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.
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
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
Vacation Home
Top of the line Mobile home unit located at Islamorada resort. Full restaurant
Beautiful Mobile home fully loaded with all ameneties. breathtaking views just steps away from the Gulf of Mexico and the Atlantic Ocean. Unit will sleep 5 people comfortably. Queen bed in the rear bedroom plus two pull out beds in the main hall. Ev ....
1 Bedroom(s)
1 Bath(s) Mobile Home - Sleeps 5
Islamorada, FL
Angler's Reef
Angler's Reef Resort Villa 136, a 2 Bedroom with Balcony Ocean View
The Angler's Reef Resort's villa 136 will provide your group with more than enough space to ensure their comfort and privacy. Complimentary covered parking will keep your mind at ease knowing your vehicle is well-protected. Just outside the living ar ....
3 Bedroom(s)
3 Bath(s) Vacation Rental - Sleeps 6
Islamorada, FL
Vacation Home
Bay Harbour - Developer Unit Every Upgrade Possible!!***7 DAY MINIMUM RENTAL***
***NOTWITHSTANDING ANYTHING IN THE RATES PAGE THE MINIMUM RENTAL IS 7 DAYS***IF YOU SEARCH LESS THAN 7 DAYS MY PROPERTY DOES NOT APPEAR***THE MINIMUM RENTAL PERIOD IS 7 DAYS*** Bay Harbour Luxuriously appointed condo located at Mile Marker 75 on t ....
3 Bedroom(s)
3 Bath(s) Condo - 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
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
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
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
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
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
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
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
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
Vacation Home
ISLAMORADA PARADISE - Welcome to 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
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
2 bedroom 2 bath home in the HEART of Islamorada, Florida Keys-- walk festivals & more!
2 bedroom 2 bath home in the HEART of Islamorada, Florida Keys-- walk festivals & more!
Mile Marker 81. Cute and cozy two bedroom, two bathroom home located off the main streets, in the heart of Islamorada. A full porch wraps around the front and back yard, for relaxing and entertaining in the Florida Keys weather. Natural sunlight ....
2 Bedroom(s)
2 Bath(s) Vacation Rental
Islamorada, FL
Vacation Home
Luxury Florida Keys Estate
Ocean Front, Lush Gardens, Private Beach, Deep-Water Dockage, Brand new Pool with Spa. This luxurious and newly renovated home is situated on the very desirable Lower Matecumbe Beach in Islamorada. This gated home offers supreme peace and privacy ov ....
3 Bedroom(s)
3 Bath(s) Large Estate Home - Sleeps 6
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
La Jolla Resort
3 Bedroom Private Oceanfront House - Bahia
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 ....
3 Bedroom(s)
3 Bath(s) Vacation Rental - Sleeps 8
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
San Roc
***Ocean Front, Pool, Spa, Dock, 2.5 Acres, Gated
San Roc is a beautiful 4 bedroom 3 bath home situated on over 2.5 acres with secluded woods. The Atlantic Ocean water views are spectacular. Located in Islamorada and the most sought after area known as "Millionaires Row" San Roc is a 2 level home. T ....
4 Bedroom(s)
3 Bath(s) Vacation Rental
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
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
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
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
Tarpon Bay Castaway
Brand New / Totally Renovated Luxurious Home New To Rental Market.
PLEASE inquire directly with us about the specific rate based on the length of stay (SHORTER or LONGER)! Located in Islamorada the premier Key of the Florida Keys, which is known as the Sports Fishing Capital of the world. Islamorada is actually mad ....
3 Bedroom(s)
2 Bath(s) Vacation Rental - Sleeps 9
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
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
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
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.