Islamorada Florida Vacation Rentals, Hotels & Resorts

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Rentals in Islamorada, FL

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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.

Islamorada house

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

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Islamorada house

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

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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

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

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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 house

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

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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 Rental
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 Rental
Islamorada, FL

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Islamorada house

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

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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 house

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

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Islamorada condo

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

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Islamorada house

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

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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 Rental - 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 Rental
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

Vacation Home

Lush Tropical Waterfront Oasis With Heated Pool, Dock And WiFi

This tropical oasis includes a heated pool and dock that reaches out onto a protected lagoon that opens into the Florida Bay. There are 3 bedrooms and two bathrooms upstairs, and a downstairs bedroom suite with private bathroom that opens onto the po ....

4 Bedroom(s) 3 Bath(s) Vacation Rental - Sleeps 8
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

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

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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 Rental
Islamorada, FL

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Islamorada house

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

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Islamorada estate

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

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Islamorada house

The Last Resort

Islamorada Oceanfront Estate | Pool, Beach & Dock | Next Availability Aug 2019

Islamorada Rental License: VR - 065 CHECK OUT A FEW WORDS FROM THE OWNERS BELOW INITIAL INFORMATION... 4 bed/5 bath beachfront on over 1 acre with a private beach, heated pool & dock Separate upstairs Den area sleeps up to 6 kids. * 7 Day minimum ....

4 Bedroom(s) 5 Bath(s) Vacation Rental - Sleeps 12
Islamorada, FL

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Islamorada house

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

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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 Rental - Sleeps 8
Islamorada, FL

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Islamorada house

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

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Islamorada condo

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

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Islamorada house

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

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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 townhome

Windy Cove #1

Wonderful 3 Bedroom Oceanfront Townhome with Pool - Windy Cove #1

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 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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