Islamorada Vacation Rentals & House Rentals - 34 Rentals Available
34 Vacation rentals
Secluded Stunning Oceanview Townhome
Islamorada Townhouse
- 2 bedrooms 2
- 3 bathrooms
- Sleeps 6 6
- 7 nights min
- Beach/lakeside relaxation
- Ask about children
- Air conditioning
$200
from $200 / night
Waterfront Paradise
Islamorada House
- 3 bedrooms 3
- 2 bathrooms
- Sleeps 10 10
- 30 nights min
- Beach/lakeside relaxation
- Ask about children
- Air conditioning
$214
from $214 / night
Luxurious Waterfront with Two Masters, Pool, Hot Tub, Tennis, Gym, Dock, Bikes
Islamorada Condo
- 2 bedrooms 2
- 3 bathrooms
- Sleeps 4 4
- 7 nights min
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$200
from $200 / night
Islamorada Luxury Home Ocean & Bay Access
Islamorada House
- 3 bedrooms 3
- 3 bathrooms
- Sleeps 8 8
- Min stay varies
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$421
from $421 / night
Florida Keys Islamorada pool/home/canal Weekly
Islamorada House
- 3 bedrooms 3
- 3 bathrooms
- Sleeps 8 8
- 7 nights min
- Swimming pool
- Ask about children
- Air conditioning
$457
from $457 / night
Villa Marlin, Renovated, Remodeled, Sandy Beach
Islamorada House
- 3 bedrooms 3
- 2 bathrooms
- Sleeps 6 6
- 30 nights min
- Beach/lakeside relaxation
- Nearest beach 1 mi
- Ask about children
$457
from $457 / night
The PERFECT Escape with pool & jacuzzi
Islamorada House
- 4 bedrooms 4
- 4 bathrooms
- Sleeps 8 8
- 7 nights min
- Beach/lakeside relaxation
- Nearest beach 3 mi
- Swimming pool
$429
from $429 / night
Islamorada Waterfront 3/2, Dockage, Pool / Jacuzzi MM75
Islamorada House
- 3 bedrooms 3
- 2 bathrooms
- Sleeps 6 6
- 30 nights min
- Beach/lakeside relaxation
- Swimming pool
- Ask about children
$500
from $500 / night
BEAUTIFUL BAYFRONT HOME - SUNSETS FROM EVERY ROOM
Islamorada House
- 3 bedrooms 3
- 3 bathrooms
- Sleeps 6 6
- 30 nights min
- Beach/lakeside relaxation
- Ask about children
- Air conditioning
$572
from $572 / night
BLUE WATER RETREAT
Islamorada House
- 3 bedrooms 3
- 3 bathrooms
- Sleeps 8 8
- Min stay varies
- Swimming pool
- Ask about children
- Pet friendly
$175
from $175 / night
BEACON REEF 501
Islamorada Apartment
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 4 4
- Min stay varies
- Swimming pool
- Ask about children
$107
from $107 / night
LYONS LANDING
Islamorada House
- 4 bedrooms 4
- 3 bathrooms
- Sleeps 10 10
- Min stay varies
- Swimming pool
- Ask about children
- Pet friendly
$217
from $217 / night
SUNSHINE PLACE
Islamorada Villa
- 1 bedroom 1
- 1 bathroom
- Sleeps 3 3
- 7 nights min
- Ask about children
- Pet friendly
$158
from $158 / night
HOUSE DORADO
Islamorada House
- 3 bedrooms 3
- 3 bathrooms
- Sleeps 8 8
- Min stay varies
- Swimming pool
- Ask about children
$617
from $617 / night
BEACON REEF 310
Islamorada Apartment
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 4 4
- Min stay varies
- Swimming pool
- Ask about children
$107
from $107 / night
MATECUMBE JEWEL
Islamorada House
- 3 bedrooms 3
- 2 bathrooms
- Sleeps 6 6
- Min stay varies
- Ask about children
- Pet friendly
$150
from $150 / night
WEST LAKE PLAZA
Islamorada House
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 5 5
- Min stay varies
- Ask about children
$134
from $134 / night
BEACON REEF 222
Islamorada Apartment
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 4 4
- Min stay varies
- Swimming pool
- Ask about children
$147
from $147 / night
MANATEE MANOR
Islamorada House
- 3 bedrooms 3
- 2 bathrooms
- Sleeps 8 8
- Min stay varies
- Swimming pool
- Ask about children
- Pet friendly
$200
from $200 / night
BROCK HAUS ON THE GULF
Islamorada Apartment
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 6 6
- 7 nights min
- Swimming pool
- Ask about children
$225
from $225 / night
MY PARADISE
Islamorada House
- 3 bedrooms 3
- 2 bathrooms
- Sleeps 6 6
- Min stay varies
- Ask about children
- Pet friendly
$227
from $227 / night
RIOLO VILLA
Islamorada House
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 6 6
- Min stay varies
- Ask about children
- Pet friendly
$117
from $117 / night
LITTLE BAY - Upper Duplex
Islamorada Villa
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 6 6
- 7 nights min
- Ask about children
- Pet friendly
$358
from $358 / night
THE PALMS 405 - 93
Islamorada Apartment
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 6 6
- Min stay varies
- Swimming pool
- Ask about children
$100
from $100 / night
LITTLE BAY - Cottage
Islamorada Villa
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 6 6
- 7 nights min
- Ask about children
$358
from $358 / night
LITTLE BAY - Lower Duplex
Islamorada Villa
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 6 6
- 7 nights min
- Ask about children
- Pet friendly
$358
from $358 / night
Your search has been expanded 4.1 miles to include more rentals
