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

Islamorada Vacation Rentals

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Islamorada vacation rentals

Exterior

1. Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
9.0 out of 10, Wonderful, (749 reviews)
"It was very cozy. I was able to relax while I was celebrating my anniversary with my wife. The bed was super comfortable. The shower was excellent, and the staff was very friendly."
United States
Dionisio
The price is AED 257
AED 347 total
includes taxes & fees
29 Sep - 30 Sep
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, (175 reviews)
"We loved sitting in the deck in the evening and again in the morning."
Canada
Molly
The price is AED 360
AED 922 total
includes taxes & fees
23 Sep - 24 Sep
Treasure Harbor
Private beach, sun loungers, beach umbrellas, beach towels

3. Island Bay Resort

Island Bay Resort
2.5 star property
Tavernier
9.8 out of 10, Exceptional, (183 reviews)
"Amazing vacation spot!!"
United States
Katie Lyn
The price is AED 736
AED 828 total
includes taxes & fees
29 Sep - 30 Sep
Island Bay Resort
Exterior

4. Florida Keys Getaway - Slps 4 - Ocean View

Florida Keys Getaway - Slps 4 - Ocean View
Tavernier
9.8 out of 10, Exceptional, (39 reviews)
"Great place to stay down on the keys."
United States
GJ W.
The price is AED 303
AED 1,116 total
includes taxes & fees
23 Sep - 24 Sep
Florida Keys Getaway - Slps 4 - Ocean View
Pool

5. Amazing Ocean view condo

Amazing Ocean view condo
Tavernier
9.6 out of 10, Exceptional, (52 reviews)
"Excellent accommodations. Unit was even nicer than it looked in pictures, everything was clean and in working order. Enjoyed our stay very much and would definitely stay here again!"
United States
Jerad E.
The price is AED 496
AED 1,265 total
includes taxes & fees
23 Sep - 24 Sep
Amazing Ocean view condo
Beach nearby

6. 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 AED 547
AED 1,424 total
includes taxes & fees
23 Sep - 24 Sep
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Beach nearby

7. 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.
3212 Across from Pool * King & Queen/Twin Bunk Bed
Pool

8. 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, (30 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 AED 627
AED 1,643 total
includes taxes & fees
25 Sep - 26 Sep
Starfish Seas Ocean Pointe 1302 King/Queen 2BA 2BR
Exterior

9. Flamingo Flats Ocean Pointe 5306 2BR/2BA

Flamingo Flats Ocean Pointe 5306 2BR/2BA
Tavernier
9.6 out of 10, Exceptional, (9 reviews)
"Great location and prompt support with all questions we had. "
United States
Jim I.
The price is AED 535
AED 1,520 total
includes taxes & fees
25 Sep - 26 Sep
Flamingo Flats Ocean Pointe 5306 2BR/2BA
A heated pool

10. Dazzling Ocean View Suite w/heated pool, beach, marina, tennis/pickleball

Dazzling Ocean View Suite w/heated pool, beach, marina, tennis/pickleball
Tavernier
9.0 out of 10, Wonderful, (103 reviews)
"Great visit!"
United States
Leigh D. H.
The price is AED 694
AED 1,266 total
includes taxes & fees
24 Sep - 25 Sep
Dazzling Ocean View Suite w/heated pool, beach, marina, tennis/pickleball
Lobby

11. The Happy Reef 4209 King & Queen

The Happy Reef 4209 King & Queen
Tavernier
9.8 out of 10, Exceptional, (186 reviews)
"Very well thought out accommodations"
United States
Mary Jo W.
The price is AED 630
AED 1,645 total
includes taxes & fees
23 Sep - 24 Sep
The Happy Reef 4209 King & Queen
Terrace/patio

12. Serene Oceanfront Keys Condo

Serene Oceanfront Keys Condo
Tavernier
9.8 out of 10, Exceptional, (44 reviews)
"Condo was exactly as pictured. The location was great and close to everything we needed. The amenities and property grounds were beautiful and well kept. We thoroughly enjoyed spending time by the pool."
United States
Alexandra F.
The price is AED 752
AED 1,591 total
includes taxes & fees
23 Sep - 24 Sep
Serene Oceanfront Keys Condo
Beach

