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 destinations for tropical villas, beach condos, secluded cabins. Don't forget about our exciting All Inclusive Packages, Wedding Destinations, Adult Only Getaways, Dude Ranches 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.
CHOOSE YOU FLORIDA KEYS DESTINATION:
EXCLUSIVE SHOWCASE COLLECTION:
FUN IN THE FLORIDA KEYS and KEY WEST...
Above & BELOW ADVENTURES - Florida Keys Fishing Charters
WHERE ADVENTURE STARTS – FISH FLORIDA'S BEST!
Reel in an Unforgettable Fishing Adventure with Capt. Jose at Above & Below Adventures – Your Go-To for Florida Key’s Best Outdoor Adventures! Discover the best fishing charter in Florida with Above & Below Adventures: Our expert guides, top-quality equipment, and picturesque surroundings guarantee the ultimate fishing experience.
HISTORIC KEY WEST VACATION RENTALS - EXPLORE KEY WEST
Explore the vibrant charm of Key West with our comprehensive area guide. From sun-soaked beaches and water adventures to iconic festivals and historic landmarks, this island paradise offers something for everyone. Discover the best places to eat, drink, and explore, and stay up-to-date with local events and insider tips.
FLORIDA KEYS SHOWCASE PARTNERS...
VACATION RENTALS OF THE FLORIDA KEYS
Locally owned and operated, Vacation Rentals of the Florida Keys's team will assist you in finding the perfect vacation rental home, villa or condo in the Upper, Middle and Lower Keys. We offer weekly vacation rentals, monthly vacation rentals and seasonal rental properties.
FLORIDA KEYS VACATION HOUSES
An Extraordinary Florida Keys Vacation Experience that brings you a wide variety of vacation homes and condo’s in the Florida Middle Keys including Marathon and Key Colony Beach. Escape for a romantic couples getaway or grab your family and friends for a fun and exciting Florida Keys Vacation!
KEY COLONY BEACH PROPERTIES...
Reel ‘Em In
8 Guests | 3 Bedrooms | 2 Bathrooms | Beautiful Key Colony Vacation Home
Starting at $2000 per Week
3/2 open air SFH ready for you to spend your vacation! 30 foot dock can easily handle your boat with quick access to Vaca Cut to head out to the bay or to the Atlantic. Dive, snorkel and fish within minutes…
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“FLORIDA KEYS VACATIONS”
Fisherman's Delight
8 Guests | 3 Bedrooms | 2.5 Bathrooms | Beautiful Key Colony Vacation Condo
Please Call for Best Rates: 305-393-0205
14 NIGHT MINIMUM STAY Each unit is fully furnished and has two bedrooms, two bathrooms, dining area, full kitchen, washer/dryer, central heat/air conditioning and a private patio or balcony. This unit has a great corner view of the ocean! …
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“FLORIDA KEYS VACATIONS”
204 Oceanview Casa
4 Guests | 2 Bedrooms | 2 Bathrooms | Beautiful Key Colony Vacation Condo
Please Call for Best Rates: 305-393-0205
14 NIGHT MINIMUM STAY Each unit is fully furnished and has two bedrooms, two bathrooms, dining area, full kitchen, washer/dryer, central heat/air conditioning and a private patio or balcony. This unit has a great corner view of the ocean!…
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“FLORIDA KEYS VACATIONS”
371 Pool for You
8 Guests | 3 Bedrooms | 2 Bathrooms | Charming Key Colony Vacation Home
Please Call for Best Rates: 305-393-0205
Absolutely charming, warm and inviting home. Single family home on lovely 12th Street in Key Colony Beach with Cabana Club privileges. Quick access to the ocean or gulf, with 80′ of deep water dock-age…
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“FLORIDA KEYS VACATIONS”
CHARMING HOME IN KEY COLONY
8 Guests | 3 Bedrooms | 2 Bathrooms | Gorgeous Waterfront Vacation Home
Starting at $1700 per Week
This 3 bedroom home has just been extensively remodeled with new tile floors throughout, all new kitchen appliances, new hall bath and the living area has been opened up to the outdoors with window walls of patio French doors opening on to a new patio…
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Kitty Whalton of
“FLORIDA KEYS VACATION RENTALS”
Sailfish Point
8 Guests | 3 Bedrooms | 3 Bathrooms | Amazing Pool & Boat Dockage
CLICK HERE for Rates & Availability
This beautiful Key Colony Beach home is the ultimate tropical escape. Enjoy an amazing private pool, great dockage for your boat, and all the amenities you need for a relaxing stay. This home is your ideal base for fun and adventure in the Florida Keys!..
