Islamorada vacation rentals

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Best Islamorada vacation rentals

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$85 - $1,279$1,279 - $2,472$2,472 - $3,665$3,665 - $4,858$4,858+ per night

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Most recommended vacation rentals in Islamorada

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Islamorada Paradise Overlooking the Fabulous Florida Bay. - Islamorada - Pool
Islamorada Paradise Overlooking the Fabulous Florida Bay.
Islamorada, FL
9.7Wonderful(24)
Parking
Free Wi-Fi
Pool
$337+
Check availability
A 57-foot trawler in Islamorada - Islamorada - Balcony
A 57-foot trawler in Islamorada
Islamorada, FL
Free Wi-Fi
Pet friendly
$389+
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Executive Bay Islamorada By Sofla Vacations - Islamorada - Living room
Executive Bay Islamorada By Sofla Vacations
Islamorada, FL
7.7Good(2)
Parking
Free Wi-Fi
Pool
Pet friendly
$203+
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Outdoor Resorts, Long Key, Fl - Islamorada - Pool
Outdoor Resorts, Long Key, Fl
Islamorada, FL
Pool
$107+
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Incredible Beach Cottage Rental with Heated Swimming Pool in Islamorada, Florida - Islamorada - Patio
Incredible Beach Cottage Rental with Heated Swimming Pool in Islamorada, Florida
Islamorada, FL
9.6Wonderful(15)
Free Wi-Fi
Spa
$748+
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Beautiful Studio Apartment - Summer Sea Condo #230 - Islamorada - Beach
Beautiful Studio Apartment - Summer Sea Condo #230
Islamorada, FL
$155+
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Ocean Views from Balcony, Living Room and Bedroom. Islamorada License 24-0380 - Islamorada - Pool
Ocean Views from Balcony, Living Room and Bedroom. Islamorada License 24-0380
Islamorada, FL
8.6Very good(20)
Free Wi-Fi
Pool
$223+
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Islamorada Modern Penthouse with Private Beach - Islamorada - Pool
Islamorada Modern Penthouse with Private Beach
Islamorada, FL
9.0Wonderful(1)
Parking
Free Wi-Fi
Pool
$1,547+
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Beautiful water front home, private dock in Islamorada, World Fishing Capital - Islamorada - Living room
Beautiful water front home, private dock in Islamorada, World Fishing Capital
Islamorada, FL
Free Wi-Fi
$226+
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The Oasis - Islamorada - Living room
The Oasis
Islamorada, FL
Parking
Pool
Pet friendly
$2,202+
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Key Lime Cottage in the heart of Islamorada - Islamorada
Key Lime Cottage in the heart of Islamorada
Islamorada, FL
9.4Wonderful(29)
Parking
Free Wi-Fi
Pool
$412+
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Oceanfront Oasis - Pinch me am I dreaming - Islamorada
Oceanfront Oasis - Pinch me am I dreaming
Islamorada, FL
$4,858+
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Islamorada Affordable 2023 2/2\n Ocean Views\nneighborhood Jetty & Tiki -Sunsets\n - Islamorada
Islamorada Affordable 2023 2/2\n Ocean Views\nneighborhood Jetty & Tiki -Sunsets\n
Islamorada, FL
$184+
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Modern Oceanview Paradise at Islamorada - Islamorada
Modern Oceanview Paradise at Islamorada
Islamorada, FL
$2,513+
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Penthouse Paradise Developer Unit with Every Upgrade Possible - Islamorada
Penthouse Paradise Developer Unit with Every Upgrade Possible
Islamorada, FL
Pool
Spa
$1,924+
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Islamorada Home Plus Bunkhouse - Islamorada
Islamorada Home Plus Bunkhouse
Islamorada, FL
Pool
$219+
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KAYAK’s insights for vacation rentals in Islamorada

Discover seasonal trends, ideal booking windows, and other data-driven tips to plan your stay in Islamorada with confidence.

Which month has the cheapest vacation rental rates in Islamorada?

Vacation rentals are cheapest in Islamorada in August, with average rates of $106. In comparison, December is the most expensive month, with prices at $5,869.

What is the cheapest day of the week to book a vacation rental in Islamorada?

Friday offers the lowest rates in Islamorada, with an average nightly price of $526. The highest prices are found on Wednesday, with average rates at $4,610.
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Good to know

Low season

August

High season

December

Average price (weeknight)

$1,626

Average price (weekend night)

$688
Cheapest month to stay with an average 90% drop in price.
Most expensive month to stay with an average 437% rise in price.
Average Sun - Thu price over the last 2 weeks.
Average Fri & Sat price over the last 2 weeks.

KAYAK's top tips for finding Islamorada vacation rental deals

  • Pet friendly, beachfront, and pool are the most popular vacation rental property amenities in Islamorada
  • Vacation rentals in Islamorada are around 61% more expensive than hotels on average. Search here to compare prices for all accommodation types in Islamorada.
  • The best vacation rental properties in Islamorada are Spectacular Top Floor Oceanfront View Condo (9.8, 27 reviews), Islamorada Paradise Overlooking the Fabulous Florida Bay. (9.7, 24), and Anglers Reef Paradise (9.7, 74), based on ratings and reviews from real travelers.
  • If you’re looking for a cheap vacation rental in Islamorada, you should consider visiting during the low season. The cheapest vacation homes in Islamorada can be found in August and January.
  • The cheapest night for renting a vacation home in Islamorada is Friday. In contrast, the most expensive is Wednesday.
  • Vacation rentals are a popular choice for both long and short-term stays. KAYAK users usually book their vacation rental in Islamorada for 22 days.
  • The cheapest Islamorada vacation rental found on KAYAK in the last 2 weeks was $242, while the most expensive was $361.

FAQs when booking a vacation home in Islamorada

  • How much is a vacation rental for a week in Islamorada?

    The average price for a weekly Islamorada vacation rental found by KAYAK users in the last 2 weeks is $1,361.

  • How much is a vacation rental for a month in Islamorada?

    The average price for a monthly Islamorada vacation rental found by KAYAK users in the last 2 weeks is $5,835.

  • What types of vacation rentals are available in Islamorada?

    There are loads of different property types that you can make your vacation home in Islamorada. You’ll find apartments, caravans, condos, cottages, houses, holiday parks, houseboats, recreational vehicles and villas.

  • What are some of the most-loved vacation rentals available in Islamorada?

    There are many types of properties available for Islamorada vacation rentals. If you’re looking for something special, vacation rentals most loved by KAYAK users are Fiesta Key Rv Resort Premium Room 3 and Fiesta Key Rv Resort Standard Room 8.

  • Are there any pet-friendly vacation rentals in Islamorada?

    There are a number of dog and pet-friendly Islamorada vacation rentals, with around 16% allowing you to bring your pet along with you.

  • How much is a vacation rental in Islamorada for this weekend?

    In the last 72 hours, users have found Islamorada vacation rentals for this weekend for as low as $886 per night. Search here for similar prices

  • How can I find vacation rentals near me in Islamorada?

    Take a look at our vacation rentals map to find the best vacation rental homes near you.

Where to stay in Islamorada?

Our map will help you find the perfect place to stay in Islamorada by showing you the exact location of each vacation rental.

Everything you need to know for your stay in Islamorada

Islamorada vacation rental deals. Search for vacation homes, apartments, condos, cabins, cottages, villas and more in Islamorada. Find cheap vacation homes to rent in Islamorada. KAYAK searches hundreds of travel sites to help you find and book a vacation rental in Islamorada that suits you best.

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