13. Aqua Vista Ocean Pointe 3307

Aqua Vista Ocean Pointe 3307
Tavernier
9.6 out of 10, Exceptional, (4 reviews)
"Beautiful & perfect place for a getaway. Really enjoyed our stay. Highly recommend."
United States
Michelle
The price is AED 531
AED 1,531 total
includes taxes & fees
18 Oct - 19 Oct
Aqua Vista Ocean Pointe 3307
Pool

14. 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 AED 627
AED 1,643 total
includes taxes & fees
23 Sep - 24 Sep
Lazy Daze Double King Suite Ocean Pointe 2310
TV

15. Sunrise Sanctuary - Top Floor Ocean Pointe 2415

Sunrise Sanctuary - Top Floor Ocean Pointe 2415
Tavernier
9.8 out of 10, Exceptional, (18 reviews)
"Great stay"
United States
Blain R.
Sunrise Sanctuary - Top Floor Ocean Pointe 2415
Sport court

16. 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 AED 590
AED 1,593 total
includes taxes & fees
23 Sep - 24 Sep
Marina to Ocean View Key Largo Ocean Pointe 5308
Coffee/tea maker, fridge, microwave, oven

17. 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)
"Very cute cozy house boat. Well equipped and close to restaurant. Enjoyable weekend stay. Heidi the host is very welcoming."
United States
Michelle P.
The price is AED 926
AED 1,620 total
includes taxes & fees
23 Sep - 24 Sep
Fla Keys Luxury Houseboat, Prime Location-Steps to Fun, Food & Water Adventures
Marina

18. 2BR Oceanfront Suite w/ Beach & Marina Access

2BR Oceanfront Suite w/ Beach & Marina Access
Key Largo
10.0 out of 10, Exceptional, (1 review)
"This was a great place to stay. Incredibly clean and homey feel. I felt super safe walking the area after dinner at night"
United States
Alyssa H.
The price is AED 683
AED 860 total
includes taxes & fees
27 Sep - 28 Sep
2BR Oceanfront Suite w/ Beach & Marina Access
Marina

19. 2BR Condo w/ Ocean View, Pool & Tropical Setting

2BR Condo w/ Ocean View, Pool & Tropical Setting
Tavernier
9.6 out of 10, Exceptional, (4 reviews)
" centrally located for keys travel"
United States
Gary
2BR Condo w/ Ocean View, Pool & Tropical Setting
A heated pool

20. Ocean view condo with balcony/marina view

Ocean view condo with balcony/marina view
Tavernier
8.6 out of 10, Excellent, (46 reviews)
"Wonderful stay! Beautiful view from the balcony"
United States
Katy T.
The price is AED 655
AED 1,465 total
includes taxes & fees
23 Sep - 24 Sep
Ocean view condo with balcony/marina view
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

8/10 Good
"Very quiet and peaceful stay. Amazing water and beach views from the balcony."
Michelle 4-night trip
Posted 7 hours ago
Chesapeake Beach Resort

Frequently asked questions

Can I find a vacation rental in Islamorada?

Yes, we have vacation rentals in Islamorada close to MoradaWay Arts & Cultural District, or you can select a secluded option if you want 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 vacation home rentals that Islamorada has to offer?

Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada: This Islamorada vacation home rental offers an outdoor pool, a balcony, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. Make the most of the garden in this rental home to help you unwind. Some other homes for rent in Islamorada include 7 Bedroom with Dockage, Pool, Firepit, Paddle Boards & Kayaks and Bungalow #3 - 2 Bed/1 Bath & Pool in Islamorada.

How many vacation rentals are there in Islamorada?

With 405 Expedia vacation rentals, you're sure to find just the right place for your Islamorada stay.

What can I see and do in Islamorada?

Anne's Beach and Fiesta Key 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 vacation rental in Islamorada like?

A vacation rental is a private property where you can stay for a couple of days or more in Islamorada. Vacation rentals provide amenities such as kitchens and laundry facilities so you'll have a home away from home. If you're concerned about cleanliness, a vacation rental can provide a sense of safety away from shared hotel elevators and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular option for family trips or small group gatherings.