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“COCO PLUM VACATION RENTALS”
Aqua Vista
8 Guests | 4 Bedrooms | 4 Bathrooms | Private Heated Pool
CLICK HERE for Rates & Availability
This home offers an expansive layout. A welcoming living room complements the layout, providing a comfortable space for relaxation and entertainment. The outdoor area of this property is designed for relaxation and adventure, featuring a spacious heated pool, waterfall, and boat dock…
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“COCO PLUM VACATION RENTALS”
Flamingo Bay
5 Guests | 2 Bedrooms | 2 Bathrooms | Stunning Backyard Oasis
CLICK HERE for Rates & Availability
Welcome to your new home away from home in Key Colony Beach! This charming, newly renovated half-duplex features a stunning backyard oasis, complete with a paver patio and a refreshing concrete in-ground pool—ideal for entertaining and relaxation…
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“COCO PLUM VACATION RENTALS”
Oceanside Manor
10 Guests | 5 Bedrooms | 3 Bathrooms | Stunning Backyard Oasis
CLICK HERE for Rates & Availability
Oceanside Manor is a spacious vacation rental located at the tranquil end cap of a canal in Key Colony Beach. This beautiful property features a private heated pool, stunning waterfront views, direct canal access for boating…
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“COCO PLUM VACATION RENTALS”
Tranquil Retreat
8 Guests | 4 Bedrooms | 2 Bathrooms | Pet Friendly Waterfront Home
CLICK HERE for Rates & Availability
Escape to a tranquil haven in the heart of the Florida Keys! This beautiful 4-bedroom, 2-bathroom home in Key Colony Beach offers a peaceful getaway with its recent renovation, canal-front location, and exclusive membership access for up to 6 guests to the nearby Cabana club…
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“COCO PLUM VACATION RENTALS”
Casa Blanca
9 Guests | 3 Bedrooms | 3 Bathrooms | Vacation Pool Home
CLICK HERE for Rates & Availability
The perfect Florida Keys vacation rental is one that offers easy access to convenient and luxurious amenities — both within the house itself and the community nearby. This Key Colony vacation home does so effortlessly and flawlessly…
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“COCO PLUM VACATION RENTALS”
My Beach Key
4 Guests | 2 Bedrooms | 2 Bathrooms | Pet Friendly Waterfront Home
CLICK HERE for Rates & Availability
This charming 2-bedroom, 2-bathroom half duplex is the perfect escape for families or couples looking for a relaxing getaway. Located on a serene canal, this rental comes complete with a private dock, perfect for fishing or docking your boat…
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“COCO PLUM VACATION RENTALS”
Turtle Tides
10 Guests | 4 Bedrooms | 3 Bathrooms | Luxury Waterfront Paradise
CLICK HERE for Rates & Availability
Welcome to your private waterfront paradise in Key Colony Beach, Florida Keys — the ultimate destination for relaxation, boating, and world-class fishing. This single-story waterfront vacation rental features 50 feet of private dockage, a heated pool, and tropical landscaping throughout…
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“COCO PLUM VACATION RENTALS”
Casita Blanca
4 Guests | 2 Bedrooms | 2 Bathrooms | Pet Friendly Canal Front Home
CLICK HERE for Rates & Availability
Welcome to your tropical escape in Key Colony Beach! This charming 2-bedroom, 2-bathroom duplex is nestled along a tranquil canal, providing you with the ultimate waterfront vacation experience. This duplex is designed for comfort and relaxation…
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“COCO PLUM VACATION RENTALS”
Tropical Therapy
5 Guests | 2 Bedrooms | 2 Bathrooms | Waterfront Luxury Condo
CLICK HERE for Rates & Availability
