAN EAST BEAUTY
8 Guests | 3 Bedrooms | 2 Bathrooms | Canal Front Cozy Cottage with Pool
Starting at $5500 per Week
Lovely 3 bedroom, 2 bathroom single family home on a deep canal with instant access to the ocean. Freshly decorated, cozy Keys cottage! Quiet, corner lot location! Enjoy the open waters of the Atlantic Ocean…
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“FLORIDA KEYS VACATION RENTALS “
SEASIDE POOL HOME ON VACA CUT
6 Guests | 3 Bedrooms | 2 Bathrooms | Waterfront Vacation Pool Home
Starting at $2400 per Week
Sitting on the edge of Vaca Cut as it opens to the Gulf of Mexico this home has fabulous views of the Gulf of Mexico and immediate boating access to the Gulf or through the Cut to the Ocean…
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CHARMING HOME IN KEY COLONY
8 Guests | 3 Bedrooms | 2 Bathrooms | Waterfront Vacation Home
Starting at $1600 per Week
Located on 11th Street in Key Colony Beach this 3 bedroom, 2 bath home has just been extensively remodeled with new tile floors throughout, all new kitchen appliances and granite counters…
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Vista Del Mar
8 Guests | 3 Bedrooms | 3 Bathrooms | Pet Friendly Waterfront Pool Home
Starting at $700 per Night
Located on a serene private canal, this property offers the ultimate combination of tranquility and adventure. Prepare to be captivated by the stunning open ocean views that will greet you each morning and provide the perfect backdrop for unforgettable sunsets in the evenings…
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Aqua Vista
6 Guests | 2 Bedrooms | 2 Bathrooms | Pool Home with Tiki Hut
Starting at $250 per Night
Aqua Vista – A 2 bedroom, 2 bathroom, single family, private pool home in Marathon. This home is a stilt style home accessible by stairs located at the front and back of the house. Inside you'll find tasteful decor and comfortable furnishings…
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Paradise Cove
8 Guests | 3 Bedrooms | 2 Bathrooms | Pet Friendly Waterfront Pool Home
Starting at $392 per Night
Luxurious Waterfront Retreat with Private Pool and Dockage. Welcome to our exquisite 3-bedroom, 2-bathroom vacation home nestled in the heart of paradise! This upscale waterfront retreat offers an unforgettable blend of comfort, style, and convenience…
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Tropical Retreat at Coral Lagoon
8 Guests | 3 Bedrooms | 2.5 Bathrooms | Pet Friendly Waterfront Pool Home
Starting at $250 per Night
Tropical Retreat at Coral Lagoon – A 3 bedroom, 2.5 bathroom, villa with resort pool at Coral Lagoon. Stunning and tranquil is the coral lagoon resort located immediately adjacent to Key Colony Beach. This unit does have a dedicated boat slip…
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Casa Playa
10 Guests | 4 Bedrooms | 3.5 Bathrooms | Elite Luxury Pool Home
Starting at $697 per Night
Casa Playa – A 4 bedroom, 4 bathroom, single family, private pool home in Marathon. With technology throughout, stunning views, and a carefully designed outdoor recreation area, Casa Playa is a Luxury Marathon Vacation Rental you must see for yourself…
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LITTLE VENICE GEM
6 Guests | 3 Bedrooms | 2 Bathrooms | Single Family Vacation Home
Starting at $1400 per Week
Little Venice Gem! Right in the heart of Marathon sits this adorable 2 bedroom, 2 bathroom single family home just seconds from the open Atlantic and Vaca Cut! Situated on a corner lot, this home has 55 ft of deep water dockage…
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COCO PLUM WATERWAY
8 Guests | 3 Bedrooms | 2 Bathrooms | Canal Front Vacation Home
Starting at $1650 per Week
Fresh, clean, updated and excellent deep-water boating with expansive canal views is what you will find in our newest addition to our Coco Plum Beach neighborhood!…
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OCEANSIDE SPACIOUS GROUND LEVE
8 Guests | 3 Bedrooms | 2 Bathrooms | Canal Front Single Family Home
Starting at $1500 per Week
Oceanside canal-front single family home with dockage awaits you! Spacious 3 bedroom, 2 bath ground level home with deep water dockage on a quiet street in the heart of Marathon…
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CHARMING GULFSIDE POOL HOME
4 Guests | 2 Bedrooms | 2 Bathrooms | Second Floor End Unit Condo Rental
Starting at $2100 per Week
Cute 2 bedroom, 2 bath end unit condo on the second floor at Harbor House, overlooking Boot Key Harbor. The screened wrap-around balcony offers great views of the active Harbor…
