Islamorada (54) Filter Cancel
Loading...
view of house from canal
1 / 22

Islamorada Home
2 BR / 2 BA / Sleeps 6 2 6 7 night min stay
Home / 2 Bedrooms / Sleeps 6
2 bedrooms 2 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
Located on the peaceful, northern end of Islamorada, in the quite residential neighborhood of Venetian Shores. Just 75 miles from Miami Airport and 86 miles from Key West. Venetian Tropics boasts large rooms furnishe...
(2) Excellent (2 reviews)
Islamorada Florida Vacation Rentals - Condo
1 / 22

Islamorada Condo
2 BR / 2 BA / Sleeps 4 2 4 7 night min stay
Condo / 2 Bedrooms / Sleeps 4
2 bedrooms 2 bathrooms Sleeps 4
High Speed Internet • Dishwasher • Microwave
A Vacation Rental for View Lovers! Best Location in the Complex. Located at MM 90 in Islamorada. Enjoy beautiful panoramic ocean views from your condo 24/7. This condo in this art- deco inspired complex is located i...
(1) Excellent (1 review)
Islamorada Florida Vacation Rentals - Home
1 / 26

Islamorada Home
3 BR / 2 BA / Sleeps 4 3 4 Min stay varies
Home / 3 Bedrooms / Sleeps 4
3 bedrooms 2 bathrooms Sleeps 4
TV (Cable/Satellite) • Private Pool • Parking Included
Minimum Stay 29 Days. Beautiful Canal Front Stilt Home With Heated Pool - For The Guest Who Expects Perfection This Is It. This Home Was Completely Remodeled In 2013. There Is 936 Square Feet Of Living Area On The Main ...
1 / 24

Islamorada Townhouse
2 BR / 2.5 BA / Sleeps 6 2 6 Min stay varies
Townhouse / 2 Bedrooms / Sleeps 6
2 bedrooms 2.5 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
This oceanfront resort is a boutique complex of 52 homes inspired by Native Conch & British West Indies architecture built in 2007. Quaint streets & walking paths wind through this village- styled retreat. Amenities incl...
1 / 6

Islamorada Townhouse
3 BR / 2 BA / Sleeps 6 3 6 30 night min stay
Townhouse / 3 Bedrooms / Sleeps 6
3 bedrooms 2 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
Call Property Manager for Best Rate. Located on Windley Key this gated 5 unit complex has the best of the Keys with a private pool sandy Beachfront, fishing pier with flats boat dockage (drawing 24" or less) locat...
(7) Excellent (7 reviews)
Front View
1 / 29

Islamorada Home
3 BR / 2 BA / Sleeps 6 3 6 30 night min stay
Home / 3 Bedrooms / Sleeps 6
3 bedrooms 2 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
Location: Islamorada, Islamorada Area, Florida Keys, Florida, USA Accommodations: House, 3 Bedrooms, 2 Baths , Sleeps 6 122 Nautilus Drive, Islamorada, Florida Keys mile marker 74. 5 bay side, White Marl...
(10) Excellent (10 reviews)
Islamorada Florida Vacation Rentals - Home
1 / 23

Islamorada Home
3 BR / 3 BA / Sleeps 8 3 8 Min stay varies
Home / 3 Bedrooms / Sleeps 8
3 bedrooms 3 bathrooms Sleeps 8
High Speed Internet • TV (Cable/Satellite) • Private Pool
Minimum Rental: 1 Month Location, location, location! This home has it all - ocean side Lower Matecumbe location, remodeled in 2009. Relax by the cocktail pool or sunbathe in the private roof top sunning area. There...
View from Balcony
1 / 12

