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Vacation Rentals in Islamorada Area
Find the perfect Cheap Vacation Rentals, Vacation Rental Deals and Luxury Villas in Florida, Colorado, California, Hawaii, South Carolina, Outerbanks and more! Get Last Minute Deals on Beach Houses, Ski cabins, Family Vacation Rentals and Pet Friendly Vacation Rentals now at How2Vacation.com!
Featured Vacation Rental Companies
Key West's Most Meticulously Furnished & Maintained 1-7 Bedroom Vacation Homes
We feel a special responsibility to anyone who has chosen to vacation in the Keys. We want every one of our guests to come away feeling the same magic that we felt ourselves when we first came to Key West. That is why each of the homes on our website has been designed and furnished with that unique "Conch Republic" flavor, but also with the idea that our guests should feel right at home. With so many vacation homes making do with the barest of essentials, each of the homes we have to offer will come as a pleasant surprise. We also pride ourselves in the service we provide for our guests, whether it's just recommending a great restaurant, or dealing with a maintenance issue in the least amount of time possible. Whatever your needs while you are here, our guest services staff will take care of them. If you have any questions, you can call us at any time.Phone Number: 305.305.9675
Beautiful Bayfront Condo with Marina, Pool and Beach (Futura Yacht Club) Quiet gated community at mile marker 88.5 bayside in Islamorada with world class fishing and diving,2 lighted tennis courts, large heated pool, large 65 slip marina, boat dockage and launch ramp, parking area for boat trailers, wonderful snorkeling and fishing from our private beach, charming updated kitchen and master bedroom and bath with breakfast bar, large bait freezer for fish or bait, spectacular oceanside restaurants and bars which you may travel to by boat or car.
Your Best Choice For Islamorada and Upper Keys Rentals - Vacation or Long TermPhone Number: 305 664-8808
Florida Keys Vacation Rentals & Condos
Welcome to Florida Keys Vacation Rentals! You'll find everything you need here to plan the perfect Florida Keys vacation, an absolutely wonderful vacation destination at any time of year. Florida Keys Vacation Rentals is dedicated to help visitors plan and enjoy their vacation in the Florida Keys through providing vacation rental homes, townhomes, and condos for rent in the Florida Keys including Key West, Islamorada, Key Largo, the Lower Keys and the Middle Keys.Phone Number: 888-743-5635
Vacation Rentals in Islamorada Area
The Palms 402
- 2 Bedrooms, 2 Bathrooms, Sleeps 5
- MINIMUM STAY: 28 DAYS Pure pleasure will be yours in this beautifully remodeled and immaculate condo. You’ll love the uncluttered…
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- $2200
monthly
The Palms 415
- 3 Bedrooms, 2 Bathrooms, Sleeps 8
- Enjoy unobstructed and panoramic views of the Atlantic Ocean from your own private balcony! This 3 bedroom/2 bath condo unit…
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- $2900
monthly
THE PALMS 506
- 2 Bedrooms, 2 Bathrooms, Sleeps 4
- Wonderfully inviting condo at one of Islamorada's favorite condo complexes. This unit is tastefully decorated with a nautical theme -…
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- $1800
monthly
VALENCIA GETAWAY
- 3 Bedrooms, 2 Bathrooms, Sleeps 8
- Bring your boat your dog and the kids! Relax on the patio or swim in the canal. You will love…
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- $3400
monthly
THE PALMS 509
- 2 Bedrooms, 2 Bathrooms, Sleeps 6
- Enjoy the magnificent ocean views from this wonderful 5th floor condo. Use the telescope to watch the ships and fishing…
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- $1933
monthly
SEA GULLS 506
- 2 Bedrooms, 2 Bathrooms, Sleeps 4
- Charming 5th floor condo with panoramic views of the Atlantic Ocean from the balcony. New owner has just refurbished this…
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- $800
monthly
PLANTATION BY THE SEA
- 2 Bedrooms, 2 Bathrooms, Sleeps 6
- Enjoy this beautifully remodeled two bedroom condo at Plantation by the Sea. Brand new kitchen (12/2010) with all new appliances…
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- $1900
monthly
Palm Harbor
- 4 Bedrooms, 3 Bathrooms, Sleeps 8
- MINIMUM RENTAL: 28 DAYS Totally charming private villa with pool and dock. Gently swaying palm trees greet you at the…
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- $11000
monthly
The Palms 301
- 2 Bedrooms, 2 Bathrooms, Sleeps 6
- This exceptional condo has been impeccably maintained and is located in one of the finest condo complexes in Islamorada. It…
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- $1900
monthly
THE PALMS 308
- 2 Bedrooms, 2 Bathrooms, Sleeps 7
