Islamorada Vacation Rentals

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Vacation Rentals in Islamorada

Our top choices for Islamorada vacation rentals

Treasure Harbor

3.0 star property
8.8 out of 10, Excellent, (102)
"Unique House boat experience, friendly staff. "
The price is CA $125
CA $336 total
includes taxes & fees
Sep 2 - Sep 3
Treasure Harbor

Breezy Palms Resort

2.5 star property
8.8 out of 10, Excellent, (513)
"Best kept secret, love staying here,!"
The price is CA $107
CA $192 total
includes taxes & fees
Sep 15 - Sep 16
Breezy Palms Resort

The Islands of Islamorada

4.0 star property
9.8 out of 10, Exceptional, (66)
"Absolutely outstanding resort. Legitimate 5 star property. "
The price is CA $765
CA $937 total
includes taxes & fees
Aug 23 - Aug 24
The Islands of Islamorada

Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada

9.6 out of 10, Exceptional, (30)
"Nice property . Well kept. Good management "
Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada

Oceanfront 165ft beach-Dock-Heated pool-4K sq.ft 4 bed/5 bath-Next avail 8.9.25

10.0 out of 10, Exceptional, (84)
"Everything just great except need better vaccum"
Oceanfront 165ft beach-Dock-Heated pool-4K sq.ft 4 bed/5 bath-Next avail 8.9.25

OCEANFRONT ANGLERS REEF in ISLAMORADA -Pool, Dock, Beach, Kayaks, Paddle Boards

10.0 out of 10, Exceptional, (185)
"Lodgings first rate. Boat access to Mahi and Grouper catches."
OCEANFRONT ANGLERS REEF in ISLAMORADA -Pool, Dock, Beach, Kayaks, Paddle Boards

Venetian Tropics weekly Pvt home w/heated Pool, 3 bedroom /70ft dock w/canal

9.6 out of 10, Exceptional, (58)
"The property is central location in Islamorada, best location....The outdoor area is perfect,pool heated very enjoyable.. great neighborhood..Friendly Host JoAnn is amazing, and prompt response, a delightful person, and a wonderful host!"
Venetian Tropics weekly Pvt home w/heated Pool, 3 bedroom /70ft dock w/canal

Private Oceanfront: Heated Pool, Paddleboards & Kayaks - 180 degree ocean views

10.0 out of 10, Exceptional, (105)
"We loved everything about this house! The outdoor areas were perfect. We had everything we needed to have a great time at the house but close enough to venture out and explore the keys if we wanted. Owners were responsive and great to work with"
Private Oceanfront: Heated Pool, Paddleboards & Kayaks - 180 degree ocean views

7 Bedroom with Dockage, Pool, Firepit, Paddle Boards & Kayaks

10.0 out of 10, Exceptional, (57)
"We have stayed in one of this Hosts properties for 5 years in a row. Always clean, always great communication and we always have a great time. We highly recommend."
7 Bedroom with Dockage, Pool, Firepit, Paddle Boards & Kayaks

FALL SPECIALS! Islamorada Anglers Reef Oceanview: Private Beach, Pool, Marina

10.0 out of 10, Exceptional, (3)
"Our stay was nothing but amazing! The area/community is beautiful and Al was a wonderful host! Will definitely be staying here again next year!!"
FALL SPECIALS! Islamorada Anglers Reef Oceanview: Private Beach, Pool, Marina

5 bedroom - Deep Dockage & Heated Pool in Islamorada.

10.0 out of 10, Exceptional, (117)
"Love Chausie and her properties! Top notch! "
5 bedroom - Deep Dockage & Heated Pool in Islamorada.

WOW! WATERFRONT CANAL HOME-RELAXING, FRESH & CLEAN-FISH, SWIM, SNORKEL CLOSE BY!

9.6 out of 10, Exceptional, (82)
"Great stay, lovely setting and location! Our second time here!"
WOW! WATERFRONT CANAL HOME-RELAXING, FRESH & CLEAN-FISH, SWIM, SNORKEL CLOSE BY!

OCEAN VIEW ANGLERS REEF - POOL, DOCK, BEACH. Walk or Bike to local food + bars

10.0 out of 10, Exceptional, (195)
"Great location. Beautiful, comfortable accommodations. Would absolutely return. "
OCEAN VIEW ANGLERS REEF - POOL, DOCK, BEACH. Walk or Bike to local food + bars

NEW - Oceanfront FL Keys Home w/Pool, Free Dockage, Gameroom, Private Balcony

10.0 out of 10, Exceptional, (1)
"This property was amazing basically brand new definitely recommend "
NEW - Oceanfront FL Keys Home w/Pool, Free Dockage, Gameroom, Private Balcony

Islamorada Boaters Paradise with 70' Dock and private beach access..

10.0 out of 10, Exceptional, (23)
"We loved this house. It had plenty of space for all 8 of us. We enjoyed fishing off the dock, the pool and the private beach. "
Islamorada Boaters Paradise with 70' Dock and private beach access..

Spectacular Ocean Front Home In Beautiful Islamorada!Slip,Com Pool, & Prv Bch

10.0 out of 10, Exceptional, (43)
"Loved the time with family- great location "
Spectacular Ocean Front Home In Beautiful Islamorada!Slip,Com Pool, & Prv Bch

BeachFront Paradise/By The Glam Homes

BeachFront Paradise/By The Glam Homes

Bungalow #3 - 2 Bed/1 Bath & Pool in Islamorada

9.2 out of 10, Wonderful, (16)
"We love to stay in these cottages in Islamorada! This cottage was very clean, did a great job with organizing and creating extra space for storage, and was beautifully decorated! It was perfect for our family of 4. We enjoyed the pool as well which is clean and nicely accessorized with lots of seating and umbrellas. We will definitely be returning to this cottage! "
Bungalow #3 - 2 Bed/1 Bath & Pool in Islamorada

Peacock Shores Islamorada - Vacation On The Beach!

10.0 out of 10, Exceptional, (38)
"Great place! Second time staying here. Comfortable, very clean, quiet and close to many great restaurants."
Peacock Shores Islamorada - Vacation On The Beach!

Paradise in Venetian Shores Pool / SPA - Heater / Chiller & Commercial Ice Maker

10.0 out of 10, Exceptional, (38)
"Was a nice property and pleasant enough for our stay."
Paradise in Venetian Shores Pool / SPA - Heater / Chiller & Commercial Ice Maker
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

Frequently asked questions

Can I find a vacation rental in Islamorada?

Yes, we have vacation rentals close to well known points of interest in Islamorada, or you can choose a more remote 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 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 barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. Some other homes for rent in Islamorada include Venetian Tropics weekly Pvt home w/heated Pool, 3 bedroom /70ft dock w/canal and Oceanfront 165ft beach-Dock-Heated pool-4K sq.ft 4 bed/5 bath-Next avail 8.9.25.

How many vacation rentals are there in Islamorada?

With 575 Expedia vacation rentals, you're sure to find just the right place for your Islamorada stay.

What can I see and do in Islamorada?

Enjoy the outdoors at Islamorada County Park and Anne's Beach, or simply take in cultural attractions like History of Diving Museum and MoradaWay Arts & Cultural District. Other places in town to visit include Bud n' Mary's Dive Center and Fiesta Key.

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.