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

Islamorada Holiday Rentals

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Check prices for these dates

In two weeks
31 Jul - 2 Aug
In two months
11 Sept - 13 Sept
In three months
9 Oct - 11 Oct
In four months
6 Nov - 8 Nov

Our top choices for Islamorada holiday rentals

Exterior

Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (708 reviews)
"Enjoyed this place."
United States
Christopher
The price is HK$510
HK$980 total
includes taxes & fees
13 Aug - 14 Aug
Breezy Palms Resort
25-inch flat-screen TV with digital channels, TV

Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (163 reviews)
"everything was good"
United States
ROGELIO
The price is HK$1,404
HK$2,682 total
includes taxes & fees
3 Aug - 4 Aug
Treasure Harbor
Balcony view

The Islands of Islamorada

The Islands of Islamorada
4.0 star property
Matecumbe
9.6 out of 10, Exceptional, (78 reviews)
"Love this property! Our family had the most amazing time in the villas. The location is great and the property is really well kept with amazing staff. We enjoyed the pool, the kids game area, pickle ball and relaxing in the home. Highly recommend!!"
United States
Christian
The price is HK$3,912
HK$4,833 total
includes taxes & fees
2 Aug - 3 Aug
The Islands of Islamorada
Private beach, sun-loungers, beach umbrellas, beach towels

Island Bay Resort

Island Bay Resort
2.5 star property
Tavernier
10.0 out of 10, Exceptional, (173 reviews)
"The place is beautiful"
United States
Adriana
The price is HK$2,007
HK$2,258 total
includes taxes & fees
2 Aug - 3 Aug
Island Bay Resort
Exterior

Florida Keys Getaway - Slps 4 - Ocean View

Florida Keys Getaway - Slps 4 - Ocean View
Tavernier
9.8 out of 10, Exceptional, (34 reviews)
"A comfortable little condo, conveniently located for exploring the Keys. There’s a nice pool and small beach area with a bar/restaurant that are well maintained."
United States
Stephen
The price is HK$690
HK$2,469 total
includes taxes & fees
17 Aug - 18 Aug
Florida Keys Getaway - Slps 4 - Ocean View
Beach nearby

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 HK$1,482
HK$3,455 total
includes taxes & fees
20 Jul - 21 Jul
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Pool

Amazing Ocean view condo

Amazing Ocean view condo
Tavernier
9.6 out of 10, Exceptional, (50 reviews)
"Walking around ground to beach and dock in evening and see osprey nest with two babes was unbelievable."
United States
FRANK S.
The price is HK$1,388
HK$3,086 total
includes taxes & fees
11 Aug - 12 Aug
Amazing Ocean view condo
Smart TV

Charming Home in Key Largo

Charming Home in Key Largo
Key Largo
9.8 out of 10, Exceptional, (38 reviews)
"Very clean and nice location."
United States
Melinda V.
The price is HK$1,129
HK$3,226 total
includes taxes & fees
25 Jul - 26 Jul
Charming Home in Key Largo
Exterior

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)
"Super clean and neat location!"
United States
Christopher R.
The price is HK$1,329
HK$3,499 total
includes taxes & fees
18 Aug - 19 Aug
Paradise Palms 2 Bedroom Condo Ocean Pointe 1206
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, (35 reviews)
"Loved the beach and pool."
United States
Haley P.
Lazy Daze Double King Suite Ocean Pointe 2310
Beach

Aqua Vista Ocean Pointe 3307

Aqua Vista Ocean Pointe 3307
Tavernier
9.6 out of 10, Exceptional, (4 reviews)
"All staff gave off a good vibe - happy-wanting to help - friendly. Amenities were as shown on the website and we all had a good time"
United States
Diane D.
The price is HK$1,227
HK$3,339 total
includes taxes & fees
19 Aug - 20 Aug
Aqua Vista Ocean Pointe 3307
Exterior

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, (29 reviews)
"Beautiful condo with nice decor. We enjoyed the pool and was nice having a restaurant on site. I would definitely stay there again "
United States
Cathy
The price is HK$1,329
HK$3,514 total
includes taxes & fees
19 Aug - 20 Aug
Starfish Seas Ocean Pointe 1302 King/Queen 2BA 2BR
Beach nearby

