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Villas in Islamorada

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    Travellers to Islamorada are booking July dates now. Secure your holiday rental today, and have the perfect trip.
    All 168 Rentals in Islamorada
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    2 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    5 Bedrooms, 5 Bathrooms, Sleeps 16 Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Comfortable Venetian Shores canal home that has two bedroom/one bath upstairs and a one bedroom/one bath apartment downstairs.  The downstairs apartment has a complete kitchen and living room and separate bedroom.   There is a screened in porch of the living room upstairs.  The home has awesome...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    OCEANFRONT pool30'DockGatedPrivate7niteMin6ppl max1 / 49
    (6)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Unheated)
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    • Waterfront
    • Satellite TV
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    Pet friendly
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    Smoking allowed
    About this property
    FOR ADDITIONAL REVIEWS GO TO "HOMEAWAY.COM" LISTING #341722 TO AVOID SCAM WE URGE YOU TO PLEASE CONTACT OWNER BY PHONE BEFORE FINALIZING ANY ARRANGEMENTS IF YOU GET A RESPONSE FROM BESTHOLIDAYRENTALS.COM **** IGNORE IT **** SCAM MINIMUM STAY 7 NIGHTS, MAXIMUM OCCUPANCY 6 PPL, NO PETS, RENTAL...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Privately owned condominium unit at the Futura Yacht Club in the Village of Islamorada. Futura is located on the Gulf of Mexico and is a gated complex consisting of 70 units. Enjoy wonderful Bay views and sunsets from our two bedroom / two bath condominium unit that sleeps up to 6 people. Stay in...
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    Islamorada, Florida Keys 33070
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
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    • Balcony
    • Ocean Views
    • Waterfront
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    Pet friendly
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    Smoking allowed
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    Watch the sunrise from the spacious balcony overlooking the Atlantic Ocean. This brand new three bedroom, two and-a-half bath condominium sleeps eight people. Master bedroom has a king bed with access to the balcony. Second bedroom has a queen bed and third one has two twin beds. TVs in every...
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    Islamorada, Florida Keys 33036
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    This charming condo is located in the Futura Yacht Club community, located at mile marker 88.5 on the bay side in Islamorada. The unit comes fully furnished with a full kitchen, dining room, large living room with sleeper sofa, expansive balcony with great views of the Florida Bay and the...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Terrace
    • Hot Tub
    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    *** Owner is highly motivated to rent! Contact us for discounts *** Infinite ocean views from the large balcony at this modern and luxurious oceanfront condo at mile marker 87. BOAT SLIP INCLUDED which can accommodate up to a 30' boat. SLEEPING ARRANGEMENTS (Sleeps 4) Master Bedroom: - King Size...
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    Islamorada, Florida Keys 33036
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    Pet friendly
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    Smoking allowed
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    Lower Matecumbe Key condo description Welcome to paradise! This beautiful three bedroom, two and a half bath end unit condominium sleeps 6 people. Master bedroom has a king bed with direct access to the water front balcony. Second bedroom has a queen bed and the third has two twin beds. Brand new...
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    Islamorada, Florida Keys 33036
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Private Garden
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    Pet friendly
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    About this property
    Beautiful home with 3 bedrooms and 2 bathrooms,everything renovated,kitchen remodeled with stainless steels appliances ,the house have comforted beds for 10 people's ,backyard area with BBQ ,private parking inside the house for 6 cars,private ramp for boat and jetski inside the house,beautiful...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Waterfront
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    About this property
    Please call or email to inquire about specific dates. We can be accommodating depending on your dates and needs. Come experience the Keys vibe the way locals do it. This cute, cozy and totally remodeled mobile home is located in the heart of the Keys. It is close to everything (shops,...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Three story home 100 feet deep water dock big pool1 / 20
    (3)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Patio
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    • Private Outdoor Pool (Unheated)
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    • Waterfront
    • DVD Player
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    Pet friendly
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    About this property
    Please contact us if you have any policy questions since we do not agree with this website forcing us to choose policies they dictate. We have our own polices so please ignore what's posted in the policies section on this website. Beautiful three story luxury home in the heart of Islamorada the...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
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    Pet friendly
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    About this property