Islamorada Condo
2 BR / 2 BA / Sleeps 5 2 5 30 night min stay
Condo / 2 Bedrooms / Sleeps 5
2 bedrooms 2 bathrooms Sleeps 5
Dishwasher • Microwave • Washer/Dryer
Located at Mile Marker 90 in the Florida Keys our 2 Bedroom/2 Bath Condo offers unobstructed views of the Atlantic Ocean. The complex offers a heated pool, tennis court, gym, water front beach, elevators, parking an...
(21) Excellent (21 reviews)
Ocean View, 3 houses from the open ocean. Upstairs covered patio
1 / 14

Islamorada Home
4 BR / 2 BA / Sleeps 8 4 8 30 night min stay
Home / 4 Bedrooms / Sleeps 8
4 bedrooms 2 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
30DAY MIN RENTALThis is a newly remodeled 4 bedroom 2 bath private home on the ocean side (just 3 houses from the open ocean) with ocean views, pool, tiki hut ice machine and all the comforts of home. This home is perf...
1 / 16

Islamorada Condo
2 BR / 2.5 BA / Sleeps 4 2 4 No min stay
Condo / 2 Bedrooms / Sleeps 4
2 bedrooms 2.5 bathrooms Sleeps 4
High Speed Internet • Dishwasher • Microwave
FEELS LIKE YOU ARE LIVING RIGHT ON TOP THE WATER! ! ! Great View! Please take the time to read our client reviews! No less then 7 day rental. Great location! ! ! Tropical waterfront gated community, heated p...
Back View
1 / 15

Islamorada Home
3 BR / 3 BA / Sleeps 8 3 8 30 night min stay
Home / 3 Bedrooms / Sleeps 8
3 bedrooms 3 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
Special vacation rental rates for off- season bookings and also for some last minute dates! Call us now for details. Located in Islamorada the fishing capitol of the world, this is a beautiful home decorated with Islan...
(9) Excellent (9 reviews)
Sunset Deluxe
1 / 9

Islamorada Townhouse
2 BR / 2.5 BA / Sleeps 4 2 4 7 night min stay
Townhouse / 2 Bedrooms / Sleeps 4
2 bedrooms 2.5 bathrooms Sleeps 4
High Speed Internet • Microwave • Washer/Dryer
Sunset view, tennis courts, heated pool, recently remodeled, fish from the dock, boat slip right in front of unit. quiet gated community, monthly $3850. 00 in season, $2850. 00 out of season Weekly $1450 per week ...
(6) Excellent (6 reviews)
Islamorada Florida Vacation Rentals - Home
1 / 25

Islamorada Home
3 BR / 2 BA / Sleeps 8 3 8 Min stay varies
Home / 3 Bedrooms / Sleeps 8
3 bedrooms 2 bathrooms Sleeps 8
High Speed Internet • TV (Cable/Satellite) • Private Pool
MINIMUM STAY: 28 DAYS NEW OPPORTUNITY to LIVE THE LIFE! This 3 Bedrooms and 2 ½ Baths home with POOL, Dock, and all new furnishings make this your opportunity to experience The Florida Keys at its best. Convenientl...
Islamorada Florida Vacation Rentals - Townhouse
1 / 27

Islamorada Townhouse
2 BR / 2.5 BA / Sleeps 6 2 6 7 night min stay
Townhouse / 2 Bedrooms / Sleeps 6
2 bedrooms 2.5 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
Enjoy the spectacular view of the Florida Bay from this elegant, tasteful, completely remodelled townhome. 2 bedrooms, 2. 5 bathrooms with balconies off the living room and master bedroom. Fully furnished and equipped...
Islamorada Florida Vacation Rentals - Home
1 / 6

Islamorada Home
2 BR / 1 BA / Sleeps 5 2 5 30 night min stay
Home / 2 Bedrooms / Sleeps 5
2 bedrooms 1 bathroom Sleeps 5
High Speed Internet • Dishwasher • Microwave
Choose between two seperate suites (2bed/lbath) or (1bed/1bath) The upstairs (The Lighhouse Suite) is on the second floor and will accommodate five people. There are two bedrooms and one bath, an eat- in kitchen with...
(4) Excellent (4 reviews)
Islamorada Florida Vacation Rentals - Home
1 / 20