Welcome to Tropical Therapy – Sit back and enjoy some tropical therapy in beautiful Key Colony Beach, known as the ‘Gem of the Florida Keys.' Within minutes of all the conveniences of Marathon, this little island paradise will quickly become your home away from home…
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“KEYS OCEAN VACATION RENTALS”
Manatee Bay
10 Guests | 5 Bedrooms | 4.5 Bathrooms | Luxury Waterfront Pool Home
CLICK HERE for Rates & Availability
The Manatee Bay home is an expansive, five-bedroom, four-and-a-half-bath home located in the quiet neighborhood of Key Colony Beach. This home has something for everyone in the family and offers plenty of room for the perfect Keys getaway…
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“KEYS OCEAN VACATION RENTALS”
KCB Beach House
6 Guests | 3 Bedrooms | 2 Bathrooms | Waterfront Vacation Home
CLICK HERE for Rates & Availability
Welcome to KCB Beach House, a spacious 3-bedroom, 2-bathroom waterfront home that comfortably accommodates six guests. While you'll find the indoors comfortable, you'll likely spend most of your time outside, and this home provides all you need for outdoor enjoyment…
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“KEYS OCEAN VACATION RENTALS”
The Veranda House
8 Guests | 4 Bedrooms | 3 Bathrooms | Waterfront Pool Home
CLICK HERE for Rates & Availability
The Veranda House- This Key West-style home boasts open-air balconies that encircle the tropical residence, offering picturesque views of the pool and waterway. With 30 feet of dockage, this home is a dream come true for fishing enthusiasts…
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“KEYS OCEAN VACATION RENTALS”
KEY LARGO BEACH PROPERTIES...
Twice The Charm
10 Guests | 4 Bedrooms | 3 Bathrooms | Waterfront Vacation Pool Home
CLICK HERE for Rates & Availability (28 night minimum)
“Twice the Charm” is a gorgeous newly remodeled single family home. You’ll love the convenient location in the Ocean Shores area of Key Largo. There is room to dock a boat of 30′ in length or less. The canal offers easy ocean access…
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“KEYS HOLIDAY RENTALS”
Ocean Paradise Point 11
6 Guests | 3 Bedrooms | 3 Bathrooms | Ocean Front Single Family Home
CLICK HERE for Best Rates & Availability
Escape to this brand new, coastal modern 3-bedroom, 3-bathroom home located in a gated, intimate community right on the Atlantic Ocean. Enjoy breathtaking views and the tranquility of the Atlantic Ocean from your balcony or rooftop deck…
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“STAR PROPERTIES DESTINATIONS”
Key Largo luxurious coastal Retreat
6 Guests | 3 Bedrooms | 2 .5 Bathrooms | Ocean Front Pool Home
CLICK HERE for Best Rates & Availability
Escape to this brand new, coastal modern 3-bedroom, 2.5-bathroom home located in a gated, intimate community right on the Atlantic Ocean. Enjoy breathtaking views and the tranquility of the Atlantic Ocean from your balcony…
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“STAR PROPERTIES DESTINATIONS”
Bayside Catch at Buttonwood Bay
5 Guests | 2 Bedrooms | 1.5 Bathrooms | Townhome on the Bay
CLICK HERE for Best Rates & Availability
Welcome to your perfect getaway at Buttonwood Bay! This inviting 2-bedroom, 1.5-bath 2 story updated townhouse has been comfortably and tastefully decorated. Located on Buttonwood Bay's private waterway known for it's unique and relaxing canal view…
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“STAR PROPERTIES DESTINATIONS”
Tiki Time Hideaway
6 Guests | 3 Bedrooms | 2 Bathrooms | Canal Front Paradise
CLICK HERE for Best Rates & Availability
Get ready to kick back, relax, and live your best island life at this fun-filled waterfront retreat in sunny Key Largo! Tucked along a quiet canal with direct access to both the Gulf and the Atlantic Ocean, this home is a dream come true for anyone looking to soak up the Keys lifestyle…
