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 Keys 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
BIG PINE KEY PROPERTIES...
Our Island Thing
8 Guests | 4 Bedroom | 2 Bathroom | 2 Story Pool Home
Starting at $7500 per Month
A get away to “Our Island Thing” will be unforgettable vacation for everyone. Huge 1,900 square-foot house with lots of room for the whole family and kids. Four bedrooms and two bathrooms, this two level concrete home is roomy and airy…
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Breeze Swept
6 Guests | 3 Bedroom | 2 Bathroom | Pet Friendly Pool Home
Starting at $6800 per Month
Magnificent open water views in this beautiful 3 Bedroom, 2 bath home on Big Pine Key! This home boasts decor by an award winning Key West decorator. Enjoy a swim in the new, heated pool after a long day on the water…
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Conch Out
6 Guests | 3 Bedroom | 2 Bathroom | Pet Friendly Waterfront Home
Starting at $5200 per Month
“Conch Out” on your tropical vacation at this spacious and comfortable 3 bedroom canalfront home on Big Pine Key. Relax on a swing under your private tiki hut, entertain in the large screened porch with your own built-in grill…
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Manatee Bay
6 Guests | 3 Bedroom | 2 Bathroom | Pet Friendly Gulf-Side Home
Starting at $3900 per Month
Manatee Bay located in the Port Pine Height area is just the right spot to bring your family and friends for an unbelievable Keys vacation. Great Gulf-side boating is at your fingertips and just a short run out to the Atlantic…
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Mango House
4 Guests | 2 Bedroom | 1.5 Bathroom | Canal Front Vacation Home
Starting at $3600 per Month
Simple and sweet with no muss, no fuss. It's all right here – Gulf Side! This quaint two bedroom vacation home offers views, a deep-water boating and swimming canal and a protective seawall…
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Tropical Sunset
4 Guests | 1 Bedroom | 2 Bathroom | Canal Front Duplex | MM30
Starting at $2900 per Month
Just the perfect Florida Keys get a way. Cute and super comfortable 2 bedroom duplex in Big Pine Key. All totally updated in 2018 with new appliances, furnishings and accessories for a comfy place to enjoy our wonderful area…
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Angelfish Cove
6 Guests | 3 Bedrooms | 2.5 Bathrooms | Pet Friendly Pool Home
Starting at $4300 per Month
Pack your floral shirts, swimming gear and sandals and come on down to Angelfish Cove. Fun is the order of the day. Enjoy the beautiful crystal clear swimming pool (heated) or jump in your boat to go explore some of the best fishing…
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Hideaway Bay
4 Guests | 2 Bedrooms | 2 Bathrooms | Pet Friendly Waterfront Home
Starting at $3500 per Month
Come hideaway with us in the beautiful Florida Keys at Hideaway Bay. Located in the Port Pine Heights area of Big Pine Key with quiet streets and where our cute Key Deer roam every evening…
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Island Time - Full Property
10 Guests | 5 Bedrooms | 2 Bathrooms | Pet Friendly Canal Front Home
Starting at $6800 per Month
Truly remarkable Big Pine Key vacation home. Rare Duplex on over an acre in the Doctors Arm area. A huge boat basin and direct access to Bogie channel. Rent one or both sides for the best family vacation destination in the Keys…
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Island Time 1
4 Guests | 2 Bedrooms | 1 Bathrooms | Pet Friendly Canal Front Home
Starting at $3700 per Month
Fully fenced for privacy and lots of yard space for everyone to enjoy outdoor activities. Just down the street from the Old Wooden Bridge marina for easy boat launch, gas and boat rentals. The interiors are expertly decorated in Keys Island motif…
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Island Time 2
6 Guests | 3 Bedrooms | 1 Bathrooms | Pet Friendly Canal Front Home
Starting at $3800 per Month
Fully fenced for privacy and lots of yard space for everyone to enjoy outdoor activities. Just down the street from the Old Wooden Bridge marina for easy boat launch, gas and boat rentals. The interiors are expertly decorated in Keys Island motif…
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KEYS TO THE TROPICS