- Enjoy the magnificent ocean views from this wonderful 3rd floor condo. This unit is ready for your arrival. The décor…
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- $2069
monthly
LITTLE BAY COTTAGE
- 2 Bedrooms, 2 Bathrooms, Sleeps 4
- MINIMUM RENTAL: 3 DAYS. This is one of three rental units on this property. The cottage is a ground level…
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- $350
nightly
Beautiful Bayfront Condo with Marina, Pool and Beach (Futura Yacht…
- 3 Bedrooms, 2 Bathrooms, Sleeps 7
- Quiet gated community at mile marker 88.5 bayside in Islamorada with world class fishing and diving,2 lighted tennis courts, large…
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- $700
weekly
The Palms 305
- 2 Bedrooms, 2 Bathrooms, Sleeps 6
- MINIMUM STAY: 28 DAYS Relax in this immaculate and spacious two bedroom condo with ocean views. This unit is well…
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- $2000
monthly
Bayside- A 1st Floor Condo on Florida Bay
- 1 Bedroom, 2 Bathrooms, Sleeps 4
- An easy 90 minute drive from Miami International Airport, the property is located in the heart of Islamorada, directly on…
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- $1095
weekly
Islamorada Keys Kottage
- 2 Bedrooms, 2 Bathrooms, Sleeps 8
- An easy 90 minute drive from Miami International Airport, the Keys Kottage is located in the heart of Islamorada. Completely…
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- $1095
weekly
THE PERFECT ESCAPE with dockage, pool & jacuzzi
- 4 Bedrooms, 4 Bathrooms, Sleeps 8
- Islamorada is the fishing capital of the world. You are practically surrounded by water with ALL sorts of water activities…
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- $2500
weekly
FUTURA YACHT CLUB CONDOS - 2 UNITS OCEAN VIEW
- 2 Bedrooms, 2 Bathrooms, Sleeps 6
- Futura Yacht Club Condominium Units Two privately owned condominium units at the Futura Yacht Club in the Village of Islamorada.…
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- $700
weekend
Islamorada Plantation Key Oceanside
- 2 Bedrooms, 2 Bathrooms, Sleeps 4
- We have two condominimums offering all the amenities of home with the bonus of breathtaking oceanfront view: Full ocean view…
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- $875
weekly
Beacon Reef 306
- 2 Bedrooms, 2 Bathrooms, Sleeps 4
- MINIMUM STAY: 28 DAYS Enjoy a relaxing summer and fall here in the Keys at this immaculate and charming two…
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- $4000
monthly
Angler's Reef
- 2 Bedrooms, 2.5 Bathrooms, Sleeps 6
- MINIMUM STAY: 7 DAYS Extraordinary 2-story single family home in a Key West style neighborhood. This gated ocean front community…
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- $1800
weekly
Secluded Oceanview Townhome with Private Dock
- 2 Bedrooms, 2.5 Bathrooms, Sleeps 6
- Experience total seclusion in a ten-unit, luxury, oceanfront complex called Port of Call, nestled along Millionaire's Row on Plantation Key,…
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- $1100
weekly
The Palms #417
- 1 Bedroom, 2 Bathrooms, Sleeps 2
- Minimum Rental one month. TOTALLY remodeled in 2007-2008. Everything in this unit is new - furnishings, linens, kitchen, appliances, and…
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- $2000
monthly
The Mermaid's Cottage
- 3 Bedrooms, 2 Bathrooms, Sleeps 6
- Absolutely Enchanting! Words are hard to find to accurately describe the charm and tropical personality found in this home. Your…
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- $3000
monthly
Villa Venetian Shores
- 4 Bedrooms, 3 Bathrooms, Sleeps 10
- Villa Venetian Shores is located in Islamorada, FL. Islamorada is the sport fishing capital of the world. It is located…
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- $175
weekly
The Palms 317
- 1 Bedroom, 1.5 Bathrooms, Sleeps 2
- MINIMUM RENTAL: 27 NIGHTS (ONE MONTH) This Condo Complex is located directly on the Atlantic Ocean and this one bedroom…
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- $1800
monthly
Little Bay
- 2 Bedrooms, 2 Bathrooms, Sleeps 18
- This is a lush tropical setting in a gated compound and located directly on the Florida Bay. Protected dockage in…
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- $7200
monthly
The Palms #402
- 2 Bedrooms, 2 Bathrooms, Sleeps 5
- MINIMUM STAY: 28 DAYS Pure pleasure will be yours in this beautifully remodeled and immaculate condo. You’ll love the uncluttered…
- from
- Contact Owner
LITTLE BAY - Lower Duplex
- 2 Bedrooms, 2 Bathrooms, Sleeps 6
- MINIMUM RENTAL: 3 NIGHTS Lower Duplex This is one of three rental units on this fabulous property. The Little Bay…
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- $350
nightly
LITTLE BAY - Upper Duplex
- 2 Bedrooms, 2 Bathrooms, Sleeps 6
