Rentals in Islamorada, FL
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Search hundreds of Beachfront Vacation Rentals in Islamorada, Florida Keys
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We have partnered with a major provider for Vacation Rentals by Owner, directly through Vacation Places To Stay. There are many home rentals to choose from, and we now have the selection and value to offer our visitors going to Islamorada, FL. Browse hundreds of Homes and Condos with Wi-Fi, Pool, Oceanview, Beachfront and other amenities they have to offer.
Executive Bay G5
Tastefully Renovated Townhome with Great Community Amenities - Executive Bay G5
This townhome at Executive Bay will sure make your home away from home! This unit has been completely renovated and decorated beautifully. This 2 bedrooms and 3 bathrooms has a (1) King Bed, (1) Queen Bed and there is a bonus room off the Master ....
2 Bedroom(s)
3 Bath(s) Townhome
Islamorada, FL
102 Columbus
Charming 2 Bedroom Canalfront Home in Islamorada - 102 Columbus Dr.
Cute, comfortable home in Lower Matecumbe, Mile Marker 76.5, Oceanside. Wake up to the sun and water each morning from either bedroom at our charming stilt house. Take time to relax with all the conveniences of home with a full kitchen, washer/dryer ....
2 Bedroom(s)
2 Bath(s) Vacation Rental
Islamorada, FL
4BR Canal front home with splash pool, patios, boat slip & more!
4BR Canal front home with splash pool, patios, boat slip & more!
4BR Canal front home with splash pool, patios, boat slip & more! Seas the day is a fun, 4 bedroom house set on Lower Matecumbe Key in the beautiful Islamorada. On visiting the property, you'll first notice that it's just 3 small lots away from the At ....
4 Bedroom(s)
4 Bath(s) Vacation Rental
Islamorada, FL
454 Palm Drive LLC
Beautiful 3/3 Islamorada Waterfront Home
Our home is in Islamorada, in the middle Florida Keys. To be more specific, we are on Lower Matecumbe Key, which is the southernmost island in Islamorada, at exactly Mile Marker 74, on the bayside. Our home is a 3/3, and can comfortably sleep six, ....
3 Bedroom(s)
3 Bath(s) Vacation Rental - Sleeps 6
Islamorada, FL
A8 Islamorada
Florida Keys' Jewel - Executive Bay Club
An ample 1,400 sq ft. town home in the heart of Islamorada. Two bedrooms and one bathroom upstairs. One bedroom has two queen beds and cable television. Second bedroom is set up with one queen bed and cable television. Sofabed and bathroom downstairs ....
2 Bedroom(s)
2 Bath(s) Townhome
Islamorada, FL
ENTIRE BEACH HOUSE TWO IN ONE
W AVAILABLE BOAT Separate & Together Duplex 70' Concrete Dock w Private Beach
****************************************** Copy and paste the link below into a browser so you can see the 3D video tour of my amazing property ****************************************** https://my.matterport.com/show/?m=Cc7CWBsnjpA&brand=0 Enter ....
4 Bedroom(s)
2 Bath(s) Vacation Rental - Sleeps 12
Islamorada, FL
Vacation Home
Perfect Home for a get away! Private homeowners beach, enjoy Islamorada.
Perfect home for a get away! Home is located in Islamorada. 3 bedroom 3 bath gorgeous private homeowners beach and private dock, close to the best restaurants, and sight seeing. Peaceful, quiet and relaxing! Just what is needed to take your mind off ....
3 Bedroom(s)
3 Bath(s) Vacation Rental - Sleeps 6
Islamorada, FL
Executive Bay - Q4
**Winter Promo** Fully Renovated Executive Bay Club Condo with Modern Décor, Pool & Beach
We help make the most of your vacation by providing Free Admission to some of the area's top attractions each and every day! Create exciting memories, have more fun, and truly experience your destination! ***Free Fun Rules and Restrictions App ....
3 Bedroom(s)
2 Bath(s) Townhome
Islamorada, FL
Executive Bay - A7
**Winter Promo** Modern Executive Bay Club Condo with Pool & Beach
We help make the most of your vacation by providing Free Admission to some of the area's top attractions each and every day! Create exciting memories, have more fun, and truly experience your destination! ***Free Fun Rules and Restrictions App ....
3 Bedroom(s)
2 Bath(s) Townhome
Islamorada, FL
Angler's Reef Resort & Villas
4 Bedroom House In Angler's Reef, Includes 31' Boat Slip
Beautiful 4 bedroom, 3.5 bath home for rent in Angler's Reef. This house has a bedroom with a queen bed and an ensuite bathroom downstairs. There is also a half-bath downstairs. The gourmet kitchen has marble counter tops, a wine cooler and a bar. Th ....