    Escape to your own Bayside Vacation Villa in Islamorada. We offer brand new 3 bedroom, 3.5 bathroom villas in the Islamorada Art District on the Florida Bay. These Bayside villa rentals are located closest to the pool, dock and fresh, clear bay waters. The villas are very near our iconic marinas...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful 3 bedroom / 2 bath in the heart of Islamorada. With a pool. A short walk to Chica Lodge and Moorings Village and all the best restaurants in the Keys like Morada Bay.<BR><BR>Located in the best location of the Florida Keys. The house has many different places to relax, lounge and forget...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    VILLA RIOLO1 / 25
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Terrace
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    Pet friendly
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    Smoking allowed
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    Minimum Rental: 28 Days "Villa Riolo" is an updated single family stilt home and perfect for your next holiday in Islamorada! It comfortably sleeps 6 in two bedrooms. This home has been meticulously cared for over the years and for the first time the owners are offering you an opportunity to...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Hot Tub
    • Patio
    • Terrace
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    • Balcony
    • Satellite TV
    • Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Minimum Rental: 28 Days "The Palms #309" is an exceptional condo with panoramic views of the Atlantic Ocean. This condo is in one of the most popular condo complexes in Islamorada - The Palms of Islamorada. Comfortably furnished and ready for your arrival this unit offers an updated kitchen...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Central Heating
    • Waterfront
    • Ocean Views
    • Washer
    • DVD Player
    • Terrace
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Your awe moment begins as you drive through the gates of the Moja Draga Estate, located on a beautiful 2 acre parcel of prime ocean front property in the village of Islamorada. Moja Draga is where your vacation dreams begin. Your island vacation home is well appointed with all that you need for a...
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    Islamorada, Florida Keys 33070
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Osprey Lagoon Half Duplex House, 28 night minimum1 / 12
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Air Conditioning
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    Pet friendly
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    Smoking allowed
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    Half Duplex Home Are you seeking a beautiful hideaway close to all the amenities? This delightful 1 bedroom half duplex vacation home has deep water dockage for your boat in the back yard with the view of a beautiful lagoon. This lagoon has schools of tarpon to test your angling skills, and...
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    Islamorada, Florida Keys 33070
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Ocean-Front Caribbean Home.1 / 21
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Ocean Views
    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Royal Palm, South - Ocean Front Home ( recent fraud. NEVER wire us money. Payment for reservations can only be done via the phone, not online or via wire) Catch Bonefish and Tarpon from Our 450-Foot Fishing Pier. Inspired by owner Phil with nothing compromised this luxurious Caribbean home...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    **Summer Promo** Ocean Front Keys Home with Private Beach - Great for Kite1 / 25
    (2)Average
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
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    Pet friendly
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    Smoking allowed
    About this property
    Beautiful four bedroom, Ocean Front home with private beach in sunny Islamorada (near Key Largo, on mile marker 74). Welcome to our little slice of paradise in the Florida Keys! Come and relax at our beautiful ocean front home with breathtaking, panoramic views of the Atlantic ocean. This spit...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Escape to your own Bayside Vacation Villa in Islamorada. We offer brand new 3 bedroom, 3.5 bathroom villas in the Islamorada Art District on the Florida Bay. These Bayside villa rentals are located closest to the pool, dock and fresh, clear bay waters. The villas are very near our iconic marinas...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Hot Tub
    • Patio
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    • Balcony
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Minimum Rental: 28 Days "The Palms #405" is a diamond! Be among the first to rent this gorgeous two bedroom condo. It has been completely renovated from floor to ceiling. The floors have been replaced with tile and the old popcorn ceilings are gone. You'll adore the comfortable living room...
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    Islamorada, Florida Keys 33036
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    LITTLE BAY - Lower Duplex1 / 23
    (4)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Satellite TV
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    Minimum Rental: 7 Days Little Bay's Lower Duplex is one of three rental units on this fabulous property. The Little Bay property is a one acre lush tropical setting in a gated compound located directly on Florida Bay. The units are available for rent by the week, or month. Each unit sleeps...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Satellite TV
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    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ENJOYABLE, CENTRAL LOCATION, PLANTATION KEY, 3 bedroom + loft, 2 bath; 1400 sf 2 story, all bedrooms and 1 full bath are upstairs & downstairs is the living area and 1 additional full bath. The unit is clean, comfortable, quiet and restful. The community is gated with security, no pets are allowed;...
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    Islamorada, Florida Keys 33036
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Patio
    • Hot Tub
    • Ocean Views
    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautifully furnished 2 BR 2 BA Condo on second floor.(First is parking only) Spiral Staircase directly down to lushly landscaped grounds. Only this floor has the stairs, others have to go through a lobby with a key. Wander around among our beautiful tropical gardens, bring your drink down to the...
