Islamorada vacation rentals

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Booking Insights
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Best Islamorada vacation rentals

Charming 2 Bedroom Ground Level Home with Bay Views - Islamorada - Beach
Charming 2 Bedroom Ground Level Home with Bay Views
Islamorada, FL
10Wonderful(4)
House
$618+
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A True Islamorada Oasis with Breathtaking Bay Views - Islamorada - Living room
A True Islamorada Oasis with Breathtaking Bay Views
Islamorada, FL
10Wonderful(4)
House
$1,745+
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Little Bay Compound - Islamorada - Living room
Little Bay Compound
Islamorada, FL
6.0Okay(1)
House
Parking
Free Wi-Fi
Pet friendly
Spa
$2,167+
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Beautiful Home located in Downtown Islamorada - Islamorada - Pool
Beautiful Home located in Downtown Islamorada
Islamorada, FL
House
Free Wi-Fi
$373+
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Breathtaking Bay Views - Islamorada - Living room
Breathtaking Bay Views
Islamorada, FL
7.4Good(7)
House
$747+
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Cozy Cottage in the Heart of Islamorada - Islamorada - Living room
Cozy Cottage in the Heart of Islamorada
Islamorada, FL
House
$611+
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Hidden Gem Islamorada | 1st Floor - Islamorada - Beach
Hidden Gem Islamorada | 1st Floor
Islamorada, FL
10Wonderful(29)
Apartment
$615+
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Bungalow #5 - 2 Bed/1 Bath & Pool in Islamorada - Islamorada - Pool
Bungalow #5 - 2 Bed/1 Bath & Pool in Islamorada
Islamorada, FL
9.4Wonderful(11)
House
Pool
$502+
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Anglers Reef Paradise - Islamorada
Anglers Reef Paradise
Islamorada, FL
9.7Wonderful(75)
House
Parking
Free Wi-Fi
Pool
$563+
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Fiesta Key RV Resort Waterfront Cottage 33 - Long Key
Fiesta Key RV Resort Waterfront Cottage 33
Long Key, FL
8.6Very good(65)
Holiday Park
Parking
$431+
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Beacon Reef 310 - Islamorada
Beacon Reef 310
Islamorada, FL
House
Parking
Free Wi-Fi
Spa
$329+
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Little Bay Lower - Islamorada
Little Bay Lower
Islamorada, FL
Apartment
Parking
Free Wi-Fi
Pet friendly
Spa
$756+
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Little Bay Cottage - Islamorada
Little Bay Cottage
Islamorada, FL
House
Parking
Free Wi-Fi
Spa
$695+
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Palms 309 - Islamorada
Palms 309
Islamorada, FL
House
Parking
Free Wi-Fi
Pool
Spa
$218+
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Fiesta Key Rv Resort Premium Room 3 - Long Key
Fiesta Key Rv Resort Premium Room 3
Long Key, FL
8.5Very good(32)
Holiday Park
Parking
$323+
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Anglers Reef Getaway - Islamorada
Anglers Reef Getaway
Islamorada, FL
9.2Wonderful(41)
Villa
$512+
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Booking Insights

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 June, with average rates of $218. In comparison, March is the most expensive month, with prices at $706.

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 $411. The highest prices are found on Thursday, with average rates at $633.

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Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

June
March
$560
$439
Cheapest month to stay with an average 53% drop in price.
Most expensive month to stay with an average 51% 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

  • Pool, air-conditioned, beachfront, pet friendly, and wifi are the most popular vacation rental property amenities in Islamorada
  • Vacation rentals in Islamorada are around 48% 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 Hidden Gem Islamorada | 1st Floor (10.0, 29 reviews), Castaway Island Vacation Bungalow (9.9, 55), and Serenity by the Sea!! Anglers Reef with Boat Slip Available!! (9.9, 32), 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 June and April.
  • The cheapest night for renting a vacation home in Islamorada is Friday. In contrast, the most expensive is Thursday.
  • Vacation rentals are a popular choice for both long and short-term stays. KAYAK users usually book their vacation rental in Islamorada for 24 days.

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 $2,591.

  • 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 $11,105.

  • 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, condos, cottages, houses, holiday parks, houseboats, recreational vehicles and villas.

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

    There are a number of dog and pet-friendly Islamorada vacation rentals, with around 5% allowing you to bring your pet along with you.

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

    In the last 72 hours, users have found Islamorada vacation rentals for tonight for as low as $328. Search here for similar prices

  • 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 $1,164 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