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INDIGO REEF 5
6 Guests | 3 Bedrooms | 2.5 Bathrooms | 2 Story Townhome
Starting at $2595 per Week
This gorgeous, villa boasts amazing, private unobstructed views, excellent furnishings. You feel like you’re on the water from inside your home and can enjoy the sunset from inside the unit, or outside on the upstairs or downstairs porches…
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OSPREY POINTE
6 Guests | 2 Bedrooms | 2.5 Bathrooms | Luxury Gulf Front Condo
Starting at $2100 per Week
2/2.5 Condo Unit, Direct Gulffront views – Wrap-around balconies Osprey Point at Gulfpointe II is a wonderful vacation property that boasts 180-degree views of the Gulf of Mexico and Vaca Cut…
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Sun of a Beach
16 Guests | 7 Bedrooms | 5 Bathrooms | Pet Friendly Waterfront Home
Starting at $715 per Night
FRIDAY TO FRIDAY ONLY – Enjoy this beautiful split level home in the heart of the Florida Keys. This unique property can sleep up to 16 guests in 7 bedrooms. Two families can enjoy privacy with a split floor plan…
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Palm Point
8 Guests | 3 Bedrooms | 2 Bathrooms | Waterfront Vacation Home
Starting at $325 per Night
Beautiful three bedroom, two bath home in Marathon has a fantastic Gulf view and quick, easy access to open water! Very spacious, concrete dock, sundeck on top of home makes for spectacular sunrise and sunset scenes…
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Mahi Mahi House
8 Guests | 3 Bedrooms | 4 Bathrooms | Waterfront Vacation Home
Starting at $495 per Night
Mahi Mahi House is a stunning modern 3 bedroom / 4 full bathroom single family home with a heat optional pool and dockage with spectacular water views! This home offers ample living space on the lower level with open concept living room & dining area…
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Ocean's Paradise
10 Guests | 4 Bedrooms | 3 Bathrooms | Pet Friendly Vacation Pool Home
Starting at $750 per Night
Looking for the perfect vacation retreat? Look no further! This stunning 4 bedroom home has it all! Located in the very desirable neighborhood of Sombrero Beach and within walking distance to the beach itself, this home does not disappoint…
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Shangri-La
8 Guests | 3 Bedrooms | 3 Bathrooms | Pet Friendly Water Front Pool Home
Starting at $572 per Night
Shangri-La, Grand upscale beautiful home in the quiet Marathon Florida Keys neighborhood. The Lighted pool area with automatic mosquito control. Outside bait freezer convenient to the dock. Fish cleaning table with water and power…
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Casa De Tiki
8 Guests | 4 Bedrooms | 3 Bathrooms | Waterfront Pool Home
Starting at $300 per Night
Imagine waking up each morning of your vacation to an amazing water view like this. This 4/3 duplex in Marathon, FL has it all. It is a BRAND NEW unit that has been professionally decorated. The unit boasts a family size spacious layout of about 1700 square feet…
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Casa Del Mar
10 Guests | 4 Bedrooms | 5 Bathrooms | Exclusive Elite Luxury Pool Home
Starting at $500 per Night
Marathon Florida Keys vacation rental with Fantastic outdoor entertainment area with outdoor bar and private heated pool. This is the home to turn that dream of a Florida Keys vacation home into reality!…
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Cobia House
8 Guests | 3 Bedrooms | 2 Bathrooms | Pet Friendly Waterfront Vacation Home
Starting at $283 per Night
Welcome to Cobia House ~ Located in the Heart of the Florida Keys! Picture yourself enjoying sea breezes from your balcony overlooking the canal. The open and airy layout of this home provides an inviting and relaxing atmosphere…
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Reel Relaxin'
12 Guests | 5 Bedrooms | 4 Bathrooms | Pet Friendly Luxury Pool Home
Starting at $350 per Night
This professionally decorated, 3430 square foot home, is located in prestigious Sombrero Isles and close to famed Sombrero Beach. The upscale, coastal chic decor will leave you feeling pampered and relaxed on your Florida Keys Vacation…
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Dolphin Cove
6 Guests | 2 Bedrooms | 2.5 Bathrooms | Pet Friendly Townhome
Starting at $209 per Night