8 Guests | 3 Bedrooms | 2 Bathrooms | Water Front Vacation Home
Starting at $5150 per Month
This unique home is situated on a quiet street, with a desirable corner canal location in Port Pine Heights, Big Pine Key. Bringing your boat along? No problem, plenty of dock space here! …
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Mi Sueno
7 Guests | 3 Bedrooms | 2 Bathrooms | Water Front Pool Home
Starting at $4500 per Month
If you’re looking for the tropical vacation home of your dreams, look no further! Mi Sueno “My Dream” is just the place for you and your guests. This is a 3 bedroom and 2-bathroom house with beautiful Key West style interior …
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MONTERO HOUSE
8 Guests | 3 Bedrooms | 2 Bathrooms | Water Front Pool Home
Starting at $7200 per Month
This spectacular home is located in the desirable Pine Channel Estates subdivision located on Big Pine Key. You will be more than delighted with this canal front home. After a long day on out on the water, dock your boat just feet away from your own private pool and dive in…
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The Lost Lobster
8 Guests | 3 Bedrooms | 2 Bathrooms | Pet Friendly Pool Home
Starting at $235 per Night
Discover The Lost Lobster: A Captivating 3-Bedroom/2-Bathroom Family Home on Big Pine Key! The heart of this home embraces an open-concept design, where the living room, dining area, and kitchen seamlessly meld together…
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Palmetto Retreat
4 Guests | 2 Bedrooms | 2 Bathrooms | Water Front Vacation Home
Starting at $3800 per Month
This relaxing retreat is situated in a very private part of Port Pine Heights on Big Pine Key. Great boating, fishing, and snorkeling can be easily accessed, just a short boat ride down the canal to Pine Channel…
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SUNSET TIKI
4 Guests | 2 Bedrooms | 2 Bathrooms | Pet Friendly Water Front Vacation Home
Starting at $4700 per Month
What a great sunset view from this house! Fun in the sun surrounds this spot right on a wide canal with excellent access to fishing either the Gulf or the Atlantic side. We will see you soon at the tiki hut!…
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TROPICAL SUNSET
4 Guests | 2 Bedrooms | 1 Bathrooms | Water Front Vacation Home
Starting at $2900 per Month
Just the perfect Florida Keys get a way. Cute and super comfortable 2 bedroom 1 bath ½ duplex in Big Pine Key. So, put this one on the top of your list for an affordable Keys Vacation…
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Water's Edge
4 Guests | 2 Bedrooms | 2 Bathrooms | Pet Friendly Water Front Vacation Home
Starting at $4600 per Month
You and your family will feel right at home in this charming Big Pine Key home. Soft sea colors and coastal décor make this a totally comfortable home away from home…
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BIG TORCH KEY PROPERTIES...
Big Torch Retreat
6 Guests | 3 Bedrooms | 2 Bathrooms | Canalfront Vacation Home
Starting at $4200 per Week
Enjoy the ultimate peace and quiet offered on Big Torch Key. This pristine area is a true treasure of the lower Keys. This home is nicely remodeled and boasts large spacious room and comfortable furnishing…
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INTO THE MYSTIC
12 Guests | 6 Bedrooms | 6 Bathrooms | Waterfront Vacation Home
Starting at $10,000 per Month
Peace and serenity abound at “Into the Mystic on Big Torch Key”. Enjoy the quiet and peaceful drive from Highway 1 to this property along with some of the greatest views over the Niles Channel and salt ponds…
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CUDJOE KEY PROPERTIES...
5 O'Clock Somewhere
4 Guests | 2 Bedrooms | 2 Bathrooms | Canalfront Vacation Home
Starting at $3800 per Month
It's always 5 O'Clock here at this wonderful Florida Keys vacation spot. Start your day off with refreshing Mimosas or Bloody Marys as you enjoy sitting out on the screened porch overlooking the nice boating canal…
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Hawkins Heaven
4 Guests | 2 Bedrooms | 2 Bathrooms | Pet Friendly Oceanview Home
Starting at $3900 per Month
Come stay at this heavenly oasis. Pull up to a fully fenced 2 bedroom Florida Keys home. The home offers beautiful, vaulted wood ceilings throughout with a cozy living room, a well-appointed kitchen. ..
