Vacation Rentals in Islamorada Area

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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…
  • from
  • $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…
  • from
  • $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 -…
  • from
  • $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…
  • from
  • $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…
  • from
  • $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…
  • from
  • $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…
  • from
  • $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…
  • from
  • $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…
  • from
  • $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…
  • from
  • $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…
  • from
  • $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…
  • from
  • $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…
  • from
  • $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…
  • from
  • $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…
  • from
  • $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…
  • from
  • $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.…
  • from
  • $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…
  • from
  • $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…
  • from
  • $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…
  • from
  • $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,…
  • from
  • $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…
  • from
  • $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…
  • from
  • $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…
  • from
  • $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…
  • from
  • $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…
  • from
  • $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…
  • from
  • $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…
  • from
  • $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…
  • from
  • $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…
  • from
  • $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…
  • from
  • $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…
  • from
  • $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…
  • from
  • $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…
  • from
  • $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…
  • from
  • $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…
  • from
  • $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…
  • from
  • $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…
  • from
  • $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…
  • from
  • $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…
  • from
  • $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.…
  • from
  • $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…
  • from
  • $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…
  • from
  • $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…
  • from
  • $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…
  • from
  • $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…
  • from
  • $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…
  • from
  • $5200
    monthly

 

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