4 Bedroom(s)
4 Bath(s) Vacation Rental - Sleeps 8
Islamorada, FL
141 Ocean Lane
3 Bedroom Home with Ocean Views and Canal Dockage - 141 Ocean Ln.
"The Beach Fixes Everything".That's the sign that greets visitors as they enter the living room of this newest Freewheeler Vacations home. But while the beach certainly is nice, an awesome vista doesn't hurt either. Located on a narrow resident ....
3 Bedroom(s)
3 Bath(s) Vacation Rental
Islamorada, FL
Beach Dream House
Beach Dream House, relax and enjoy the clear waters of Islamorada FL
Welcome to our Dream Beach House where you can enjoy the most panoramic views in Islamorada, Florida. Enjoy the sun rising over the Atlantic Ocean and superb views from every room in the house: 360 degrees of glass and a wraparound balcony . Pool and ....
3 Bedroom(s)
2 Bath(s) Vacation Rental - Sleeps 6
Islamorada, FL
Lo Key Estates
BEAUTIFUL 5 BDR HOUSE
*VIEW VIDEO* https://www.youtube.com/watch?v=LQFOSPnfS4Y&feature=youtu.be Lo-Key Estate is truly a luxury Keys home situated on a private 400’ waterfront peninsula with the use of a tropical swimming pool w/waterfall and hot tub(shared w/guest ho ....
5 Bedroom(s)
6 Bath(s) Large Estate Home - Sleeps 10
Islamorada, FL
Little Palm Caribbean Home
Little Palm Home - Enjoy Boat Harbor & Fishing Pier
Guests enjoy the beautiful Caribbean décor and high, open ceilings. Solid wood Anderson doors and windows, chiseled stone flooring. Open living and dining area all add to your tropical experience. Comfortable lounging chairs create a seamless trans ....
1 Bedroom(s)
1 Bath(s) Vacation Rental - Sleeps 4
Islamorada, FL
La Jolla Resort
3 Bedroom Private Oceanfront House - Sol
Nestled in the tropical setting of La Jolla Resort in Islamorada, Florida, this 3 bedroom private oceanfront house overlooks the bay, with unparalleled privacy and nearly 2 acres of tropical trees, private boat docks and some of the best unobstructed ....
4 Bedroom(s)
3 Bath(s) Vacation Rental - Sleeps 8
Islamorada, FL
Ocean Harbour M43
**Winter Promo** Luxurious Ocean View Condo w/Heated Pool & Jacuzzi
*** Owner is highly motivated to rent! Contact us for discounts *** Infinite ocean views from the large windows at this modern and luxurious oceanfront condo at mile marker 87. Accommodation - Sleeps 4 Master Bedroom: - King Size Bed - Nig ....
2 Bedroom(s)
2 Bath(s) Condo
Islamorada, FL
Windy Cove #3
Great 3 Bedroom Oceanfront Town Home with Pool - Windy Cove #3
Relax in this great townhouse style condo, which overlooks the sparkling Atlantic Ocean. This condo features 3 bedrooms and 2 bathrooms, a balcony off the living room, a private balcony off the master bedroom, and the quaintness of only 4 other units ....
3 Bedroom(s)
2 Bath(s) Townhome
Islamorada, FL
The Island Dog Villa
The World Famous Island Dog Villa of Islamorada in the Florida Keys
Perfect location for your Florida Keys Vacation Newly remodeled Villa in the beautiful Florida Keys. The Villa offers 2 Bedrooms, Boat Storage, Private Community Boat Ramp with Private Ocean Channel Access, Heated Pool, Private Community, LED Flat ....
2 Bedroom(s)
1 Bath(s) Villa - Sleeps 5
Islamorada, FL
Dream Escape at Anglers Reef in Islamorada
Dream Escape at Anglers Reef in Islamorada
2 Bedroom and 2.5 Bath Villa, in Anglers Reef. An upscale gated community with resort living in the Florida Keys. Everything you need for your vacation is here,: gorgeous private beach, heated resort style pool, private back yard terrace with barbe ....
3 Bedroom(s)
3 Bath(s) Vacation Rental
Islamorada, FL
121 Anglers Way, Islamorada FL
Islamorada home in Anglers Reef with Ocean Views, Dock, Com Pool & Private Beach
This magnificent home with ocean views from all 4 balconies is located in Islamorada at Mile Marker 85 in the exclusive gated community of Angler's Reef, a quiet oceanfront community in the Florida Keys. Anglers Reef is a boutique complex of 52 home ....
3 Bedroom(s)
3 Bath(s) Vacation Rental
Islamorada, FL
132 Atlantic Lane
Beautifully Renovated 2 Bedroom Oceanfront Home - 132 Columbus
Looking for your next Home away from Home? You can not go wrong in this recently renovated 2 bedroom and 2 bath canal home in Lower Matecumbe at the 76 Mile Marker. This home has everything you need for your next get-away in Islamorada. Only one pr ....