Beautiful townhome in Bonefish Yacht Club by Coco Plum Vacation Rentals Marathon Florida Keys. Whether you're seeking a romantic escape or a family adventure, this 2-bedroom, 2-bathroom, 3-level townhome promises an unforgettable experience…
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R & Ks Marathon Paradise
6 Guests | 2 Bedrooms | 2 Bathrooms | Waterfront Pet Friendly Duplex
Starting at $215 per Night
Boaters, fishermen, families, and YES even your 4 legged friends will enjoy our beautiful 2 bedroom/2 bath open floor plan duplex. Property is located on the widest and deepest canal in Marathon. Features easy access to both the Gulf of Mexico and the Atlantic Ocean…
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The Beach House
6 Guests | 2 Bedrooms | 2 Bathrooms | Single Family Pool Home
Starting at $280 per Night
The Beach House is a stunning and spacious 2bed/2bath with private pool & walking distance to Sombrero Beach! This home offers an open concept living, kitchen and dining area. The living room is spacious with comfortable furnishings…
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Tequila Sunrise
8 Guests | 3 Bedrooms | 3 Bathrooms | Waterfront Pool Home
Starting at $525 per Night
Tequila Sunrise does not disappoint with 3 bedrooms, 3.5 baths, a well appointed kitchen, large spacious living room, large pool and a half a mile from the picturesque Sombrero Beach…
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Pozitively Bliss
8 Guests | 3 Bedrooms | 2 Bathrooms | Waterfront Pool Home
Starting at $300 per Night
This home is spectacular inside and out. Beautifully updated, this home is full of modern amenities with a laid back style located in the desirable Sombrero Beach neighborhood. It offers an open concept living…
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Villa Bella
7 Guests | 3 Bedrooms | 2 Bathrooms | Waterfront Vacation Home
Starting at $285 per Night
Villa Bella 3bed/2bath single family waterfront home in Key Colony Beach with easy kayak launch, dockage & cabana club access! The property is stilted and the main living space is located upstairs. When you walk in, you are greeted with open water views…
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Harbor Hideaway
6 Guests | 2 Bedrooms | 2 Bathrooms | Waterfront Vacation Home
Starting at $175 per Night
Harbor Hideaway is a quaint 2bed/2bath near the Seven Mile Bridge. It features an open concept living rooms, dining and kitchen. There are 2 bedrooms and 2 bathrooms. Plenty of parking and great outdoor space that overlooks the canal….
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Tipsy Turtle
10 Guests | 4 Bedrooms | 3 Bathrooms | Waterfront Pool Home
Starting at $315 per Night
Sombrero Beach is right down the road from this beautiful and well-maintained home in the Heart of Marathon. Close to grocery stores, restaurants and fun things to do. Sombrero Light is right offshore for your snorkeling and diving pleasure….
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Casa Mare
12 Guests | 5 Bedrooms | 6.5 Bathrooms | Luxury Oceanfront Pool Home
Starting at $1375 per Night
The property has 120 feet of sandy ocean beachfront on a 1.1-acre lot. The beach is totally private. A treasure on the Ocean in the heart of the Florida Keys. A private white sandy beach on the Atlantic Ocean….
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BOOT KEY HARBOR HIDEAWAY
4 Guests | 2 Bedrooms | 2 Bathrooms | Waterfront Beach Cottage
Starting at $1100 per Week
Boot Key dream boating location! Fisherman’s paradise on Boot Key Harbor has instant open Atlantic Access and Gulf acces via Seven Mile Bridge. 2 bedroom 2 bathroom charming waterfront home boasts an open floor plan….
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“FLORIDA KEYS VACATION RENTALS”
THE COCO PALM HOUSE
10 Guests | 4 Bedrooms | 3 Bathrooms | Waterfront Beach Home
Starting at $2800 per Week
This 4 bedroom, 3 bathroom home is located in the Coco Plum Beach neighborhood, which is known for excellent boating access with deep, wide canals. Newly built with beauitful tile floors, tall ceilings, a sophisticated and clean amibance and incredibly decorated….
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“FLORIDA KEYS VACATION RENTALS”
SALTY MERMAID
8 Guests | 4 Bedrooms | 3 Bathrooms | Waterfront Pool Home
Starting at $1995 per Week
Check out Anglers at Sombrero Canal Front Townhome with a private pool and 30 ft of dockage! Just minutes to the stunning Sombrero Beach, this Villa-style home is perfectly located in the heart of the Florida Keys….
