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

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
Jul 10 - Jul 12
In two months
Aug 21 - Aug 23
In three months
Sep 18 - Sep 20
In four months
Oct 16 - Oct 18

Our top choices for Islamorada vacation rentals

25-inch flat-screen TV with digital channels, TV

Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (159 reviews)
The price is ￥25,749
￥51,713 total
includes taxes & fees
Jul 11 - Jul 12
Treasure Harbor
Exterior

Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (703 reviews)
"Enjoyed this place."
United States
Christopher
The price is ￥15,087
￥25,358 total
includes taxes & fees
Jul 6 - Jul 7
Breezy Palms Resort
Exterior

Caloosa Cove Resort by CoolVacay

Caloosa Cove Resort by CoolVacay
3.0 star property
Matecumbe
9.8 out of 10, Exceptional, (6 reviews)
"Easy check in if you come After business hours. Kayaks and sport equipment available. Has a small beach which is unique to the Keys. Pool pretty much vacant at all times. Great views. Highly recommend."
United States
Dana
The price is ￥40,429
￥50,941 total
includes taxes & fees
Jun 30 - Jul 1
Caloosa Cove Resort by CoolVacay
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
Florida Keys Getaway - Slps 4 - Ocean View
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 traveler
The price is ￥17,613
￥38,414 total
includes taxes & fees
Jun 29 - Jun 30
Cozy 1-bedroom apartment with kitchen in peaceful Tavernier/Key largo
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 ￥23,291
￥66,556 total
includes taxes & fees
Jun 30 - Jul 1
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 ￥30,569
￥70,944 total
includes taxes & fees
Jul 22 - Jul 23
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 ￥28,101
￥64,214 total
includes taxes & fees
Jul 5 - Jul 6
Amazing Ocean view condo
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 ￥33,974
￥75,915 total
includes taxes & fees
Jul 8 - Jul 9
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
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 ￥42,710
￥58,362 total
includes taxes & fees
Jun 29 - Jun 30
Flip-Flops & Sunshine: Islamorada Studio Escape
Beach nearby

Flamingo Flats Ocean Pointe 5306 2BR/2BA

Flamingo Flats Ocean Pointe 5306 2BR/2BA
Tavernier
9.6 out of 10, Exceptional, (8 reviews)
"Great location and prompt support with all questions we had. "
United States
Jim I.
The price is ￥32,025
￥78,650 total
includes taxes & fees
Jul 13 - Jul 14
Flamingo Flats Ocean Pointe 5306 2BR/2BA
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 ￥35,259
￥83,270 total
includes taxes & fees
Jul 27 - Jul 28
Reel Key Largo Escape Ocean Pointe 5209
Marina

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 ￥28,635
￥73,856 total
includes taxes & fees
Jul 22 - Jul 23
Starfish Seas Ocean Pointe 1302 King/Queen 2BA 2BR
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 ￥33,974
￥75,915 total
includes taxes & fees
Jul 8 - Jul 9
4 Flr |2 Mastr |Oceanview |Jacuzzi |Beach |Marina
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 ￥25,231
￥69,349 total
includes taxes & fees
Jul 20 - Jul 21
Aqua Vista Ocean Pointe 3307
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 ￥43,346
￥93,773 total
includes taxes & fees
Jul 28 - Jul 29
Modern and Coastal Ocean Pointe 2307
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 ￥28,312
￥73,800 total
includes taxes & fees
Jul 19 - Jul 20
Lazy Daze Double King Suite Ocean Pointe 2310
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 ￥47,325
￥53,240 total
includes taxes & fees
Jun 30 - Jul 1
Island Bay Resort
Marina

1BR Oceanfront Suite w/ Beach & Marina Access

1BR Oceanfront Suite w/ Beach & Marina Access
Key Largo
The price is ￥27,981
￥35,523 total
includes taxes & fees
Jul 7 - Jul 8
1BR Oceanfront Suite w/ Beach & Marina Access
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.
Boho Chic Ocean Pointe 3214 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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Islamorada Hotel Reviews

Breezy Palms Resort

Breezy Palms Resort

10/10 Excellent
"We stayed in a cottage. The room was clean and spacious. It had a full kitchen and the cabnets had plates, silverwear, pans, dish detergent. It had a full size refrigerator. There is a separate living room and kichenette from bedroom. The staff was very friendly. There was enough parking for everyone on the day we were there (June). We would definitely stay there again."
Marie 2-night trip
Posted 13 hours ago
Breezy Palms 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
  • Use the map to find apartments and other holiday homes in the Islamorada neighbourhood you prefer
  • 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 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 Bungalow #3 - 2 Bed/1 Bath & Pool in Islamorada and 5 bedroom - Deep Dockage & Heated Pool in Islamorada..

How many vacation rentals are there in Islamorada?

With 415 Expedia vacation rentals, you're sure 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 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.