Islamorada Vacation Rentals

35 Rentals

List Map
Sort:

8BR / 5.5BA - Sleeps 16 - Islamorada Home

The Florida Keys Largest, Most Prestigious Vacation Rental Home Available! ! Come stay in your own...

$536 - $858 / nt

Sunset Deluxe

2BR / 2.5BA - Sleeps 4 - Islamorada Townhouse

Sunset view, tennis courts, heated pool, recently remodeled, fish from the dock, boat slip right...

$158 / nt

4 Reviews
Waterfront II

4BR / 3BA - Sleeps 12 - Islamorada Home

The Great Islamorada Getaway features a spectacular canal front home on an over- sized property with...

$386 - $429 / nt

15 Reviews
Islamorada Florida Vacation Rentals - Townhouse
Linda

2BR / 1.5BA - Sleeps 6 - Islamorada Townhouse

Vacation in beautiful peaceful Islamorada, in the Florida Keys. Islamorada, "Fishing Capital of the...

$94 / nt

4 Reviews
Back View

3BR / 3BA - Sleeps 8 - Islamorada Home

Special vacation rental rates for off- season bookings and also for some last minute dates! Call us...

$230 / nt

3 Reviews
Islamorada Florida Vacation Rentals - Townhouse

3BR / 2BA - Sleeps 6 - Islamorada Townhouse

Call Property Manager for Best Rate. Located on Windley Key this gated 5 unit complex has the best...

$100 / nt

3 Reviews

4BR / 4BA - Sleeps 8 - Islamorada Home

This spacious pool home comes with all the amenities to turn your dream vacation into a reality, including...

$358 / nt

Islamorada Florida Vacation Rentals - Guesthouse

2BR / 2BA - Sleeps 8 - Islamorada Guesthouse

Amazing five acre ocean front lot with incredible historic houseboat residence where President Truman...

$286 / nt

Islamorada Florida Vacation Rentals - Townhouse

2BR / 2.5BA - Sleeps 8 - Islamorada Townhouse

Come enjoy a slice of paradise in this beautiful ocean front property settled in a private, gated and...

$315 / nt

EXTERIOR OF HOUSE

4BR / 4BA - Sleeps 8 - Islamorada Home

This beautiful 4 bedroom/ 4 bathroom home has a 70' dock directly behind the home . Canal leads out to...

3 Reviews
Islamorada Florida Vacation Rentals - Apartment

3BR / 2BA - Sleeps 6 - Islamorada Apartment

MINIMUM STAY: 29 DAYS Enjoy unobstructed and panoramic views of the Atlantic Ocean from your own private...

$117 - $150 / nt

Islamorada Florida Vacation Rentals - Apartment

2BR / 2BA - Sleeps 4 - Islamorada Apartment

Minimum Rental: 1 Month This exceptional 2 bedroom and 2 bath condo is located in one of the most popular...

$80 - $127 / nt

Islamorada Florida Vacation Rentals - Apartment

2BR / 2BA - Sleeps 4 - Islamorada Apartment

Minimum Rental: 1 Month Extraordinary ocean front condo with panoramic views of the Atlantic Ocean. Relax...

$134 - $160 / nt

Islamorada Florida Vacation Rentals - Villa

2BR / 2BA - Sleeps 6 - Islamorada Villa

Minimum Rental: 7 Nights Upper Duplex - This is one of three rental units on this fabulous property....

$343 / nt

Islamorada Florida Vacation Rentals - Apartment

2BR / 2BA - Sleeps 6 - Islamorada Apartment

Minimum Rental: 1 Month A Diamond! Be among the first to rent this gorgeous two bedroom condo. It has...

$92 - $127 / nt

Islamorada Florida Vacation Rentals - Villa

2BR / 2BA - Sleeps 6 - Islamorada Villa

Minimum Rental: 7 Nights Cottage - This is one of three rental units on this property. The cottage is...

$343 / nt

Islamorada Florida Vacation Rentals - Villa

2BR / 2BA - Sleeps 6 - Islamorada Villa

Minimum Rental: 7 Nights Lower Duplex - This is one of three rental units on this fabulous property....

