Islamorada Holiday Rentals

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Check prices for these dates

In two weeks
30 Jan - 1 Feb
In two months
13 Mar - 15 Mar
In three months
10 Apr - 12 Apr
In four months
8 May - 10 May

Our top choices for Islamorada holiday 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, (124 reviews)
"Great spot! Will be back someday hopefully. "
Canada
Diane
Treasure Harbor
Exterior
Breezy Palms Resort

Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (606 reviews)
"Property was nice and easy to navigate, ocean view room was extra nice to have!"
United States
Lisa
The price is HK$1,167
HK$1,717 total
includes taxes & fees
14 Jan - 15 Jan
Breezy Palms Resort
On the beach, sun-loungers, beach umbrellas, beach towels
The Islands of Islamorada

The Islands of Islamorada

The Islands of Islamorada
4.0 star property
Matecumbe
9.8 out of 10, Exceptional, (70 reviews)
"Amazing stay, can’t wait to stay there again!"
United States
Anonymous traveller
The price is HK$4,747
HK$5,770 total
includes taxes & fees
13 Jan - 14 Jan
The Islands of 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 reviews)
"Would stay there again."
Canada
jamie g.
The price is HK$1,832
HK$3,815 total
includes taxes & fees
28 Jan - 29 Jan
Boho Style Florida Keys Condo Ocean Views
Marina
Island Sanctuary Islamorada

Island Sanctuary Islamorada

Island Sanctuary Islamorada
Tavernier
9.8 out of 10, Exceptional, (13 reviews)
"It exceeded our expectations, and we are so glad we found this location!"
United States
Jenn H.
The price is HK$2,069
HK$3,246 total
includes taxes & fees
20 Jan - 21 Jan
Island Sanctuary Islamorada
Beach
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 review)
"Beautiful & perfect place for a getaway. Really enjoyed our stay. Highly recommend."
United States
Michelle
The price is HK$2,034
HK$4,377 total
includes taxes & fees
11 Feb - 12 Feb
Aqua Vista Ocean Pointe 3307
Fridge, microwave, oven, stovetop
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 reviews)
"Absolutely wonderful property in every way!"
United States
Christopher K.
The price is HK$2,338
HK$3,928 total
includes taxes & fees
16 Jan - 17 Jan
Fla Keys Luxury Houseboat, Prime Location-Steps to Fun, Food & Water Adventures
On the beach, sun-loungers, beach towels
Coastal comfort in Ocean Pointe Suites.

Coastal comfort in Ocean Pointe Suites.

Coastal comfort in Ocean Pointe Suites.
Tavernier
10.0 out of 10, Exceptional, (33 reviews)
"Very clean, lots of things to do for the kids on property - large pool and hot tub, tennis and pickle ball courts, and a small beach. "
United States
Robert F.
The price is HK$1,988
HK$5,201 total
includes taxes & fees
13 Jan - 14 Jan
Coastal comfort in Ocean Pointe Suites.
Property grounds
NEW ! Lagoon-front townhouse with Marina! Day Dreams Key Largo.

NEW ! Lagoon-front townhouse with Marina! Day Dreams Key Largo.

NEW ! Lagoon-front townhouse with Marina! Day Dreams Key Largo.
2.0 star property
Key Largo
10.0 out of 10, Exceptional, (46 reviews)
"Good location. Lagoon and pool right outside door. "
United States
Debra C.
The price is HK$2,105
HK$4,581 total
includes taxes & fees
13 Jan - 14 Jan
NEW ! Lagoon-front townhouse with Marina! Day Dreams Key Largo.
Interior
Top Floor w Amazing Ocean Views!! Resort Style Pool, Beach, Marina, & Cafe!

Top Floor w Amazing Ocean Views!! Resort Style Pool, Beach, Marina, & Cafe!

Top Floor w Amazing Ocean Views!! Resort Style Pool, Beach, Marina, & Cafe!
2.0 star property
Tavernier
10.0 out of 10, Exceptional, (1 review)
"The property was just as pictured on the site! We loved the view from the balconies (yes, two!!!). The host was superior in supplying our basic needs upon arrival. More importantly, she was extremely responsive to our questions during our stay (usually responding within a few minutes--even on Christmas day!!). The property is conveniently located in the keys so it's not too far to Miami or Key West. We absolutely loved our stay! If we come back to the Keys, we will definitely stay here again!!!"
United States
Mark W.
The price is HK$1,434
HK$3,130 total
includes taxes & fees
19 Jan - 20 Jan
Top Floor w Amazing Ocean Views!! Resort Style Pool, Beach, Marina, & Cafe!
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 reviews)
"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 HK$1,473
HK$3,630 total
includes taxes & fees
27 Jan - 28 Jan
Island Time at Ocean Pointe Luxe 2 King Spa BR/BA, 2 Balcony
Beach
2BR Condo w/ Ocean Views, Private Beach & Pool

