Islamorada Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
27 Feb - 1 Mar
In two months
10 Apr - 12 Apr
In three months
8 May - 10 May
In four months
5 Jun - 7 Jun

Our top choices for Islamorada holiday rentals

25-inch flat-screen TV with digital channels, TV

Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (129 reviews)
"Very peaceful and comfortable stay! Dallas and Hannah were amazing hosts! Thank you so much !"
United States
Nick
Treasure Harbor
Smart TV

Charming Home in Key Largo

Charming Home in Key Largo
Key Largo
9.8 out of 10, Exceptional, (31 reviews)
"Great location. Very clean very nice, stay there again"
United States
Mark B.
The price is HK$1,491
HK$3,895 total
includes taxes & fees
23 Feb - 24 Feb
Charming Home in Key Largo
Exterior

Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (618 reviews)
"Friendly staff, beautiful peaceful beach, great room with a big comfy bed and all that you might need. "
United States
Alexander
The price is HK$1,667
HK$2,280 total
includes taxes & fees
18 Mar - 19 Mar
Breezy Palms Resort
Marina

Island Sanctuary Islamorada

Island Sanctuary Islamorada
Tavernier
9.8 out of 10, Exceptional, (15 reviews)
"An amazing place to switch gears. Great host. Win/win."
United States
Alex Z.
The price is HK$2,075
HK$3,263 total
includes taxes & fees
24 Feb - 25 Feb
Island Sanctuary Islamorada
On the beach

Serenity In The Sun Condo Fabulous Ocean View

Serenity In The Sun Condo Fabulous Ocean View
Tavernier
10.0 out of 10, Exceptional, (109 reviews)
"Fantastic place to stay! Very clean and great hosts. Will stay again. "
United States
Les
The price is HK$2,189
HK$4,338 total
includes taxes & fees
10 Mar - 11 Mar
Serenity In The Sun Condo Fabulous Ocean View
Pool

Amazing Ocean view condo

Amazing Ocean view condo
Tavernier
9.6 out of 10, Exceptional, (44 reviews)
"Exceeded expectations, exceptionally clean, great for kids (they loved the pool), perfect for our Keys trip"
United States
Natalie M.
The price is HK$1,688
HK$3,490 total
includes taxes & fees
1 Mar - 2 Mar
Amazing Ocean view condo
Exterior

Florida Keys Getaway - Slps 4 - Ocean View

Florida Keys Getaway - Slps 4 - Ocean View
Tavernier
9.6 out of 10, Exceptional, (21 reviews)
"Everything was just as described in the condo listing. We enjoyed the pool and hot tub. Wonderful location to explore the Keys. "
United States
Michele G.
The price is HK$1,574
HK$3,514 total
includes taxes & fees
25 Feb - 26 Feb
Florida Keys Getaway - Slps 4 - Ocean View
Beach nearby

Paradise Palms 2 Bedroom Condo Ocean Pointe 1206

Paradise Palms 2 Bedroom Condo Ocean Pointe 1206
Tavernier
9.8 out of 10, Exceptional, (6 reviews)
"Thanks for your great hospitality."
United States
richard
The price is HK$1,454
HK$3,675 total
includes taxes & fees
4 Mar - 5 Mar
Paradise Palms 2 Bedroom Condo Ocean Pointe 1206
Beach nearby

3212 Across from Pool * King & Queen/Twin Bunk Bed

3212 Across from Pool * King & Queen/Twin Bunk Bed
Tavernier
9.8 out of 10, Exceptional, (152 reviews)
"Great stay lovely home "
United States
Yezenia
The price is HK$1,720
HK$4,027 total
includes taxes & fees
4 Mar - 5 Mar
3212 Across from Pool * King & Queen/Twin Bunk Bed
Beach nearby

Reel Key Largo Escape Ocean Pointe 5209

Reel Key Largo Escape Ocean Pointe 5209
Tavernier
9.4 out of 10, Exceptional, (6 reviews)
"Great area"
United States
Yesenia
The price is HK$1,962
HK$4,289 total
includes taxes & fees
25 Feb - 26 Feb
Reel Key Largo Escape Ocean Pointe 5209
Beach nearby

Blue Haven Key Largo | Ocean Pointe 1315

Blue Haven Key Largo | Ocean Pointe 1315
Tavernier
9.8 out of 10, Exceptional, (16 reviews)
"Loved this condo. Had all the amenities we needed and was super clean and tidy. Will definitely be staying here again. "
United States
Rodney B.
The price is HK$1,571
HK$3,829 total
includes taxes & fees
4 Mar - 5 Mar
Blue Haven Key Largo | Ocean Pointe 1315
Beach nearby

Lazy Daze Double King Suite Ocean Pointe 2310

Lazy Daze Double King Suite Ocean Pointe 2310
Tavernier
9.8 out of 10, Exceptional, (26 reviews)
"Everything was exceptionally nice. Would definitely book again."
United States
Sharon
The price is HK$2,056
HK$4,439 total
includes taxes & fees
11 Mar - 12 Mar
Lazy Daze Double King Suite Ocean Pointe 2310
Beach nearby

Starfish Seas Ocean Pointe 1302 King/Queen 2BA 2BR

Starfish Seas Ocean Pointe 1302 King/Queen 2BA 2BR
Tavernier
9.8 out of 10, Exceptional, (26 reviews)
"Accommodation and location are excellent! Listing is accurate and the resort amenities are very enjoyable after a day out exploring the Keys (or just having at least one whole day at the resort, as we did). "
United States
Jenny G.
The price is HK$1,704
HK$3,977 total
includes taxes & fees
3 Mar - 4 Mar
Starfish Seas Ocean Pointe 1302 King/Queen 2BA 2BR
Property grounds