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SEVENTH HEAVEN
4 Guests | 2 Bedrooms | 2 Bathrooms | Luxury Waterfront Pool Home
Starting at $8000 per Month
This home is situated on a beautiful canal in the prestigious Cudjoe Gardens. It is impressive from the moment you pull in the driveway! There is a tropical grand entryway leading into the spacious and beautifully furnished living room…
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Lafitte Landing
4 Guests | 2 Bedrooms | 2 Bathrooms | Pet Friendly Canalfront Home
Starting at $3800 per Month
Lafitte Landing is the perfect destination for your Florida Keys vacation. Very nicely appointed 2 bedroom, 2 bathroom canal front home is very comfortable and spacious. A very affordable spot to spend your next vacation!…
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Pirate's Cove
4 Guests | 2 Bedrooms | 1 Bathrooms | Pet Friendly Canalfront Home
Starting at $2900 per Month
Kick back and relax in this Island vacation home. Or, enjoy the spacious deck located off the kitchen area, and take in the warm tropical breezes, canal and spectacular sunset skies…
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Quiet Waters
6 Guests | 3 Bedrooms | 2 Bathrooms | Canalfront Vacation Home
Starting at $4200 per Month
This Cudjoe Key home is neat as a pin with all the comforts of home. Bright and shiny kitchen with everything you may need to create wonderful get togethers. Lovely screened porch and a patio area downstairs by the dock with a gas grill…
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Catch of the Day
6 Guests | 2 Bedrooms | 2 Bathrooms | Pet Friendly Canalfront Home | MM22
Starting at $3600 per Month
Come enjoy Paradise in the comfortable island style of Catch of the Day! This 2 bedroom 2 bathroom canal front home on Cudjoe Key offers the casual lifestyle of the Lower Keys…
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VENTURE OUT 434
4 Guests | 2 Bedrooms | 1 Bathrooms | Pet Friendly Pool Home
Starting at $1500 per Week
For your next Florida Keys vacation, reserve a stay at this waterfront home located on a canal with easy access to either the Atlantic or the Gulf. This home has everything you need to enjoy a relaxing vacation with resort amenities at your backdoor…
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Pelican Perch
6 Guests | 3 Bedrooms | 2 Bathrooms | Pet Friendly Waterfront Home
Starting at $4800 per Month
This comfortable 3-bedroom 2 bath stilt home provides, the outdoor island lifestyle; upstairs 2 wide open decks on either side of a screened in porch, and at ground level a full seawall with fish cleaning station and immaculate tropical grounds…
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GARDENS GETAWAY
6 Guests | 3 Bedrooms | 2 Bathrooms | Pet Friendly Waterfront Home
Starting at $6400 per Month
Let this Cudjoe Gardens home be the location of your next getaway! Situated on a beautiful, clear deep canal with ample space for your boat, you will enjoy quick access to some of the best fishing, diving and snorkeling in the Florida Keys…
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ALOE HOUSE
6 Guests | 3 Bedrooms | 3 Bathrooms | Pet Friendly Waterfront Home
Starting at $5400 per Month
Make your memories at the Aloe House on Cudjoe Key! This home is located on a beautiful crystal clear canal with plenty of dockage for up to a 25 foot boat. The canals here provide great access to some of the best fishing in the Florida Keys…
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DUCK KEY PROPERTIES...
