Key Holiday Rentals
Your Best Choice For Islamorada and Upper Keys Rentals - Vacation or Long TermPhone Number: 305 664-8808
Website: http://keysholidayrentals.com/
Phone: 305-664-8808
Website: http://keysholidayrentals.com/
Phone: 305-664-8808
Key Holiday Rentals Properties on How2Vacation
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 Angler's ReefMINIMUM STAY: 7 DAYS Extraordinary 2-story single family home in a Key West style neighborhood. This gated ocean front community offers charming narrow winding streets, colorful 2 story detached homes and is ideally located in Islamorada, the sport fishing capital… | $1,800 More Info |
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My Paradise Minimum Rental 29 Days. Direct oceanfront home with large sandy beach, protected dockage , handicap accessible and located in the Fishing Capital of the World - Islamorada. Realize your dreams - a beach house located on a swimmable beach and… | $5,500 More Info |
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Twice the Charm Enjoy your stay in this gorgeous single family home. You'll love the convenient location in the Ocean Shores area of Key Largo. There's easy ocean access from this 90' concrete dock. Water, electricity, fish cleaning station and gas barbecue grill… | $1,800 More Info |
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Blue Water Retreat Minimum Rental 29 Days. Location, location, location! This home has it all - ocean side Lower Matecumbe location, totally remodeled in 2009. Relax by the cocktail pool or sunbath in the private roof top sunning area. There are blue water… | $5,000 More Info |
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Beacon Reef 319 Minimum Rental One Month. Gorgeous oceanfront condo in one of Islamorada's premier condominium complexes. Direct ocean view - nothing between you and the water views - from the balcony, your living room, the master suite, and the kitchen! This oceanfront… | $5,000 More Info |
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Ocean Shores Villa Come Sail Away! Let your daydreams take you on an adventure as you relax on one of the balconies and gaze out at the incredible panoramic ocean views. Watch the sail boats pass on the Atlantic Ocean, take pleasure in… | $3,500 More Info |
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Moon Bay Condo A206 Whether you plan to fish or dive on your next visit to the Keys, you will find these exceptional accommodations first class and affordable. World famous dive sites are minutes away and phenomonal fishing is at your door step. Bring… | $895 More Info |
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BROCK HAUS ON THE GULF MINIMUM STAY: 7 DAYS (SAT to SAT) End unit townhouse on the water's edge with water views on 3 sides! The front faces the Florida Bay, one side faces the inlet leading to the marina basin and the back faces… | $1,200 More Info |
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Beacon Reef 306 MINIMUM STAY: 28 DAYS Enjoy a relaxing summer and fall here in the Keys at this immaculate and charming two bedroom and two bath condo. While the owners attend to their other property “up north” you can relish all the… | $4,000 More Info |
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EMERALD COVE MINIMUM STAY: 29 DAYS Enjoy unobstructed and panoramic views of the Atlantic Ocean from your own private balcony! This 3 bedroom/2 bath condo unit features direct ocean views from the living room, balcony and two of the three bedrooms. Tropical… | $5,500 More Info |
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The Palms 201 Minimum Rental: 30 days Enjoy the magnificent ocean views of this wonderful condominium complex. You'll love the newly completed renovations. The kitchen has been totally remodeled with all new cabinets and appliances. The livingroom furniture is brand new and there's… | $2,000 More Info |
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Coco Plum MINIMUM RENTAL: 28 DAYS Spacious canal front home in fabulous location. This home offers an easy commute to Homestead or Lower Keys. You'll love the updated kitchen with snack bar and the family room overlooking the dock and canal. Additional… | $1,800 More Info |
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THE PALMS 314 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. You'll be able to see cruise ships… | $1,837 More Info |
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LITTLE BAY COTTAGE MINIMUM RENTAL: 3 DAYS. This is one of three rental units on this property. The cottage is a ground level dwelling separate from two duplex units. It offers a unique floor plan with the main living area in the center… | $350 More Info |
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Little Bay This is a lush tropical setting in a gated compound and located directly on the Florida Bay. Protected dockage in the "Little Bay" will keep your 30' boat (or smaller) safe. There's a "sunning" area with lounge chairs on the… | $7,200 More Info |
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The Palms 317 MINIMUM RENTAL: 27 NIGHTS (ONE MONTH) This Condo Complex is located directly on the Atlantic Ocean and this one bedroom unit is perfectly proportioned - large living area and large bedroom plus great views of Florida Bay. It has been… | $1,800 More Info |