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    Islamorada, Florida Keys 33036
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
    • Private Outdoor Pool (Heated)
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    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 heated pool / spa was added in 2015 and is surrounded...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Balmy weather, sunshine and a little magic await you in the Florida Keys… Look no further than this exquisite Islamorada vacation rental home as your own personal oasis during your upcoming tropical getaway! Nestled in the exclusive oceanfront gated community of Angler’s Reef in Islamorada on...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Escape to your own Bayside Vacation Villa in Islamorada. We offer brand new 3 bedroom, 3.5 bathroom villas in the Islamorada Art District on the Florida Bay. These Bayside villa rentals are located closest to the pool, dock and fresh, clear bay waters. The villas are very near our iconic marinas...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Wi-Fi
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    • Balcony
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    • Washer
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful and spacious home with three bedrooms, two and half baths, huge new kitchen, new bathrooms, and screened in porches facing East and West. There are great views from every room!!! Tastefully furnished with all linens, comfortable memory foam mattresses, all new appliances, and completely...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    LITTLE BAY - Upper Duplex1 / 25
    (3)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Minimum Rental: 7 Days Little Bay's Upper Duplex is one of three rental units on this fabulous property. The Little Bay property is a one acre lush tropical setting in a gated compound located directly on Florida Bay. This is one of 3 separate units for rent by the week or month. Each unit...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 2 Bathrooms, Sleeps 6 Quick View
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    Located just off US-1 behind a gated fence awaits a Fantastic Keys Getaway. Little Bay is a private compound situated on a beautiful 1-acre piece of paradise on the Florida Bay. The property has a total of three separate rental units. The Cottage is a bright and airy 1,250 sq ft unit with a huge...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    About this property
    Dubbed Aguazul, the home has four bedrooms and three bathrooms. There's also a small bungalow off the pool deck, meaning the property can comfortably sleep nine. Two separate kitchens, one on each of the home's two levels, are another unique feature. Cool off in the home's oceanfront swimming pool,...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    BLUE WATER RETREAT1 / 26
    (2)Average
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
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    About this property
    Minimum Rental: 28 Days "Blue Water Retreat" is all about the location, location, location! This home has it all - ocean side Lower Matecumbe location, remodeled in 2009. Relax by the cocktail pool or sunbathe in the private roof top sunning area. There are blue water ocean views from almost...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Shared Outdoor Pool (Unheated)
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    Islamorada Oceanfront Pool home! Wake up in the morning to a gorgeous sunrise.  This home is a 3 bedroom 2 bath home with vaulted wood ceilings, decorated with a cottage feel.  The porch is perfectly shaded and overlooking the Atlantic Ocean. Relax in the heated swimming pool or swing in the...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    SANCTUARY IN PARADISE1 / 21
    (3)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Hot Tub
    • DVD Player
    • Washer
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    • Air Conditioning
    • Waterfront
    • Wi-Fi
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    Pet friendly
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    About this property
    WWW.SCHOONERHAMMOCK.COM This unique property offers : -master suite -apartment -cottage -3 full kitchens On Atlantic Ocean. Simple, sweet, and serene sanctuary. Please contact Andy Cancela 828 808 1693 We love The Lord and look forward to sharing our home with you.
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    Islamorada, Florida Keys 33070
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    This 2 bedroom, 2 bathroom condo located directly on the Florida Bay is the perfect sunny getaway! Situation with perfect views of the community pool, community marina, and open bay, you'll enjoy coffee in the morning while watching the boaters head out for their perfect catch and enjoy a sunset...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Mina Bay - Oceanfront "Million Dollar View"1 / 19
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Ocean Views
    • DVD Player
    • Terrace
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    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Mina Bay - vacation rental with "the million dollar view"! Truly OCEANFRONT on the sandy beach and feet from the pier and dock. Sparkling water's and brilliant sunsets complete this 2 Bd 1.5 Ba plus loft Unit I-1 townhouse. 28 DAY MIMIMUM RENTAL for all guests.  Accommodates a family of 8 perfectly...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    LITTLE BAY - Cottage1 / 24
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Minimum Rental: 7 Days "Little Bay's Cottage" is one of three rental units on this property. The cottage is a ground level dwelling separate from two duplex units. It offers a unique floor plan with the main living area in the center of the house with kitchen, dining area, sitting area and a...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    • Shared Outdoor Pool (Unheated)
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    About this property
    This is a beautiful Venetian Shores home... It truly is a must see! The interior is clean and nicely decorated. The large porch on the back allows you to see the famous Florida Keys sunsets from your own home! Located a few houses down from Snake Creek, you'll have quick ocean and bay access. Deep...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    This is a very spacious and very well-maintained 4 bedroom, 3 bathroom home toward the mouth of the canal on a quiet street in Plantation Key (Tavernier). You and your group will enjoy stunning views from the main level, master suite, & rooftop sundeck. There is approximately 20ft concrete dockage....
