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
4 Sept - 6 Sept
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

Our top choices for Islamorada holiday rentals

Exterior

1. Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (727 reviews)
"Great place to stay rooms were really nice nice boat ramp plenty of parking restaurants right down the street to eat at no complaints nice pool everybody was friendly room was ice cold from the air condition full kitchen nice balcony looking out over the ocean great stay"
United States
roger
The price is HK$805
HK$1,031 total
includes taxes & fees
1 Sept - 2 Sept
Breezy Palms Resort
25-inch flat-screen TV with digital channels, TV

2. Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (171 reviews)
"We loved sitting in the deck in the evening and again in the morning."
Canada
Molly
The price is HK$911
HK$2,128 total
includes taxes & fees
20 Aug - 21 Aug
Treasure Harbor
Private beach, sun-loungers, beach umbrellas, beach towels

3. Island Bay Resort

Island Bay Resort
2.5 star property
Tavernier
10.0 out of 10, Exceptional, (179 reviews)
"Very pleased with our stay"
United States
Vernon Micheal
The price is HK$2,009
HK$2,260 total
includes taxes & fees
24 Aug - 25 Aug
Island Bay Resort
Marina

4. Island Sanctuary Islamorada

Island Sanctuary Islamorada
Tavernier
9.4 out of 10, Exceptional, (26 reviews)
"We had a great experience. Loved watching the sunset from the top deck. Great to cruise around in the electric catamaran. Kelly’s recommendations were great. We found the sand bar and the Dive restaurant at Mangrove Marina was fun with the live music."
United States
Carrie S.
The price is HK$2,083
HK$3,337 total
includes taxes & fees
20 Aug - 21 Aug
Island Sanctuary Islamorada
Marina

5. Ocean Pointe condo ocean view sleeps 6 in Florida keys building 4 top floor

Ocean Pointe condo ocean view sleeps 6 in Florida keys building 4 top floor
Tavernier
9.6 out of 10, Exceptional, (33 reviews)
"The apartment was perfect, great location over looking the ocean, and nice and clean. They had everything we needed for our stay, The pool and the hot tub at the resort where clean and welcoming."
United States
Kimberly P.
The price is HK$1,177
HK$3,977 total
includes taxes & fees
24 Aug - 25 Aug
Ocean Pointe condo ocean view sleeps 6 in Florida keys building 4 top floor
Property grounds

6. 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$1,295
HK$3,238 total
includes taxes & fees
20 Aug - 21 Aug
4 Flr |2 Mastr |Oceanview |Jacuzzi |Beach |Marina
Terrace/patio

7. Serene Oceanfront Keys Condo

Serene Oceanfront Keys Condo
Tavernier
9.8 out of 10, Exceptional, (44 reviews)
"We very much enjoyed our stay! The condo was comfortable and had most everything we needed. We loved the proximity to the pool and the small beach. Property was nice and clean and communicating with the owner was easy. "
United States
Christy W.
The price is HK$1,607
HK$3,463 total
includes taxes & fees
19 Aug - 20 Aug
Serene Oceanfront Keys Condo
Sun-loungers, beach towels

8. Your Happy Place - gorgeous 2 bed/2 bath oceanfront suite with full kitchen

Your Happy Place - gorgeous 2 bed/2 bath oceanfront suite with full kitchen
Tavernier
9.8 out of 10, Exceptional, (25 reviews)
"The property was in a great location, close to several beach bars and restaurants, the condo was so cute and the host was accessible throughout the entire process before and after our stay."
United States
Alicia
The price is HK$1,603
HK$3,823 total
includes taxes & fees
19 Aug - 20 Aug
Your Happy Place - gorgeous 2 bed/2 bath oceanfront suite with full kitchen
Beach nearby

9. 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$1,483
HK$3,433 total
includes taxes & fees
13 Sept - 14 Sept
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Beach

10. 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$1,530
HK$3,533 total
includes taxes & fees
23 Aug - 24 Aug
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Beach nearby