Duck Key Darling
6 Guests | 2 Bedrooms | 2 Bathrooms | Townhouse Villa in Hawks Cay | MM61
Starting at $325 per Night
Duck Key Darling is a 2 bed 2 bath Townhouse Villa in Hawks Cay that over looks beautiful Tom's Harbor! This unit has gorgeous water views from both the main living space downstairs and the master bedroom upstairs…
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“VACATION RENTALS OF THE FLORIDA KEYS”
Duck Key Tarpon
12 Guests | 5 Bedrooms | 3 Bathrooms | Waterfront Pool Home
Starting at $567 per Night
Exquisite Home on Duck Key with 5 bedrooms and 3 baths. Nice pool with outdoor living space TV and Grill area, Bar and fantastic views of the channel. There is a Tiki Hut at the dock with a large fish cleaning station…
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Duck Key Retreat
8 Guests | 3 Bedrooms | 2 Bathrooms | Pet Friendly Waterfront Pool Home
Starting at $535 per Night
Beautifully appointed home with Open Floor plan, tropically decorated living spaces, The Cathedral ceilings make the living areas feel extra large. A large screened in porch. Large pool with a shallow area for small children. Large tiki hut and domino table right off the pool area…
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The Come Back Shack
6 Guests | 3 Bedrooms | 3 Bathrooms | Pet Friendly Oceanfront Pool Home
Starting at $607 per Night
Your Coastal Sheek Duck Key Getaway! Beautifully appointed home with Open Floor plan. Cathedral ceilings and views from every room of the ocean. The house has a huge yard for privacy, and a swimming pool and Tiki Hut, plus a putting green. Bring your putter! …
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The South Face on Duck Key
8 Guests | 3 Bedrooms | 2.5 Bathrooms | Pet Friendly Oceanfront Pool Home
Starting at $750 per Night
Welcome to this Oceanfront beauty in Duck Key! Enjoy the South Exposure with the sun all day, while having your toes in the pool and enjoying the ocean view and breezes. This oceanfront property is Florida Keys living at its finest…
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Sunset Island
8 Guests | 3 Bedrooms | 2 Bathrooms | Stunning Vacation Home
Starting at $235 per Night
Sunset Island is a stunning 3bed/2bath single family in desirable Duck Key. This property was recently remodeled and features new modern furnishing. Spend your time in the Florida Keys enjoying a spacious home…
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The Glamorous Entertainer
12 Guests | 5 Bedrooms | 4 Bathrooms | Luxurious Family Pool Home | MM61
Starting at $715 per Night
The Glamorous Entertainer….Beautifully appointed Spacious Duck Key home with Cathedral Ceilings, wet bar, Kitchen has Subzero size refrigerator, with Three master suites with a king size bed in each, 2 bedrooms for the kids…
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Hook Wine & Sinker
8 Guests | 3 Bedrooms | 3 Bathrooms | Beautiful Canalfront Pool Home | MM61
Starting at $322 per Night
This Beautiful 3 bedroom 2 bath canal front home with private pool is your perfect tropical paradise. Featuring a beautiful pool with jacuzzi built onto the pool, while also featuring a deep water 75 foot dock…
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Reel Sunset
8 Guests | 3 Bedrooms | 2.5 Bathrooms | Cana Front Pool Home | MM61
Starting at $629 per Night
Pets Allowed! Beautiful 3 bedroom 2.5 bath canalfront home with private pool. Seaside decor and casual elegance defines this comfortable home on Duck Key. Open floor plan and spacious well-equipped kitchen…
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Turtle Time
8 Guests | 3 Bedrooms | 3 Bathrooms | Waterfront Pool Home | MM61
Starting at $535 per Night
Pets Allowed! Beautifully appointed home with Open Floor plan, tropically decorated living spaces, plantation shutters and nice screened in porch off living areas. This home has a 75 foot dock for a boat up to a 3 foot draft…
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GRASSY KEY PROPERTIES...
