Islamorada Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Islamorada vacation rentals

A beach with palm trees, thatched-roof huts, and lounge chairs.

1. Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
9.0 out of 10, Wonderful, (780 reviews)
"Such a great place to stay!!"
United States
Gavin
The price is AED 254
AED 476 total
includes taxes & fees
10 Nov - 11 Nov
Breezy Palms Resort
A modern kitchen with white cabinets, a microwave, and a dining area with a table and chairs.

2. Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (181 reviews)
"Had a very enjoyable stay at Hemingway House. The place was spotless! All staff were very friendly and helpful. Would highly recommend staying here!"
United States
Diane
The price is AED 393
AED 959 total
includes taxes & fees
8 Nov - 9 Nov
Treasure Harbor
A beachfront hotel with two palm trees, a flag, and a pool area with lounge chairs.

3. Florida Keys Getaway - Slps 4 - Ocean View

Florida Keys Getaway - Slps 4 - Ocean View
Tavernier
9.8 out of 10, Exceptional, (43 reviews)
"great stay and value! glad we went with this place for our trip, everyone loved it! beautiful, clean and the pool was great too!"
Canada
Nick
The price is AED 487
AED 1,356 total
includes taxes & fees
16 Nov - 17 Nov
Florida Keys Getaway - Slps 4 - Ocean View
A modern kitchen with white cabinets, a black refrigerator, and a dining area with a black table and two black chairs.

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

Cozy 1-bedroom apartment with kitchen in peaceful Tavernier/Key largo
Tavernier
9.8 out of 10, Exceptional, (6 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 traveler
The price is AED 364
AED 1,040 total
includes taxes & fees
9 Nov - 10 Nov
Cozy 1-bedroom apartment with kitchen in peaceful Tavernier/Key largo
A swimming pool with clear blue water, surrounded by lounge chairs and umbrellas, and a covered pavilion in the background.

5. Amazing Ocean view condo

Amazing Ocean view condo
Tavernier
9.6 out of 10, Exceptional, (53 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 1,221 total
includes taxes & fees
15 Nov - 16 Nov
Amazing Ocean view condo
A beach with palm trees, thatched umbrellas, and beach chairs.

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

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Tavernier
10.0 out of 10, Exceptional, (171 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 AED 459
AED 1,325 total
includes taxes & fees
15 Nov - 16 Nov
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
A beach with palm trees, thatched umbrellas, and beach chairs.

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

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Tavernier
10.0 out of 10, Exceptional, (116 reviews)
"Fantastic place to stay! Very clean and great hosts. Will stay again. "
United States
Les
The price is AED 477
AED 1,353 total
includes taxes & fees
19 Nov - 20 Nov
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
A beach with palm trees, thatched umbrellas, and beach chairs.

8. 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.
4 Flr |2 Mastr |Oceanview |Jacuzzi |Beach |Marina
A marina with boats docked, a swimming pool, and a building with a blue roof.

9. Flamingo Flats | Marina View | Ocean Pointe 5306

Flamingo Flats | Marina View | Ocean Pointe 5306
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 591
AED 1,525 total
includes taxes & fees
14 Nov - 15 Nov
Flamingo Flats | Marina View | Ocean Pointe 5306
A marina with boats docked, a swimming pool, and a building with a blue roof.

10. Aqua Vista | Ocean View 2BR | Ocean Pointe 3307

Aqua Vista | Ocean View 2BR | 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 591
AED 1,551 total
includes taxes & fees
10 Nov - 11 Nov
Aqua Vista | Ocean View 2BR | Ocean Pointe 3307
A marina with boats docked, a swimming pool, and a building with a blue roof.

11. 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)
"My host is amazing and the property was incredible. Highly recommended."
United States
Jean V.
The price is AED 693
AED 1,671 total
includes taxes & fees
17 Nov - 18 Nov
Lazy Daze | Double King Suite | Ocean Pointe 2310
A modern living room with a flat-screen TV, a black leather sofa, and a white ottoman.