Boho Style Florida Keys Condo Ocean Views

Boho Style Florida Keys Condo Ocean Views
Tavernier
9.8 out of 10, Exceptional, (44 reviews)
"Would stay there again."
Canada
jamie g.
The price is HK$2,228
HK$4,359 total
includes taxes & fees
9 Mar - 10 Mar
Boho Style Florida Keys Condo Ocean Views
Terrace/patio

Serene Oceanfront Keys Condo

Serene Oceanfront Keys Condo
Tavernier
10.0 out of 10, Exceptional, (24 reviews)
"Great stay, amazing pool and property, "
United States
Abbigail R.
The price is HK$2,400
HK$4,584 total
includes taxes & fees
5 Mar - 6 Mar
Serene Oceanfront Keys Condo
Sun-loungers, beach towels

Your Happy Place - gorgeous 2 bed/2 bath oceanfront suite with full kitchen

Your Happy Place - gorgeous 2 bed/2 bath oceanfront suite with full kitchen
Tavernier
10.0 out of 10, Exceptional, (12 reviews)
"Perfect Stay."
United States
suhaela s.
The price is HK$2,572
HK$5,015 total
includes taxes & fees
10 Mar - 11 Mar
Your Happy Place - gorgeous 2 bed/2 bath oceanfront suite with full kitchen
Marina

Reel Large END Unit in Ocean Pointe Suites - Newly Renovated!

Reel Large END Unit in Ocean Pointe Suites - Newly Renovated!
Tavernier
9.4 out of 10, Exceptional, (17 reviews)
"We love our family vacations there."
United States
Francis M.
The price is HK$2,110
HK$5,583 total
includes taxes & fees
24 Feb - 25 Feb
Reel Large END Unit in Ocean Pointe Suites - Newly Renovated!
TV

Sunrise Sanctuary - Top Floor Ocean Pointe 2415

Sunrise Sanctuary - Top Floor Ocean Pointe 2415
Tavernier
9.6 out of 10, Exceptional, (13 reviews)
"Clean and great location "
United States
Michael P.
The price is HK$1,626
HK$3,878 total
includes taxes & fees
9 Mar - 10 Mar
Sunrise Sanctuary - Top Floor Ocean Pointe 2415
TV

Keys Bohemian 2 BR 2 BA at Ocean Pointe 1312

Keys Bohemian 2 BR 2 BA at Ocean Pointe 1312
Tavernier
10.0 out of 10, Exceptional, (1 review)
The price is HK$1,727
HK$4,031 total
includes taxes & fees
4 Mar - 5 Mar
Keys Bohemian 2 BR 2 BA at Ocean Pointe 1312
Beach nearby

Ocean View Overlooking Marina Ocean Pointe 5305

Ocean View Overlooking Marina Ocean Pointe 5305
Tavernier
10.0 out of 10, Exceptional, (24 reviews)
"This was a wonderful place to stay in the Florida Keys. The location was beautiful. We watched sunrise each morning from the balcony. The unit faced the ocean. We would certainly stay here again."
United States
Donald
The price is HK$2,079
HK$4,467 total
includes taxes & fees
7 Mar - 8 Mar
Ocean View Overlooking Marina Ocean Pointe 5305
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Islamorada Hotel Reviews

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

10/10 Excellent
"The was nice, clean and comfortable. All staff we encountered was extremely friendly and courteous. The amenities were excellent. "
Sheila 6-night trip
Posted 2 days ago
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

Find out more about Islamorada

Search for holiday rentals in Islamorada on Expedia! You can easily find your home rentals, villas, holiday apartments in Islamorada using one of the methods below:

  • View our selection of featured holiday rentals in Islamorada
  • Use the map to find apartments and other holiday homes in the Islamorada neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Islamorada while they last

Look no further and take a look at our great range of rental properties in Islamorada!

Frequently asked questions

Can I find a holiday rental in Islamorada?

Yes, there are holiday rentals close to the most popular sights in Islamorada, or you can select a more secluded option if you're looking for a relaxing stay. Visitors to Islamorada like the scenic seaside and entertainment choices this destination is known for. While you're here, grab a bite or have a drink at the seafood restaurants.

What are some of the best holiday rentals that Islamorada has to offer?

Bungalow #3 - 2 Bed/1 Bath & Pool in Islamorada: This highly rated holiday home rental in Islamorada offers an outdoor pool, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. Some other homes for rent in Islamorada include Private Oceanfront: Heated Pool, Paddleboards & Kayaks - 180 degree ocean views and Single Family Home In Angler's Reef Gated Community, Beaches,Marina,Heated Pool.

How many holiday rentals are there in Islamorada?

With 463 Expedia holiday rentals, you're guaranteed to find just the right place for your Islamorada stay.

What can I see and do in Islamorada?

Enjoy the outdoors at Everglades National Park and Islamorada County Park, or simply take in cultural attractions like History of Diving Museum and MoradaWay Arts & Cultural District. Other places in town to visit include Bud n' Mary's Dive Center and Anne's Beach.

What’s a holiday rental in Islamorada like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Islamorada. Holiday rentals feature extras like laundry facilities and kitchens so your stay will be comfortable. If you're concerned about a sanitised environment, holiday rentals can offer a sense of privacy away from shared hotel lifts and bustling concierge desks while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a hotel, which makes a holiday rental a great option for family trips.