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“FLORIDA KEYS VACATION RENTALS”
DOLPHIN OASIS
10 Guests | 4 Bedrooms | 3.5 Bathrooms | Waterfront Pool Home
Starting at $3600 per Week
Sleeps 10, large heated pool, Hot tub, Sandy Beach area, 90′ Dock, Ocean Kayaks This 4 bedroom 3 Bath House has ample sleeping options for every type of family/friend gathering and provides parking for several vehicles…
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“FLORIDA KEYS VACATION RENTALS”
Sea Haven
8 Guests | 3 Bedrooms | 2 Bathrooms | Pet Friendly Pool Home
Starting at $350 per Night
A 3 bedroom, 2 bathroom, single-family, updated, private pool home. Sea Haven is the perfect Marathon vacation home with a private pool, updated kitchen, dock, and expansive outdoor living space with beach volleyball, outdoor games, and kayaks included!…
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Pier Pressure
10 Guests | 4 Bedrooms | 4 Bathrooms | Luxury Pool Home
Starting at $371 per Night
Located on the water and not far from the beach, Pier Pressure embraces the waterfront vacation lifestyle, with plenty of room for the entire family or a group of friends traveling together. Pier Pressure is the ideal base for your Luxury Florida Keys Vacation Rental retreat…
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Adventures in Paradise
10 Guests | 4 Bedrooms | 3 Bathrooms | Pet Friendly Luxury Pool Home
Starting at $400 per Night
“Adventures in Paradise” is located just a short walk or drive down to famed Sombrero beach. Located right off the main beach strip this home is centrally located to everything you need for a fantastic Florida Keys vacation…
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Barracuda Bungalow
6 Guests | 2 Bedrooms | 1 Bathrooms | Pet Friendly Waterfront Retreat
Starting at $232 per Night
Welcome to Barracuda Bungalow ~ Located in the Heart of the Florida Keys! Picture yourself enjoying sea breezes from your balcony overlooking the canal. The open and airy layout of this home provides an inviting and relaxing atmosphere…
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Indigo Reef Pirates Cove
8 Guests | 3 Bedrooms | 2.5 Bathrooms | Waterfront Town Home
Starting at $261 per Night
Escape to paradise and enjoy all the comforts of home in this stunning 3-bedroom, 2.5-bathroom townhouse in the desirable Indigo Reef community. Boasting elegant coastal decor and luxurious amenities…
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Serenity
12 Guests | 5 Bedrooms | 4 Bathrooms | Oceanfront Pool Home
Starting at $600 per Night
Large, Luxurious, Open Water View. Enjoy life at Serenity with unobstructed views of the Vaca Cut from this amazing home! Located on the ocean side, it’s the perfect place to create memories on your vacation. It comfortably sleeps 12…
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5 Seas Retreat
10 Guests | 4 Bedrooms | 2 Bathrooms | Waterfront Pool Home
Starting at $429 per Night
Sandy Beach a Rarety for the Keys. Gorgeous open water sunset views await you at this fully furnished tropical waterfront vacation home. This home is located right on Vaca Cut and facing West for the sunsets every night!…
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Vista Marquesa
10 Guests | 4 Bedrooms | 3 Bathrooms | Pet Friendly Oceanfront Pool Home
Starting at $625 per Night
The Vista Marquesa offers the most expansive open ocean view of almost 180 degrees. It features four bedrooms and three bathrooms, a huge private pool, a deck extending out over the Atlantic Ocean, and over 50 feet of dockage…
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Bob's Harbor
6 Guests | 2 Bedrooms | 2 Bathrooms | Pet Friendly Canal Front Home
Starting at $195 per Night
Bob's Harbor View is a quaint 2bed/2bath near the Seven Mile Bridge. It features 2 living rooms, kitchen, 2 bedrooms, 2 bathrooms and great outdoor space that overlooks the canal. Seven night minimum – no exceptions…
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Seas The Day
8 Guests | 3 Bedrooms | 2.5 Bathrooms | Pet Friendly Vacation Home
Starting at $208 per Night
