Islamorada Holiday Rentals

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Our top choices for Islamorada holiday rentals

Houseboat in Islamorada

Treasure Harbor
3.0 star property
9.0 out of 10, Wonderful, (123)
"Great spot! Will be back someday hopefully. "
Canada
Diane
Treasure Harbor

Aparthotel in Matecumbe

Breezy Palms Resort
2.5 star property
8.8 out of 10, Excellent, (606)
"Property was nice and easy to navigate, ocean view room was extra nice to have!"
United States
Lisa
The price is HK$1,006
HK$1,536 total
includes taxes & fees
14 Jan - 15 Jan
Breezy Palms Resort
9.6 out of 10, Exceptional, (19)
"Everything was just as described in the condo listing. We enjoyed the pool and hot tub. Wonderful location to explore the Keys. "
United States
Michele G.
The price is HK$1,370
HK$3,278 total
includes taxes & fees
2 Feb - 3 Feb
Florida Keys Getaway - Slps 4 - Ocean View
2.5 star property
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 HK$1,619
HK$3,730 total
includes taxes & fees
1 Feb - 2 Feb
Aqua Vista Ocean Pointe 3307
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 HK$1,246
HK$3,367 total
includes taxes & fees
3 Feb - 4 Feb
Blue Haven Key Largo | Ocean Pointe 1315
10.0 out of 10, Exceptional, (108)
"Fantastic place to stay! Very clean and great hosts. Will stay again. "
United States
Les
The price is HK$1,675
HK$3,622 total
includes taxes & fees
21 Jan - 22 Jan
Serenity In The Sun Condo Fabulous Ocean View
9.6 out of 10, Exceptional, (5)
"Thanks for your great hospitality."
United States
richard
The price is HK$1,238
HK$3,311 total
includes taxes & fees
25 Jan - 26 Jan
Paradise Palms 2 Bedroom Condo Ocean Pointe 1206
10.0 out of 10, Exceptional, (1)
"Host was very helpful and place was very nice and very clean. Would definitely recommend. "
United States
Amy E.
The price is HK$1,035
HK$2,679 total
includes taxes & fees
12 Jan - 13 Jan
Private 1-bedroom apartment in peaceful Tavernier with kitchen, key Largo
9.2 out of 10, Wonderful, (35)
"Great place, comfortable, clean and good location. "
United States
Joshua P.
The price is HK$1,285
HK$5,695 total
includes taxes & fees
26 Jan - 27 Jan
Tavernier Oceanfront Resort Condo-Pool, Dockage, Kayaks, Onsite Restaurant & Bar

Houseboat in Tavernier

Island Sanctuary Islamorada
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 HK$2,067
HK$3,165 total
includes taxes & fees
20 Jan - 21 Jan
Island Sanctuary Islamorada

Condo in Tavernier

Amazing Ocean view condo
9.6 out of 10, Exceptional, (43)
"Exceeded expectations, exceptionally clean, great for kids (they loved the pool), perfect for our Keys trip"
United States
Natalie M.
The price is HK$1,241
HK$2,881 total
includes taxes & fees
19 Jan - 20 Jan
Amazing Ocean view condo
10.0 out of 10, Exceptional, (123)
"We enjoyed our stay!"
United States
Halley R.
The price is HK$1,207
HK$3,236 total
includes taxes & fees
19 Jan - 20 Jan
Modern and Coastal Ocean Pointe 2307

Apartment in Tavernier

Boho Chic Ocean Pointe 3214
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 HK$1,355
HK$3,387 total
includes taxes & fees
20 Jan - 21 Jan
Boho Chic Ocean Pointe 3214
9.8 out of 10, Exceptional, (26)
"Everything was exceptionally nice. Would definitely book again."
United States
Sharon
The price is HK$1,222
HK$3,169 total
includes taxes & fees
21 Jan - 22 Jan
Lazy Daze Double King Suite Ocean Pointe 2310
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 HK$1,526
HK$3,737 total
includes taxes & fees
2 Feb - 3 Feb
Sunrise Oasis - Top Floor 2 BR 2 BA Condo 2411
9.4 out of 10, Exceptional, (6)
"Great area"
United States
Yesenia
The price is HK$1,900
HK$4,224 total
includes taxes & fees
2 Feb - 3 Feb
Reel Key Largo Escape Ocean Pointe 5209
The price is HK$1,339
HK$3,511 total
includes taxes & fees
13 Jan - 14 Jan
Keys Bohemian 2 BR 2 BA at Ocean Pointe 1312
9.4 out of 10, Exceptional, (24)
"Unit was everything we hoped for, building was nice, quiet, and had good amenities, and the grounds and pool were great. Would absolutely stay here again on future trips."
United States
Jacob W.
The price is HK$1,403
HK$5,853 total
includes taxes & fees
16 Jan - 17 Jan
Ocean Pointe 2BR Retreat Ocean View, Pool, Marina & Resort Amenities
10.0 out of 10, Exceptional, (1)
"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$1,246
HK$2,947 total
includes taxes & fees
12 Jan - 13 Jan
Top Floor w Amazing Ocean Views!! Resort Style Pool, Beach, Marina, & Cafe!
2.0 star property
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 HK$1,417
HK$3,546 total
includes taxes & fees
14 Jan - 15 Jan
Ocean View Gem Ocean Pointe 3406 2BA/2BR 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

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 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.