Islamorada Vacation Rentals & House Rentals - 78 Rentals Available
78 Vacation rentals
Dream Home In The Keys
Islamorada House
- 5 bedrooms 5
- 3 bathrooms
- sleeps 12 12
- 7 nights min
- Beach/lakeside relaxation
- Swimming pool
- Ask about children
Responds fast! Avg. 3 hours 14 minutes
$409.00
from $409.00 / 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
$322.00
from $322.00 / night
Beautiful Oceanfront, heated pool, free wifi
Islamorada House
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- 7 nights min
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$458.00
from $458.00 / night
Islamorada Luxury Home Ocean & Bay Access
Islamorada House
- 3 bedrooms 3
- 3 bathrooms
- sleeps 8 8
- 7 nights min
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$533.00
from $533.00 / night
MATECUMBE JEWEL
Islamorada House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Ask about children
- Pet friendly
$157.00
from $157.00 / night
BEACON REEF 310
Islamorada Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- min stay varies
- Swimming pool
- Ask about children
$110.00
from $110.00 / night
LITTLE BAY - Upper Duplex
Islamorada Villa
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 7 nights min
- Ask about children
- Pet friendly
$358.00
from $358.00 / night
LYONS LANDING
Islamorada House
- 4 bedrooms 4
- 3 bathrooms
- sleeps 10 10
- min stay varies
- Swimming pool
- Ask about children
- Pet friendly
$246.00
from $246.00 / night
LITTLE BAY - Cottage
Islamorada Villa
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 7 nights min
- Ask about children
$358.00
from $358.00 / night
BROCK HAUS ON THE GULF
Islamorada Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Ask about children
$225.00
from $225.00 / night
SUNSHINE PLACE
Islamorada Villa
- 1 bedroom 1
- 1 bathroom
- sleeps 3 3
- 7 nights min
- Ask about children
- Pet friendly
$172.00
from $172.00 / night
FLAMINGO COTTAGE
Islamorada House
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Ask about children
- Pet friendly
$101.00
from $101.00 / night
THE PALMS 405 - 93
Islamorada Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Ask about children
$103.00
from $103.00 / night
MY PARADISE
Islamorada House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- min stay varies
- Ask about children
- Pet friendly
$261.00
from $261.00 / night
LITTLE BAY - Lower Duplex
Islamorada Villa
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 7 nights min
- Ask about children
- Pet friendly
$358.00
from $358.00 / night
HOUSE DORADO
Islamorada House
- 3 bedrooms 3
- 3 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Ask about children
$616.00
from $616.00 / night
SUNRISE ON SUNSET
Islamorada House
- 3 bedrooms 3
- 3 bathrooms
- sleeps 12 12
- min stay varies
- Ask about children
- Pet friendly
$300.00
from $300.00 / night
BEACON REEF 222
Islamorada Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- min stay varies
- Swimming pool
- Ask about children
$146.00
from $146.00 / night
BLUE WATER RETREAT
Islamorada House
- 3 bedrooms 3
- 3 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Ask about children
- Pet friendly
$183.00
from $183.00 / night
BEACON REEF 501
Islamorada Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- min stay varies
- Swimming pool
- Ask about children
$110.00
from $110.00 / night
ANCIENT PLACE
Islamorada House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- min stay varies
- Ask about children
- Pet friendly
$173.00
from $173.00 / night
MANATEE MANOR
Islamorada House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Ask about children
- Pet friendly
$198.00
from $198.00 / night
WEST LAKE PLAZA
Islamorada House
- 2 bedrooms 2
- 2 bathrooms
- sleeps 5 5
- min stay varies
- Ask about children
$133.00
from $133.00 / night
GULFVIEW GETAWAY
Islamorada House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 10 10
- min stay varies
- Ask about children
$401.00
from $401.00 / night
RIOLO VILLA
Islamorada House
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- min stay varies
- Ask about children
- Pet friendly
$122.00
from $122.00 / night
Your search has been expanded 18.6 miles to include more rentals
Beautiful One Bedroom Cottage at Riptide RV Resort in Key Largo
Key Largo Cottage - 10.4 miles away
- 1 bedroom 1
- 1 bathroom
- sleeps 4 4
- 3 nights min
- Child friendly
- Air conditioning
$168.00
from $168.00 / night
Paradise By The Bay
Key Largo House - 18.6 miles away
- 3 bedrooms 3
- 3 bathrooms
- sleeps 8 8
- 30 nights min
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$160.00
from $160.00 / night
Diving, Fishing, Snorkeling, Kayaking Paradise
Key Largo Townhouse - 11.4 miles away
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- min stay varies
- Beach/lakeside relaxation
- Child friendly
- Air conditioning
$250.00
from $250.00 / night
Florida Keys Cottage w/ Amazing Sunsets and Access to Kayaks, Sailboats and More
Key Largo Cottage - 11.9 miles away
- 1 bedroom 1
- 1 bathroom
- sleeps 5 5
- 5 nights min
- Nearest beach 0 mi
- Child friendly
- Air conditioning
Responds fast! Avg. 4 minutes
$255.00
from $255.00 / night
Cottage w/ Docks for Sailing, Kayaking, Snorkeling, Amazing Sunsets all Free
Key Largo Cottage - 11.9 miles away
- 1 bedroom 1
- 1 bathroom
- sleeps 4 4
- 5 nights min
- Nearest beach 0 mi
- Child friendly
- Air conditioning
Responds fast! Avg. 4 minutes
$255.00
from $255.00 / night
Cottage w/ Amazing Sunsets, Manatee Visits, Free Sailing & Lots of Adventures
Key Largo Cottage - 11.9 miles away
- 1 bedroom 1
- 1 bathroom
- sleeps 4 4
- 5 nights min
- Nearest beach 0 mi
- Child friendly
- Air conditioning
Responds fast! Avg. 4 minutes
$281.00
from $281.00 / night
Cottage w/ Free Paddle Boards, Kayaks, Sailboats, Water Toys, Docks & Sunsets
Key Largo Cottage - 11.9 miles away
- 1 bedroom 1
- 1 bathroom
- sleeps 4 4
- 5 nights min
- Nearest beach 0 mi
- Child friendly
- Air conditioning
Responds fast! Avg. 4 minutes
$281.00
from $281.00 / night
Florida Sailing Adventures, Cottage w/ Free use of Sailboat, Kayaks, Water Toys
Key Largo Cottage - 11.9 miles away
- 1 bedroom 1
- 1 bathroom
- sleeps 2 2
- 5 nights min
- Child friendly
Responds fast! Avg. 4 minutes
$292.00
from $292.00 / night
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.
What is Certificate of Excellence?
TripAdvisor gives a Certificate of Excellence to accommodations, attractions and restaurants that consistently earn great reviews from travelers.