Islamorada Home
3 BR / 3 BA / Sleeps 8 3 8 7 night min stay
Home / 3 Bedrooms / Sleeps 8
3 bedrooms 3 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
Oceanfront splendor on the Atlantic ocean. Has a 350' pier that can accomodate most any size boat. Just relax by the pool on those hot days or take a dip in the ocean. The pool is heated for the winter months. Th...
(21) Excellent (21 reviews)
Islamorada Florida Vacation Rentals - Home
1 / 9

Islamorada Home
4 BR / 4 BA / Sleeps 8 4 8 full period
Home / 4 Bedrooms / Sleeps 8
4 bedrooms 4 bathrooms Sleeps 8
High Speed Internet • Microwave • Washer/Dryer
This beautiful 4 bedroom/ 4 bathroom home has a 70' dock directly behind the home . Canal leads out to Snake Creek and has immediate Ocean and Bay access. The home is located in one of the finest neighborhoods of the Flo...
(7) Excellent (7 reviews)
Islamorada Florida Vacation Rentals - Home
1 / 30

Islamorada Home
4 BR / 3 BA / Sleeps 10 4 10 30 night min stay
Home / 4 Bedrooms / Sleeps 10
4 bedrooms 3 bathrooms Sleeps 10
High Speed Internet • Dishwasher • Microwave
MINIMUM STAY: 29 DAYS Lyons Landing is an exceptional VENETIAN SHORES single family home with pool, dock, boat lift and outdoor living area! Everything you need for a spectacular holiday awaits you in this extraordina...
Waterfront II
1 / 17

Islamorada Home
4 BR / 3 BA / Sleeps 12 4 12 30 night min stay
Home / 4 Bedrooms / Sleeps 12
4 bedrooms 3 bathrooms Sleeps 12
High Speed Internet • Dishwasher • Microwave
The Great Islamorada Getaway features a spectacular canal front home on an over- sized property with 136 feet of dock space and an in ground pool (heater/chiller optional). Large outside patio with gas grill and upstairs...
(18) Excellent (18 reviews)
Islamorada Florida Vacation Rentals - Home
1 / 16

Islamorada Home
4 BR / 4.5 BA / Sleeps 8 4 8 30 night min stay
Home / 4 Bedrooms / Sleeps 8
4 bedrooms 4.5 bathrooms Sleeps 8
Dishwasher • Microwave • Washer/Dryer
Gorgeous home in the premier gated community in Islamorada. Bonefish Bay, an enclave of 12 Key West- style homes with all the amenities of a large resort. White sand beach, tennis court, boat ramp & dockage with beaut...
1 / 20

Islamorada Home
6 BR / 3 BA / Sleeps 12 6 12 30 night min stay
Home / 6 Bedrooms / Sleeps 12
6 bedrooms 3 bathrooms Sleeps 12
High Speed Internet • Air Conditioning • Private Pool
This is a huge 6 bedroom pool home with direct dockage just off Snake Creek. Home has 2 kings, 3 queens, and 2 twins. Located at mile marker 86 on the bay side I only take payment by personal check made out to owner...
Islamorada Florida Vacation Rentals - Townhouse
1 / 20

Islamorada Townhouse
2 BR / 2 BA / Sleeps 6 2 6 30 night min stay
Townhouse / 2 Bedrooms / Sleeps 6
2 bedrooms 2 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
Townhouse Totally Renovated And Furnished Terraces Off Every Room (4) Bayfront With Dock, Pool Tiki Hut , Carport For Two Cars, Central Air, Washer And Dryer, Wifi, Dishwasher, Microwave And Cable Tv For 3 Tvs ...
1 / 13

