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EXPERIENCE THE BEST OF KEY WEST RELAXED - TROPICAL ISLAND STYLE LIVING THE PERFECT DESTINATION FOR YOUR VACATION

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 PackagesWedding DestinationsResort Vacation PackagesFamily 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.

BIG PINE KEY PROPERTIES...

Our Island Thing

8 Guests | 4 Bedroom | 2 Bathroom | 2 Story Pool Home
Starting at $6950 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…

brought to you by
“ACTION KEYS REALTY”

Breeze Swept

6 Guests | 3 Bedroom | 2 Bathroom | Pet Friendly Pool Home
Starting at $6500 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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“ACTION KEYS REALTY”

Conch Out

6 Guests | 3 Bedroom | 2 Bathroom | Pet Friendly Waterfront Home
Starting at $4900 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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“ACTION KEYS REALTY”

Manatee Bay

6 Guests | 3 Bedroom | 2 Bathroom | Pet Friendly Gulf-Side Home
Starting at $3500 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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“ACTION KEYS REALTY”

Mango House

4 Guests | 2 Bedroom | 1.5 Bathroom | Canal Front Vacation Home
Starting at $2800 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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“ACTION KEYS REALTY”

Tropical Sunset

4 Guests | 1 Bedroom | 2 Bathroom | Canal Front Duplex | MM30
Starting at $2800 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…

brought to you by
“ACTION KEYS REALTY”

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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“ACTION KEYS REALTY”

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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“ACTION KEYS REALTY”

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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“ACTION KEYS REALTY”

Island Time 1

4 Guests | 2 Bedrooms | 1 Bathrooms | Pet Friendly Canal Front Home
Starting at $3500 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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“ACTION KEYS REALTY”

Island Time 2

6 Guests | 3 Bedrooms | 1 Bathrooms | Pet Friendly Canal Front Home
Starting at $3550 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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“ACTION KEYS REALTY”

KEYS TO THE TROPICS

8 Guests | 3 Bedrooms | 2 Bathrooms | Water Front Vacation Home
Starting at $4800 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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“ACTION KEYS REALTY”

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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“ACTION KEYS REALTY”

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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“ACTION KEYS REALTY”

SUNSET TIKI

4 Guests | 2 Bedrooms | 2 Bathrooms | Pet Friendly Water Front Vacation Home
Starting at $4500 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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“ACTION KEYS REALTY”

TROPICAL SUNSET

4 Guests | 2 Bedrooms | 1 Bathrooms | Water Front Vacation Home
Starting at $2800 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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“ACTION KEYS REALTY”

Water's Edge

4 Guests | 2 Bedrooms | 2 Bathrooms | Pet Friendly Water Front Vacation Home
Starting at $4300 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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“ACTION KEYS REALTY”

BIG TORCH KEY PROPERTIES...

Big Torch Retreat

6 Guests | 3 Bedrooms | 2 Bathrooms | Canalfront Vacation Home
Starting at $3900 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…

brought to you by
“ACTION KEYS REALTY”

CUDJOE KEY PROPERTIES...

5 O'Clock Somewhere

4 Guests | 2 Bedrooms | 2 Bathrooms | Canalfront Vacation Home
Starting at $3300 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…

brought to you by
“ACTION KEYS REALTY”

Hawkins Heaven

4 Guests | 2 Bedrooms | 2 Bathrooms | Pet Friendly Oceanview Home
Starting at $3800 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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“ACTION KEYS REALTY”

Lafitte Landing

4 Guests | 2 Bedrooms | 2 Bathrooms | Pet Friendly Canalfront Home
Starting at $3375 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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“ACTION KEYS REALTY”

Pirate's Cove

4 Guests | 2 Bedrooms | 1 Bathrooms | Pet Friendly Canalfront Home
Starting at $2700 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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“ACTION KEYS REALTY”

Quiet Waters

6 Guests | 3 Bedrooms | 2 Bathrooms | Canalfront Vacation Home
Starting at $3900 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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“ACTION KEYS REALTY”

Waterside Bay

6 Guests | 3 Bedrooms | 3 Bathrooms | 3 Story Custom Vacation Home
Starting at $5300 per Month

Come enjoy the breathtaking open water views from the multi-level porches of Waterside Bay! This 3 story custom home has 3 bedroom and 3 baths and has upscale yet comfortable living…

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“ACTION KEYS REALTY”