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“STAR PROPERTIES DESTINATIONS”
Gary's Paradise Cove
6 Guests | 3 Bedrooms | 3 Bathrooms | Waterfront Pool Home with Dock
CLICK HERE for Best Rates & Availability
Escape to a tropical oasis at Gary's Paradise Cove, a stunning 3-bedroom, 3-bathroom retreat designed for relaxation and adventure. Nestled among beautifully manicured tropical foliage, this property offers breathtaking views of the bay and a host of luxurious amenities…
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“STAR PROPERTIES DESTINATIONS”
Rock Harbor Club #P-8
6 Guests | 2 Bedrooms | 2 Bathrooms | Beautiful Bayfront Town Home
CLICK HERE for Rates & Availability (28 night minimum)
Bayfront townhouse located in the lush tropical setting of Rock Harbor Club in Key Largo. You’ll love the open water views from the two oversized screened balconies – one off the main living area and the other off the master suite…
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“KEYS HOLIDAY RENTALS”
MOON BAY A410
5 Guests | 2 Bedrooms | 1.5 Bathrooms | Waterfront Corner Unit Condo
CLICK HERE for Rates & Availability (7 night minimum)
“Moon Bay #A410” is a 4th floor end unit in one of Key Largo's finest bay front condominium complexes offers a beautiful view of the Florida Bay and lots of natural light. New linens and fresh paint add to the desirability of this condo…
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“KEYS HOLIDAY RENTALS”
BAY THERAPY
8 Guests | 3 Bedrooms | 3 Bathrooms | Waterfront Vacation Home
CLICK HERE for Rates & Availability (28 night minimum)
“Bay Therapy” invites happy vacationing. Owners call their special getaway “Bay Therapy” for many reasons. It is located in a great neighborhood in Key Largo. It is convenient to the mainland and is the gateway to the Keys…
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“KEYS HOLIDAY RENTALS”
Ocean Paradise Point 10
6 Guests | 3 Bedrooms | 2 Full -1 1/2 Bathrooms | Ocean Front Vacation Home
CLICK HERE for Best Rates & Availability
Spanning three stories, this home features expansive windows that frame unparalleled ocean vistas, filling almost every room with natural light. Step inside to discover coastal modern, high-end finishes throughout with an elevator for access across all levels…
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“STAR PROPERTIES DESTINATIONS”
Bahia Vista
6 Guests | 2 Bedrooms | 2 Bathrooms | Luxury Waterfront Condo
CLICK HERE for Best Rates & Availability
Bahia Vista is a rare end unit within the Moon Bay community, boasting exquisite water bay views from nearly every room and window. This unit has the perfect location within the community with a short walk to the beachy area and pool…
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“STAR PROPERTIES DESTINATIONS”
Marlin house at Mariner's Club
6 Guests | 2 Bedrooms | 2 Bathrooms | Luxury Resort Condo
CLICK HERE for Best Rates & Availability
Nestled in a secluded and quiet lush tropical setting. This is a Two bedroom, two bath 2nd floor condo with gorgeous marbled floors, cathedral ceilings and an open floor plan with wonderful Tommy Bahama furniture and decor…
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“STAR PROPERTIES DESTINATIONS”
Key Largo Treasure at Kawama Yacht Club
6 Guests | 2 Bedrooms | 2 Bathrooms | Luxury Waterfront Condo
CLICK HERE for Best Rates & Availability
Two bedrooms, each with their own balconies, one overlooks the pool, the other State Park Hardwood Hammock. There is plenty of room for the family to spread out in the living room. Four upstairs/downstairs porches/balconies give this townhouse such a comfortable feel!..
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“STAR PROPERTIES DESTINATIONS”
LITTLE TORCH KEY PROPERTIES...