THE GULF FRONT HAVEN
10 Guests | 4 Bedrooms | 2 Bathrooms | Luxury Oceanfront Pool Home
Starting at $2800 per Week
This 4 bedroom home is located on a half acre of Gulf Front property with a waterside pool and a spa on the pool deck. Steps away is a pier dock, great for fishing. Spectacular sunset color. The perfect spot for a memorable vacation! …
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“FLORIDA KEYS VACATION RENTALS”
GULF FRONT REFUGE
6 Guests | 3 Bedrooms | 2 Bathrooms | Luxurious Gulf Front Pool Home
Starting at $2900 per Week
Spectacular Views of the Gulf of Mexico! A Beautiful 3 Bedroom, 2 Bath Gulf Front Home on Morton Street in Grassy Key! Just yards from the edge of the Gulf this home is the perfect location for a memorable vacation!…
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“FLORIDA KEYS VACATION RENTALS”
THE DREAM HOUSE POOL HOME
12 Guests | 5 Bedrooms | 3 Bathrooms | Luxury Gulf House with Private Pool
Starting at $4500 per Week
Fabulous Views of the Gulf of Mexico, 40′ pool waterside with built in spa, great dockage for boating or fishing and lovely tropical grounds! A gracious beachside style home with casual elegance, and all the amenities for a great family vacation…
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“FLORIDA KEYS VACATION RENTALS”
SEA SPELL GULF FRONT POOL HOME
10 Guests | 4 Bedrooms | 4 Bathrooms | Fabulous Gulf Front Estate | Pool
Starting at $3700 per Week
Your stay at this 4 Bedroom residence will be a vacation to remember! Driving through the gates and up the winding driveway all you see is the lush tropical landscaping until you come to the house where the property opens up to the waterfront…
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Kitty Whalton of
“FLORIDA KEYS VACATION RENTALS”
ISLAMORADA PROPERTIES...
LYONS LANDING
10 Guests | 4 Bedrooms | 3 Bathrooms | Gulf Front Family Pool Home
Starting at $349 per Night (28 night minimum)
“Lyons Landing” is an exceptional VENETIAN SHORES single family home with pool, dock, boat lift and outdoor living area! Everything you need for a spectacular holiday awaits you in this extraordinary home…
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BLUE WATER RETREAT
6 Guests | 3 Bedrooms | 3 Bathrooms | Waterfront Pool Home
Starting at $358 per Night (28 night minimum)
This home has it all – ocean side Lower Matecumbe location. Relax by the splash pool or sunbathe on the roof top and enjoy the spectacular views. There are blue water ocean views from almost every room in this home….
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HARBOR HOUSE
8 Guests | 4 Bedrooms | 3 Bathrooms | Waterfront Vacation Home
Starting at $286 per Night (28 night minimum)
This is a very special single family home with many amenities. Relax on the open porch and watch the boats come and go from the marina and keep an eye on your boat at the same time. Spend your Keys holiday in this upscale Venetian Shores located in Islamorada!…
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PALMS 309
5 Guests | 2 Bedrooms | 2 Bathrooms | Ocean View Luxury Condo
Starting at $122 per Night (28 night minimum)
an exceptional condo with panoramic views of the Atlantic Ocean. This condo is in one of the most popular condo complexes in Islamorada – The Palms of Islamorada. Comfortably furnished and ready for your arrival…
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PALMS 317
3 Guests | 1 Bedrooms | 1.5 Bathrooms | Ocean View Condo
Starting at $83 per Night (28 night minimum)
The Palms of Islamorada is a condo complex consisting of 84 units and is located directly on the Atlantic Ocean. The complex features separate his and hers mini-gyms, heated pool, hot tub, tiki for gatherings…
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VILLA RIOLO
6 Guests | 2 Bedrooms | 2 Bathrooms | Luxury Waterfront Stilt Home
Starting at $170 per Night (28 night minimum)
“Villa Riolo” is an updated single family stilt home and perfect for your next holiday in Islamorada! It comfortably sleeps 6 in two bedrooms. The back yard is charming. Enjoy a snack or drink under the Tiki. Bring your boat!…
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LITTLE BAY - Cottage
4 Guests | 2 Bedrooms | 2 Bathrooms | Ground Level Gulfside Cottage
Starting at $429 per Night (7 night minimum)
“Little Bay's Cottage” is one of three rental units on this property. The cottage is a ground level dwelling separate from two duplex units. The Little Bay property is an acre of lush tropical plantings in a gated compound located directly on Florida Bay …