Catch of the Day

6 Guests | 2 Bedrooms | 2 Bathrooms | Pet Friendly Canalfront Home | MM22
Starting at $3300 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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“ACTION KEYS REALTY”

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…

brought to you by
“ACTION KEYS REALTY”

Sunny Lei

6 Guests | 3 Bedrooms | 2 Bathrooms | Pet Friendly Pool Home
Starting at $4500 per Month

Please come visit this tastefully decorated tropical themed home on Cudjoe Key. This 3-bedroom 2 bath house has been completely redecorated both in and out with island style furniture which is both functional and fun…

brought to you by
“ACTION KEYS REALTY”

Pelican Perch

6 Guests | 3 Bedrooms | 2 Bathrooms | Pet Friendly Waterfront Home
Starting at $4500 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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“ACTION KEYS REALTY”

GARDENS GETAWAY

6 Guests | 3 Bedrooms | 2 Bathrooms | Pet Friendly Waterfront Home
Starting at $6200 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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“ACTION KEYS REALTY”

ALOE HOUSE

6 Guests | 3 Bedrooms | 3 Bathrooms | Pet Friendly Waterfront Home
Starting at $5000 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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“ACTION KEYS REALTY”

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”

Mel's Fishing Paradise

6 Guests | 2 Bedrooms | 2 Bathrooms | Pet Friendly Pool Home | MM61
Starting at$10,863 per Month (28 night minimum)

Looks like South Beach Living but in The Florida Keys, this home is completely renovated and ready for your fishing and diving adventures. Fantastic large kitchen and Open Floor plan. Large open deck overlooking the pool and the beautiful canals of Duck Key…

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“VACATION RENTALS OF THE FLORIDA KEYS”

The Glamorous Entertainer

12 Guests | 5 Bedrooms | 4 Bathrooms | Luxurious Family Pool Home | MM61
Starting at$29,693 per Month (28 night minimum)

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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“VACATION RENTALS OF THE FLORIDA KEYS”

Duck Key Summit

16 Guests | 5 Bedrooms | 5 Bathrooms | Exquisite Waterfront Pool Home | MM61
Starting at $29,809 per Month (28 night minimum)

Pets Allowed! Exquisite Home on Duck Key with 5 bedrooms and 5 baths with marble floors and tile throughout. Large pool, Tiki Hut, and Jacuzzi. Gaming table, ping pong table. Bar, with mini refrigerator…

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“VACATION RENTALS OF THE FLORIDA KEYS”

Hook Wine & Sinker

8 Guests | 3 Bedrooms | 3 Bathrooms | Beautiful Canalfront Pool Home | MM61
Starting at $10,901 per Month (28 night minimum)

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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“VACATION RENTALS OF THE FLORIDA KEYS”

Luxurious Fanta-sea

8 Guests | 3 Bedrooms | 3 Bathrooms | Luxury Waterfront Pool Home | MM61
Starting at $10,500 per Month (28 night Minimum)

Pets Allowed! This Beautiful home located on Tom's Harbour with the ocean waters flowing from the Atlantic to the Gulf of Mexico. Two sides of waterfront with great fishing off the dock. The private yard is your perfect tropical getaway…

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“VACATION RENTALS OF THE FLORIDA KEYS”

Oceanfront Jewel

6 Guests | 3 Bedrooms | 2 Bathrooms | Waterfront Pool Home | MM61
Starting at $21,365 per Month (60 night minimum)

Pets Allowed! Your island escape is here! Meticulously renovated home with everything you can want in a vacation get away. Oceanfront with views enjoyed from every living area…

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“VACATION RENTALS OF THE FLORIDA KEYS”

Reel Sunset

8 Guests | 3 Bedrooms | 2.5 Bathrooms | Cana Front Pool Home | MM61
Starting at $14,339 per Month (28 night minimum)

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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“VACATION RENTALS OF THE FLORIDA KEYS”

Turtle Time

8 Guests | 3 Bedrooms | 3 Bathrooms | Waterfront Pool Home | MM61
Starting at $13,210 per Month (28 night minimum)

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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“VACATION RENTALS OF THE FLORIDA KEYS”

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! …

brought to you by
Kitty Whalton of
“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!…

brought to you by
Kitty Whalton of
“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…

brought to you by
Kitty Whalton of
“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…

brought to you by
Kitty Whalton of
“FLORIDA KEYS VACATION RENTALS”

ISLAMORADA PROPERTIES...

