A beach with white lounge chairs, a covered pavilion, and palm trees.

Islamorada Vacation Rentals

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Islamorada vacation rentals

A beach with palm trees, thatched-roof huts, and lounge chairs.

1. Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
9.0 out of 10, Wonderful, (753 reviews)
"Great Florida style resort, clean and nice staff. Close to everything in Islamorada!"
United States
Debra
The price is ￥12,858
￥16,976 total
includes taxes & fees
Sep 29 - Sep 30
Breezy Palms Resort
A modern kitchen with white cabinets, a microwave, and a dining area with a table and chairs.

2. Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (175 reviews)
"We loved sitting in the deck in the evening and again in the morning."
Canada
Molly
The price is ￥16,844
￥41,068 total
includes taxes & fees
Sep 28 - Sep 29
Treasure Harbor
A beachside lounge with wooden lounge chairs and blue umbrellas, overlooking a calm sea and docked boats.

3. Island Bay Resort

Island Bay Resort
2.5 star property
Tavernier
9.8 out of 10, Exceptional, (183 reviews)
"Amazing vacation spot!!"
United States
Katie Lyn
The price is ￥31,530
￥35,471 total
includes taxes & fees
Sep 29 - Sep 30
Island Bay Resort
A beachfront hotel with two palm trees, a flag, and a pool area with lounge chairs.

4. Florida Keys Getaway - Slps 4 - Ocean View

Florida Keys Getaway - Slps 4 - Ocean View
Tavernier
9.8 out of 10, Exceptional, (39 reviews)
"Great place to stay down on the keys."
United States
GJ W.
The price is ￥14,773
￥48,075 total
includes taxes & fees
Oct 4 - Oct 5
Florida Keys Getaway - Slps 4 - Ocean View
A swimming pool with clear blue water, surrounded by lounge chairs and umbrellas, and a covered pavilion in the background.

5. Amazing Ocean view condo

Amazing Ocean view condo
Tavernier
9.6 out of 10, Exceptional, (52 reviews)
"Excellent accommodations. Unit was even nicer than it looked in pictures, everything was clean and in working order. Enjoyed our stay very much and would definitely stay here again!"
United States
Jerad E.
The price is ￥21,233
￥51,805 total
includes taxes & fees
Sep 28 - Sep 29
Amazing Ocean view condo
A beach with clear shallow waters, a row of blue lounge chairs, and palm trees.

6. Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Tavernier
10.0 out of 10, Exceptional, (115 reviews)
"Everything was wonderful! We enjoyed our stay very much. "
United States
Colleen D.
The price is ￥23,435
￥57,821 total
includes taxes & fees
Sep 28 - Sep 29
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ

7. 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, (160 reviews)
"Perfect place for family to get away. Plenty of room"
United States
Aaron H.
The price is ￥28,255
￥68,421 total
includes taxes & fees
Sep 28 - Sep 29
3212 Across from Pool * King & Queen/Twin Bunk Bed
A swimming pool with lounge chairs and umbrellas, surrounded by palm trees.

8. 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, (30 reviews)
"The space was family friendly and worked well for our stay. The pool area was very clean and the Island Grill on site was great for snacks and drinks while we swam."
United States
Miranda J.
The price is ￥26,840
￥66,751 total
includes taxes & fees
Oct 27 - Oct 28
Starfish Seas Ocean Pointe 1302 King/Queen 2BA 2BR
A waterfront property with a dock leading to a building with a blue roof.

9. Flamingo Flats Ocean Pointe 5306 2BR/2BA

Flamingo Flats Ocean Pointe 5306 2BR/2BA
Tavernier
9.6 out of 10, Exceptional, (9 reviews)
"Great location and prompt support with all questions we had. "
United States
Jim I.
The price is ￥22,908
￥61,803 total
includes taxes & fees
Sep 27 - Sep 28
Flamingo Flats Ocean Pointe 5306 2BR/2BA
A pool area with a palm tree, a showerhead, and blue lounge chairs.

10. Dazzling Ocean View Suite w/heated pool, beach, marina, tennis/pickleball

Dazzling Ocean View Suite w/heated pool, beach, marina, tennis/pickleball
Tavernier
9.0 out of 10, Wonderful, (103 reviews)
"Great visit!"
United States
Leigh D. H.
The price is ￥29,726
￥51,866 total
includes taxes & fees
Sep 28 - Sep 29
Dazzling Ocean View Suite w/heated pool, beach, marina, tennis/pickleball
A wooden pier extending into the water with a thatched-roof structure at one end.

11. The Happy Reef 4209 King & Queen

The Happy Reef 4209 King & Queen
Tavernier
9.8 out of 10, Exceptional, (186 reviews)
"Very well thought out accommodations"
United States
Mary Jo W.
The price is ￥26,997
￥66,811 total
includes taxes & fees
Sep 27 - Sep 28
The Happy Reef 4209 King & Queen
A wooden deck with thatched roof and benches overlooking the sea.

12. Serene Oceanfront Keys Condo

Serene Oceanfront Keys Condo
Tavernier
9.8 out of 10, Exceptional, (44 reviews)
"Condo was exactly as pictured. The location was great and close to everything we needed. The amenities and property grounds were beautiful and well kept. We thoroughly enjoyed spending time by the pool."
United States
Alexandra F.
The price is ￥32,203
￥67,833 total
includes taxes & fees
Sep 27 - Sep 28
Serene Oceanfront Keys Condo

13. Aqua Vista Ocean Pointe 3307

Aqua Vista Ocean Pointe 3307
Tavernier
9.6 out of 10, Exceptional, (4 reviews)
"Beautiful & perfect place for a getaway. Really enjoyed our stay. Highly recommend."
United States
Michelle
The price is ￥22,908
￥61,803 total
includes taxes & fees
Sep 28 - Sep 29
Aqua Vista Ocean Pointe 3307
A beachside resort with a thatched umbrella, palm trees, and a dock.