2 Bedroom(s)
2 Bath(s) Vacation Rental
Islamorada, FL
Vacation Home
Enjoy the lifestyle of the Key in Islamorada. Monthly rent have 32.5%discount
Very nice and clean Houseboat in the beautiful Islamorada in the 82 Mile The boat have one bedroom with a queen bed and a TV, another bedroom with a queen mattress, complete bathroom , kitchen, living room with TV also and a sofa bed queen, dining r ....
1 Bedroom(s)
1 Bath(s) Vacation Rental - Sleeps 4
Islamorada, FL
Islamorada Paradise
Islamorada Home In Paradise - NO HURRICANE DAMAGE TO HOUSE OR COMMUNITY
NO HURRICANE DAMAGE TO HOUSE OR COMMUNITY!!! This beautiful villa, 106 Anglers Reef, is fully licensed by the Village of Islamorada for Vacation Rentals, license # VR-224. It is located in the exclusive oceanfront gated community of Angler's Reef ....
2 Bedroom(s)
3 Bath(s) Villa - Sleeps 6
Islamorada, FL
Vacation Home
NEW RENTAL! Venetian Shores waterfront dream with pool and plenty of dockage.
This Venetian Shores pool home has 4,209 sq. ft. of living to spread out and enjoy your Keys vacation. This includes 2 living levels, with 2 bedrooms/1 bath on the first level and 3 bedrooms/2 baths on the second floor. Beautiful living room, update ....
5 Bedroom(s)
3 Bath(s) Vacation Rental
Islamorada, FL
Little Bay Compound
A True Islamorada Oasis with Breathtaking Bay Views - Little Bay Compound
Located just off US-1 behind a gated fence awaits a Fantastic Keys Getaway. Little Bay is a private compound situated on a beautiful 1-acre piece of paradise on the Florida Bay. The property has a total of three separate rental units, accommodating a ....
5 Bedroom(s)
6 Bath(s) Vacation Rental
Islamorada, FL
75731 Overseas Highway
Gorgeous Key West Style 4 Bedroom Oceanfront Pool Home - 75731 Overseas Hwy.
Islamorada is the Spiritual Center of the Keys, the Sportfishing Capital of the World, and home to the largest fleet of charter boats in the Keys. Fish deep water or the back bay. Snorkeling and SCUBA sites abound. Restaurants, art galleries, and oth ....
4 Bedroom(s)
4 Bath(s) Vacation Rental
Islamorada, FL
PARADISEPOINT
OceanfrontPeninsula Pool Dock water3sides 7nite min 6ppl max
MINIMUM stay 7 nights, MAXIMUM occupancy 6 people, rental pattern saturday to Saturday, SORY NO PETS COMMENTS AT HOMEAWAY #341722, VRBO #311382 A SLICE OF PARADISE. This is it...Search no More -you have found the needle in the hay stack. You are in ....
3 Bedroom(s)
3 Bath(s) Vacation Rental - Sleeps 6
Islamorada, FL
Bay Harbour A304
Stunning 3 Bedroom Condo with Basin & Ocean Views Located in Lower Matecumbe - Bay Harbour A304
Beautiful 3 bedroom and 2.5 luxury condo located at mile marker 74.5 bayside. This condo is nicely decorated and very spacious for you and your family. The unit has a great screened in porch off the living room. The complex has 2 tennis courts, wei ....
3 Bedroom(s)
3 Bath(s) Condo
Islamorada, FL
Islamorada's Tropical Paradise
Tropical Paradise in Venetian Shores. Luxury Heated Pool / Spa, 4 Bikes & Kayak
Located in prestigious Venetian Shores Islamorada's premier waterfront community! This home was completely remodeled in 2014/15 so everything is tasteful, high quality, spotless and NEW!! HI SPEED WIFI and NetFlix is INCLUDED! A brand new luxury he ....
3 Bedroom(s)
3 Bath(s) Vacation Rental - Sleeps 8
Islamorada, FL
Vacation Home
ISLAMORADA PARADISE! Welcome to your private heaven on earth!
Built in 2012 and designed by well-known Miami architect to mirror the curved shoreline of the beach, this private custom contemporary beach home is a one of a kind, unique design with gated entry, large private beach, and gorgeous panoramic ocean vi ....
3 Bedroom(s)
4 Bath(s) Vacation Rental - Sleeps 6
Islamorada, FL
Islamorada Florida Keys Vacation Rentals, Hotels & Resorts
Plan your Islamorada Florida Vacation here and get the best value possible for the trip! Find affordable Resort Hotels with oceanfront condo rentals, pool and much more. We have a great selection of 2,3 or 4 bedroom villas, condos or cottages that offer you the best available places to stay in Islamorada, Florida Keys.
Our Vacation Rentals, including Pet Friendly Rentals, let you get the most from your vacation in Islamorada and the Florida Keys.
Spend quality time with your family and friends at cheap low rates you can afford, all while near the beach, nightlife, entertainment and a wide variety of beach activities. If you visit Key West in October, make sure to book your Vacation Rental here for Fantasy Fest. Hundreds of properties to choose from, search for availability, photos, descriptions and best price.