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LITTLE BAY - Lower Duplex MINIMUM RENTAL: 3 NIGHTS Lower Duplex This 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. The units are… | $350 More Info |
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LITTLE BAY - Upper Duplex MINIMUM RENTAL: 3 NIGHTS Upper Duplex This 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. This is one… | $350 More Info |
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The Palms 402 MINIMUM STAY: 28 DAYS Pure pleasure will be yours in this beautifully remodeled and immaculate condo. You’ll love the uncluttered and modern décor along with the recent renovations. Enjoy the picturesque views of Aligator Reef and the Atlantic Ocean from… | $2,200 More Info |
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Sunset Hammock 4B MINIMUM STAY: 60 DAYS New on the rental market in 2011. Immaculate townhouse in prestigious Sunset Hammock in Tavernier. You’ll enjoy your time in the Keys in this charming and spacious two-story townhouse. Relax on one of the overstuffed sofas… | $2,200 More Info |
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Boater's Delight Beautifully furnished, this almost new single family stilt home sits on an ocean side canal front lot. Bring your boat and your swim suit! This 2 bedroom, 2 bath home has everything you need - including a laundry room with… | $3,500 More Info |
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The Mermaid's Cottage Absolutely Enchanting! Words are hard to find to accurately describe the charm and tropical personality found in this home. Your comfort and enjoyment has been carefully anticipated and provided for. If you must stay intouch with the office, wireless internet… | $2,700 More Info |
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The Palms #417 Minimum Rental one month. TOTALLY remodeled in 2007-2008. Everything in this unit is new - furnishings, linens, kitchen, appliances, and bath rooms. Great views of Florida Bay and our fabulous Keys sunsets. This complex is conveniently located just steps from… | $2,000 More Info |
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Matecumbe Jewel Minimum stay 29 Days. You will love this home! This is a new listing - make your reservations now before someone else books your dates! This is a jewel of a home. Located in Lower Matecumbe this charming canal front… | $4,000 More Info |
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The Palms 214 Gorgeous 2 bedroom, 2 bath condo. The Palms of Islamorada is gated for privacy and located directly on the Atlantic Ocean. This unit has unobstructed views of the ocean from the master suite and the private balcony. Wake up every… | $1,900 More Info |
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Enchanted Fish Camp Enchanted Fish Camp is a wonderful single family home which exemplifies the charm and character of the Florida Keys. If fishing or boating is your passion, you?ll be very pleased with the almost instant access to the Atlantic Ocean via… | $4,000 More Info |
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Venetian Dream Minimum Rental 29 Days. Venetian Dream is a new single family home and is located on a deep water canal in the heart of Islamorada. Venetian Shores is a waterfront community with beautiful homes and is located on Plantation Key… | $5,200 More Info |
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MOON BAY A206 MINIMUM RENTAL: 7 NIGHTS CALLING ALL FISHERMEN AND DIVERS… Whether you plan to fish or dive on your next visit to the Keys, you will find these exceptional accommodations first class and affordable. World famous dive sites are minutes away… | $795 More Info |
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THE PALMS 509 Enjoy the magnificent ocean views from this wonderful 5th floor condo. Use the telescope to watch the ships and fishing vessels cruise past Alligator Reef. This unit is ready for your arrival. The two bedrooms, one with a king bed… | $1,933 More Info |
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SEA GULLS 506 Charming 5th floor condo with panoramic views of the Atlantic Ocean from the balcony. New owner has just refurbished this unit with new furnishings and all new linens. Each of the two bedrooms has access to the open air balcony… | $800 More Info |
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SUMMER SEA 305 An "efficient" little condo unit in one of the nicest condos in the area. This bayfront gated condominium complex offers spacious gathering areas with comfortable seating arrangements, a billiard room, library area, exercise facilities, a swimming pool and a wading… | $1,400 More Info |
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PLANTATION BY THE SEA Enjoy this beautifully remodeled two bedroom condo at Plantation by the Sea. Brand new kitchen (12/2010) with all new appliances and granite counters. The two full baths have been totally updated (12/2010). New carpet in the bedrooms and linens. Roomy… | $1,900 More Info |
