Islamorada Florida Vacation Rentals, Hotels & Resorts

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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 of vacation rentals, 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.

Islamorada house

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 Rentals
Islamorada, FL

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Islamorada townhome

Executive Bay - M3

**Winter Promo** Experience the Keys like a Local at Executive Bay - Townhouse with Beach & Pool!

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 ....

2 Bedroom(s) 2 Bath(s) Townhome
Islamorada, FL

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Islamorada house

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 Rentals - Sleeps 6
Islamorada, FL

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Islamorada house

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 Rentals
Islamorada, FL

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Islamorada cottage

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

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Islamorada townhome

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

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Islamorada house

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 Rentals - Sleeps 5
Islamorada, FL

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Islamorada estate

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

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Islamorada house boat

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

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Islamorada house

Vacation Home

Gorgeous Canalfront, Ocean View 3 Bedroom 3.5 Bath Home- Water Enthusiasts Dream

Welcome to Paradise! This fabulous Old Florida Style home with Tommy Bahama décor throughout is a Fisherman & Water Enthusiast's Dream! ***Ask about reduced seasonal rates Sept thru Nov! Located in a beautiful, quiet cul-de-sac, on a deep water ca ....

3 Bedroom(s) 4 Bath(s) Vacation Rentals - Sleeps 10
Islamorada, FL

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Islamorada house

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 Rentals
Islamorada, FL

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Islamorada apartment

Bay Harbour D114

Stunning 3 Bedroom Condo with Oceanviews Located in Lower Matecumbe - Bay Harbour D114

Beautiful modern luxury unit with 3 bedrooms and 2 full bathrooms, along with a half guest-bath! Plasma TV, VCR and DVD player in the living room. This unit does have Wi-Fi. The Bay Harbour Complex comes complete with two tennis courts, weight room, ....

3 Bedroom(s) 3 Bath(s) Apartment
Islamorada, FL

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Islamorada condo

Bay Harbour Condominium #204

??Luxury 3 Bedroom Condo -Amazing Views, Sunrise, Pool/Hot Tub, Kayak/Gym/Bikes

Located in Islamorada, Florida, this beautiful condominium is located in Lower Matecumbe Key, and feels like old Florida. Our home is a 3 bedroom, 2.5 bath and sleeps 6 people comfortably. The 3 bedroom unit includes an extra large living area and ba ....

3 Bedroom(s) 3 Bath(s) Condo - Sleeps 6
Islamorada, FL

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Islamorada house

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 Rentals
Islamorada, FL

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Islamorada house

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 Rentals - Sleeps 8
Islamorada, FL

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Islamorada house

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 Rentals - Sleeps 8
Islamorada, FL

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Islamorada house

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 Rentals
Islamorada, FL

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Islamorada townhome

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

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Islamorada townhome

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

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Islamorada mobile home

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

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Islamorada house

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 Rentals - Sleeps 4
Islamorada, FL

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Islamorada villa

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

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Islamorada house

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 Rentals - Sleeps 6
Islamorada, FL

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Islamorada house

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 Rentals - Sleeps 6
Islamorada, FL

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Islamorada house

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 Rentals - Sleeps 6
Islamorada, FL

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Islamorada house

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 Rentals
Islamorada, FL

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Islamorada townhome

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

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Islamorada townhome

Executive Bay - T2

**Winter Promo** Family Friendly Executive Bay Townhome with Beach & Pool

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

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Islamorada house

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 Rentals
Islamorada, FL

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Islamorada townhome

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

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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.

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