Islamorada Vacation Rentals

(57 rentals)
Palms #314 - Ocean Views from the Balcony, Living Room and Master Suite

$80

per night

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Casa Dorado - Exceptional home located directly on Bay.

$617

per night

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Dream Home in the Keys House perfect from storm!!

$357

per night

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Little Bay Duplex - Gated Bayfront Property Shared with 2 Other Rental Units

$357

per night

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Paradise - Ultimate vacation home!

$1000

per night

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The PERFECT Escape with pool & jacuzzi

$429

per night

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Palms #402 - Ocean Front Condo Complex - Great Ocean Views from Balcony

$80

per night

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Islamorada Luxurious Private Sandy Beach Access Tiki Huts Hammocks & more

Islamorada Luxurious Private Sandy Beach Access Tiki Huts Hammocks & more

3 BR | 2 BA | Sleeps 6 | Quick View

2

$457

per night

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Ocean Front building with Ocean Front pool in beautiful Islamorada!

$129

per night

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Ocean Breeze, at Bay Harbour

Ocean Breeze, at Bay Harbour

2 BR | 2.5 BA | Sleeps 6 | Quick View

$300

per night

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Pool Home - Fisherman's Dream and Wife and Kids Will Love it!

$167

per night

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Islamorada water front with free boat tie-up. Available weekly, Saturday to Sat

Islamorada water front with free boat tie-up. Available weekly, Saturday to Sat

1 BR | 2 BA | Sleeps 4 | Quick View

8

$171

per night

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The Perfect Getaway with Heated Swimming Pool, Jacuzzi and Boat Slip

$357

per night

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Beacon Reef 406 - Charming condo with lovely views of the ocean and pool.

$100

per night

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Beacon Reef #501 - Beautiful condo with views of the Atlantic Ocean.

$110

per night

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Beacon Reef 522 - Oceanfront 5th floor (top floor) condo at Beacon Reef.

$147

per night

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Palms #417 - Elegant 1 bedroom unit with Florida Bay Views from Balcony

$67

per night

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My Paradise - Oceanfront beach house with protected dockage.

$227

per night

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Lyons Landing - Exceptional VENETIAN SHORES home with pool, dock and boat lift.

Lyons Landing - Exceptional VENETIAN SHORES home with pool, dock and boat lift.

4 BR | 3 BA | Sleeps 10 | Quick View

$232

per night

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Little Bay Cottage- Gated Bayfront Property Shared with 2 Other Rental Units

$357

per night

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Mitchell's Keys Villa - Private, Secluded House on the Bay

Mitchell's Keys Villa - Private, Secluded House on the Bay

2 BR | 1 BA | Sleeps 4 | Quick View

$185

per night

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Paradise Found - Sandy Beach, Beachside Bar, Great Views, And Dock

$286

per night

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Beautiful Ocean Sunrise Views!

Beautiful Ocean Sunrise Views!

3 BR | 2.5 BA | Sleeps 6 | Quick View

1

$321

per night

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Mitchell's Bayview Villa - Islamorada House on the Bay

$242

per night

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Beacon Reef #310 - Beautiful condo with lovely views of the ocean.

$107

per night

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Antigua Place - Charming vacation home located in Port Antigua.

$173

per night

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Sea Grape - Serene, quaint part of paradise that the entire family will enjoy..

$400

per night

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W. Plaza del Lago - Promises to be a favorite!

$133

per night

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Palms #405 - Totally Remodeled Condo with Ocean Views

$103

per night

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Villa Riolo - Updated home and perfect for your next holiday in Islamorada

$117

per night

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Beacon Reef #222 - Gorgeous condo with panoramic views of the Atlantic Ocean.

$147

per night

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Little Bay Lower Duplex - Gated Bayfront Property Shared w/ 2 Other Rental Units

$357

per night

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Matecumbe Jewel - 3 bedroom home with pool and dockage is a jewel of a home!

$150

per night

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Gulfview Getaway - Bayfront Home with Private Beach

$400

per night

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Blue Water Retreat - Location!!!! Gorgeous house with Pool and Ocean Views.

$183

per night

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Palms #301 - Darling condo with panoramic views of the Atlantic Ocean.

$73

per night

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Palms #214 - Lovely condo with panoramic views of the Atlantic Ocean.

$73

per night

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Sunshine Place - Ground Level Unit with Ocean Views.

$157

per night

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2 Master Bedrooms, Waterfront, Pool, Hot Tub, Gym/Tennis, Marina, Bikes, Jacuzzi

$171

per night

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BAYSIDE CONDO, MARINA, POOL AND BEACH

$114

per night

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Palms #407 - Beautiful condo with panoramic views of the Atlantic Ocean.

$97

per night

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Pool Home Fisherman's Dream Ocean Side

$150

per night

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Palms #309 - Exceptional condo with panoramic views of the Atlantic Ocean.

