Islamorada Vacation Rentals

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Check prices for these dates

Tonight
Dec 28 - Dec 29
Tomorrow
Dec 29 - Dec 30
Next weekend
Jan 2 - Jan 4
In two weeks
Jan 9 - Jan 11

Our top choices for Islamorada vacation rentals

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

Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (118)
"I am obsessed with tiny houses and this one floats! It was so relaxing to sit on the deck and enjoy the view. The bed was very comfy and the gentle motion of the water put me right to sleep. The staff are friendly and helpful. Islamorada is beautiful and fun to explore."
United States
Mary
Treasure Harbor
Exterior
Breezy Palms Resort

Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (596)
"Property was nice and easy to navigate, ocean view room was extra nice to have!"
United States
Lisa
The price is ￥23,933
￥35,041 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Breezy Palms Resort
2 outdoor pools, open 8:00 AM to 6:00 PM, sun loungers
The Islands of Islamorada

The Islands of Islamorada

The Islands of Islamorada
4.0 star property
Matecumbe
9.8 out of 10, Exceptional, (70)
"Great for family vacation with kids. love it"
United States
Dixania
The price is ￥95,351
￥115,901 total
includes taxes & fees
Jan 5 - Jan 6, 2026
The Islands of Islamorada
Private beach, sun loungers, beach umbrellas, beach towels
Island Bay Resort

Island Bay Resort

Island Bay Resort
2.5 star property
Tavernier
10.0 out of 10, Exceptional, (141)
"Very quiet and the outdoor spaces are very nice. Staff was very friendly also."
United States
Jacob
The price is ￥64,325
￥72,366 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Island Bay Resort
2 bedrooms, in-room safe, desk, bed sheets
Island Sanctuary Islamorada

Island Sanctuary Islamorada

Island Sanctuary Islamorada
Tavernier
9.8 out of 10, Exceptional, (13)
"It exceeded our expectations, and we are so glad we found this location!"
United States
Jenn H.
The price is ￥41,569
￥65,358 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Island Sanctuary Islamorada
Property grounds
Boho Style Florida Keys Condo Ocean Views

Boho Style Florida Keys Condo Ocean Views

Boho Style Florida Keys Condo Ocean Views
Tavernier
9.8 out of 10, Exceptional, (43)
"Would stay there again."
Canada
jamie g.
Boho Style Florida Keys Condo Ocean Views
Pool
Amazing Ocean view condo

Amazing Ocean view condo

Amazing Ocean view condo
Tavernier
9.6 out of 10, Exceptional, (42)
"Exceeded expectations, exceptionally clean, great for kids (they loved the pool), perfect for our Keys trip"
United States
Natalie M.
The price is ￥25,083
￥58,514 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Amazing Ocean view condo
A heated pool
Serenity In The Sun Condo Fabulous Ocean View

Serenity In The Sun Condo Fabulous Ocean View

Serenity In The Sun Condo Fabulous Ocean View
Tavernier
10.0 out of 10, Exceptional, (108)
"Fantastic place to stay! Very clean and great hosts. Will stay again. "
United States
Les
Serenity In The Sun Condo Fabulous Ocean View
Pool
Aqua Vista Ocean Pointe 3307

Aqua Vista Ocean Pointe 3307

Aqua Vista Ocean Pointe 3307
2.5 star property
Tavernier
10.0 out of 10, Exceptional, (1)
"Beautiful & perfect place for a getaway. Really enjoyed our stay. Highly recommend."
United States
Michelle
The price is ￥32,880
￥77,725 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Aqua Vista Ocean Pointe 3307
Fridge, microwave, oven, stovetop
Charming Home in Key Largo

Charming Home in Key Largo

Charming Home in Key Largo
Key Largo
9.8 out of 10, Exceptional, (29)
"It was clean and a very nice place to stay. Plenty of room and awesome amenities."
United States
Eric M.
The price is ￥25,223
￥71,375 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Charming Home in Key Largo
Pool
Modern and Coastal 3212 is Across from Pool

Modern and Coastal 3212 is Across from Pool

Modern and Coastal 3212 is Across from Pool
Tavernier
9.8 out of 10, Exceptional, (150)
"Great stay lovely home "
United States
Yezenia
The price is ￥30,688
￥75,611 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Modern and Coastal 3212 is Across from Pool
Property grounds
Fla Keys Luxury Houseboat, Prime Location-Steps to Fun, Food & Water Adventures

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, (210)
"Heidi has a little bit of paradise on her houseboat! You must plan on staying!!"
United States
Toni M.
The price is ￥46,971
￥78,442 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Fla Keys Luxury Houseboat, Prime Location-Steps to Fun, Food & Water Adventures
Pool
Ocean View Gem Ocean Pointe 3406 2BA/2BR King/Queen

