Islamorada vacation rentals

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Best Islamorada vacation rentals

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$85 - $1,085$1,085 - $2,085$2,085 - $3,085$3,085 - $4,084$4,084+ 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(26)
Parking
Free Wi-Fi
Pool
$397+
Check availability
A 57-foot trawler in Islamorada - Islamorada - Balcony
A 57-foot trawler in Islamorada
Islamorada, FL
8.3Very good(19)
Free Wi-Fi
$438+
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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
$1,469+
Check availability
Beautiful Studio Apartment - Summer Sea Condo #230 - Islamorada - Beach
Beautiful Studio Apartment - Summer Sea Condo #230
Islamorada, FL
10Wonderful(1)
$154+
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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(21)
Free Wi-Fi
$688+
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The Oasis - Islamorada - Living room
The Oasis
Islamorada, FL
8.0Very good(1)
Parking
Pool
Pet friendly
$2,068+
Check availability
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
8.9Very good(30)
Free Wi-Fi
$225+
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Discover the Charm of Island Living - Islamorada - Pool
Discover the Charm of Island Living
Islamorada, FL
9.5Wonderful(14)
Free Wi-Fi
$304+
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Executive Bay Islamorada By Sofla Vacations - Islamorada
Executive Bay Islamorada By Sofla Vacations
Islamorada, FL
7.7Good(2)
Parking
Free Wi-Fi
Pool
Pet friendly
$448+
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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(35)
Free Wi-Fi
$345+
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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(31)
Free Wi-Fi
$397+
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Castaway Island Vacation Bungalow - Islamorada - Bedroom
Castaway Island Vacation Bungalow
Islamorada, FL
9.9Wonderful(53)
Parking
Free Wi-Fi
Pet friendly
$738+
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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(31)
$1,072+
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Spectacular Top Floor Oceanfront View Condo - Islamorada - Pool
Spectacular Top Floor Oceanfront View Condo
Islamorada, FL
9.8Wonderful(38)
$210+
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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(30)
Parking
Free Wi-Fi
Pool
$413+
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Escape to the Keys - Islamorada
Escape to the Keys
Islamorada, FL
Pool
$143+
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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 December, with average rates of $319. In comparison, February is the most expensive month, with prices at $783.
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Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

December
February
$393
$583
Cheapest month to stay with an average 39% drop in price.
Most expensive month to stay with an average 50% 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, beachfront, and pet friendly are the most popular vacation rental property amenities in Islamorada
  • Vacation rentals in Islamorada are around 55% 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, 28), and Keys Kottage: Bayside villa W/ free onsite boat ramp marina & trailer parking. (10.0, 35), 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 December and September.
  • The cheapest night for renting a vacation home in Islamorada is Thursday. In contrast, the most expensive is Saturday.
  • 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.
  • The cheapest Islamorada vacation rental found on KAYAK in the last 2 weeks was $284, while the most expensive was $416.

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

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