LYONS LANDING

10 Guests | 4 Bedrooms | 3 Bathrooms | Gulf Front Family Pool Home
Starting at $8750 per Month (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…

brought to you by
“KEYS HOLIDAY RENTALS”

VILLA RIOLO

6 Guests | 2 Bedrooms | 2 Bathrooms | Luxury Waterfront Stilt Home
Starting at $4300 per Month (29 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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“KEYS HOLIDAY RENTALS”

LITTLE BAY - Cottage

6 Guests | 2 Bedrooms | 2 Bathrooms | Ground Level Gulfside Cottage
Starting at $3000 per Week (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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“KEYS HOLIDAY RENTALS”

LITTLE BAY - Lower Duplex

6 Guests | 2 Bedrooms | 2 Bathrooms | Lower Level Gulfside Vacation Rental
Starting at $3000 per Week (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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“KEYS HOLIDAY RENTALS”

LITTLE BAY - Upper Duplex

6 Guests | 2 Bedrooms | 2 Bathrooms | Upper Level Gulfside Vacation Rental
Starting at $3000 per Week (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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“KEYS HOLIDAY RENTALS”

Martin Family Fish Camp

12 Guests | 4 Bedrooms | 3 Bathrooms | Two Cottages on a Peninsula
Starting at $3800 per Week (7 night minimum)

Saturday to Saturday 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…

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“KEYS HOLIDAY RENTALS”

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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“FLORIDA KEYS LUXURY RENTALS”

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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“FLORIDA KEYS LUXURY RENTALS”

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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“FLORIDA KEYS LUXURY RENTALS”

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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“FLORIDA KEYS LUXURY RENTALS”

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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“FLORIDA KEYS LUXURY RENTALS”

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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“FLORIDA KEYS LUXURY RENTALS”

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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“FLORIDA KEYS LUXURY RENTALS”

The Palms #301

6 Guests | 2 Bedrooms | 2 Bathrooms | Luxury Oceanfront Condo Rental
Starting at $2800 per Month (28 night minimum)

This 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…

brought to you by
“KEYS HOLIDAY RENTALS”

The Palms #407

6 Guests | 2 Bedrooms | 2 Bathrooms | Luxury Oceanfront Condo Rental
Starting at $2400 per Month (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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“KEYS HOLIDAY RENTALS”

BROCK HAUS ON THE GULF

6 Guests | 2 Bedrooms | 2.5 Bathrooms | Oceanview End Unit Townhome
Starting at $1595 per Week (7 night minimum)

Saturday to Saturday* “Brock Haus on the Gulf” is an end unit townhouse on the water's edge with water views on 3 sides! The panoramic open water views from this unit are incredible!…

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“KEYS HOLIDAY RENTALS”

Beacon Reef #222

6 Guests | 2 Bedrooms | 2 Bathrooms | Extraordinary Oceanfront Condo Rental
Starting at $4000 per Month (30 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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“KEYS HOLIDAY RENTALS”

MY PARADISE

6 Guests | 3 Bedrooms | 2 Bathrooms | Beautiful Oceanfront Beach House
Starting at $8250 per Month (28 night minimum)

“My Paradise” is an oceanfront beach house with protected dockage and located in the Fishing Capital of the World – Islamorada. Realize your dreams – a beach home located on a swimmable beach and a place to dock your boat…

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“KEYS HOLIDAY RENTALS”

Beacon Reef #522

6 Guests | 2 Bedrooms | 2 Bathrooms | Beautiful Oceanfront Condo Rental
Starting at $4650 per Month (30 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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“KEYS HOLIDAY RENTALS”

PALMS 417

2 Guests | 1 Bedrooms | 2 Bathrooms | Condo Rental on the Florida Bay
Starting at $2100 per Month (27 night minimum)

“The Palms #417” has great views of Florida Bay and our fabulous Keys sunsets. This complex is conveniently located just steps from a full service marina and 2 highly acclaimed restaurants…

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“KEYS HOLIDAY RENTALS”

SUNSHINE PLACE

3 Guests | 1 Bedrooms | 1.5 Bathrooms | Romantic Oceanfront Vacation
Starting at $1465 per Week (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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“KEYS HOLIDAY RENTALS”