Ocean View Gem Ocean Pointe 3406 2BA/2BR King/Queen

Ocean View Gem Ocean Pointe 3406 2BA/2BR King/Queen
2.0 star property
Tavernier
10.0 out of 10, Exceptional, (3)
"Great place! Condo was clean l and was as described. Property and pool area was fun and very clean."
United States
Kevin W.
The price is ￥36,794
￥83,749 total
includes taxes & fees
Jan 15 - Jan 16, 2026
Ocean View Gem Ocean Pointe 3406 2BA/2BR King/Queen
Beach
Island Time at Ocean Pointe Luxe 2 King Spa BR/BA, 2 Balcony

Island Time at Ocean Pointe Luxe 2 King Spa BR/BA, 2 Balcony

Island Time at Ocean Pointe Luxe 2 King Spa BR/BA, 2 Balcony
2.0 star property
Blue Waters
10.0 out of 10, Exceptional, (2)
"Beautifully high-end decorated & furnished like brand new! Very clean and appointed with everything one could want for a perfect stay. First floor convenience (building elevated on piers) but no water view Would definitely return! "
United States
Peter A. Z.
The price is ￥32,723
￥76,915 total
includes taxes & fees
Jan 19 - Jan 20, 2026
Island Time at Ocean Pointe Luxe 2 King Spa BR/BA, 2 Balcony
Terrace/patio
NEW ! Lagoon-front townhouse with Marina in Key Largo

NEW ! Lagoon-front townhouse with Marina in Key Largo

NEW ! Lagoon-front townhouse with Marina in Key Largo
2.0 star property
Key Largo
10.0 out of 10, Exceptional, (46)
"Good location. Lagoon and pool right outside door. "
United States
Debra C.
The price is ￥52,294
￥103,610 total
includes taxes & fees
Jan 12 - Jan 13, 2026
NEW ! Lagoon-front townhouse with Marina in Key Largo
Pool
Sea View Farm Style Ocean front Condo Views

Sea View Farm Style Ocean front Condo Views

Sea View Farm Style Ocean front Condo Views
Tavernier
10.0 out of 10, Exceptional, (154)
"The property was excellent."
United States
June M.
The price is ￥31,314
￥69,830 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Sea View Farm Style Ocean front Condo Views
Terrace/patio
Ocean Pointe Condo ~ Beach, Pool, Hot Tub & Tennis

Ocean Pointe Condo ~ Beach, Pool, Hot Tub & Tennis

Ocean Pointe Condo ~ Beach, Pool, Hot Tub & Tennis
2.0 star property
Key Largo
The price is ￥32,058
￥69,376 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Ocean Pointe Condo ~ Beach, Pool, Hot Tub & Tennis
Beach
1BR w/ Pool, Beach, Near Marine & Bird Sanctuaries

1BR w/ Pool, Beach, Near Marine & Bird Sanctuaries

1BR w/ Pool, Beach, Near Marine & Bird Sanctuaries
2.0 star property
Tavernier
The price is ￥35,111
￥63,220 total
includes taxes & fees
Jan 4 - Jan 5, 2026
1BR w/ Pool, Beach, Near Marine & Bird Sanctuaries
Marina
Sunrise Sanctuary - Top Floor Ocean Pointe 2415

Sunrise Sanctuary - Top Floor Ocean Pointe 2415

Sunrise Sanctuary - Top Floor Ocean Pointe 2415
Tavernier
9.6 out of 10, Exceptional, (11)
"Clean and great location "
United States
Michael P.
The price is ￥28,965
￥73,425 total
includes taxes & fees
Jan 13 - Jan 14, 2026
Sunrise Sanctuary - Top Floor Ocean Pointe 2415
Pool
Captains Quarters Ocean Pointe 4405

Captains Quarters Ocean Pointe 4405

Captains Quarters Ocean Pointe 4405
Tavernier
10.0 out of 10, Exceptional, (13)
"We had a very pleasant weekend away with all the comforts of home, yet even better with the amazing view! Great communication with the host with quick pleasant responses. The property is conveniently located and easy to get around. "
United States
Debbie W.
The price is ￥30,531
￥75,427 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Captains Quarters Ocean Pointe 4405
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

Breezy Palms Resort

Breezy Palms Resort

10/10 Excellent
"Property was nice and easy to navigate, ocean view room was extra nice to have!"
Lisa 3-night trip
Posted 21 hours ago
Breezy Palms 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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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 close to well known points of interest in Islamorada, or you can choose a more remote 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 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 barbecue grill, 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 Now booking late 2026 and 2027. Oceanfront - Heated Pool - Dock - Over 1 acre and Bungalow #3 - 2 Bed/1 Bath & Pool in Islamorada.

How many vacation rentals are there in Islamorada?

With 483 Expedia vacation rentals, you're sure 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 Founders Park, or simply take in cultural attractions like History of Diving Museum and MoradaWay Arts & Cultural District. Other places in town to visit include Florida Keys Brewing Co. and Bud n' Mary's Dive Center.

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.