Islamorada Vacation Rentals

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Check prices for these dates

Tonight
Dec 27 - Dec 28
Tomorrow
Dec 28 - Dec 29
Next weekend
Jan 2 - Jan 4
In two weeks
Jan 9 - Jan 11

Our top choices for Islamorada vacation rentals

Exterior
Breezy Palms Resort

Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (596)
"we stayed in the beach front cottage kitchen was stocked room was clean and the views were great friendly staff "
United States
Terry
The price is ￥23,933
￥35,041 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Breezy Palms Resort
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
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
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 ￥37,264
￥82,735 total
includes taxes & fees
Jan 18 - Jan 19, 2026
Aqua Vista Ocean Pointe 3307
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
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
￥63,377 total
includes taxes & fees
Jan 4 - Jan 5, 2026
1BR w/ Pool, Beach, Near Marine & Bird Sanctuaries
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
￥71,532 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Charming Home in Key Largo
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
Pool
Ocean View 2BR - Pool, Private Beach & Near Parks

Ocean View 2BR - Pool, Private Beach & Near Parks

Ocean View 2BR - Pool, Private Beach & Near Parks
Tavernier
8.2 out of 10, Very Good, (48)
"Very nice unit. Great ocean view and location. It was close to everything we wanted to do. "
United States
Mike B.
The price is ￥48,028
￥85,797 total
includes taxes & fees
Jan 27 - Jan 28, 2026
Ocean View 2BR - Pool, Private Beach & Near Parks
Pool
Sunrise Oasis - Top Floor 2 BR 2 BA Condo 2411

Sunrise Oasis - Top Floor 2 BR 2 BA Condo 2411

Sunrise Oasis - Top Floor 2 BR 2 BA Condo 2411
Tavernier
10.0 out of 10, Exceptional, (4)
"The condo was very clean, comfortable and had everything we needed. We appreciated the close location to the pool. "
United States
Erica T.
The price is ￥37,890
￥84,100 total
includes taxes & fees
Jan 22 - Jan 23, 2026
Sunrise Oasis - Top Floor 2 BR 2 BA Condo 2411
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
Pool
Key Largo Oasis Oceanfront with Pool & Hot Tub

Key Largo Oasis Oceanfront with Pool & Hot Tub

Key Largo Oasis Oceanfront with Pool & Hot Tub
Key Largo
10.0 out of 10, Exceptional, (4)
"Loved the location and views, house is amazing"
United States
Dan L.
The price is ￥63,973
￥135,082 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Key Largo Oasis Oceanfront with Pool & Hot Tub
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
Exterior
Boho Chic Ocean Pointe 3214

Boho Chic Ocean Pointe 3214

Boho Chic Ocean Pointe 3214
Tavernier
10.0 out of 10, Exceptional, (12)
"It was clean, well organized and communication was great. Had a good time."
United States
Shirl
The price is ￥32,097
￥76,646 total
includes taxes & fees
Jan 27 - Jan 28, 2026
Boho Chic Ocean Pointe 3214
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 ￥34,289
￥78,603 total
includes taxes & fees
Jan 14 - Jan 15, 2026
Ocean View Gem Ocean Pointe 3406 2BA/2BR King/Queen
Pool
Lazy Daze Double King Suite Ocean Pointe 2310

Lazy Daze Double King Suite Ocean Pointe 2310

Lazy Daze Double King Suite Ocean Pointe 2310
Tavernier
9.8 out of 10, Exceptional, (26)
"Everything was exceptionally nice. Would definitely book again."
United States
Sharon
The price is ￥33,976
￥78,547 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Lazy Daze Double King Suite Ocean Pointe 2310
Pool
Salty Mermaid Ocean Pointe 4406

Salty Mermaid Ocean Pointe 4406

Salty Mermaid Ocean Pointe 4406
Tavernier
10.0 out of 10, Exceptional, (1)
Salty Mermaid Ocean Pointe 4406
Pool
Blue Haven Key Largo | Ocean Pointe 1315

Blue Haven Key Largo | Ocean Pointe 1315

Blue Haven Key Largo | Ocean Pointe 1315
Tavernier
9.6 out of 10, Exceptional, (15)
"This condo was everything we needed. Lots of space, bug comfy beds, hreat shower and the pool at the complex was great in the late afternoon after a day exploring the upper keys. There were works going on at the conplex when we were there which took the edge off things as 9am drilling on Monday morning wasnt welcome but I only knocked 1 star off - otherwise wouldnt hesitate to recommend!"
United Kingdom
Philippa
The price is ￥27,869
￥71,347 total
includes taxes & fees
Jan 21 - Jan 22, 2026
Blue Haven Key Largo | Ocean Pointe 1315
Pool
Key Largo Sunrise Resort Style Ocean Pointe 5315

Key Largo Sunrise Resort Style Ocean Pointe 5315

Key Largo Sunrise Resort Style Ocean Pointe 5315
Tavernier
10.0 out of 10, Exceptional, (6)
"4 friends in town for a wedding. Would stay again!"
United States
Jody H.
Key Largo Sunrise Resort Style Ocean Pointe 5315
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 12 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.