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Islamorada Luxury Vacation Rentals

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    Travellers to Islamorada are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    22 Matching Rentals in IslamoradaView all 148 rentals
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    75731 Overseas Highway1 / 32
    (13)Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Oceanfront Oasis with Quintessential Island Living1 / 44
    (5)Excellent
    5 Bedrooms, 6 Bathrooms, Sleeps 11 Quick View
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    Ocean-Front Caribbean Home.1 / 21
    (2)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Venetian Tropics 3 bedroom pool home on sailboat canal weekly vacation rental1 / 38
    (28)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Washer
    • Air Conditioning
    • Waterfront
    • Ocean Views
    • Patio
    • DVD Player
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 19, 2016
    Over the years, we have stayed here 4 times, and each time gets better due to the improvements to the property. The location is perfect and relaxing for folks who like to fish...
    Reviewed March 28, 2016
    This is my fourth year at the property and it has only gotten better. There were some criticism of the deck conditions and lack of refrigerator at the outside Tiki hut. Those...
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    About this property
    Private heated pool vacation home located on deep canal with immediate access to ocean and bay. Mile Marker 86 in prestigious Venetian Shores. Pet friendly Vacation Rental License. No VR-001 106 San Remo Drive, Islamorada, Florida, 33036 Please email me for the application. Weekly vacation rental...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Incredible Luxury Home with Waterfront!! Paradise1 / 19
    (2)Excellent
    5 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Waterfront
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Wi-Fi
    • Washer
    • Hot Tub
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed December 5, 2017
    Cannot even express in words how great of an experience my family had! The house is unbelievable, with two apartments downstairs and three bedrooms upstairs. The yard is amazing...
    Reviewed December 5, 2017
    I loved having everyone at one location and with the 3 separate living areas, there was plenty of space! Easy access to a great bike/walking path. Great restaurants just a...
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    About this property
    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 house) There are Ocean Views from the 2 & 3rd floors. Lo-Key is a custom 5 bedroom/5 bath home that opens onto Florida Bay...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 12
    140 Atlantic Lane1 / 147
    (8)Very good
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 12, 2015
    We seven people (3 couples and one single) stayed here for one week. This big house is located right on the Atlantic Ocean, but it has no beech. It has a great wraparound porch...
    Reviewed August 12, 2014
    The home that we stayed at was incredible! The accommodations, the view, the boat dock space was all great. It was fast in and out to the Atlantic Ocean to be able to scuba...
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    About this property
    You'll fall in love with this little piece of paradise. Amazing ocean views can be enjoyed from every room in this beautiful home and separate guest quarters. With an open concept living, kitchen and dining room, a large wrap around porch, 5 bedrooms and 4 bathrooms, this house has everything you...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
    82754 Overseas Highway1 / 29
    (4)Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Hot Tub
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 7, 2017
    We have been staying in the keys for 5 years in a row & this was the best rental property we found. We are 4 guys (over 50) who want to go fishing and relax and this property...
    Reviewed May 9, 2017
    Our family (three generations) wanted a place in Islamorada with 5 bedrooms. We rented the Osprey Bay Villa for a week and it was a perfect fit. The bay side location provided...
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    About this property
    OSPREY BAY VILLA! Wonderful bayfront home in the heart of Islamorada in the fabulous Florida Keys for rent by the week or monthly. Offering 5 bedrooms and 3 full baths on 2 living levels overlooking the Florida Bay with its incredible sunset views. Sleeps 10 people comfortably. Spacious fully...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
    SANCTUARY IN PARADISE1 / 21
    (5)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Hot Tub
    • DVD Player
    • Washer
    • Grill
    • Air Conditioning
    • Waterfront
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 9, 2017
    We booked Sanctuary in Paradise as there were three families (9 people) traveling together. It was perfect as each family had separate sleeping quarters. We were able to...
    Reviewed October 23, 2014
    My family/extended family stayed here in June 2012 for two weeks and it was beyond wonderful. The owner ALWAYS was quick to respond to emails even if it was to say "you're...
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    About this property
    This unique property offers : -master suite -apartment -cottage -3 full kitchens On Atlantic Ocean. Simple, sweet, and serene sanctuary. We love The Lord and look forward to sharing our home with you. Whether your vacation ideal is relaxing in a hammock in view of the ocean with a good book or...
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    Location Information
    Islamorada, Florida Keys 33070
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
    Paradise Beach Sandy Oceanfront1 / 46
    (3)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Balcony
    • Waterfront
    • Hot Tub
    • Terrace
    • Washer
    • Ocean Views
    • Patio
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 23, 2019
    My family just spent a fun filled week in Islamorada and our accommodations at Paradise Beach were fantastic! The house is impeccably designed with a pool that kept us outside...
    Reviewed April 20, 2019
    The house is beautiful, views are amazing, and it has everything you need or will ever need. Our whole family enjoyed a week of relaxation, and we spent some memorable time...
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    About this property
    Endless open water views with spectacular sunrises and sunset colored skies await in this private gated estate. Sink your toes into the natural sand beach. Enjoy your privacy at the heated pool and spa among lush tropical vegetation and palm trees. This Key West styled house offers stunning...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
    Beautiful Bayside View with Swimming Pool1 / 49
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Washer
    • Grill
    • DVD Player
    • Patio
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 7, 2018
    My family just LOVED this house. The backyard is amazing with a beautiful view and plenty of space for boat-dockage. My family had fun paddle boarding, kayaking, and...
