Islamorada vacation rentals

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Best Islamorada vacation rentals

Islamorada Paradise Overlooking the Fabulous Florida Bay. - Islamorada - Pool
Islamorada Paradise Overlooking the Fabulous Florida Bay.
Islamorada, FL
9.6Wonderful(26)
Condo
Parking
Free Wi-Fi
Pool
$397+
Check availability
Islamorada Modern Penthouse with Private Beach - Islamorada - Pool
Islamorada Modern Penthouse with Private Beach
Islamorada, FL
9.0Wonderful(1)
House
Parking
Free Wi-Fi
Pool
$2,511+
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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
9.7Wonderful(22)
Cottage
Free Wi-Fi
$811+
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Beautiful Studio Apartment - Summer Sea Condo #230 - Islamorada - Beach
Beautiful Studio Apartment - Summer Sea Condo #230
Islamorada, FL
10Wonderful(1)
Apartment
$151+
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The Oasis - Islamorada - Living room
The Oasis
Islamorada, FL
8.0Very good(1)
House
Parking
Free Wi-Fi
Pool
Pet friendly
$2,480+
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Castaway Island Vacation Bungalow - Islamorada - Bedroom
Castaway Island Vacation Bungalow
Islamorada, FL
9.9Wonderful(54)
House
Free Wi-Fi
$902+
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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
9.0Wonderful(32)
Condo
Free Wi-Fi
$192+
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Discover the Charm of Island Living - Islamorada - Pool
Discover the Charm of Island Living
Islamorada, FL
9.5Wonderful(14)
Condo
Free Wi-Fi
$355+
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Keys Kottage: Bayside villa W/ free onsite boat ramp marina & trailer parking. - Islamorada - Bedroom
Keys Kottage: Bayside villa W/ free onsite boat ramp marina & trailer parking.
Islamorada, FL
10Wonderful(36)
Villa
Free Wi-Fi
$398+
Check availability
Serenity by the Sea!! Anglers Reef with Boat Slip Available!! - Islamorada - Patio
Serenity by the Sea!! Anglers Reef with Boat Slip Available!!
Islamorada, FL
9.9Wonderful(32)
Villa
Free Wi-Fi
$432+
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Anglers Reef Direct Ocean, 4 bedroom, Dock, Comm Pool & Beach - Islamorada - Living room
Anglers Reef Direct Ocean, 4 bedroom, Dock, Comm Pool & Beach
Islamorada, FL
9.8Wonderful(32)
House
$701+
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Affordable luxury yacht charters. - Islamorada - Dining room
Affordable luxury yacht charters.
Islamorada, FL
10Wonderful(27)
Houseboat
$1,275+
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Studio w/2 Queen Beds, Kitchenette, Pool, Free Parking & Pet Friendly - Islamorada - Pool
Studio w/2 Queen Beds, Kitchenette, Pool, Free Parking & Pet Friendly
Islamorada, FL
10Wonderful(1)
Villa
Free Wi-Fi
$753+
Check availability
Truly Oceanfront-Panoramicoceanviews-Wraparounddecks-Quietlocation-Availableslip - Islamorada - Building
Truly Oceanfront-Panoramicoceanviews-Wraparounddecks-Quietlocation-Availableslip
Islamorada, FL
9.7Wonderful(16)
House
Free Wi-Fi
$791+
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Executive Bay Islamorada By Sofla Vacations - Islamorada
Executive Bay Islamorada By Sofla Vacations
Islamorada, FL
7.7Good(3)
House
Parking
Free Wi-Fi
Pool
Pet friendly
$576+
Check availability
Escape to the Keys - Islamorada
Escape to the Keys
Islamorada, FL
Apartment
Pool
$143+
Check availability
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 April, with average rates of $235. In comparison, January is the most expensive month, with prices at $1,232.

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 $267. The highest prices are found on Sunday, with average rates at $733.

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Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

April
January
$500
$393
Cheapest month to stay with an average 56% drop in price.
Most expensive month to stay with an average 130% 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, pet friendly, and beachfront are the most popular vacation rental property amenities in Islamorada
  • Vacation rentals in Islamorada are around 60% 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 Affordable luxury yacht charters. (10.0, 27 reviews), Hidden Gem Islamorada | 1st Floor (10.0, 29), and Keys Kottage: Bayside villa W/ free onsite boat ramp marina & trailer parking. (10.0, 36), 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 April and September.
  • The cheapest night for renting a vacation home in Islamorada is Sunday. In contrast, the most expensive is Tuesday.
  • 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

  • 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 6% 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 $409. 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 $1,122 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