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, (10 reviews)
"Such a beautiful condo! We loved our stay."
United States
Bethany B.
The price is HK$1,329
HK$3,499 total
includes taxes & fees
18 Aug - 19 Aug
Sunrise Oasis - Top Floor 2 BR 2 BA Condo 2411
Beach

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

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Tavernier
10.0 out of 10, Exceptional, (169 reviews)
"Beautifully appointed, clean and comfortable. This place is worth it! We had a great stay. Location is also excellent. Would definitely stay here again. "
United States
Erica C.
The price is HK$1,450
HK$3,427 total
includes taxes & fees
5 Aug - 6 Aug
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
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, (158 reviews)
"Perfect place for family to get away. Plenty of room"
United States
Aaron H.
The price is HK$1,533
HK$3,763 total
includes taxes & fees
18 Aug - 19 Aug
3212 Across from Pool * King & Queen/Twin Bunk Bed
Property grounds

4 Flr |2 Mastr |Oceanview |Jacuzzi |Beach |Marina

4 Flr |2 Mastr |Oceanview |Jacuzzi |Beach |Marina
Tavernier
9.8 out of 10, Exceptional, (48 reviews)
"We were two couples staying in this space with plenty of room. All the amenities on this property (pool, beach restaurant and bar)made this a terrific stay. "
United States
Donna B.
The price is HK$1,545
HK$3,549 total
includes taxes & fees
4 Aug - 5 Aug
4 Flr |2 Mastr |Oceanview |Jacuzzi |Beach |Marina
Beach nearby

Reel Key Largo Escape Ocean Pointe 5209

Reel Key Largo Escape Ocean Pointe 5209
Tavernier
9.6 out of 10, Exceptional, (10 reviews)
"We had a great time and the property was the center-point of our stay. Thanks for making it easy!"
United States
Ty L.
The price is HK$1,164
HK$3,281 total
includes taxes & fees
18 Aug - 19 Aug
Reel Key Largo Escape Ocean Pointe 5209
Marina

1BR Suite w/ Partial Ocean View & Beach Access

1BR Suite w/ Partial Ocean View & Beach Access
Key Largo
The price is HK$1,552
HK$1,935 total
includes taxes & fees
26 Jul - 27 Jul
1BR Suite w/ Partial Ocean View & Beach Access
Interior

Private 3-bedroom brand new apartment in Tavernier, Key Largo

Private 3-bedroom brand new apartment in Tavernier, Key Largo
Tavernier
9.8 out of 10, Exceptional, (6 reviews)
"Everything as advertised. Very efficient property. Easy in, easy out. You an is great to work with. "
United States
Michael W.
The price is HK$1,799
HK$4,225 total
includes taxes & fees
20 Jul - 21 Jul
Private 3-bedroom brand new apartment in Tavernier, Key Largo
Interior

Boho Chic Ocean Pointe 3214 King & Queen

Boho Chic Ocean Pointe 3214 King & Queen
Tavernier
9.8 out of 10, Exceptional, (15 reviews)
"The condo was nice and clean. The view from the balcony is very nice. The property is also nice with things to do but not too busy. The host was great and responsive. "
United States
Anthony F.
The price is HK$1,329
HK$3,428 total
includes taxes & fees
19 Aug - 20 Aug
Boho Chic Ocean Pointe 3214 King & Queen
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

10/10 Excellent
"T was so fun and I love all activities you have there. The location was amazing and the views. It has something for everyone in the family. I love how they give you lil surprises outside by the pool. Such great staff checking you in as you come inside. I can’t remember their names. But T really helped out on activities paddle boards , kayaks etc . We Love it and will be back."
Sandy 4-night trip
Posted 3 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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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 in Islamorada close to MoradaWay Arts & Cultural District, 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?

Private Beachfront Paradise: This highly rated holiday home rental in Islamorada is located on the beach, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday. Some other homes for rent in Islamorada include 5 bedroom - Deep Dockage & Heated Pool in Islamorada. and Peacock Shores Islamorada - Vacation On The Beach!.

How many holiday rentals are there in Islamorada?

With 415 Expedia holiday rentals, you're guaranteed to find just the right place for your Islamorada stay.

What can I see and do in Islamorada?

Everglades National Park and Founders Park 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 Florida Keys Brewing Co. and Bud n' Mary's Dive Center.

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.