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Oasis Not an ordinary rental! Oasis is a beautiful 2002 quality built single family home located directly on the bay and tucked neatly into a very private lot. From the moment you enter the ground level foyer and walk up to… | $2,750 More Info |
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Key Largo Townhome MINIMUM STAY: 30 DAYS Exceptional 3 story townhouse located in a quiet oceanfront complex with heated pool and marina. Inspiring ocean views from two balconies and a ground level patio to BBQ. Protected marina and deeded boat slip easily accommodates… | $3,200 More Info |
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BEACON REEF 302 MINIMUM RENTAL: 27 NIGHTS (ONE MONTH) Beautiful condo - new on the rental market. You'll be so glad the owners have decided to share their piece of paradise! You will love the spacious rooms of this 2 bedroom and 2… | $3,577 More Info |
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Palm Harbor MINIMUM RENTAL: 28 DAYS Totally charming private villa with pool and dock. Gently swaying palm trees greet you at the gated entrance to this wonderful home. The ground level entry features a billiard/game room, bedroom and full bath. An open… | $11,000 More Info |
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The Palms 301 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. This unit is ready for your arrival. Be sure to… | $1,900 More Info |
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THE PALMS 308 Enjoy the magnificent ocean views from this wonderful 3rd floor condo. This unit is ready for your arrival. The décor is light and bright with a totally remodeled kitchen and updated baths. This unit offers 2 bedrooms each with en… | $2,069 More Info |
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VALENCIA GETAWAY Bring your boat your dog and the kids! Relax on the patio or swim in the canal. You will love this ground level single family home located in prestigious Venetian Shores. It has been completely renovated and awaits your arrival.… | $3,400 More Info |
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VILLA BELLA 13 Villa Bella is a fabulous 3 BR/3 BA two-story townhouse. This end unit townhome “lives” on the 2nd floor. The kitchen, dining and living areas are all open to each other in a great room with a gorgeous vaulted ceiling.… | $1,350 More Info |
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THE PALMS 506 Wonderfully inviting condo at one of Islamorada's favorite condo complexes. This unit is tastefully decorated with a nautical theme - an antique ship's light over the dining table and a ship's wheel is hung on the wall to name a… | $1,800 More Info |
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BEACON REEF 211 This is a very special unit in a premier condominium complex located directly on the Atlantic Ocean and in the heart of Islamorada. This unit is situated close to the pool and beach and provides spectacular ocean views. It is… | $3,500 More Info |
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BEACON REEF 314 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. Picture yourself relaxing on your… | $2,200 More Info |
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The Palms 415 Enjoy unobstructed and panoramic views of the Atlantic Ocean from your own private balcony! This 3 bedroom/2 bath condo unit features direct ocean views from the living room, balcony and two of the three bedrooms. Tropical furnishings create a warm… | $2,900 More Info |
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BEACON REEF 222 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… | $4,640 More Info |
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FUTURA YACHT CLUB 122 MINIMUM RENTAL: 7 NIGHTS Exceptional end unit townhouse with endless bay views from two balconies - one off the living area one off the master bedroom suite. Bring your boat and dock it directly in front of your unit. This… | $950 More Info |
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MOON BAY B404 MINIMUM RENTAL: 7 NIGHTS Unwind and enjoy the Sunsets on the Florida Bay! Full wall of glass overlooking the pool and the bay from the living room in this updated unit provides panoramic views of the pools and the bay.… | $750 More Info |
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The Palms #402 MINIMUM STAY: 28 DAYS Pure pleasure will be yours in this beautifully remodeled and immaculate condo. You’ll love the uncluttered and modern décor along with the recent renovations. Enjoy the picturesque views of Aligator Reef and the Atlantic Ocean from… | n/a More Info |
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Sunshine Place MINIMUM STAY: 28 DAYS You can have it all – 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. The ground level living area… | $3,300 More Info |
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The Palms 305 MINIMUM STAY: 28 DAYS Relax in this immaculate and spacious two bedroom condo with ocean views. This unit is well appointed with comfortable furnishings, flat screen TV in the living room, large dining table, and both baths have been updated.… | $2,000 More Info |