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
83003 Old Highway
Beautiful Oceanfront Oasis with Pool - 83003 Old Hwy.
Two adorable, private cottages right on the Atlantic Ocean. Located in the heart of Islamorada at mile marker 83. This stunning property is truly a tropical paradise with a private, sandy beach and observing pier. Relax at the beach or cool down in ....
4 Bedroom(s)
3 Bath(s) Vacation Rental
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
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
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
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
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
Angler's Reef
Oceanside Resort Home for the best getaway in luxurious Angler's Reef!
Our house is located in Islamorada, FL, the fishing capital of the world. Our single-family, Key-style home is located in an exclusive gated community of 50 island homes called Angler's Reef. The community includes a beautiful oceanfront pool, a priv ....
2 Bedroom(s)
3 Bath(s) Vacation Rental - Sleeps 4
Islamorada, FL
151 Anglers Way
Islamorada Oceanfront Home In Anglers Reef Ocean Views, Dock, Comm Pool & Beach
This magnificent home with amazing direct ocean views from the master bedroom, living room and balconies is located in Islamorada at Mile Marker 85 in the exclusive gated community of Angler's Reef. Home also overlooks the community pool. Anglers Ree ....
2 Bedroom(s)
3 Bath(s) Vacation Rental - Sleeps 6
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
Paradise Cottage
RELAX in your PRIVATE Oceanfront Cottage!
1/1 cottage with breathtaking oceanfront views. Sleeps four comfortably. Private bedroom with queen bed. Living room has two full size futons. New kitchen with all stainless steel appliances. Very cozy and great views to enjoy in your dream vac ....
1 Bedroom(s)
1 Bath(s) Cottage - Sleeps 4
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
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
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
91 West Plaza del Lago
Tastefully Renovated 3 Bedroom Canal Front in Port Antigua - 91 West Plaza Del Lago
Awesome renovated home in Port Antigua. The upstairs has 3 bedroooms and 2 baths. The kitchen has granite counter tops, stainless steel appliances, along with a serving window if you are out on the balcony. The downstairs has a great tv room with ....
3 Bedroom(s)
3 Bath(s) Vacation Rental
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
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
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
75130 Overseas Highway
Unique 2 Bedroom Bay Front Home with Roof Top Terrace - 75130 Overseas Hwy.
Great house in Lower Matecumbe (south side of Islamorada) at the 75 mile marker on the bayside. This house has fabulous sunset views in a nice quiet part of town. There is a small beach area in the back with palm trees giving you a little more privac ....
2 Bedroom(s)
2 Bath(s) Vacation Rental
Islamorada, FL
Angler's Reef
Angler's Reef's Villa 119, a 2 Bedroom and 2.5 Bath Bungalow
Start your day with a refreshing plunge in the sparkling pool or an invigorating kayaking trip on the Atlantic Ocean. At Angler's Reef Villa 119 you can pamper yourself in the sun on the ocean front private beach while seagulls and pelicans grace the ....
3 Bedroom(s)
3 Bath(s) Townhome - Sleeps 6
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
Vacation Home
Islamorada Luxury Home deep water dock
Huge 40 foot swimming pool recently added. This is an incredible home featuring nothing but the best in high-end Florida Keys style décor and amenities. The location is spectacular with this home being just two minutes to either the ocean or bay. Pl ....
4 Bedroom(s)
3 Bath(s) Vacation Rental - Sleeps 8
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
122 Valencia Dr
Unique Venetian Shores Home with 3 Bedrooms and Dockage - 122 Valencia Dr.
Charming canalfront home in prestigous Venetian Shores. A simple yet lovely, ground level 3 bedroom, 2 bath home with direct access to ocean and bay via Snake Creek. With 70 feet of dockage, a fish cleaning station, gas grill, and great outside patio ....
3 Bedroom(s)
2 Bath(s) Apartment
Islamorada, FL
Summer Sea Condominium
Kick Back In Islamorada!
Remodeled 2 Bedroom unit includes air conditioning, private balcony, cable TV, DVD player, full kitchen with cooking utensils, pots & pans, silverware, plates, glasses, microwave, coffee maker, dishwasher, iron, ironing board, blow dryer and refriger ....
2 Bedroom(s)
2 Bath(s) Condo - Sleeps 6
Islamorada, FL
113 Sunset Drive
Charming Beach Front Home in Lower Matecumbe - 113 Sunset Dr.
Near the house is the small Anne's Beach. There are nature trails, board walks to small lunch and BBQ areas, private sandy areas hidden in the mangroves and parking. The home is also near Robbie's Marina (where they feed the Tarpon), Bud n' Mary's Ma ....
4 Bedroom(s)
3 Bath(s) Vacation Rental
Islamorada, FL
The White Marlin Beach House
RATES REDUCED!! White Marlin Beach House, Islamorada
Contact owner for rates and availability at (305-431-2006). Relax in Islamorada, Florida Keys... 'Sport Fishing Capital of the World.' Enjoy deep blue water or back country fishing. Dive, snorkel, and swim on a clear, white, sandy beach (rare in th ....
2 Bedroom(s)
2 Bath(s) Vacation Rental - Sleeps 5
Islamorada, FL
100 Palo De Oro Drive
Beautiful Pool Home Located In Desirable Venetian Shores- 100 Palo De Oro
Looking for an amazing home in Venetian Shores? This home has everything - 4 bedroom, 4 bath home that has been updated. The kitchen is amazing, suited for any type of entertaining. The 3rd floor floor is a lofted master bedroom suite with a walk- ....
4 Bedroom(s)
4 Bath(s) Vacation Rental
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
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
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.