2BR Condo w/ Ocean Views, Private Beach & Pool

2BR Condo w/ Ocean Views, Private Beach & Pool
2.0 star property
Tavernier
10.0 out of 10, Exceptional, (1 review)
"A good place to relax."
United States
gildas m.
2BR Condo w/ Ocean Views, Private Beach & Pool
Beach
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, (157 reviews)
"The property was excellent."
United States
June M.
The price is HK$1,559
HK$3,476 total
includes taxes & fees
19 Jan - 20 Jan
Sea View Farm Style Ocean front Condo Views
Beach
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 reviews)
"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 HK$1,426
HK$3,598 total
includes taxes & fees
14 Jan - 15 Jan
Ocean View Gem Ocean Pointe 3406 2BA/2BR King/Queen
Beach nearby
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 reviews)
"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 HK$1,512
HK$3,707 total
includes taxes & fees
2 Feb - 3 Feb
Sunrise Oasis - Top Floor 2 BR 2 BA Condo 2411
Interior
Private 3-bedroom brand new apartment in Tavernier, Key Largo

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

Private 3-bedroom brand new apartment in Tavernier, Key Largo
2.0 star property
Tavernier
10.0 out of 10, Exceptional, (1 review)
"The amenities and location were nice for being close to Key Largo. There is a small park that faces the Atlantic side which is a 1 minute walk from the apartment. "
United States
Kathleen A.
The price is HK$2,058
HK$4,496 total
includes taxes & fees
14 Jan - 15 Jan
Private 3-bedroom brand new apartment in Tavernier, Key Largo
On the beach
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 reviews)
"Fantastic place to stay! Very clean and great hosts. Will stay again. "
United States
Les
The price is HK$1,676
HK$3,670 total
includes taxes & fees
21 Jan - 22 Jan
Serenity In The Sun Condo Fabulous Ocean View
On the beach, sun-loungers, beach towels
NEW! CASA PALMA OCEANSIDE -GOLF CART, 2 KING SUITES, POOL, BEACH, PICKLE, KAYAKS

NEW! CASA PALMA OCEANSIDE -GOLF CART, 2 KING SUITES, POOL, BEACH, PICKLE, KAYAKS

NEW! CASA PALMA OCEANSIDE -GOLF CART, 2 KING SUITES, POOL, BEACH, PICKLE, KAYAKS
Key Largo
9.8 out of 10, Exceptional, (170 reviews)
"Everything was clean and in good condition. The owner responded right away to any questions. Golf Cart is a plus! "
United States
Anonymous traveller
The price is HK$5,012
HK$8,962 total
includes taxes & fees
29 Jan - 30 Jan
NEW! CASA PALMA OCEANSIDE -GOLF CART, 2 KING SUITES, POOL, BEACH, PICKLE, KAYAKS
Interior
Boho Chic Ocean Pointe 3214

Boho Chic Ocean Pointe 3214

Boho Chic Ocean Pointe 3214
Tavernier
10.0 out of 10, Exceptional, (12 reviews)
"It was clean, well organized and communication was great. Had a good time."
United States
Shirl
The price is HK$1,559
HK$3,598 total
includes taxes & fees
27 Jan - 28 Jan
Boho Chic Ocean Pointe 3214
Terrace/patio
Spectacular Ocean-Marina Views - Free Kayaks Pickleball

Spectacular Ocean-Marina Views - Free Kayaks Pickleball

Spectacular Ocean-Marina Views - Free Kayaks Pickleball
Key Largo
Spectacular Ocean-Marina Views - Free Kayaks Pickleball
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

Amara Cay Resort

Amara Cay Resort

10/10 Excellent
"This resort exceed our expectations. Wonderful for families , very clean and amazing staff. We did a free fishing lesson with captain Patrick and he was wonderful-also great with kids. Loved the free water taxi to visit the sister resorts . We will definitely be back "
Susan 1-night trip
Posted 3 days ago
Amara Cay 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 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 #4 - 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 Oceanfront 4-BR w/ private 31' Boat Slip Included, Pool & Beach, gourmet kitchen and Bungalow #3 - 2 Bed/1 Bath & Pool in Islamorada.

How many holiday rentals are there in Islamorada?

With 486 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 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 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.