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Islamorada vacation rentals

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Best Islamorada vacation rentals

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, United States
9.7Wonderful(24)
Parking
Free Wi-Fi
Pool
C$ 371+
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A 57-foot trawler in Islamorada - Islamorada - Balcony
A 57-foot trawler in Islamorada
Islamorada, FL, United States
Free Wi-Fi
Pet friendly
C$ 606+
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Executive Bay Islamorada By Sofla Vacations - Islamorada - Living room
Executive Bay Islamorada By Sofla Vacations
Islamorada, FL, United States
7.7Good(2)
Parking
Free Wi-Fi
Pool
Pet friendly
C$ 281+
Check availability
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, United States
9.6Wonderful(15)
Free Wi-Fi
Spa
C$ 1,041+
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, United States
8.6Very good(20)
Free Wi-Fi
Pool
C$ 365+
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Outdoor Resorts, Long Key, Fl - Islamorada - Pool
Outdoor Resorts, Long Key, Fl
Islamorada, FL, United States
Pool
C$ 148+
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Beachfront Villa At Islamorada By The Gl - Islamorada - Stairs
Beachfront Villa At Islamorada By The Gl
Islamorada, FL, United States
Free Wi-Fi
Pet friendly
Spa
C$ 5,653+
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The Oasis - Islamorada - Living room
The Oasis
Islamorada, FL, United States
Parking
Pool
Pet friendly
C$ 3,128+
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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, United States
Free Wi-Fi
C$ 313+
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Discover the Charm of Island Living - Islamorada - Pool
Discover the Charm of Island Living
Islamorada, FL, United States
Free Wi-Fi
Pool
C$ 429+
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Oceanfront Oasis - Pinch me am I dreaming - Islamorada
Oceanfront Oasis - Pinch me am I dreaming
Islamorada, FL, United States
C$ 6,724+
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Modern Oceanview Paradise at Islamorada - Islamorada
Modern Oceanview Paradise at Islamorada
Islamorada, FL, United States
C$ 3,478+
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Penthouse Paradise Developer Unit with Every Upgrade Possible - Islamorada
Penthouse Paradise Developer Unit with Every Upgrade Possible
Islamorada, FL, United States
Pool
Spa
C$ 2,663+
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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, United States
C$ 255+
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Key Lime Cottage in the heart of Islamorada - Islamorada
Key Lime Cottage in the heart of Islamorada
Islamorada, FL, United States
9.4Wonderful(29)
Parking
Free Wi-Fi
Pool
C$ 711+
Check availability
Luxurious Ph 5br 3.5ba Gym/ Pool & Jacuzzi/ Sauna - Islamorada
Luxurious Ph 5br 3.5ba Gym/ Pool & Jacuzzi/ Sauna
Islamorada, FL, United States
Pool
C$ 3,524+
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Good to know

Low season

December

High season

March
Cheapest month to stay with an average 27% drop in price.
Most expensive month to stay with an average 14% rise in price.

KAYAK's top tips for finding Islamorada holiday rental deals

  • Beachfront, pool, and pet friendly are the most popular vacation rental property amenities in Islamorada
  • Vacation rentals in Islamorada are around 67% 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 Serenity by the Sea!! Anglers Reef with Boat Slip Available!! (10.0, 22 reviews), 4 Bedroom House in Angler's Reef, Includes 31' Boat Slip. Islamorada, FL (10.0, 45), and The Real Liveaboard Experience. Lets Go Cruising! (10.0, 24), 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 January.
  • Vacation rentals are a popular choice for both long and short-term stays. KAYAK users usually book their vacation rental in Islamorada for 7 days.
See more tips

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, caravans, condos, cottages, houses, vacation villages, 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 17% 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 C$ 1,928 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.

See more FAQs

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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