$82

per night

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Flamingo Cottage - Adorable 2 bedroom, 2 bath cozy cottage with pool.
BEAUTIFUL 3 BEDROOM VACATION HOME LOCATED ON DEEP CANAL W/OCEAN & BAY ACCESS

BEAUTIFUL 3 BEDROOM VACATION HOME LOCATED ON DEEP CANAL W/OCEAN & BAY ACCESS

3 BR | 3 BA | Sleeps 8 | Quick View

$457

per night

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Islamorada 3/2 Canalfront with Pool and Dockage

Islamorada 3/2 Canalfront with Pool and Dockage

3 BR | 2 BA | Sleeps 6 | Quick View

$400

per night

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Anglers Reef-Rent Now for Summer- May/June Special

$243

per night

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New Interior, Oceanfront End Unit, Pool, WiFi, Great Ocean Views

New Interior, Oceanfront End Unit, Pool, WiFi, Great Ocean Views

2 BR | 2 BA | Sleeps 4 | Quick View

$129

per night

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Bayside: 1st Floor Apartment in Native Hammock on Florida Bay

Bayside: 1st Floor Apartment in Native Hammock on Florida Bay

1 BR | 2 BA | Sleeps 4 | Quick View

$214

per night

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Osprey Lagoon Half Duplex House, 28 night minimum

$67

per night

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Local Weather

 | 

75°  62°
JANUARY
Ocean 74°
76°  62°
FEBRUARY
Ocean 74°
78°  65°
MARCH
Ocean 76°
82°  70°
APRIL
Ocean 79°
85°  74°
MAY
Ocean 81°
87°  77°
JUNE
Ocean 83°
89°  79°
JULY
Ocean 85°
89°  78°
AUGUST
Ocean 87°
87°  77°
SEPTEMBER
Ocean 85°
84°  74°
OCTOBER
Ocean 83°
80°  70°
NOVEMBER
Ocean 79°
76°  65°
DECEMBER
Ocean 76°

The “Village of Islands” awaits you: Islamorada vacation rentals by owner


Sunny, friendly Islamorada is a smart choice for those who want a quiet escape away from the hustle and bustle of the major Florida hot spots. Located between Mile Marker 91 and Mile Marker 74, Islamorada is situated halfway between Miami and Key West along Florida’s scenic Route 1. Islamorada itself is spread out over six islands, each surrounded by tranquil ocean and soft sands.

Next time you’re looking for fun & sun, skip the traditional beachside hotel and opt for a vacation rental in Islamorada instead from FloridaRentals.com. When staying in a beach condo instead of hotel, you’ll have much more space and privacy, plus cost savings when booking a property for a large group. Some of our rentals even come with special amenities like a backyard pool, washer/dryer units, and bicycles. Whether you’re looking for a super-sized modern villa with an indoor pool, or a cozy beachfront bungalow, you can find it on our site.

Islamorada, Florida travel advice


This destination is a tropical paradise for those looking to get away from it all. In fact, celebrities have made the secluded Islamorada a second home for decades, including the island’s most famed resident, baseball player Ted Williams. Be careful, or you might just fall in love with the area, too.

With a tropical climate and daytime temperatures that rarely dip below the 70s (F), Islamorada is a fantastic vacation spot any time of the year. During the summer, temperatures typically hover in the upper 80s. The ocean breeze cools temps down in the afternoon, and the conditions are just perfect for fishing (more on this below).

Getting here from Miami International Airport or Key West Airport is easy with a rental car, and the views on Route 1 and connecting bridges are incredible. Worth the drive! Once you’ve arrived, island hopping via boat is a fun way to see the entire area.

Named by early Spanish explorers, Islamorada literally translates to “purple isles” – a nod to the colors one might see during one of the legendary sunsets.

Top activities and attractions


The sport fishing capital of the world, this city offers activities for anglers of all ages and skill levels. The surrounding ocean and shallow bays teem with a variety of fish, including sailfish, bonefish, swordfish, marlin and tarpon. Hop aboard a deep sea fishing charter to try your hand at grabbing one of these fish and cooking your own catch for dinner. If you’d rather stay on land, explore try fly fishing in the backcountry.

Fishing not your thing? That’s fine, there’s plenty of other activities in the area. Grab a towel and head to Anne’s Beach for a full day of sand castles and snorkeling. It’s also private and quiet, so you will feel a long way away from the crowds on South Beach. If you’re feeling adventurous, try your hand at kite surfing since the shallow waters here provide an ideal environment.

Bring your family to the Theater of the Sea and take a live snorkeling tour or swim with dolphins. If you prefer nature surroundings, Windley Key Fossil Reef Geological State Park has nature trails for hiking. Don’t miss the underwater shipwreck site at San Pedro Preserve where scuba divers love the scenery and adventure.

Music lovers enjoy warm, tropical evenings and daylong music festivals on the lawn of the outdoor, waterfront ICE Amphitheater located inside Islamorada Founders Park, a 40-acre expanse that features an Olympic-sized pool, shallow water beach, water sports rentals, ball fields, fishing jetty, exercise opportunities, skatepark and a dog park.

Dining


Known for delicious seafood, Islamorada’s restaurants serve up the day’s freshest catch. Starting at breakfast, stop in to the Midway Cafe & Coffee Bar where guests can start their day off with an omelette or pancakes. For lunch, grab a wrap at Chef Michael’s where they feature daily seafood dishes that “wow” eaters. Want to eat with a view? Grab an outside table at Morada Bay and watch the palm trees sway as you grub. Lastly, the Green Turtle Inn has more seafood dishes and soups that come with rave reviews.

Islamorada homes for rent on FloridaRentals.com


Islamorada condo rentals on FloridaRentals.com can save you up to 20% over our competitors. Plus, we have a wide array of inventory appealing to any group size or traveler tastes. Happy planning!