Seas the Day is a stunning 3bed/2.5bath townhouse style single family home right in the heart of Marathon. The home features an open floor plan for the living, dining & kitchen. This property is “dog friendly”…
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Refuge on the Reef at Coco Plum Beach
12 Guests | 5 Bedrooms | 5 Bathrooms | Pet Friendly Pool Home
Starting at $375 per Night
Waterfront Coco Plum Beach home with a private resort-style pool, 75′ dock. Relax your cares away at Refuge on the Reef! Read a book in the shady outdoor hammock, take a lazy day to float in the pool or enjoy your margarita poolside under the tiki hut…
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Sunsets in Paradise
12 Guests | 5 Bedrooms | 3 Bathrooms | Pet Friendly Oceanfront Pool Home
Starting at $400 per Night
A Florida Keys vacation starts with the right accommodations, and Sunsets in Paradise delivers. Picture yourself enjoying the sunset on the Gulf of Mexico from your own private patio and private. With all of the amenities available at this property directly on the water, you may not need to go anywhere…
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Bonefish Bliss
8 Guests | 3 Bedrooms | 3 Bathrooms | Townhome in Bonefish Marina
Starting at $350 per Night
Beautiful Bonefish Yacht Club townhome! Overlooking the marina, this 3 story townhome, end unit has been thoughtfully updated and curated for a tranquil hotel experience with all the comforts of home…
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Serenity Bay
8 Guests | 3 Bedrooms | 2 Bathrooms | Pet Friendly Waterfront Home
Starting at $200 per Night
Serenity Bay features a newly remodeled interior and exterior that accentuates the open, breezy floor plan of the home. With two living areas this home is spacious and airy providing plenty of space to enjoy your stay here in paradise…
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Mermaid Manor
10 Guests | 4 Bedrooms | 2.5 Bathrooms | Pet Friendly Waterfront Home
Starting at $300 per Night
Mermaid Manor offers the privacy, space, and amenities of a modern island retreat you would expect in your Florida Keys Vacation Rental. With four bedrooms, multiple common spaces, and island decor, you will feel refreshed in no time!…
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Casa Blanca By the Gulf
12 Guests | 5 Bedrooms | 3 Bathrooms | Pet Friendly Pool Home
Starting at $650 per Night
Casa Blanca By The Gulf is a Florida Keys Paradise for Everyone. This is a modern design home with sleek lines, spacious decks and Crystal waters of the Gulf of Mexico a hop skip and a jump from your back door. The modern and nautical theme reminds you to relax and enjoy the sun…
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Snorkel Shack
10 Guests | 4 Bedrooms | 3 Bathrooms | Pet Friendly Waterfront Pool Home
Starting at $500 per Night
This home is located landside of Sombrero Light. If you take your boat or rent a boat it is a Lighthouse located on the incredible Living reef right off of Marathon and located in the Atlantic Ocean which has incredible Snorkeling and Diving….
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Paradise Palms
10 Guests | 4 Bedrooms | 3 Bathrooms | Waterfront Pool Home
Starting at $515 per Night
Paradise Palms is an updated 4 bedroom, 3 bath single family home that overlooks Sister's Creek. This home is perfect for beach lovers, golfers and boaters! The home offers 50 feet of deep water dockage with direct access to the Atlantic Ocean…
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Seaglass Cottage
10 Guests | 4 Bedrooms | 3 Bathrooms | Pet Friendly Oceanfront Pool Home
Starting at $700 per Night
Oceanfront White Sand Beach Home with a dock for your boat and Ocean views from practically every room. Three single Kayaks included. This Modern 4 bedroom, 3 bath Oceanfront Home on Coco Plum Beach has the sound of the ocean lapping on the shore…
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Gulfstream and Sunsets
14 Guests | 6 Bedrooms | 4 Bathrooms | Pet Friendly Oceanfront Pool Home
Starting at $775 per Night
Delightful location on the Gulf of Mexico! Sunsets every night from this home, facing west.