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LITTLE BAY - Lower Duplex
6 Guests | 2 Bedrooms | 2 Bathrooms | Lower Level Gulfside Vacation Rental
Starting at $429 per Night (7 night minimum)
Little Bay's Lower Duplex is one of three rental units on this fabulous property. The Little Bay property is a one acre lush tropical setting in a gated compound located directly on Florida Bay…
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LITTLE BAY - Upper Duplex
6 Guests | 2 Bedrooms | 2 Bathrooms | Upper Level Gulfside Vacation Rental
Starting at $429 per Night (7 night minimum)
Little Bay's Upper Duplex is one of three rental units on this fabulous property. The Little Bay property is a one acre lush tropical setting in a gated compound located directly on Florida Bay…
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Martin Family Fish Camp
12 Guests | 4 Bedrooms | 3 Bathrooms | Two Cottages on a Peninsula
Starting at $643 per Night (7 night minimum)
The Martin Family Fish Camp is located on a private peninsula and offers two cottages named Bonefish and Tarpon. Each cottage offers two private bedrooms. Both houses are cozy, comfortable and well maintained…
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Pineapple Beach
12 Guests | 5 Bedrooms | 4 Bathrooms | Luxury Oceanfront Pool Home
Starting at $17,500 per Week (7 night minimum)
Ever have a dream of sitting at your very own oceanfront private pool, overlooking a beautiful white sandy beach and crystal-clear waters…look no further! Pineapple Beach is nestled on over 3 acres in the heart of Islamorada…
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A Pirates Great Escape
6 Guests | 3 Bedrooms | 2 Bathrooms | Oceanfront Penthouse Condo
Starting at $272 per Night
Oceanfront Penthouse Condo with a Private Boat slip. Small Gated Community on the southern tip of Islamorada. We look forward to having you create your own family memories, as our family has done for generations.
Get your Great Escape started and contact us now…
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Turtle Nest Estate
12 Guests | 4 Bedrooms | 4.5 Bathrooms | Luxury Oceanfront Estate
Starting at $10,000 per Week (7 night minimum)
Enjoy all the beauty of Islamorada's clear blue waters from your private beach front estate. Turtle Nest Estate features an exotic wood deck surrounding a custom pool overlooking a private sugar sand beach on the Atlantic Ocean…
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Serenity
8 Guests | 3 Bedrooms | 3 Bathrooms | Luxury Oceanfront Pool Home
Starting at $20,000 per Month (28 night minimum)
Ocean Front…Pool…Dockage…It’s all hear at Serenity, in beautiful Islamorada. This beautiful three bedroom, three bath home will sleep 8 people very comfortably. Let Serenity be your next Keys vacation home, you will want to come back…
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Midnight Runner
10 Guests | 5 Bedrooms | 4.5 Bathrooms | Luxury Oceanfront Pool Home
Starting at $10,000 per Week (7 night minimum)
Step out the door to your private ocean front beach with pool and dock at Midnight Runner. The property features 5 bedrooms, two living room/seating areas with large screen TV's, full kitchen and mini kitchen…
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Karapan
10 Guests | 5 Bedrooms | 5.5 Bathrooms | Luxury Oceanfront Pool Home
Starting at $11,500 per Week (7 night minimum)
Islamorada's oceanfront Karapan 5 bedroom luxury estate will have you never wanting to leave this tropical paradise. Situated on 4 lush acres in the heart of Islamorada. Enjoy the view and ocean breezes from one of the wrap around porches or private beach…
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Sea Oats Beach
10 Guests | 5 Bedrooms | 5 Bathrooms | Luxury Oceanfront Pool Home
Starting at $24,000 per Month (28 night minimum)
Everything you could possibly need to enjoy your vacation is here at Sea Oats Beach. Enjoy your own private beach, waterfront pool or hang out inside with the family and enjoy a game of pool or movie on one of the large screen TV's…
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Mango Oasis
8 Guests | 3 Bedrooms | 2 Bathrooms | Luxury Waterfront Pool Home
Starting at $14,000 per Month (28 night minimum)
Beautiful 3 bedroom home on wide canal with access to bay or ocean. Home features three bedrooms and two bathrooms upstair. Enjoy an amazing outdoor space with your private pool, waterfall and lush landscape…
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The Palms #407
4 Guests | 2 Bedrooms | 2 Bathrooms | Luxury Oceanfront Condo Rental