Islamorada Townhouse
2 BR / 1.5 BA / Sleeps 2 2 2 30 night min stay
Townhouse / 2 Bedrooms / Sleeps 2
2 bedrooms 1.5 bathrooms Sleeps 2
Dishwasher • Microwave • Washer/Dryer
Come to Paradise and Enjoy it with Comfort, and Style! Located on Mile Marker 87 in Islamorada ( Fishing Capital of the World ), part of the Wonderful Florida Keys. Executive Bay Club is a Private Gated Community with...
Islamorada Florida Vacation Rentals - Estate
1 / 24

Islamorada Estate
3 BR / 2.5 BA / Sleeps 10 3 10 7 night min stay
Estate / 3 Bedrooms / Sleeps 10
3 bedrooms 2.5 bathrooms Sleeps 10
High Speed Internet • Dishwasher • Microwave
Two Oceanfront villas on two beautiful acres. It has a total of three bedrooms and two and half baths. Sleeps 8- 10 comfortably. One King bed, two queen beds, two twin beds, and two queen size pull out sofas. Both vil...
Islamorada Florida Vacation Rentals - Condo
1 / 19

Islamorada Condo
3 BR / 2 BA / Sleeps 6 3 6 7 night min stay
Condo / 3 Bedrooms / Sleeps 6
3 bedrooms 2 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
Welcome to our beautiful, private and secure gated community with all of the amenities to make your vacation as relaxing or exciting as you wish. Located on Plantation Key in Islamorada at mile marker 88. 5 on the bay s...
Islamorada Florida Vacation Rentals - Home
1 / 18

Islamorada Home
2 BR / 2.5 BA / Sleeps 4 2 4 7 night min stay
Home / 2 Bedrooms / Sleeps 4
2 bedrooms 2.5 bathrooms Sleeps 4
High Speed Internet • Dishwasher • Microwave
This Property is fully insured for rentals and licensed by the Village of Islamorada, license #VR- 228. Welcome to 134 Anglers, a newly renovated luxurious escape for your vacation needs. Perfect for families, cou...
Islamorada Florida Vacation Rentals - Home
1 / 9

Islamorada Home
3 BR / 2 BA / Sleeps 6 3 6 30 night min stay
Home / 3 Bedrooms / Sleeps 6
3 bedrooms 2 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
Local laws prohibit advertising this rental for less than 30 days. There are restrictions for weekly rentals. Enjoy your own beautiful solar heated pool with Jacuzzi! ! ! You also will have access to a private homeowner...
(7) Excellent (7 reviews)
1 / 14

Islamorada Home
3 BR / 2 BA / Sleeps 10 3 10 30 night min stay
Home / 3 Bedrooms / Sleeps 10
3 bedrooms 2 bathrooms Sleeps 10
High Speed Internet • Dishwasher • Microwave
The house is perfect for those traveling with different age groups, in- laws, teenagers or 2 families. The house is extra clean and has modern furnishings. It has 3 bedrooms, 2 baths. Upstairs there are 2 bedrooms, 1...
Islamorada Florida Vacation Rentals - Home
1 / 23

Islamorada Home
2 BR / 2 BA / Sleeps 6 2 6 Min stay varies
Home / 2 Bedrooms / Sleeps 6
2 bedrooms 2 bathrooms Sleeps 6
High Speed Internet • TV (Cable/Satellite) • Parking Included
MINIMUM STAY: 28 DAYS Villa Riolo is an updated single family stilt home and perfect for your next holiday in Islamorada! It comfortably sleeps 6 in two bedrooms. This home has been meticulously cared for over the years...
Islamorada Florida Vacation Rentals - Villa
1 / 27

Islamorada Villa
2 BR / 2 BA / Sleeps 6 2 6 7 night min stay
Villa / 2 Bedrooms / Sleeps 6
2 bedrooms 2 bathrooms Sleeps 6
High Speed Internet • TV (Cable/Satellite) • Parking Included
Minimum Rental: 7 Nights Lower Duplex - This is one of three rental units on this fabulous property. The Little Bay property is a one acre lush tropical setting in a gated compound located directly on Florida Bay. The u...
1  2 
12
page 1 of 2
LoadingLoading...

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.