Spacious 6 bedroom, 4 bath home with large open living and dining room area. Open views of the Open water and pool can be observed from practically every room in the house…
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The Garden Villa
3 Guests | 1 Bedrooms | 1 Bathrooms | Quaint Pool Villa
Starting at $130 per Night
The Garden Villa is a stunning 1bed/1bath unit with its own private pool. This unit has fresh paint, all new furniture and landscaping! It is a tranquil getaway for a small family or a couple…
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Seaside Cottage
4 Guests | 1 Bedrooms | 1 Bathrooms | Pet Friendly Waterfront Cottage
Starting at $129 per Night
Beautiful Conch Cottage, the most adorable 1 bedroom 1 bath waterfront Doll house in the Middle of Marathon, with Ocean views from the Dock. Your own Jacuzzi to watch the stars at night. One level home with a big deck off of the back of the house…
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Reel Knotty
10 Guests | 4 Bedrooms | 4 Bathrooms | Pet Friendly Pool Home
Starting at $550 per Night
A 4 bedroom, 4 bathroom, single family, private pool home in the heart of Coco Plum. With gorgeous coastal decor, stunning views, and a carefully designed outdoor recreation area, Reel Knotty is a Luxury Marathon Vacation Rental you must see for yourself…
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One Particular Harbor
8 Guests | 3 Bedrooms | 3 Bathrooms | Pet Friendly Pool Home
Starting at $330 per Night
Located in the quiet residential neighborhood of Coco Plum Beach so you can spend your day relaxing on the beach, worryfree. This home offers a private heated pool with deck and abundant poolside seating…
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Seas the Day
8 Guests | 3 Bedrooms | 2 Bathrooms | Pet Friendly Pool Home
Starting at $350 per Night
Seas the day is a single-family Florida Keys Vacation Rental Home with a private pool that was recently built-in 2018. This home was built with luxury and comfort in mind! From the oversized outdoor living spaces to the high-end finishes…
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Lionfish Lodge
6 Guests | 2 Bedrooms | 1 Bathrooms | Pet Friendly Waterfront Home
Starting at $239 per Night
Picture yourself enjoying sea breezes from your balcony overlooking the canal. Watch the sunset overlooking the canal to end the perfect day. This unit is part of a triplex that is perfect for large groups! All 3 units have a occupancy of 20 people combined, with 7 bedrooms and 4 bathrooms…
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Duck Key Summit Too
12 Guests | 5 Bedrooms | 5 Bathrooms | Pet Friendly Waterfront Pool Home
Starting at $715 per Night
Exquisite Home on Duck Key with 5 bedrooms and 5 baths with marble floors and tile throughout. Large pool, Tiki Hut, and Jacuzzi. 2 kayaks and 2 paddle boards included. Gaming table, ping pong table. Bar, with mini refrigerator. Deep water dockage…
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I-Guana Hang By The Sea
12 Guests | 5 Bedrooms | 5 Bathrooms | Pet Friendly Waterfront Pool Home
Starting at $415 per Night
I-Guana Hang By The Sea Walking distance to Sombrero Beach. Easy boating access to the Ocean and a short distance to the Gulf of Mexico. A short distance to Sombrero Beach. You can't beat this location. 60 ft of dockage. Private Pool and Hot Tub…
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Island Adventure I
8 Guests | 4 Bedrooms | 4.5 Bathrooms | Waterfront Pool Home
Starting at $600 per Night
“Island Adventure” was built-in 2021, with Family, Fun, Luxury, and Water Sports Lovers in Mind. The home is located in Marathon, with ample parking space for a boat trailer up to 35 ft and 2 cars. The home faces the Ocean, with immediate access to open water…
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Our Happy Place
4 Guests | 2 Bedrooms | 2 Bathrooms | Boot Key Harbor Condo
Starting at $143 per Night
Our Happy Place with Sunsets and Open water views of Boot Key Harbor. This condo is a 2 bedroom 2 bath with elevator access. Located on the Top floor in unit 302. There is a large shared heated pool with a grill on property…
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Island Adventure II
8 Guests | 4 Bedrooms | 4.5 Bathrooms | Waterfront Pool Home
Starting at $643 per Night
“Island Adventure” was built-in 2021, with Family, Fun, Luxury, and Water Sports Lovers in Mind. The home is located in Marathon, with ample parking space for a boat trailer up to 37 ft and 2 cars. The home faces the Ocean, with immediate access to open water…
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Vaca Cove unit A Shore Thang
10 Guests | 4 Bedrooms | 4 Bathrooms | Waterfront Pool Home