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Oceanfront Luxury Islamorada Estate - 4 bed/pool1 / 45
    (2)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Waterfront
    • Internet Access
    • Private Outdoor Pool (Heated)
    • Washer
    • Air Conditioning
    • Grill
    • Satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    * 7 Day Rental minimum - Saturday to Saturday * Please check the calendar prior to inquiry Sleeps 8 adults plus up to 4 children under 6 allowed (fire code regs)...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Located just off US-1 behind a gated fence awaits a Fantastic Keys Getaway. Little Bay is a private compound situated on a beautiful 1-acre piece of paradise on the Florida Bay. The property has a total of three separate rental units. The Lower Duplex is a 1,500 sq ft unit with 2 bedrooms, 2 full...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Balcony
    • Washer
    • Terrace
    • Waterfront
    • Patio
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    THIS HOME ONLY OFFERS MONTHLY RENTALS. Islamorada is known as the 'Sport Fishing Capital of the World.' This property is located just minutes from the Atlantic Ocean, where you can head off shore to the Gulf Stream and reel in the big game, or travel into the Florida Bay, where you will find vast...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Islamorada Oceanfront Executive Rental1 / 11
    (5)Very good
    5 Bedrooms, 4 Bathrooms, Sleeps 9 Quick View
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    • Private Outdoor Pool (Heated)
    • DVD Player
    • Waterfront
    • Washer
    • Satellite TV
    • Air Conditioning
    • Internet Access
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Millionaire's Row! Beautiful home with private heated swimming pool directly on the ocean in Islamorada. This home offers excellent views of the ocean from many rooms. 5 bedroom, 4 bath owners home is beautifully furnished with ocean views from patio, living room (upper and lower), and dining room...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 9
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    Luxury Home Ocean & Bay Access in minutes!1 / 14
    (9)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Internet Access
    • Satellite TV
    • Private Outdoor Pool (Unheated)
    • Patio
    • Waterfront
    • Washer
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Special vacation rental rates for off-season bookings and also for some last minute dates! Call us now for details. Located in Islamorada the fishing capitol of the world, this is a beautiful home decorated with Island style decor. Over 3,000 square feet of living space. 100' of dock, less than two...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Islamorada 2-bedroom Condo1 / 6
    (4)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Grill
    • Waterfront
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    • Satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If you’ve been to Islamorada you know it as the sportfishing capital of the world, a place where you’ll find every water-related activity imaginable, with fine restaurants to crab shacks serving local fare, and plenty of nightlife for both the young and young at heart. If you’ve never been here, a...
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    Islamorada, Florida Keys 33070
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Park Model mobile home located oceanside on beautiful Windley Key in Islamorada, Florida Keys, the 'sport fishing capital of the world.' This is a great spot for relaxing, fishing and/or exploring the Keys, situated 75 miles from Miami and 85 miles from Key West. 1 BR plus upstairs sleeping or...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Islamorada Waterfront Paradise Getaway!1 / 28
    (31)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Patio
    • Ocean Views
    • Air Conditioning
    • DVD Player
    • Waterfront
    • Satellite TV
    • Wi-Fi
    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Please contact us for all of our rates for different length of stays! For shorter stays...make sure you have a minimum of 28 days entered in your contact form! DO NOT BOOK THROUGH FLIPKEY! Booking instructions will be provided when you send your inquiry, saving you significant FlipKey booking...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Internet Access
    • Hot Tub
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    Pet friendly
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    Smoking allowed
    About this property
    Enjoy a little European elegance combined with Florida Keys Charm at this Lower Matecumbe Key oceanfront property.  The main home has four bedrooms and 4.5 baths.  A separate bungalow contains a king suite with kitchenette, as well as its own patio overlooking the Atlantic.  Spend your vacation...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 10
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