$343 / nt

Islamorada Florida Vacation Rentals - Home

3BR / 3BA - Sleeps 8 - Islamorada Home

Minimum Rental: 1 Month Enjoy the tranquil setting of this single family home located directly on the...

$184 - $250 / nt

Islamorada Florida Vacation Rentals - Home

3BR / 2BA - Sleeps 6 - Islamorada Home

Minimum Rental: 1 Month Beautiful Canal Front Stilt Home With Heated Pool - For The Guest Who Expects...

$127 - $167 / nt

Islamorada Florida Vacation Rentals - Apartment

2BR / 2BA - Sleeps 4 - Islamorada Apartment

Description….. MINIMUM STAY: Minimum Rental: 1 Month 5th Floor unit at one of Islamorada's favorite...

$60 - $117 / nt

Islamorada Florida Vacation Rentals - Apartment

2BR / 2BA - Sleeps 5 - Islamorada Apartment

Minimum Rental: 1 Month Sensational oceanfront views are yours from both the master bedroom and the balcony...

$74 - $127 / nt

Islamorada Florida Vacation Rentals - Home

2BR / 2BA - Sleeps 4 - Islamorada Home

MINIMUM STAY: 28 DAYS Villa Riolo is an updated single family stilt home and perfect for your next holiday...

$100 - $134 / nt

Islamorada, FL Travel Tips

Islamorada vacation rentals are a great choice for families visiting this tropical island. There are fun things to do, see, and explore. Activities are water-based and the family that loves fishing will have plenty of fun in the sun. Boating is a popular activity as well as snorkeling and scuba diving. Islamorada is in the Florida Keys and on the Atlantic Ocean and Florida Bay. Islamorada rentals enable families to enjoy their vacations while keeping the comforts of home. You will need a car to get around the island, so rent one if you are not driving from Miami or other surrounding cities.
Neighborhoods
You can find Islamorada vacation home rentals in each of the island’s three neighborhoods. Lower Matecumbe Beach, Matecumbe, and Plantation Key are popular neighborhoods for Islamorada rentals. Oceanfront Islamorada house rentals are easy to find online and are a perfect way to visit Florida. They provide easy access to water activities without giving up comfort. Traveling families enjoy the ease of staying in a rental home or condo. By-owner properties include necessities such as washers and dryers, kitchens, and full baths. For the family that wants to save on their vacation, rentals in Islamorada, FL, are an excellent choice.
Attractions
There are many attractions in Islamorada and the Florida Keys. One of the most popular attractions is the family-friendly park Theater of the Sea. Kids can swim with dolphins. There are opportunities for interacting with sea lions and turtles as well. Theater of the Sea also provides live snorkeling tours, ensuring fun for the entire family. Coral reef diving is an exciting adventure, and there are always chances for fishing. Rent a boat or join a fishing charter with an experienced tour guide.
San Pedro Underwater Archaeological Preserve State Park is a historical shipwreck site. The water is 18 feet deep and perfect for experienced divers. Another popular family-friendly attraction is the Windley Key Fossil Reef Geological State Park. The park includes hiking and nature trails and features fossilized coral. There are picnic tables and educational tours for kids. The park is home to a variety of birds, and wildlife viewing is a popular activity.
Anne’s Beach is a great place to bring the kids. There are many coves along the white sands, making it easy to find private spots for family fun. Mangroves surround the beach, making it the perfect location to observe Florida marine life. The waters are shallow, and Anne’s Beach is a popular destination for kite-boarders. Beginning kite-boarders can test their skills on the tropical waters. As there is little wave activity, Anne’s Beach is a good choice for families with young children.
Families staying in the Florida Keys will find many advantages to choosing vacation rentals. Islamorada is a top destination in the Florida Keys and offers a wide array of activities and events. When visiting Islamorada, condo rentals are also a great choice. You can save on the total cost of your trip by choosing Islamorada vacation rentals as opposed to hotels.
Events
Islamorada has plenty of year-round events and activities to keep families entertained. Every December is the holiday festival hosted at Founders Park. In March, there is the annual art show, and the Fourth of July celebration occurs each summer. There are always family-friendly events taking place, making Islamorada a perfect destination.
Loading...
Click for larger map
Loading...
Show big map »
  • Price

  • Bedrooms

    Sleeps

  • Amenities

    • Show More...