Starting at $108 per Night(28 night minimum)
Charming 2 bedroom condo with updated kitchen and baths. Walk out onto your balcony and enjoy the sea breezes and ever changing ocean views. The comfortable furnishings and convenient floor plan provide an inviting place to call home…
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BROCK HAUS ON THE GULF
6 Guests | 2 Bedrooms | 2 Bathrooms | Oceanview End Unit Townhome
Starting at $285 per Night (7 night minimum)
Water views on 3 sides! The main living area faces the Florida Bay, one side faces the inlet leading to the marina basin and the back faces the marina. The panoramic open water views from this unit are incredible! !…
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Beacon Reef #222
6 Guests | 2 Bedrooms | 2 Bathrooms | Extraordinary Oceanfront Condo Rental
Starting at $160 per Night (28 night minimum)
Extraordinary ocean front condo with panoramic views of the Atlantic Ocean. Relax on your private balcony or use the spiral stairs to access the sandy beach below. This condo is located in one of the most prestigious condo complexes in Islamorada…
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Beacon Reef #522
6 Guests | 2 Bedrooms | 2 Bathrooms | Beautiful Oceanfront Condo Rental
Starting at $167 per Night (28 night minimum)
“Beacon Reef 522” offers magnificent 180 degree oceanfront views. Enjoy the sea breezes as your relax on your private balcony and gaze at the water. Whether staying one month or more you will be more than happy with your choice to stay here…
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PALMS 417
3 Guests | 1 Bedrooms | 2 Bathrooms | Condo Rental on the Florida Bay
Starting at $90 per Night (28 night minimum)
This one bedroom unit has partial views of the ocean and a good view of the Florida Bay. It is perfectly proportioned – large living area and large bedroom. The kitchen and baths have been updated. You'll be glad you chose this unit for your holiday in the Keys…
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PALMS 301
6 Guests | 2 Bedrooms | 2 Bathrooms | Condo Rental on the Florida Bay
Starting at $100 per Night (28 night minimum)
An exceptional condo has been impeccably maintained and is located in one of the finest condo complexes in Islamorada. It features an updated kitchen, remodeled baths and is comfortably furnished. This unit is ready for your arrival…
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SUNSHINE PLACE
3 Guests | 1 Bedrooms | 1.5 Bathrooms | Romantic Oceanfront Vacation
Starting at $236 per Night (7 night minimum)
“Sunshine Place” is setup perfectly for privacy and convenience. The owners of this wonderful property called Sunshine Place are willing to share a portion of their piece of Paradise with you…
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Beacon Reef #310
4 Guests | 2 Bedrooms | 2 Bathrooms | Oceanfront Luxury Condo Rental
Starting at $161 per Night (28 night minimum)
This 2 bedroom/2 bath condo has comfortable and inviting furnishings. The interior is bright, spacious and clean. Dine in the formal dining area, outside on the balcony or pull up a stool to the kitchen counter..
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Antigua Place
6 Guests | 3 Bedrooms | 2 Bathrooms | Charming Oceanfront Vacation Home
Starting at $268 per Night (28 night minimum)
Charming vacation home located in the beautiful neighborhood of Port Antigua. You will love this home! There is a wonderful open concept floor plan. Sliding doors open from the dining area into the sunroom overlooking the canal…
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“KEYS HOLIDAY RENTALS”
Beacon Reef #406
6 Guests | 2 Bedrooms | 2 Bathrooms | Oceanfront Vacation Condo Rental
Starting at $147 per Night (28 night minimum)
“Beacon Reef 406” is an excellent choice for your vacation getaway, whether you're planning on staying a month or the entire season, this is a great unit. Beacon Reef is centrally located in the Heart of Islamorada…
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The Palms #314
5 Guests | 2 Bedrooms | 2 Bathrooms | Oceanfront Vacation Condo
Starting at $133 per Night (28 night minimum)
Sensational oceanfront views are yours from both the master bedroom and the balcony of this beautifully appointed condo. Watch the fishing charter boats as they come and go from Bud and Mary's Marina…
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Beacon Reef #501
4 Guests | 2 Bedrooms | 2 Bathrooms | Top Floor Condo with Ocean Views
Starting at $143 per Night (28 night minimum)