CAPTAIN HOUSE
8 Guests | 3 Bedrooms | 2 Bathrooms | Beautiful Waterfront Home with Boat Basin
Starting at $649 per Night
Stay in the amazing Keys and beautiful waterfront home with boat basin for your boat. The property lot is almost an acre with an island point surrounded by sea life. Stunning panoramic water views, sunrise and sunset. Steps away from ocean water!…
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“COZY COVES BEACH”
BARRY BEACH
20 Guests | 8 Bedrooms | 5 Bathrooms | Spacious Private Waterfront Home
Starting at $699 per Night
Stay in the amazing Keys and beautiful waterfront home with 200 foot dock for your boat. Exclusive heated pool to relax and enjoy the surrounding ocean view – just breath taking! The private lot is almost an acre with optional Guesthouse and guest pool…
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“COZY COVES BEACH”
BARRY BEACH GUEST HOSUE
10 Guests | 4 Bedrooms | 2 Bathrooms | Private Guest House
Starting at $95 per Night
The Guesthouse has an open living and dining room concept with queen sofa bed and recliner massage chair in each space. There's one space upstairs two bedrooms and one bath, the other on ground level same layout. Kings and trundle beds…
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“COZY COVES BEACH”
Cozy Cottage
6 Guests | 2 Bedrooms | 1 Bathrooms | Waterfront Home with Dock
Starting at $399 per Night
Stay in the amazing Keys and beautiful waterfront home with 250 foot dock, ramp, and basin for your boat. It's a must-see rustic outdoor environment and fishery experience, very typical in the Keys! Steps away from ocean water…
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“COZY COVES BEACH”
Anchor House
10 Guests | 4 Bedrooms | 2 Bathrooms | Waterfront Home with Dock
Starting at $661 per Night
Stay in the amazing Keys and beautiful waterfront home with boat basin and ramp for your boat. The property lot is almost an acre with another rental home and still very spacious. Stunning panoramic water views…
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“COZY COVES BEACH”
Haven House
8 Guests | 3 Bedrooms | 1 Bathrooms | Waterfront Home with Ramp for Boat
Starting at $399 per Night
Stay in the amazing Keys and beautiful waterfront home with boat basin and ramp for your boat. The property lot is almost an acre with another rental home and still very spacious (search for Anchor House to reserve both homes if available)…
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“COZY COVES BEACH”
Margarita Villa
6 Guests | 3 Bedrooms | 2 Bathrooms | Island Style Private Waterfront Home
CLICK HERE for Rates & Availability
Welcome to Margarita Villa! Located in Jolly Roger Estates on Little Torch Key, where you’ll find some of the best deep water boating in the Lower Keys! Decorated in fine island-style this private home is definitely a 5-star property…
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“ACTION KEYS REALTY”
BLACKBEARDS BOUNTY
6 Guests | 3 Bedrooms | 2 Bathrooms | Island Style Private Waterfront Home
CLICK HERE for Rates & Availability
Looking for a perfect sunny get away in the beautiful Florida Keys? Blackbeard’s Bounty is just the place for you and your guests! This tropical oasis is located on Little Torch Key. This home has easy access to North Pine Channel which is great for anglers and snorkelers alike!…
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“ACTION KEYS REALTY”
Agua Azul
6 Guests | 3 Bedrooms | 2.5 Bathrooms | Luxury Beach House
CLICK HERE for Rates & Availability
This waterfront home located in Coral Shores Park on Little Torch Key is a real paradise pleaser! The spacious interior is nicely decorated, completely remodeled, and has a beautiful open floor plan with views of the expansive deck and open water…
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“ACTION KEYS REALTY”
CAPTAIN KIDD'S HIDEAWAY
6 Guests | 3 Bedrooms | 2 Bathrooms | Pet Friendly Waterfront Home
CLICK HERE for Rates & Availability
“WOW!” is what you will say when you walk through the door of this Little Torch Key home. With cathedral ceilings and a large family and dining area, your whole family will be able to stretch out and relax. Sliding glass doors lead out of the living room to the outdoor dining area and tiki hut…
