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 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 condo

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

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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 Rental - Sleeps 5
Islamorada, FL

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Islamorada house

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

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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 Rental - Sleeps 6
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 Rental - Sleeps 4
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 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 villa

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

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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

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

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Islamorada house

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

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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 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

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 apartment

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

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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 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

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

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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

4 BR Villa w/ pool Canal front-- Great access to the Ocean in Islamorada, Florida

4 BR Villa w/ pool Canal front-- Great access to the Ocean in Islamorada, Florida

MM 91. Situated on a clean, clear canal with deep water access to either the bay or ocean via Tavernier Creek! Enjoy your island time in this bright and breezy hideaway ... Two bedrooms/Two baths upstairs along with open living, dining and kitchen. T ....

4 Bedroom(s) 3 Bath(s) Vacation Rental
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

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

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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 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

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

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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 Rental
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 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

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 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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