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Holiday Rentals with Pools in Cudjoe Key

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    $395 Average
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    Travellers to Cudjoe Key are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    9 Matching Rentals in Cudjoe KeyView all 30 rentals
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Oceanview Estate 15 minutes from Key West - 6 bedroom accommodate 13 guests1 / 34
    (48)Very good
    6 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    Family Retreat ocean front home with private pool1 / 18
    (13)Very good
    6 Bedrooms, 4 Bathrooms, Sleeps 18 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Hot Tub
    • Grill
    • Washer
    • Air Conditioning
    • Waterfront
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 July 2016
    The house is designed perfectly for a mixed aged family group. Lots of separate areas for different activities and also a large area for the whole group to celebrate together...
    Reviewed 19 June 2015
    12 of our family came down from NC & VA to celebrate a college graduation and fulfill some bucket list items. It was a classic road trip and the very best vacation imaginable...
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    About this property
    Oceanfront 6 bed/4 bath home with panoramic ocean view on Cudjoe Key. Sleeps 12+. Beach, Hot Tub, Floating Dock, Heated Pool, Kayaks and 540 square foot screened in porch overlooking the Atlantic ocean. This house has been very popular with large groups. Floating dock is great to fish and swim...
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    Location Information
    Cudjoe Key, Florida Keys 33042
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 18
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    Fandango1 / 25
    (12)Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Washer
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Hot Tub
    • Waterfront
    • DVD Player
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 August 2017
    Our family and friends had an amazing week at Fandango. Everything from the location, to the amenities was perfect. The house had all you needed to create unforgettable family...
    Reviewed 9 December 2016
    My daughter-in-law leased Fandango House for 3 days to celebrate the birthdays of my two children and myself. Fandango is a beautifully kept vacation rental that has all the...
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    About this property
    Designed as the ultimate vacation rental. Five Bedroom/Three Bath Oceanview Home with Heated Pool and Hot Tub. Panoramic Ocean Views. Sleeps 10+. Located on Cudjoe Key. Includes private boat dock, private beach, kayaks, and bikes. Weber BBQ grill, Lot's of lounge chairs and two hammocks....
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    Location Information
    Cudjoe Key, Florida Keys 33042
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 14
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    Oksana's Tropical Beach Oasis1 / 22
    (2)Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Private Garden
    • Air Conditioning
    • Parking
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 January 2017
    The house is very nice. They are upgrading many of the rooms...the kitchen is really nice. The view is spectacular and the large backyard is great. The fact that they allow...
    Reviewed 2 May 2016
    Our family of 3 couples and 2 singles stayed here in April and loved it. Rental process was smooth, management very nice and provided local info on places to eat and things to...
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    About this property
    Oksana's Tropical Beach Oasis is a spacious ocean front property with spectacular views and a large swimming pool with overflow spa. The beach area has not been dug out by man. We recommend you bring swim shoes to walk around in that area. The dock is currently under repairs after Hurricane Irma...
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    Location Information
    Cudjoe Key, Florida Keys 33042
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 14
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    Tropical Paradise Oceanfront Home with Pool1 / 24
    (10)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Internet Access
    • DVD Player
    • Waterfront
    • Cable/satellite TV
    • Washer
    • Air Conditioning
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 March 2017
    Our family of four loved everything about this property - the location, the kayaks and bikes that are provided, Cudjoe Bay (which is just steps from the deck), the view! So...
    Reviewed 19 July 2016
    I had originally reserved a larger house a few streets down from this one. That was when there was going to be a much larger group. However, due to the fact that some friends...
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    About this property
    2 Bedroom+/2 Bath+ Tropical Paradise Home with floating dock, small beach & heated dipping pool. This has been a popular honeymoon and anniversary celebration home for over 10 years. Very romantic. You wake up to the sunrise reflecting on the water and don't even have to get out of bed. This...
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    Location Information
    Cudjoe Key, Florida Keys 33042
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Tropical Blue Adventure Waterfront at Venture Out1 / 23
    (2)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • Waterfront
    • Hot Tub
    • DVD Player
    • Cable/satellite TV
    • Ocean Views
    • Children's Pool
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Comfortable and charming, this newer stilt home has everything you could want for a vacation for just the two of you, a few friends, or the whole family! Fantastic waterfront open canal views. Located on a 60' wide canal, you can bring your powerboat, jet ski, kayak, or what have you, and dock...
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    Location Information
    Cudjoe Key, Florida Keys 33042
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Wi-Fi
    • Washer
    • DVD Player
    • Ocean Views
    • Waterfront
    • Cable/satellite TV
    • Hot Tub
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    For your next Florida Keys vacation, reserve a stay at this waterfront home located on a canal with easy access to either the Atlantic or the Gulf. This home has everything you need to enjoy a relaxing vacation with resort amenities at your backdoor. Featuring 2 bedrooms, 1 bathroom. The master...
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    Location Information
    Cudjoe Key, Florida Keys 33042
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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