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“ACTION KEYS REALTY”
PIRATES PARADISE
6 Guests | 3 Bedrooms | 3.5 Bathrooms | Pet Friendly Waterfront Pool Home
CLICK HERE for Rates & Availability
Enjoy a luxurious space and a place to call home during your sunny Florida Keys destination. Located on the open water on Little Torch Key with gorgeous ocean views. The sunrises and moon rises are a delightful sight. Large inground ground pool with attached spa for lounging and swimming…
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“ACTION KEYS REALTY”
COCONUT CAY
6 Guests | 3 Bedrooms | 2 Bathrooms | Pet Friendly Waterfront Home
CLICK HERE for Rates & Availability
Nestled on a pristine canal-front lot, situated in Little Torch Key, this well-appointed home offers all the amenities you will need to enjoy the casual lifestyle of the Lower Keys. There is plenty of room for friends and family to enjoy outdoor cookouts…
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“ACTION KEYS REALTY”
Buccaneer Boathouse
4 Guests | 2 Bedrooms | 2 Bathrooms | Vacation Home with Private Beach
CLICK HERE for Rates & Availability
Pack your floral shirts, swimming gear and sandals and come on down to Little Torch Key in the beautiful Florida Keys. This lovely home is spacious with 2 bedrooms and 2 bathrooms. It offers a large open kitchen, dining and living area for everyone to hang-out and plan all the fun activities for the group…
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“ACTION KEYS REALTY”
Pirates Pointe
6 Guests | 3 Bedrooms | 2 Bathrooms | Canal Front Family Vacation Home
CLICK HERE for Rates & Availability
Here is the hidden treasure you have been looking for. Pirates Pointe is a great get a way for you and the family. The home is pleasantly decorated in soft leather furniture, comfy beds and crisp linens. Enjoy the porch overlooking the crystal clear canal, great for swimming…
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“ACTION KEYS REALTY”
GROUPER THERAPY
6 Guests | 3 Bedrooms | 2 Bathrooms | Canal Front Pet Friendly Home
CLICK HERE for Rates & Availability
You will be pleasantly surprised when you arrive at Grouper Therapy on Little Torch Key. One of the few ground level vacation homes. No steps here!! Dockside is lovely with a covered patio area and fish cleaning table. Lots of space with plenty of dockage and easy access out to South Pine Channel…
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“ACTION KEYS REALTY”
Serenity
4 Guests | 2 Bedrooms | 2 Bathrooms | Canal Front Pet Friendly Home
CLICK HERE for Rates & Availability
Serenity found in the Florida Keys! This home is situated on a beautiful canal in the Jolly Roger Estates of Little Torch Key. There is plenty of room for your boat with access to the best boating, fishing, diving, and snorkeling in the lower Keys…
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“ACTION KEYS REALTY”
BLUE MARLIN
6 Guests | 3 Bedrooms | 2 Bathrooms | Canal Front Pet Friendly Home
CLICK HERE for Rates & Availability
Florida Keys Vacation Rentals – Set sail for a glorious Florida Keys vacation at the Blue Marlin. Spacious and comfortable for 6 in this 3-bedroom 2 bath Little Torch Key home. Located down a private lane and overlooking the crystal blue waters of Pine channel, gulf side…
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“ACTION KEYS REALTY”
MARACAIBO MANOR
8 Guests | 3 Bedrooms | 2 Bathrooms | Pet Friendly Pool Home
CLICK HERE for Rates & Availability
Meet your perfect vacation getaway, Maracaibo Manor! Located on Little Torch Key in the highly desirable Jolly Roger Estates neighborhood, with excellent deep water access for boating, diving, fishing and snorkeling at the famous Looe Key Reef…
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“ACTION KEYS REALTY”
KEY HOUSE
5 Guests | 2 Bedrooms | 2 Bathrooms | Canal Front
CLICK HERE for Rates & Availability
Welcome to the Key House, a completely charming, canal front home located in the ultra popular Jolly Roger Estates on Little Torch Key. A cute tropical them from the outside in, you know you are in the Florida Keys! The interior is decorated so nicely that you will feel relaxed and at home…
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“ACTION KEYS REALTY”