Exceptional 5th floor (top floor) 2 bedroom 2 bath condo at Beacon Reef. Ocean views from the open air balcony. You’ll be so glad you have chosen to spend your holiday here…
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BEACON REEF 503
4 Guests | 2 Bedrooms | 2 Bathrooms | 5th Floor Condo with Ocean Views
Starting at $161 per Night (28 night minimum)
This exquisite condo has been TOTALLY remodeled and updated from top to bottom. This is a 5th floor unit with ocean views from the balcony and master bedroom suite. The furnishings are all brand new…
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PALMS 313
5 Guests | 2 Bedrooms | 2 Bathrooms | Beautiful Oceanfront Condo Rental
Starting at $129 per Night (28 night minimum)
Spectacular oceanfront views are yours from both the master bedroom and the balcony of this beautifully appointed condo. Alligator Reef Lighthouse is easily visible from your master suite or the balcony…
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BEACON REEF 307
4 Guests | 2 Bedrooms | 2 Bathrooms | Beachfront Condo Rental
Starting at $154 per Night (28 night minimum)
This like-new 2 bedroom/2 bath condo has fabulous ocean views and was totally remodeled/updated very recently. You'll love the sparkling new natural stone counter-top kitchen with stainless steel appliances, induction cook top and microwave…
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OCEAN HARBOUR K31
6 Guests | 3 Bedrooms | 2 Bathrooms | Oceanfront Condo
Starting at $322 per Night (28 night minimum)
Gorgeous 3 bedroom ocean front condo with unobstructed ocean views from the screened balcony. The complex is conveniently located in Islamorada and you'll love the amenities this upscale condo complex offers …
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WEST PLAZA DEL LAGO
5 Guests | 2 Bedrooms | 2 Bathrooms | Waterfront Vacation Home
Starting at $233 per Night (28 night minimum)
“West Plaza Del Lago” will steal your breath away the moment you pull into the drive way. Beautifully remodeled roomy single family stilt home with vaulted ceilings on a deep and wide canal. You will love the interior of this home as much as the exterior!…
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PELICAN LANDING
8 Guests | 4 Bedrooms | 32 Bathrooms | Luxury Beach House
Starting at $429 per Night (28 night minimum)
Pelican Landing is located in the prestigious neighborhood of Port Antigua on a deep and wide canal. The main floor offers 3 bedrooms and an open concept with ample seating for the entire family…
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BEACON REEF 301
6 Guests | 2 Bedrooms | 2 Bathrooms | Luxury Beach Condo
Starting at $100 per Night (28 night minimum)
“Beacon Reef 301” is a fully renovated condo that offers inspiring tropical views including the ocean from the open-air balcony accessed from the main living area and the master bedroom suite. This charming, condo has all the comforts for a wonderful vacation…
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BEACON REEF 306
4 Guests | 2 Bedrooms | 2 Bathrooms | Luxury Beach Condo
Starting at $133 per Night (28 night minimum)
Enjoy a relaxing stay here in the Keys at this immaculate and charming two bedroom and two bath condo. You can relish all the delightful amenities of their condo. This unit is beautifully appointed and offers comfortable accommodations…
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SANDGLASS 4
12 Guests | 5 Bedrooms | 3 Bathrooms | Luxury Waterfront Townhome
Starting at $500 per Night (28 night minimum)
ONE-OF-A-KIND! Magnificent two story townhouse with 5 bedrooms and 3 baths located on Lower Matecumbe in Islamorada. Sandglass is a four-unit condo complex located on Lower Matecumbe in Islamorada…
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Palms 314
5 Guests | 2 Bedrooms | 2 Bathrooms | Luxury Beach Condo
Starting at $133 per Night (28 night minimum)
This condo offers breathtaking oceanfront views. Imagine watching the sun rise as you lay comfortably in your bed or have your morning beverage on the balcony and enjoy watching the fishing boats leave for their day's adventure…
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Palms 404
5 Guests | 2 Bedrooms | 2 Bathrooms | Luxury Beach Condo
Starting at $104 per Night (28 night minimum)
This is an exceptional 2 bedroom and 2 bath condo located in one of the most popular Islamorada condo complexes – The Palms of Islamorada. The balcony is large enough to dine or recline and offers fabulous open water views…
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