Starting at $500 per Night
Vaca Cove is a private oasis compromised of 7 stilted homes facing Shelter Bay, with direct Ocean and Gulf access. Each unit has assigned 35’ of deep water dockage with electricity and water on the dock. Our guests will have access to a shared resort size in-ground Saltwater pool…
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Endless Summer451
12 Guests | 5 Bedrooms | 5.5 Bathrooms | Waterfront Pool Home
Starting at $785 per Night
Luxury in “The Reserve” on Sombrero Beach. Look no further this home has it all. Brand new construction with decks on every level. Fantastic indoor and outdoor living with Sunrise and Sunsets every night. This home has all the amenities you will need to have a fantastic vacation! …
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Vaca Cove B Sea Forever
10 Guests | 4 Bedrooms | 3 Bathrooms | Waterfront Pool Home
Starting at $500 per Night
Vaca Cove is a private oasis compromised of 7 stilted homes facing Shelter Bay, with direct Ocean and Gulf access. Each unit has assigned 35’ of deep water dockage with electricity. Our guests will have access to a shared resort size in-ground pool…
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Vaca Cove unit D Sunset Pointe
10 Guests | 4 Bedrooms | 3 Bathrooms | Waterfront Pool TownHome
Starting at $500 per Night
Vaca Cove is a private oasis compromised of 7 stilted homes facing Shelter Bay, with direct Ocean and Gulf access. Each unit has assigned 35’ of deep water dockage with electricity. Our guests will have access to a shared resort size in-ground pool…
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Vaca Cove E Endless Summer
8 Guests | 4 Bedrooms | 3 Bathrooms | Waterfront Pool TownHome
Starting at $500 per Night
Vaca Cove is a private oasis compromised of 7 stilted homes facing Shelter Bay, with direct Ocean and Gulf access. Each unit has assigned 35’ of deep water dockage with electricity. Our guests will have access to a shared resort size in-ground pool…
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Vaca Cove G Beach Daze
10 Guests | 4 Bedrooms | 3 Bathrooms | Waterfront Pool TownHome
Starting at $500 per Night
Vaca Cove is a private oasis compromised of 7 stilted homes facing Shelter Bay, with direct Ocean and Gulf access. Each unit has assigned 35’ of deep water dockage with electricity. Our guests will have access to a shared resort size in-ground pool…
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Martin's Beach House
10 Guests | 4 Bedrooms | 3 Bathrooms | Waterfront Pool Home
Starting at $458 per Night
Complete Florida Keys Living – Your Perfect Vacation Rental. Discover the epitome of Florida Keys living with this stunning vacation rental. Perfectly designed for relaxation and adventure, this modern and spacious home offers direct oceanfront access by boat…
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Marathon Bungalow
6 Guests | 2 Bedrooms | 2 Bathrooms | Waterfront Pool Home
Starting at $272 per Night
Beautifully appointed Marathon home with private pool and outdoor seating on two levels. Spend your time in the Florida Keys enjoying a spacious home with fantastic outdoor amenities. Quick access by boat to Snorkeling, fishing, and sunset cruises…
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Piece of Paradise
4 Guests | 1 Bedrooms | 1 Bathrooms | Beach Resort Condo
Starting at $190 per Night
Piece of Paradise is a beautifully decorated one bedroom & one bathroom condo in Skipjack Resort. Resort amenities: on site pool, on site gym, laundry, tiki bar, pickle ball court, restaurant, live music almost every night, and so much more!!…
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Conch Key Cottage
4 Guests | 2 Bedrooms | 1 Bathrooms | Quaint Cottage
Starting at $175 per Night
The Quintessinal Conch Cottage on Conch key, Circa 1953, this home has the Key West Vibe but in the MIddle keys. Located in a quaint fishing village on an island in the middle of the Sea. This home is set in a quiet place near the water…
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Gulfside Escape
12 Guests | 5 Bedrooms | 4 Bathrooms | Luxury Beach Pool Home
Starting at $725 per Night
Introducing Gulfside Escape: A Brand New 5 Bed/4 Bath Luxury Single-Family Home in The Tides at Vaca Cut Development. Nestled in the pristine surroundings of The Tides at Vaca Cut, Gulfside Escape is a newly built, luxurious 5-bedroom, 4-bathroom residence…
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Almost Paradise
6 Guests | 3 Bedrooms | 2 Bathrooms | Waterfront Home on Flamingo Island
Starting at $190 per Night
Welcome to Almost Paradise, a serene tropical escape featuring three bedrooms and two bathrooms on the idyllic Flamingo Island. Tucked away from the hustle and bustle, our location offers a peaceful retreat, yet it's conveniently just a few minutes from essential amenities…