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    About this property
    Bayside View is truly an amazing Florida Keys home, with great Bay views from all floors! Bayside View is a 3 bedroom/3 bath home that is directly on the Florida Bay. This location satisfies all of your fishing & water sport desires. The home is completely renovated and absolutely gorgeous. The...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Dubbed Aguazul, the home has four bedrooms and three bathrooms.  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, fish or swim from its dock, play in the sand of its private beach or merely sip a...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    San Roc - Private 150 Ft Oceanfront 2.5 Acre Millionaire Row Estate, Pool, Spa,1 / 20
    (1)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Ocean Views
    • Wi-Fi
    • Air Conditioning
    • Waterfront
    • Washer
    • Hot Tub
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 20, 2019
    We loved our stay in Islamorada. The property is spacious and gated offering lots of quiet privacy in a prime location close to everything, shopping and dining. We enjoyed...
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    About this property
    San Roc is a private home with 150 feet of oceanfront and spectacular views of open water with heated pool and spa. Beautiful 4 Bedroom 3 Bath Home situated on over 2.5 acre secluded wooded lot. Landscaped grounds in a premier area of Islamorada, Florida known as 'Millionaires Row' Enjoy...
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    Location Information
    Islamorada, Florida Keys 33070
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Alligator Reef is a truly special slice of paradise with two individual homes nestled on a privately gated oceanfront estate. The Conch House (pronounced konk), is a 3 bedroom, 2 bathroom ocean front home featuring beautiful views, ocean breezes, your own private pool, plus a private balcony to...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    100' Private Beach Front Ocean Front Estate1 / 42
    (2)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Heated)
    • DVD Player
    • Grill
    • Cable/satellite TV
    • Washer
    • Patio
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 15, 2018
    INCREDIBLE HOME ON THE BEACH!This beachfront home offered more amenities than any other home we have rented for vacation. Complete game room as well as kayaks and paddle...
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    About this property
    Welcome to Murphy’s Paradise, a one acre private gated beachfront estate in the heart of Islamorada, Florida. This home features a private beach, 5 bedrooms, 3 ½ baths, family room, living room, game rooms, pool and bar. This home can comfortably accommodate 10-12 people with room to spare....
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
    Blue Dolphin  Private Oceanfront 1.8 acre Estate on Millionaire's Row with Pool1 / 34
    (2)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Air Conditioning
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Ocean Views
    • Wi-Fi
    • Waterfront
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 28, 2019
    The location, the amenities, the house, and the pool area was perfect. Everything needed to spend a weeks vacation with your family is within this home. I bring my 3 grown...
    Reviewed April 17, 2019
    We are three families that vacation together, everyone was just amazed at the expansive ocean views and the size of the property and home. The pictures do not do justice to it...
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    About this property
    Beautiful Gated Oceanfront 1.8 Acre Estate located in Islamorada featuring amazing ocean views. 5 Bedrooms, 4 Baths, Winding Staircase, Expansive Ocean Views, Over 4000 Sq. Ft. of Living Space. Heated Pool, Sandy Back Yard, Gated Entrance Lined With Palm Trees. Enjoy the Ocean Views and...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Ocean Views
    • DVD Player
    • Waterfront
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    WELCOME TO PARADISE! 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 views from every room....
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
    CASA DORADO1 / 24
    (2)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Patio
    • Private Outdoor Pool (Heated)
    • Parking
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 11, 2018
    This is the third time we have stayed at Casa Dorado. It is a beautiful home in an amazing location. If you like fishing, boating,diving, snorkling, and amazing sunsets this is...
    Reviewed June 9, 2017
    Beautiful home with great access to boat launch and dockage at the house. Very neat and clean and every amenity you could want. Had some AC problems that Keys Holiday Rentals...
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    About this property
    <b> Minimum Rental: 28 Days </b> 'Casa Dorado' is an exceptional privately owned single family home located directly on Florida Bay on Lower Matecumbe Key in Islamorada. The house is named after the owners' favorite species of fish, the Dolphinfish, also known as Dorado in Spanish speaking...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Southern Diversion Islamorada see our fall special1 / 58
    (7)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 16 Quick View
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    • Porch
    • Cable/satellite TV
    • Parking
    • Outdoor Dining Area
    • Washer
    • Grill
    • Air Conditioning
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 18, 2015
    Our family of 13 people enjoyed a full week at this property. The house was amazing along with outstanding views. The property was well clean that includes the yard, pool and...
    Reviewed March 28, 2015
    I did not stay here but our friends did and we attended a wedding there and it was amazing. Beautiful place and very clean. I hope my kids get married there!
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    About this property
    This is an exclusive oceanfront private gated estate home with 200 feet of oceanfront on two acres. This property also features 200 feet of dock, Boat lift, Tiki hut on private beach, Heated pool and Wireless remote Internet. Southern Diversion has just been completely renovated. Brand new...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 16
    5 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    Amenities & Details
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Alligator Reef is a truly special slice of paradise with two individual homes nestled on a privately gated oceanfront estate. The Conch House (pronounced konk), is a 3 bedroom, 2 bathroom ocean front home featuring beautiful views, ocean breezes, your own private pool, plus a private balcony to...
    View all property information
    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 14
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Terrace
    • Balcony
    • Grill
    • Patio
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    'Irish Ayes' - Elegant tropical waterfront home with pool, Jacuzzi, dock and custom elevator. Plan your Keys getaway to this absolutely beautiful, spacious, tropical waterfront home located in the prestigious Venetian Shores subdivision of Islamorada. Enjoy unforgettable sunsets while relaxing on...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Little Bay Compound1 / 17
    (1)Excellent
    5 Bedrooms, 6 Bathrooms, Sleeps 18 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 20, 2019
    We searched for a perfect spot for our wedding, and we found it here. The compound was large enough for 16 people. The home and cottage were in great shape with everything you...
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    About this property
    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, accommodating a total of 18 people. The Upper Duplex &...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 18
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Parking
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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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    Location Information
    Islamorada, Florida Keys 33070
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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