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
17 Jul - 19 Jul
In two months
28 Aug - 30 Aug
In three months
25 Sept - 27 Sept
In four months
23 Oct - 25 Oct

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, (704 reviews)
"Enjoyed this place."
United States
Christopher
The price is HK$829
HK$1,339 total
includes taxes & fees
2 Aug - 3 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, (161 reviews)
"Amazing stay!"
United States
Amanda
The price is HK$1,060
HK$2,296 total
includes taxes & fees
14 Jul - 15 Jul
Treasure Harbor
Exterior

Florida Keys Getaway - Slps 4 - Ocean View

Florida Keys Getaway - Slps 4 - Ocean View
Tavernier
9.8 out of 10, Exceptional, (33 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$697
HK$2,478 total
includes taxes & fees
7 Jul - 8 Jul
Florida Keys Getaway - Slps 4 - Ocean View
Smart TV

Charming Home in Key Largo

Charming Home in Key Largo
Key Largo
9.8 out of 10, Exceptional, (38 reviews)
"The condo is extremely clean and has everything you need for your stay. "
United States
hillary w.
The price is HK$1,129
HK$3,227 total
includes taxes & fees
7 Jul - 8 Jul
Charming Home in Key Largo
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$3,432 total
includes taxes & fees
5 Jul - 6 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)
"Unit was really nice. The only complaint was the pillows were the worst we have ever used anywhere. We did find a pillow in the closet that was a little less lumpy but very stained. The pool does get very crowded. The beach area is really cute but smelled pretty bad. Overall a great place!"
United States
joleen s.
The price is HK$1,370
HK$3,090 total
includes taxes & fees
6 Jul - 7 Jul
Amazing Ocean view condo
Exterior

Caloosa Cove Resort by CoolVacay

Caloosa Cove Resort by CoolVacay
3.0 star property
Matecumbe
9.8 out of 10, Exceptional, (7 reviews)
The price is HK$1,941
HK$2,448 total
includes taxes & fees
7 Jul - 8 Jul
Caloosa Cove Resort by CoolVacay
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, (172 reviews)
"Very nice small resort."
United States
Dan
The price is HK$2,008
HK$2,259 total
includes taxes & fees
2 Aug - 3 Aug
Island Bay Resort
Exterior

Sunrise Sanctuary - Top Floor Ocean Pointe 2415

Sunrise Sanctuary - Top Floor Ocean Pointe 2415
Tavernier
9.8 out of 10, Exceptional, (17 reviews)
"Great views and very nice condo. The hosts were welcoming and helpful. we truly enjoyed our stay."
United States
Beth H.
The price is HK$1,804
HK$4,086 total
includes taxes & fees
3 Aug - 4 Aug
Sunrise Sanctuary - Top Floor Ocean Pointe 2415
Beach nearby

Modern and Coastal Ocean Pointe 2307

Modern and Coastal Ocean Pointe 2307
Tavernier
10.0 out of 10, Exceptional, (133 reviews)
"There’s plenty to do for families of all ages at Ocean Pointe, and the condo was an extremely comfortable place to do it from. The hosts made us feel welcome, and we appreciated their care. "
United States
Sherry G.
The price is HK$1,623
HK$3,897 total
includes taxes & fees
3 Aug - 4 Aug
Modern and Coastal Ocean Pointe 2307
Beach

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

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Tavernier
10.0 out of 10, Exceptional, (169 reviews)
"Condo was beautiful would definitely stay here again."
United States
Dan M.
The price is HK$1,647
HK$3,633 total
includes taxes & fees
8 Jul - 9 Jul
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
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, (47 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$1,647
HK$3,633 total
includes taxes & fees
8 Jul - 9 Jul
4 Flr |2 Mastr |Oceanview |Jacuzzi |Beach |Marina
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.
The price is HK$1,357
HK$3,528 total
includes taxes & fees
5 Jul - 6 Jul
Lazy Daze Double King Suite Ocean Pointe 2310
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)
"Great area"
United States
Yesenia
The price is HK$1,208
HK$3,345 total
includes taxes & fees
21 Jul - 22 Jul
Reel Key Largo Escape Ocean Pointe 5209
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$1,255
HK$3,408 total
includes taxes & fees
21 Jul - 22 Jul
Aqua Vista Ocean Pointe 3307
Marina

Signature 1BR Ocean View Suite w/ Beach Access

Signature 1BR Ocean View Suite w/ Beach Access
Key Largo
The price is HK$1,474
HK$1,823 total
includes taxes & fees
9 Jul - 10 Jul
Signature 1BR Ocean View Suite w/ Beach Access
Interior

Cozy 1-bedroom apartment with kitchen in peaceful Tavernier/Key largo

Cozy 1-bedroom apartment with kitchen in peaceful Tavernier/Key largo
Tavernier
10.0 out of 10, Exceptional, (4 reviews)
"Very clean with everything you could need for your time in the Florida keys! The host was very responsive and helpful. Perfect place for a weekend with our dog."
United States
Anonymous traveller
The price is HK$953
HK$1,990 total
includes taxes & fees
16 Jul - 17 Jul
Cozy 1-bedroom apartment with kitchen in peaceful Tavernier/Key largo
Pool

Flip-Flops & Sunshine: Islamorada Studio Escape

Flip-Flops & Sunshine: Islamorada Studio Escape
Matecumbe
10.0 out of 10, Exceptional, (6 reviews)
"Very nice clean place. Pool amazing with great views of ocean"
United States
Dawn S.
The price is HK$1,906
HK$2,566 total
includes taxes & fees
6 Jul - 7 Jul
Flip-Flops & Sunshine: Islamorada Studio Escape
TV, offices

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$1,247
HK$3,383 total
includes taxes & fees
8 Jul - 9 Jul
Boho Chic Ocean Pointe 3214 King & Queen
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$1,420
HK$3,633 total
includes taxes & fees
23 Jul - 24 Jul
Starfish Seas Ocean Pointe 1302 King/Queen 2BA 2BR
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

Chesapeake Beach Resort

Chesapeake Beach Resort

10/10 Excellent
"We had a great experience! Clean room, great breakfast. Only stayed one night but were very impressed with the hotel."
Nick 1-night trip
Posted 8 hours ago
Chesapeake Beach 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?

Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada: This highly rated holiday home rental in Islamorada offers an outdoor pool, a balcony and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. Make the most of garden in this rental home to help you unwind. Some other homes for rent in Islamorada include 5 bedroom - Deep Dockage & Heated Pool in Islamorada. and Private Beachfront Paradise.

How many holiday rentals are there in Islamorada?

With 412 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 Bud n' Mary's Dive Center and Robbie’s of Islamorada.

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.