14. Lazy Daze Double King Suite Ocean Pointe 2310

Lazy Daze Double King Suite Ocean Pointe 2310
Tavernier
9.8 out of 10, Exceptional, (36 reviews)
"Loved the beach and pool."
United States
Haley P.
The price is ￥26,997
￥66,937 total
includes taxes & fees
Sep 27 - Sep 28
Lazy Daze Double King Suite Ocean Pointe 2310
A balcony with a view of the ocean, a chair, a sofa, and a decorative seahorse wall art.

15. Sunrise Sanctuary - Top Floor Ocean Pointe 2415

Sunrise Sanctuary - Top Floor Ocean Pointe 2415
Tavernier
9.8 out of 10, Exceptional, (18 reviews)
"Great stay"
United States
Blain R.
The price is ￥23,537
￥62,544 total
includes taxes & fees
Sep 29 - Sep 30
Sunrise Sanctuary - Top Floor Ocean Pointe 2415
A cozy room with a bed, a table, and a chair. There's a view of the outdoors through large windows.

16. Marina to Ocean View Key Largo Ocean Pointe 5308

Marina to Ocean View Key Largo Ocean Pointe 5308
Tavernier
9.4 out of 10, Exceptional, (71 reviews)
"The host was quick to respond, condo was perfect, the view was exceptional!"
United States
Rosalie K.
The price is ￥25,424
￥64,925 total
includes taxes & fees
Sep 27 - Sep 28
Marina to Ocean View Key Largo Ocean Pointe 5308
A compact kitchen with a dishwasher, a microwave, and a sink. There is a window with a view of the outdoors, and a ceiling fan.

17. Fla Keys Luxury Houseboat, Prime Location-Steps to Fun, Food & Water Adventures

Fla Keys Luxury Houseboat, Prime Location-Steps to Fun, Food & Water Adventures
Tavernier
9.8 out of 10, Exceptional, (220 reviews)
"Very cute cozy house boat. Well equipped and close to restaurant. Enjoyable weekend stay. Heidi the host is very welcoming."
United States
Michelle P.
The price is ￥41,192
￥67,653 total
includes taxes & fees
Oct 1 - Oct 2
Fla Keys Luxury Houseboat, Prime Location-Steps to Fun, Food & Water Adventures
A waterfront property with a dock, a house with a blue roof, and a marina with boats.

18. 2BR Oceanfront Suite w/ Beach & Marina Access

2BR Oceanfront Suite w/ Beach & Marina Access
Key Largo
10.0 out of 10, Exceptional, (1 review)
"This was a great place to stay. Incredibly clean and homey feel. I felt super safe walking the area after dinner at night"
United States
Alyssa H.
The price is ￥30,313
￥38,095 total
includes taxes & fees
Oct 5 - Oct 6
2BR Oceanfront Suite w/ Beach & Marina Access

19. 2BR Condo w/ Ocean View, Pool & Tropical Setting

2BR Condo w/ Ocean View, Pool & Tropical Setting
Tavernier
9.6 out of 10, Exceptional, (4 reviews)
" centrally located for keys travel"
United States
Gary
The price is ￥20,836
￥65,120 total
includes taxes & fees
Oct 5 - Oct 6
2BR Condo w/ Ocean View, Pool & Tropical Setting
A modern showerhead with multiple water streams, a tiled wall, and a pool area with blue chairs and a palm tree.

20. Ocean view condo with balcony/marina view

Ocean view condo with balcony/marina view
Tavernier
8.6 out of 10, Excellent, (46 reviews)
"Wonderful stay! Beautiful view from the balcony"
United States
Katy T.
The price is ￥28,027
￥59,604 total
includes taxes & fees
Sep 28 - Sep 29
Ocean view condo with balcony/marina view
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.
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Top Islamorada Hotel Reviews

Islander Resort

Islander Resort

8/10 Good
"I liked the fact that our rear outside seating area was quite private because of the trees and bushes growing around the property. Very peaceful and also just a couple of minutes walk from the sea."
norman 4-night trip
Posted 19 hours ago
Islander 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
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  • 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 vacation rental in Islamorada?

Yes, we have vacation rentals in Islamorada close to MoradaWay Arts & Cultural District, or you can select a secluded option if you want 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 vacation home rentals that Islamorada has to offer?

Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada: This Islamorada vacation home rental offers an outdoor pool, a balcony, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. Make the most of the garden in this rental home to help you unwind. Some other homes for rent in Islamorada include 7 Bedroom with Dockage, Pool, Firepit, Paddle Boards & Kayaks and Bungalow #3 - 2 Bed/1 Bath & Pool in Islamorada.

How many vacation rentals are there in Islamorada?

With 405 Expedia vacation rentals, you're sure to find just the right place for your Islamorada stay.

What can I see and do in Islamorada?

Anne's Beach and Fiesta Key are a couple of scenic spots to enjoy the outdoors, whereas History of Diving Museum is one of the cultural attractions. Other places in town to visit include Bud n' Mary's Dive Center and Robbie’s of Islamorada.

What’s a vacation rental in Islamorada like?

A vacation rental is a private property where you can stay for a couple of days or more in Islamorada. Vacation rentals provide amenities such as kitchens and laundry facilities so you'll have a home away from home. If you're concerned about cleanliness, a vacation rental can provide a sense of safety away from shared hotel elevators and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular option for family trips or small group gatherings.