Beacon Reef #310

6 Guests | 2 Bedrooms | 2 Bathrooms | Oceanfront Luxury Condo Rental
Starting at $3700 per Month (30 night minimum)

Beacon Reef is one of the most desirable condominium complexes in the Upper Keys. Located in Islamorada it is convenient to everything – restaurants, fishing, diving, snorkeling, swim with the dolphin programs and much more…

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“KEYS HOLIDAY RENTALS”

Antigua Place

8 Guests | 3 Bedrooms | 2 Bathrooms | Charming Oceanfront Vacation Home
Starting at $6200 per Month (30 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 $3600 per Month (30 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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“KEYS HOLIDAY RENTALS”

The Palms #405

6 Guests | 2 Bedrooms | 2 Bathrooms | Oceanfront Vacation Condo Rental
Starting at $3100 per Month (30 night minimum)

A Diamond! Be among the first to rent this gorgeous two bedroom condo. You’ll adore the comfortable living room furnishings and the flat screen TV, not to mention the ocean views from the picture window…

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“KEYS HOLIDAY RENTALS”

The Palms #314

4 Guests | 2 Bedrooms | 2 Bathrooms | Oceanfront Vacation Condo
Starting at $3300 per Month (30 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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“KEYS HOLIDAY RENTALS”

Beacon Reef #501

4 Guests | 2 Bedrooms | 2 Bathrooms | Top Floor Condo with Ocean Views
Starting at $4000 per Month (30 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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“KEYS HOLIDAY RENTALS”

A Pirates Great Escape

8 Guests | 3 Bedrooms | 2 Bathrooms | Oceanfront Penthouse Condo
Starting at $5265 per Week (7 night minimum)

Oceanfront Penthouse Condo with a Private Boat slip. Small Gated Community on the southern tip of Islamorada. The condo has a designated 4 car covered parking. Quick boating access to the Ocean or the Gulf of Mexico thru the Channel 5 Bridge….

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“VACATION RENTALS OF THE FLORIDA KEYS”

BEACON REEF 503

4 Guests | 2 Bedrooms | 2 Bathrooms | 5th Floor Condo with Ocean Views
Starting at $4500 per Month (27 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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“KEYS HOLIDAY RENTALS”

PALMS 313

4 Guests | 2 Bedrooms | 2 Bathrooms | Beautiful Oceanfront Condo Rental
Starting at $2750 per Month (27 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 $5600 per Month (27 night minimum)

This 2 bedroom/2 bath condo with fabulous ocean views has been totally remodeled and updated. Beacon Reef is one of the most desirable condominium complexes in the Upper Keys…

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“KEYS HOLIDAY RENTALS”

OCEAN HARBOUR K31

6 Guests | 3 Bedrooms | 2 Bathrooms | Oceanfront Condo
Starting at $9000 per Month (27 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 $5500 per Month (27 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 $7900 per Month (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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CONCH HOUSE

6 Guests | 3 Bedrooms | 3 Bathrooms | Luxury Beach House
Starting at $7900 per Month (28 night minimum)

A BEACH FRONT HOME with an amazing use of space. This home offers BREATH TAKING OCEAN VIEWS from the 2nd floor open concept living area, the balcony facing the ocean and the large sun porch!…

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“KEYS HOLIDAY RENTALS”

BEACON REEF 301

4 Guests | 2 Bedrooms | 2 Bathrooms | Luxury Beach Condo
Starting at $4500 per Month (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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“KEYS HOLIDAY RENTALS”

BEACON REEF 306

4 Guests | 2 Bedrooms | 2 Bathrooms | Luxury Beach Condo
Starting at $4200 per Month (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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“KEYS HOLIDAY RENTALS”

BEACON REEF 522

4 Guests | 2 Bedrooms | 2 Bathrooms | Luxury Beach Condo
Starting at $4650 per Month (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. This 2 bedroom, 2 bath condo offers some of the most breathtaking views of the Atlantic Ocean…

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“KEYS HOLIDAY RENTALS”

SANDGLASS 4

12 Guests | 5 Bedrooms | 3 Bathrooms | Luxury Waterfront Townhome
Starting at $12,000 per Month (28 night minimum)

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 $3700 per Month (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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“KEYS HOLIDAY RENTALS”

Palms 404

5 Guests | 2 Bedrooms | 2 Bathrooms | Luxury Beach Condo
Starting at $3500 per Month (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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“KEYS HOLIDAY RENTALS”

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