Islamorada Vacation Rentals

(56 rentals)
BAYSIDE CONDO, MARINA, POOL AND BEACH

$114

per night

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Villa Paraiso Large 6 BR Bayside Home-Sunsets-Perfect for Large Groups

$500

per night

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Summer Sea Majestic Beauty

Summer Sea Majestic Beauty

1 BR | 1 BA | Sleeps 3 | Quick View

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

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Ocean Front building with Ocean Front pool in beautiful Islamorada!

$129

per night

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Islamorada Paradise Vacation Home on the Water

$229

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

6

$171

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

1

$457

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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The PERFECT Escape with pool & jacuzzi

$429

per night

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Mitchell's Bayview Villa - Islamorada House on the Bay

$242

per night

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

$357

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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SEA GRAPE

SEA GRAPE

3 BR | 3.5 BA | Sleeps 8 | Quick View

$400

per night

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FLAMINGO COTTAGE

FLAMINGO COTTAGE

2 BR | 2 BA | Sleeps 6 | Quick View

BEACON REEF 222

BEACON REEF 222

2 BR | 2 BA | Sleeps 4 | Quick View

$147

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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CASA DORADO

CASA DORADO

3 BR | 3.5 BA | Sleeps 8 | Quick View

$617

per night

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PALMS 405

PALMS 405

2 BR | 2 BA | Sleeps 6 | Quick View

$103

per night

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GULFVIEW GETAWAY

GULFVIEW GETAWAY

3 BR | 2 BA | Sleeps 10 | Quick View

$400

per night

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MATECUMBE JEWEL

MATECUMBE JEWEL

3 BR | 2 BA | Sleeps 6 | Quick View

$150

per night

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BEACON REEF 501

BEACON REEF 501

2 BR | 2 BA | Sleeps 4 | Quick View

$107

per night

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PALMS 309

PALMS 309

2 BR | 2 BA | Sleeps 5 | Quick View

$82

per night

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PALMS 214

PALMS 214

2 BR | 2 BA | Sleeps 4 | Quick View

$73

per night

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BEACON REEF 310

BEACON REEF 310

2 BR | 2 BA | Sleeps 4 | Quick View

$107

per night

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BLUE WATER RETREAT

BLUE WATER RETREAT

3 BR | 3 BA | Sleeps 8 | Quick View

$183

per night

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PALMS 314

PALMS 314

2 BR | 2 BA | Sleeps 5 | Quick View

$80

per night

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VILLA RIOLO

VILLA RIOLO

2 BR | 2 BA | Sleeps 6 | Quick View

$117

per night

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WEST PLAZA DEL LAGO

WEST PLAZA DEL LAGO

2 BR | 2 BA | Sleeps 5 | Quick View

$18

per night

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MY PARADISE

MY PARADISE

3 BR | 2 BA | Sleeps 6 | Quick View

$227

per night

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LYONS LANDING

LYONS LANDING

4 BR | 3 BA | Sleeps 10 | Quick View

$232

per night

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SUNSHINE PLACE

SUNSHINE PLACE

1 BR | 1.5 BA | Sleeps 3 | Quick View

$157

per night

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PARADISE

PARADISE

4 BR | 4.5 BA | Sleeps 10 | Quick View

$1000

per night

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PALMS 301

PALMS 301

2 BR | 2 BA | Sleeps 6 | Quick View

$73

per night

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PALMS 402

PALMS 402

2 BR | 2 BA | Sleeps 4 | Quick View

$80

per night

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PALMS 417

PALMS 417

1 BR | 2 BA | Sleeps 4 | Quick View

$67

per night

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LITTLE BAY - Cottage

LITTLE BAY - Cottage

2 BR | 2 BA | Sleeps 6 | Quick View

$357

per night

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LITTLE BAY - Lower Duplex

LITTLE BAY - Lower Duplex

2 BR | 2 BA | Sleeps 6 | Quick View

$357

per night

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PALMS 407

PALMS 407

2 BR | 2 BA | Sleeps 4 | Quick View

$80

per night

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LITTLE BAY - Upper Duplex

LITTLE BAY - Upper Duplex

2 BR | 2 BA | Sleeps 6 | Quick View

$357

per night

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Pool Home Fisherman's Dream Ocean Side

$150

per night

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PARADISEPOINT- SMACK OCEANFRONT, POOL, 30' DOCK, EASY BAY ACCESS

PARADISEPOINT- SMACK OCEANFRONT, POOL, 30' DOCK, EASY BAY ACCESS

3 BR | 2.5 BA | Sleeps 6 | Quick View

$465

per night

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ANTIGUA PLACE

ANTIGUA PLACE

3 BR | 2 BA | Sleeps 6 | Quick View

$173

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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Keys Cottage; Remodeled Villa in Native Hammock on Florida Bay

$214

per night

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Island Conch Cottage

Island Conch Cottage

2 BR | 1.5 BA | Sleeps 4 | Quick View

$125

per night

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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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Waterfront Paradise with Free Dockage - Contact us to price your stay!!

Waterfront Paradise with Free Dockage - Contact us to price your stay!!

1 BR | 1 BA | Sleeps 2 | Quick View

$171

per night

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Futura Yacht Club Bayside Condominium and Marina Dockage, Islamorada

$164

per night

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

$243

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!