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
24 Jul - 26 Jul
In two months
4 Sep - 6 Sep
In three months
2 Oct - 4 Oct
In four months
30 Oct - 1 Nov

Our top choices for Islamorada vacation rentals

Exterior

Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (705 reviews)
"Enjoyed this place."
United States
Christopher
The price is SAR 336
SAR 573 total
includes taxes & fees
19 Jul - 20 Jul
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, (162 reviews)
"Amazing stay!"
United States
Amanda
The price is SAR 571
SAR 1,170 total
includes taxes & fees
15 Jul - 16 Jul
Treasure Harbor
Exterior

Caloosa Cove Resort by CoolVacay

Caloosa Cove Resort by CoolVacay
3.0 star property
Matecumbe
9.8 out of 10, Exceptional, (8 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
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, (173 reviews)
"The place is beautiful"
United States
Adriana
The price is SAR 961
SAR 1,081 total
includes taxes & fees
9 Aug - 10 Aug
Island Bay Resort
Marina

Island Sanctuary Islamorada

Island Sanctuary Islamorada
Tavernier
9.4 out of 10, Exceptional, (25 reviews)
"Great , everything you want and need to have an amazing vacation. Kelly is just cool dude and his houseboat is well kept"
United States
Wayne M.
The price is SAR 997
SAR 1,582 total
includes taxes & fees
17 Jul - 18 Jul
Island Sanctuary Islamorada
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 SAR 710
SAR 1,658 total
includes taxes & fees
13 Jul - 14 Jul
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
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 SAR 385
SAR 1,241 total
includes taxes & fees
3 Aug - 4 Aug
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)
"Very clean and nice location."
United States
Melinda V.
The price is SAR 561
SAR 1,568 total
includes taxes & fees
13 Jul - 14 Jul
Charming Home in Key Largo
Pool

Amazing Ocean view condo

Amazing Ocean view condo
Tavernier
9.6 out of 10, Exceptional, (50 reviews)
"Exceeded expectations, exceptionally clean, great for kids (they loved the pool), perfect for our Keys trip"
United States
Natalie M.
The price is SAR 642
SAR 1,471 total
includes taxes & fees
14 Jul - 15 Jul
Amazing Ocean view condo
Marina

2BR Oceanfront Suite w/ Beach & Marina Access

2BR Oceanfront Suite w/ Beach & Marina Access
Key Largo
The price is SAR 751
SAR 931 total
includes taxes & fees
16 Jul - 17 Jul
2BR Oceanfront Suite w/ Beach & Marina Access
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.
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Beach nearby

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)
"Great location and clean"
United States
Matthew H.
The price is SAR 597
SAR 1,672 total
includes taxes & fees
15 Jul - 16 Jul
Sunrise Oasis - Top Floor 2 BR 2 BA Condo 2411
Balcony view

The Islands of Islamorada

The Islands of Islamorada
4.0 star property
Matecumbe
9.6 out of 10, Exceptional, (77 reviews)
"What a wonderful venue for our last 2 nights in the Keys. This place is a hidden gem. The entire staff, especially Edith, the bartender, were fantastic."
United States
Michael
The price is SAR 1,873
SAR 2,314 total
includes taxes & fees
9 Aug - 10 Aug
The Islands of Islamorada
Pool

Flip-Flops & Sunshine: Islamorada Studio Escape

Flip-Flops & Sunshine: Islamorada Studio Escape
Matecumbe
10.0 out of 10, Exceptional, (7 reviews)
"Very nice clean place. Pool amazing with great views of ocean"
United States
Dawn S.
Flip-Flops & Sunshine: Islamorada Studio Escape
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 SAR 456
SAR 949 total
includes taxes & fees
9 Aug - 10 Aug
Cozy 1-bedroom apartment with kitchen in peaceful Tavernier/Key largo
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, (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 SAR 747
SAR 1,708 total
includes taxes & fees
12 Jul - 13 Jul
4 Flr |2 Mastr |Oceanview |Jacuzzi |Beach |Marina
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
Reel Key Largo Escape Ocean Pointe 5209
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.
Modern and Coastal Ocean Pointe 2307
Marina

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)
The price is SAR 597
SAR 1,664 total
includes taxes & fees
19 Jul - 20 Jul
Paradise Palms 2 Bedroom Condo Ocean Pointe 1206
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
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

8/10 Good
"This was a nice place to get away from the urban Key West. The staff was very friendly and solved any issues regardless of the time (noisy neighbor, needed blanket) and the shore was close by. There was staff routinely monitoring the beach and property so it was very secure. The location has easy access to restaurants and shops if you have a car. The large pool had a bar / food and the property has a nice restaurant. The breakfast is cook to order pancakes and omelets, very nice! Pros Great staff everywhere! Ocean view is a real view if you select it We had a suite with a king bed and the teen had a separate fold out couch that was comfortable Microwave and mini-fridge were convenient Bathroom was very nice had a toilet in a separated section with a door A second pool was available with shade making it cooler in the summer Parking was easy and right outside, some covered by the buildings Elevator if you have the ocean view was very convenient Fresh omelet to order with a dozen ingredients, good yogurt options with toppings that were plentiful Balcony was very nice Reasonable price Cons - not much Next to a busy road. We could not hear it from outside the room door but there are two buildings and we were at the far building, so not bad at all for us Not much available without a car I recommend not going in June as the seaweed odor is unpleasant No one went to the beach but it was fine at the pool"
matthew 2-night trip
Posted 8 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 5 bedroom - Deep Dockage & Heated Pool in Islamorada. and Private Beachfront Paradise.

How many vacation rentals are there in Islamorada?

With 412 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.