BAYSIDE BREEZE
Tavernier House - 0.1 miles away
- 3 bedrooms 3
- 2 bathrooms
- Sleeps 6 6
- Min stay varies
- Ask about children
- Pet friendly
$127
from $127 / night
CONCH BAR SOUTH
Tavernier House - 1 miles away
- 4 bedrooms 4
- 3 bathrooms
- Sleeps 10 10
- Min stay varies
- Swimming pool
- Ask about children
- Pet friendly
$299
from $299 / night
PLANTATION ADVENTURE
Tavernier House - 2 miles away
- 4 bedrooms 4
- 3 bathrooms
- Sleeps 10 10
- Min stay varies
- Swimming pool
- Ask about children
$217
from $217 / night
BEBA'S REEF HOUSE
Tavernier House - 2.6 miles away
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 4 4
- Min stay varies
- Ask about children
$150
from $150 / night
Key Largo Vacation Condo with Fantastic Bay View
Key Largo Condo - 3.6 miles away
- 3 bedrooms 3
- 2 bathrooms
- Sleeps 6 6
- 7 nights min
- Beach/lakeside relaxation
- Ask about children
- Air conditioning
$130
from $130 / night
Casa del Sol in Tavernier, Florida Keys
Tavernier House - 4.1 miles away
- 4 bedrooms 4
- 4 bathrooms
- Sleeps 8 8
- 7 nights min
- Beach/lakeside relaxation
- Ask about children
- Air conditioning
$500
from $500 / night
1
About Islamorada
Islamorada consists of a “Village of Islands” spread out over six islands in the Florida Keys. Surrounded by cerulean ocean waters and soft sands, this destination is a tropical paradise for those looking to get away from it all. Stay in oceanfront Islamorada vacation rentals for the ultimate convenience during your beach getaway.
Climate
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, and the ocean waters provide a refreshing respite. Pack lots of sunscreen as the sun’s rays are much stronger than they are in northern parts of the U.S. Wintertime brings temperatures in the 70s – cool by Florida standards, but still comfortably warm for vacationers from other parts of the country.
Transit
Islamorada is best traveled by car or boat. Fly into Miami International Airport or Key West International Airport then rent a car to travel to Islamorada. The island roads are scenic and views from the bridges connecting each island are breathtaking. Just keep in mind that speed limits are strictly enforced in the Florida Keys. Once you’ve arrived, ditch the car and island hop via boat. Rent a boat from Islamorada Watersports Company and spend time cruising the pristine waters.
Things to Do
Islamorada is well-known as the sport fishing capital of the world, and the surrounding ocean and shallow bays teem with a variety of fish, including sailfish, bonefish, swordfish, marlin and tarpon. Embark on a fishing charter led by a knowledgeable captain from Sea Horse Private Charters or Drop Back Fishing Charters for a fun day out on the water. If you’d rather stay on land, explore try fly fishing in the backcountry.
There’s much to see and do in Islamorada besides fishing, though. Soak up sun with the family at Anne’s Beach. Here, there are many coves along the white sands, making it easy to find a quiet, private for the family, and the surrounding mangroves provide an ideal setting to observe Florida marine life. The beach also has shallow waters, and it is a popular destination for kite-boarders. Visit the Theater of the Sea, so everyone can swim with dolphins, interact with sea lions and turtles, and enjoy live snorkeling tours that the park provides.
San Pedro Underwater Archaeological Preserve State Park is a historical shipwreck site and a popular diving adventure for visitors. The 18-feet deep waters at this site are best for experienced divers, but divers of all levels will enjoy exploring nearby coral reefs underwater. Another popular attraction is the Windley Key Fossil Reef Geological State Park, which includes nature trails for hiking and features fossilized coral. There are picnic tables and educational tours for kids, and the park is home to a variety of birds and native wildlife.
Events
With ideal weather year-round, the fun never stops and Islamorada hosts events and activities to keep families entertained all year long. Visit in January for the Annual Blessing of the Fleet to kick off another year of fishing. In March, stroll throughout Islamorada during National Wildlife Week or visit the weekly farmer’s market open on Fridays. The summer brings a lively 4th of July celebration, the Spirit of Islamorada as well as numerous weekly events, while winter also brings fun holiday activities and festivals.
This island oasis beckons to vacationers all year long with its divine weather and laidback atmosphere. Islamorada vacation rentals provide easy access to the abundance of water activities without giving up comfort or any of the necessities for the perfect stay. You might even thinking about making Islamorada your permanent home.
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