Islamorada vacation rentals

KAYAK searches hundreds of travel sites at once for vacation home deals in Islamorada

Here is why travelers choose KAYAK

Free to useThere are no hidden charges or fees.

Filter your dealsFilter by free cancellation, free breakfast and more.

Millions of reviewsCheck ratings based on millions of real guest reviews.

Recommended by KAYAK
Booking Insights
Recommended by KAYAK

Best Islamorada vacation rentals

These are the best prices for Oct 31 - Nov 1.
Peninsula Villa Boat Dock Heated Pool Sunset Point - Islamorada - Pool
Peninsula Villa Boat Dock Heated Pool Sunset Point
Islamorada, FL
10Wonderful(2)
House
$2,962+
Check availability
Beautiful Home located in Downtown Islamorada - Islamorada - Pool
Beautiful Home located in Downtown Islamorada
Islamorada, FL
House
$267+
Check availability
Islamorada Modern Penthouse with Private Beach - Islamorada - Living room
Islamorada Modern Penthouse with Private Beach
Islamorada, FL
9.0Wonderful(1)
Apartment
$1,281+
Check availability
The 'Nest' Villa & Marina in the heart of beautiful Islamorada. Pet Friendly! - Islamorada - Balcony
The 'Nest' Villa & Marina in the heart of beautiful Islamorada. Pet Friendly!
Islamorada, FL
10Wonderful(7)
Villa
$608+
Check availability
Fall Discounted Prices!! Bayside Condo With Beach, Pool, Dockage, Pickle Ball - Islamorada - Pool
Fall Discounted Prices!! Bayside Condo With Beach, Pool, Dockage, Pickle Ball
Islamorada, FL
9.7Wonderful(26)
Condo
$195+
Check availability
Aquamarine Oceanview-Wall To Wall-+144/Best 5 Star Reviews+dock+pool+gym++++++ - Islamorada - Pool
Aquamarine Oceanview-Wall To Wall-+144/Best 5 Star Reviews+dock+pool+gym++++++
Islamorada, FL
9.8Wonderful(59)
Condo
$312+
Check availability
Luxurious Caribbean 2 Bedroom 2 Bath Home - Islamorada - Pool
Luxurious Caribbean 2 Bedroom 2 Bath Home
Islamorada, FL
10Wonderful(1)
House
$738+
Check availability
Stay where you play, On the water w/Boat dock & Trailer parking. Pet friendly! - Long Key - Bedroom
Stay where you play, On the water w/Boat dock & Trailer parking. Pet friendly!
Long Key, FL
9.8Wonderful(22)
Apartment
$391+
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(39)
Villa
$442+
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
9.4Wonderful(27)
Cottage
$753+
Check availability
Fiesta Key Rv Resort Waterfront Cottage 33 - Long Key
Fiesta Key Rv Resort Waterfront Cottage 33
Long Key, FL
8.1Very good(72)
Holiday Park
$450+
Check availability
Beacon Reef 310 - Islamorada
Beacon Reef 310
Islamorada, FL
House
$244+
Check availability
Little Bay Cottage - Islamorada
Little Bay Cottage
Islamorada, FL
House
$695+
Check availability
Little Bay Lower - Islamorada
Little Bay Lower
Islamorada, FL
Apartment
$704+
Check availability
Palms 309 - Islamorada
Palms 309
Islamorada, FL
House
$258+
Check availability
Martin Family Fish Camp - Islamorada
Martin Family Fish Camp
Islamorada, FL
House
$1,086+
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 June, with average rates of $176. In comparison, May is the most expensive month, with prices at $3,853.

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

Wednesday offers the lowest rates in Islamorada, with an average nightly price of $278. The highest prices are found on Friday, with average rates at $786.

How much is a vacation rental in Islamorada for this weekend by property type?

The best deal for a vacation rental in Islamorada found by KAYAK users for the upcoming weekend was $346 in a Apartment. Houses prices start at $379 and Houseboats at $1,174.

Find deals

Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

December
February
$519
$660
Cheapest month to stay with an average 59% drop in price.
Most expensive month to stay with an average 101% 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, kitchen/kitchenette, pet friendly, wifi, and beachfront are the most popular vacation rental property amenities in Islamorada
  • Vacation rentals in Islamorada are around 108% cheaper than hotels on average. Search here to compare prices for all accommodation types in Islamorada.
  • The best vacation rental properties in Islamorada are Anglers Reef Islamorada, Bikes,kayak,paddle Boards Dock Available-Pool (10.0, 21 reviews), Islamorada Waterfront Home, Spectacular View-Great Dockage-Wifi-Contact Owner (10.0, 26), and Serenity by the Sea!! Anglers Reef with Boat Slip Available!! (9.9, 39), 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 April.
  • The cheapest night for renting a vacation home in Islamorada is Wednesday. In contrast, the most expensive is Friday.
  • Vacation rentals are a popular choice for both long and short-term stays. KAYAK users usually book their vacation rental in Islamorada for 6 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 $5,321.

  • 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 $22,806.

  • 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, hotels, houseboats 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 18% 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 $271. 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 $1,174 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.

More options for your stay in Islamorada