12. Charming Home in Key Largo

Charming Home in Key Largo
Key Largo
10.0 out of 10, Exceptional, (41 reviews)
"Very clean and nice location."
United States
Melinda V.
The price is AED 529
AED 1,442 total
includes taxes & fees
9 Nov - 10 Nov
Charming Home in Key Largo
A modern showerhead with multiple water streams, a tiled wall, and a pool area with blue chairs and a palm tree.

13. 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 1,359 total
includes taxes & fees
14 Nov - 15 Nov
Ocean view condo with balcony/marina view
A beach with rows of sun loungers, a wooden pier, and a thatched-roof structure.

14. 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 AED 674
AED 1,616 total
includes taxes & fees
9 Nov - 10 Nov
Your Happy Place - gorgeous 2 bed/2 bath oceanfront suite with full kitchen
A marina with boats docked, a swimming pool, and a building with a blue roof.

15. Sunrise Sanctuary | Top Floor | Ocean Pointe 2415

Sunrise Sanctuary | Top Floor | Ocean Pointe 2415
Tavernier
9.8 out of 10, Exceptional, (20 reviews)
"Great stay"
United States
Blain R.
The price is AED 613
AED 1,572 total
includes taxes & fees
23 Nov - 24 Nov
Sunrise Sanctuary | Top Floor | Ocean Pointe 2415
Marina

16. 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 pool area with a palm tree, a showerhead, and blue lounge chairs.

17. Ocean Pointe Ocean View w/heated pool beach marina

Ocean Pointe Ocean View w/heated pool beach marina
Tavernier
8.6 out of 10, Excellent, (13 reviews)
"Great location and host is great with communication!"
United States
Mary Katherine B.
The price is AED 694
AED 1,241 total
includes taxes & fees
11 Nov - 12 Nov
Ocean Pointe Ocean View w/heated pool beach marina
A modern kitchen with white cabinets, a marble countertop, and a dining area with a round table and chairs.

18. Private 2-bedroom apartment with kitchen in lovely Tavernier, Key Largo

Private 2-bedroom apartment with kitchen in lovely Tavernier, Key Largo
Tavernier
9.6 out of 10, Exceptional, (5 reviews)
"Host was very helpful and responsive! This was our first VRBO stay so we had more questions than seasoned guests, and he was very patient and helpful. Place was as advertised. Bed/pillows were very comfortable. AC was excellent. "
United States
Denise H.
Private 2-bedroom apartment with kitchen in lovely Tavernier, Key Largo
A marina with boats docked, a swimming pool, and a building with a blue roof.

19. Tiki Time | Top Floor King | Ocean Pointe 1413

Tiki Time | Top Floor King | Ocean Pointe 1413
Tavernier
10.0 out of 10, Exceptional, (2 reviews)
"The host was excellent, they reached out often and very attentive. The condo is beautifully decorated and super clean. It is a small condo but perfect for a couple. It has numerous amenities and has lots of extras for your use. We would definitely stay here again!"
United States
Constance W.
The price is AED 609
AED 1,419 total
includes taxes & fees
29 Nov - 30 Nov
Tiki Time | Top Floor King | Ocean Pointe 1413
A waterfront property with a dock, a house with a blue roof, and a marina with boats.

20. Signature 1BR Partial Ocean View | Beach + Pool

Signature 1BR Partial Ocean View | Beach + Pool
Key Largo
10.0 out of 10, Exceptional, (1 review)
"Beautiful place, nice location"
United States
Michelle G.
The price is AED 658
AED 777 total
includes taxes & fees
30 Nov - 1 Dec
Signature 1BR Partial Ocean View | Beach + Pool
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.
View all properties

Find vacation rentals that suit your style

apart-hotel image
Aparthotels
Aparthotels
Houseboat image
Houseboats
Houseboats

Top Islamorada Hotel Reviews

A beach with palm trees, a thatched-roof structure, and kayaks.
Kona Kai Resort and Gallery - Adults Only

Kona Kai Resort and Gallery - Adults Only

Kona Kai Resort and Gallery - Adults Only
Rock Harbor

10/10 Excellent

Best getaway in the Keys. Quiet, good vibes and friendly staff. Highly recommended.
United States
Audrey
Reviewed August 4, 2025
Kona Kai Resort and Gallery - Adults Only

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 403 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.