11. 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, (160 reviews)
"Perfect place for family to get away. Plenty of room"
United States
Aaron H.
The price is HK$1,410
HK$3,649 total
includes taxes & fees
2 Sept - 3 Sept
3212 Across from Pool * King & Queen/Twin Bunk Bed
Exterior

12. 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)
"The space was family friendly and worked well for our stay. The pool area was very clean and the Island Grill on site was great for snacks and drinks while we swam."
United States
Miranda J.
The price is HK$1,346
HK$3,542 total
includes taxes & fees
17 Sept - 18 Sept
Starfish Seas Ocean Pointe 1302 King/Queen 2BA 2BR
On the beach, beach towels

13. Two Spectacular Ocean Views from the Living Room and Master Bedroom of the Condo

Two Spectacular Ocean Views from the Living Room and Master Bedroom of the Condo
Tavernier
9.6 out of 10, Exceptional, (231 reviews)
"Our stay was excellent. The home was immaculate and had everything we needed. We would definitely stay here again."
United States
Chris
The price is HK$1,263
HK$3,058 total
includes taxes & fees
12 Sept - 13 Sept
Two Spectacular Ocean Views from the Living Room and Master Bedroom of the Condo
Coffee/tea maker, fridge, microwave, oven

14. 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, (220 reviews)
"Our host was amazing! Great location with lots to do! "
United States
Jamie B.
The price is HK$2,472
HK$4,127 total
includes taxes & fees
24 Aug - 25 Aug
Fla Keys Luxury Houseboat, Prime Location-Steps to Fun, Food & Water Adventures
Beach nearby

15. Marina to Ocean View Key Largo Ocean Pointe 5308

Marina to Ocean View Key Largo Ocean Pointe 5308
Tavernier
9.4 out of 10, Exceptional, (71 reviews)
"The host was quick to respond, condo was perfect, the view was exceptional!"
United States
Rosalie K.
The price is HK$1,268
HK$3,324 total
includes taxes & fees
19 Aug - 20 Aug
Marina to Ocean View Key Largo Ocean Pointe 5308
Exterior

16. 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$1,221
HK$3,387 total
includes taxes & fees
17 Sept - 18 Sept
Paradise Palms 2 Bedroom Condo Ocean Pointe 1206
Beach nearby

17. 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$1,346
HK$3,542 total
includes taxes & fees
13 Sept - 14 Sept
Sunrise Oasis - Top Floor 2 BR 2 BA Condo 2411
Exterior

18. Florida Keys Getaway - Slps 4 - Ocean View

Florida Keys Getaway - Slps 4 - Ocean View
Tavernier
9.8 out of 10, Exceptional, (36 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$629
HK$2,394 total
includes taxes & fees
2 Sept - 3 Sept
Florida Keys Getaway - Slps 4 - Ocean View
Interior

19. 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$1,214
HK$3,331 total
includes taxes & fees
2 Sept - 3 Sept
Boho Chic Ocean Pointe 3214 King & Queen
Beach nearby

20. Lazy Daze Double King Suite Ocean Pointe 2310

Lazy Daze Double King Suite Ocean Pointe 2310
Tavernier
9.8 out of 10, Exceptional, (36 reviews)
"Loved the beach and pool."
United States
Haley P.
The price is HK$1,346
HK$3,542 total
includes taxes & fees
17 Sept - 18 Sept
Lazy Daze Double King Suite Ocean Pointe 2310
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

Cheeca Lodge & Spa

Cheeca Lodge & Spa

10/10 Excellent
"Perfect getaway spot"
John 2-night trip
Posted 13 hours ago
Cheeca Lodge & Spa

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 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?

7 Bedroom with Dockage, Pool, Firepit, Paddle Boards & Kayaks : This highly rated holiday home rental in Islamorada is located by the ocean, and has an outdoor pool, a balcony and a BBQ to put you at ease in your new surroundings. It has 7 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Some other homes for rent in Islamorada include Private Beachfront Paradise and Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada.

How many holiday rentals are there in Islamorada?

With 408 Expedia holiday rentals, you're guaranteed to find just the right place for your Islamorada stay.

What can I see and do in Islamorada?

Islamorada County 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.