- MINIMUM RENTAL: 3 NIGHTS Upper Duplex This is one of three rental units on this fabulous property. The Little Bay…
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- $350
nightly
FUTURA YACHT CLUB 122
- 2 Bedrooms, 2.1 Bathrooms, Sleeps 4
- MINIMUM RENTAL: 7 NIGHTS Exceptional end unit townhouse with endless bay views from two balconies - one off the living…
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- $950
weekly
New Bay Harbour Condominium Ocean View and Boat Dock -…
- 3 Bedrooms, 2.5 Bathrooms, Sleeps 6
- Escape the everyday stress of the mainland for the quiet, relaxed atmosphere of the Florida Keys in an exclusive gate…
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- $2000
weekly
Sunshine Place
- 1 Bedroom, 1.5 Bathrooms, Sleeps 2
- MINIMUM STAY: 28 DAYS You can have it all – privacy and convenience. The owners of this wonderful property called…
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- $3300
monthly
BEACON REEF 302
- 2 Bedrooms, 2 Bathrooms, Sleeps 4
- MINIMUM RENTAL: 27 NIGHTS (ONE MONTH) Beautiful condo - new on the rental market. You'll be so glad the owners…
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- $3577
monthly
BEACON REEF 314
- 2 Bedrooms, 2 Bathrooms, Sleeps 4
- Beacon Reef is one of the most desirable condominium complexes in the Upper Keys. Located in Islamorada it is convenient…
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- $2200
monthly
BEACON REEF 222
- 2 Bedrooms, 2 Bathrooms, Sleeps 4
- Extraordinary ocean front condo with panoramic views of the Atlantic Ocean. Relax on your private balcony or use the spiral…
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- $4640
monthly
BEACON REEF 211
- 2 Bedrooms, 2 Bathrooms, Sleeps 4
- This is a very special unit in a premier condominium complex located directly on the Atlantic Ocean and in the…
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- $3500
monthly
Enchanted Fish Camp
- 3 Bedrooms, 2 Bathrooms, Sleeps 10
- Enchanted Fish Camp is a wonderful single family home which exemplifies the charm and character of the Florida Keys. If…
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- $4000
monthly
The Palms 214
- 2 Bedrooms, 2 Bathrooms, Sleeps 4
- Gorgeous 2 bedroom, 2 bath condo. The Palms of Islamorada is gated for privacy and located directly on the Atlantic…
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- $1900
monthly
Matecumbe Jewel
- 3 Bedrooms, 2 Bathrooms, Sleeps 6
- Minimum stay 29 Days. You will love this home! This is a new listing - make your reservations now before…
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- $4000
monthly
San Marco Retreat
- 5 Bedrooms, 4 Bathrooms, Sleeps 12
- San Marco Retreat is a 5 bedroom, 4 bath contemporary house with an inground heated swimming pool and a boat…
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- $2850
weekly
Anglers Reef Anglefish
- 3 Bedrooms, 2.5 Bathrooms, Sleeps 6
- Anglers Reef Anglefish is an oceanfront beauty, This 3 bedroom, 2.5 bath Key West styled house is set in a…
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- $2000
weekly
The Palms 201
- 2 Bedrooms, 2 Bathrooms, Sleeps 6
- Minimum Rental: 30 days Enjoy the magnificent ocean views of this wonderful condominium complex. You'll love the newly completed renovations.…
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- $2000
monthly
THE PALMS 314
- 2 Bedrooms, 2 Bathrooms, Sleeps 5
- Sensational oceanfront views are yours from both the master bedroom and the balcony of this beautifully appointed condo. Watch the…
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- $1837
monthly
EMERALD COVE
- 4 Bedrooms, 3 Bathrooms, Sleeps 8
- MINIMUM STAY: 29 DAYS Enjoy unobstructed and panoramic views of the Atlantic Ocean from your own private balcony! This 3…
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- $5500
monthly
Beacon Reef 319
- 3 Bedrooms, 2.5 Bathrooms, Sleeps 6
- Minimum Rental One Month. Gorgeous oceanfront condo in one of Islamorada's premier condominium complexes. Direct ocean view - nothing between…
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- $5000
monthly
Blue Water Retreat
- 3 Bedrooms, 3 Bathrooms, Sleeps 6
- Minimum Rental 29 Days. Location, location, location! This home has it all - ocean side Lower Matecumbe location, totally remodeled…
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- $5000
monthly
My Paradise
- 3 Bedrooms, 2 Bathrooms, Sleeps 6
- Minimum Rental 29 Days. Direct oceanfront home with large sandy beach, protected dockage , handicap accessible and located in the…
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- $5500
monthly
Venetian Dream
- 3 Bedrooms, 4.5 Bathrooms, Sleeps 8
- Minimum Rental 29 Days. Venetian Dream is a new single family home and is located on a deep water canal…
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- $5200
monthly
