Best Rental Prices 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.
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
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
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
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
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
Vacation Home
2 BDR Penthouse-Breathtaking view-Designer Furnished-***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 www.bayinthekeyscom Luxuriously appointed condo located at M ....
2 Bedroom(s)
3 Bath(s) Condo
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
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
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
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
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
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
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
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
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
Vacation Home
Luxury Home Huge Pool & Dock Islamorada
Call us now for special discounts and also for rates not listed. Gorgeous three story home completely remodeled and refurnished using tropical island type colors and décor. Located on one of the only true deep water canals in Islamorada, this house ....
3 Bedroom(s)
3 Bath(s) Vacation Rental - Sleeps 8
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
Alligator Reef - Conch Home
Alligator Reef - Conch Home
Alligator Reef is a truly special slice of Paradise with 4 individual homes nestled on a privately gated oceanfront estate. This home, the Conch House (pronounced konk), is a 3 bedroom, 2 bathroom ocean front home featuring beautiful views, ocean bre ....
3 Bedroom(s)
3 Bath(s) Vacation Rental
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
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
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
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
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
Vacation Home
3/2 Waterfront home in Lower Matecumbe
Everything you need to have fun in the Keys! Traditional Keys home on an oversized lot with your own private boat ramp. Launch your boat (up to 20'), jet skies, kayaks or paddle boards into a private canal that leads to the bay. Our home has a large ....
3 Bedroom(s)
2 Bath(s) Vacation Rental - Sleeps 8
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
Executive Bay Club
Executive Bay Club unit V4 Islamorada,FL
SERVICE ANIMALS are OK, otherwise NO PETS ALLOWED 30 Day Minimum Stays 2 Bedroom, 1.5 Bathroom townhome located in Islamorada, FL. Driving distance is only 90 minutes from Miami International Airport. Centrally located within the complex to tennis ....
2 Bedroom(s)
2 Bath(s) Condo - Sleeps 10
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
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
76004 Overseas Highway
Great 4 Bedroom Home with Breathtaking Bay Views - 76004 Overseas Highway
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 M ....
4 Bedroom(s)
3 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.