Islamorada: Vacation Rental By Owner

Showing 20 Of 247 Vacation Rentals
  • Property-1 Image 1
    House $425 / Nightly
    • 4 Bed
    • 3 Baths
    Islamorada, FL

    The reasons you desire to visit the Keys can be found here! The unique location of this home near the end of the island offers protected dockage while giving... ...more

  • Property-2 Image 1
    Townhome $187 / Nightly
    • 2 Bed
    • 2 Baths
    • (3) Very Good
    Islamorada, FL

    Cozy, quaint, and peaceful townhouse with Best Location in Islamorada, Florida. Close enough yet not too far from the Top of the keys to the Southernmost Point of... ...more

  • Property-3 Image 1
    House $526 / Nightly
    • 4 Bed
    • 3 Baths
    • (26) Wonderful
    Islamorada, FL

    This beautiful, four-bedroom, three-bath house is conveniently located in the heart of Islamorada, the fishing capital of the world. Situated in a beautiful... ...more

  • Property-4 Image 1
    House $329 / Nightly
    • 2 Bed
    • 3 Baths
    • (1) Exceptional
    Islamorada, FL

    Please call me with questions. 305 . 240 . 0592 Anglers Reef had no substantial damage or flooding to the homes. They are already cleaning it up and getting... ...more

  • Property-5 Image 1
    House $444 / Nightly
    • 2 Bed
    • 2 Baths
    • (13) Exceptional
    Islamorada, FL

    Due to COVID-19 and the precedented times we are living, our home will provide hand sanitizer and have the whole house sanitized when one guest leaves and another... ...more

  • Property-6 Image 1
    House Select Dates for Price
    • 2 Bed
    • 3 Baths
    • (38) Exceptional
    Islamorada, FL

    Paradise is only a phone call away. Our 2 BR/2.5 BA conch style townhouse is available for weekly and monthly vacation rentals. Our unit has unobstructed direct... ...more

  • Property-7 Image 1
    House $339 / Nightly
    • 2 Bed
    • 3 Baths
    • (24) Excellent
    Islamorada, FL

    2 Bedrooms, 2.5 Bathrooms, Sleeps 6 VR-103# One King One Queen One futon-double Angler's reef is a luxury retreat framed by mangroves and the clear waters of... ...more

  • Property-8 Image 1
    House $348 / Nightly
    • 3 Bed
    • 3 Baths
    • (2) Exceptional
    Islamorada, FL

    Get ready to enjoy the sun on your skin and wind in your hair at this spacious, beautiful, waterfront home! Whether you're here to fish or just get away to the... ...more

  • Property-9 Image 1
    House $583 / Nightly
    • 2 Bed
    • 3 Baths
    • (50)
    Islamorada, FL

    The Keys are open... Come stay at the Salty Pelican in Angler's Reef! This magnificent home with amazing direct ocean views from the master bedroom, living room... ...more

  • Property-10 Image 1
    Condo $553 / Nightly
    • 3 Bed
    • 3 Baths
    • (10) Wonderful
    Islamorada, FL

    This fisherman's delight boasts a 30' boat slip and storage unit with a bait freezer. This is the place to come for total relaxation, boating, swimming, deep sea... ...more

  • Property-11 Image 1
    House $482 / Nightly
    • 6 Bed
    • 3 Baths
    • (2) Exceptional
    Islamorada, FL

    Located in one of the best neighborhoods in the keys!! Huge 4700 sq ft home with wonderful outdoor living areas. Pool, brand new hot tub, beautiful outdoor... ...more

  • Property-12 Image 1
    House Select Dates for Price
    • 3 Bed
    • 4 Baths
    Islamorada, FL

    Wonderful Baview Home in south Islamorada in the fabulous Florida Keys for rent by the month; offering Incredible Bay and Sunset Views. Heated pool & hot tub.... ...more

  • Property-13 Image 1
    Condo Select Dates for Price
    • 3 Bed
    • 3 Baths
    • (2) Very Good
    Islamorada, FL

    Maison Matecumbe is an exclusive gated and private boutique townhome complex. This wonderful unit offers an open floor and three inviting bedrooms and three... ...more

  • Property-14 Image 1
    Condo Select Dates for Price
    • 3 Bed
    • 2 Baths
    Islamorada, FL

    Islamorada oceanfront complex... Maison Matecumbe. The unit has one level living with 3 bedroom and 2 baths. Fully equipped kitchen with counter bar area and full... ...more

  • Property-15 Image 1
    House Select Dates for Price
    • 4 Bed
    • 4 Baths
    • (1) Exceptional
    Islamorada, FL

    Looking for an amazing home in Venetian Shores? This beautifully updated 4 bedroom, 4 bath home has everything you need for a perfect vacation. This home is... ...more

  • Property-16 Image 1
    Townhome Select Dates for Price
    • 3 Bed
    • 2 Baths
    • (4) Excellent
    Islamorada, FL

    Relax in this great townhouse style condo, which overlooks the sparkling Atlantic Ocean. This condo features 3 bedrooms and 2 bathrooms, a balcony off the living... ...more

  • Property-17 Image 1
    House Select Dates for Price
    • 2 Bed
    • 2 Baths
    • (4) Excellent
    Islamorada, FL

    Great house in Lower Matecumbe (south side of Islamorada) at the 75 mile marker on the bayside. This house has fabulous sunset views in a nice quiet part of town.... ...more

  • Property-18 Image 1
    House Select Dates for Price
    • 2 Bed
    • 2 Baths
    • (1)
    Islamorada, FL

    Cute, comfortable home in Lower Matecumbe, Mile Marker 76.5, Oceanside. Wake up to the sun and water each morning from either bedroom at our charming stilt house.... ...more

  • Property-19 Image 1
    Apartment Select Dates for Price
    • 3 Bed
    • 3 Baths
    • (1)
    Islamorada, FL

    Beautiful modern luxury unit with 3 bedrooms and 2 full bathrooms, along with a half guest-bath! Plasma TV, VCR and DVD player in the living room. This unit does... ...more

  • Property-20 Image 1
    Townhome Select Dates for Price
    • 3 Bed
    • 2 Baths
    • (2) Exceptional
    Islamorada, FL

    Relax in this great townhouse style condo, which overlooks the sparkling Atlantic Ocean. This condo features 3 bedrooms and 2 bathrooms, a balcony off the living... ...more

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Vacation Rental Filters are an easy way to help you personalize your search to find the ideal rental in Islamorada. Many accommodations in Islamorada provide "Non Smoking Only", there are 178, or there are 165 of Vacation Rentals in Islamorada with a "Fishing", there are also 165 with "Scuba Diving - Snorkling", which is another great reason to visit Islamorada.

We analyzed price data and rendered them in this graph, which shows vacation rental prices for the next twelve months in Islamorada. The most expensive month of the next 12 months is in July, where prices hit an average of $163 a night. In June, prices will hit an average low of $320 per night.