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Ideal Escape
4 Guests | 1 Bedrooms | 1 Bathrooms | Beach Condo Rental
Starting at $190 per Night
Ideal Escape is a 1bed/1bath nightly condo in Skipjack Resort. This condo is in the heart of Marathon, close to shopping, restaurants, grocery stores, and the beautiful Sombrero Beach. Marathon is the “Heart of the Keys”…
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Sandy Shores and Sunsets
10 Guests | 4 Bedrooms | 3 Bathrooms | Pet Friendly Beach House
Starting at $429 per Night
Sandy Shores is a home with a Beach and Sunsets combined it is a Rarety for the Keys. This home is located right on Vaca Cut and facing West for the sunsets every night! This home features a sandy beach backyard, gas grill, private swimming pool, and 100 foot dock…
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Aqua Vista Oceanfront Home
8 Guests | 3 Bedrooms | 3.5 Bathrooms | Pet Friendly Oceanfront Pool Home
Starting at $500 per Night
Aqua Vista – Your Waterfront Oasis in the Florida Keys. Indulge in the ultimate Florida Keys getaway with a stay at Aqua Vista. This brand-new vacation home promises a perfect blend of luxury, modern amenities, and breathtaking water views…
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Isabella on Paradise Place
6 Guests | 2 Bedrooms | 2 Bathrooms | Pet Friendly Beach Cottage
Starting at $458 per Night
Isabella on Paradise place is a Picture-perfect location in Paradise!!! The resort Pool is Amazing. As you drive into the fully fenced yard you will find a beautifully landscaped home with palm trees, a heated swimming pool with a paved deck, and a barbeque grill…
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Coco Cay House
10 Guests | 4 Bedrooms | 3 Bathrooms | Modern Pool Home
Starting at $458 per Night
The owner pulled out all the stops on this this beautiful spacious and modern home that has Fantastic open water views down the channel and direct oceanfront access by boat. The pool area has sun and shade, relax in a lounge chair or sit at the Outdoor Grill and Bar that is right next to the pool…
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Changes in Attitude
8 Guests | 3 Bedrooms | 3.5 Bathrooms | Family Pool Home
Starting at $420 per Night
Changes in Attitude is a stunning 3 bedroom and 3.5 bathroom single family home on Sombrero Boulevard. This property is warm and inviting and located in the desirable neighborhood of Sombrero Beach…
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Fisherman's Retreat
8 Guests | 3 Bedrooms | 2 Bathrooms | Canal Front Home with Jacuzzi
Starting at $286 per Night
This home is the perfect Florida Keys get-away; it truly lives up to its name FIsherman's Retreat!! A 3 Bedroom, 2 Bath, Waterfront home with a private jacuzzi, 75 ft of dockage, a ladder, a fish cleaning table, and propane grill, freshwater hose access, bait freezer…
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Bikinis & Martinis
6 Guests | 2 Bedrooms | 2.5 Bathrooms | Modern Townhome with Partial Water Views
Starting at $240 per Night
Bikinis & Martinis is a serene townhouse nestled within the Gulf Pointe II Association. Enjoy partial water vistas from both the living room and master bedroom. The main level boasts an open-concept design, featuring a kitchen, dining area, and living room…
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Captains Quarters
8 Guests | 3 Bedrooms | 3 Bathrooms | Boot Key Harbor Vacation Home
Starting at $190 per Night
Captains Quarters: Charming 3-Bed/2-Bath Home with Convenient Boot Key Harbor Access! This delightful home features an open-concept design encompassing the kitchen, living room, and dining area. The kitchen boasts modern stainless steel appliances…
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A Captains Dream
6 Guests | 2 Bedrooms | 1 Bathrooms | Waterfront Vacation Rental with Dock
Starting at $236 per Night
The Captain's Dream is located in a quiet neighborhood in Marathon. Right on the deep water with a private 50-foot dock that will accommodate a 40 ft Boat. Relax and cast a line from your waterfront patio…
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Indigo Reefs' Tarpon House
6 Guests | 3 Bedrooms | 2.5 Bathrooms | Luxury Waterfront Vacation Home
Starting at $315 per Night
One Of The Finest Locations in Indigo Reef, The boat slip is included and is steps from your door with unobstructed open water views and Sunsets Every Night! Indigo Reef 61 is an end unit, so the whole right side of the townhome has windows to enjoy the sunny skies of Marathon…
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