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Holiday Rentals with Pools in Cudjoe Key, FL

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    Travellers to Cudjoe Key are booking March dates now. Secure your holiday rental today, and have the perfect trip.
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    1 / 14
    3.5 of 5 stars (10) Average
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    1 / 24
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Amenities & Details
    • Private Outdoor...
    • Terrace
    • Air Conditioning
    • Internet Access
    • Washer
    • Balcony
    • Parking
    • Satellite TV
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    About this property
    3 Bedrooms, 3 Bathrooms, Sleeps 8 L’Anquesa – The Angel’s Key Luxury Amenities Include: Total renovation completed January 2014 2 master bedrooms suites with king beds, ensuite baths, flatscreen TVs and surround sound with incredible panoramic views 1 Guest room with 2 Queen... View all property information
    Location Information
    Cudjoe Key, Florida Keys
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • Satellite TV
    • Internet Access
    • Washer
    • DVD Player
    • Hot Tub
    • Grill
    • Air Conditioning
    • Children's Pool
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    About this property
    Tropical, Affordable Rental in Gated Community, Wi-Fi & Gas Grill Colorful tropical vacation home. The living room nicely decorated with tropical flare, has a flat screen TV with DVD, Directv W/DVR,two sofas, one is a queen size sleeper and comfortable bamboo chair. Dining area conveniently... View all property information
    Location Information
    Cudjoe Key, Florida Keys 33042
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Shared Outdoor Pool...
    • Hot Tub
    • DVD Player
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    • Waterfront
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    • Sauna
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    About this property
    For your next escape to the Florida Keys, reserve a stay at this delightful waterfront Cudjoe Key vacation rental home. Perfectly situated on a canal with easy access to the area’s most notable attractions, this serene house has everything you need for a relaxing island retreat! Featuring 2... View all property information
    Location Information
    Cudjoe Key, Florida Keys 33462
    1 / 20
    5 of 5 stars (8) Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 14 | Quick View
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    • Satellite TV
    • Washer
    • Internet Access
    • Private Outdoor...
    • Air Conditioning
    • Waterfront
    • DVD Player
    • Hot Tub
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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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.... View all property information
    Location Information
    Cudjoe Key, Florida Keys 33042
    5 of 5 stars Reviewed 12 September 2015
    This property really is wonderful. We had a fantastic 10 days here an would come back in a heart beat! The house has breath taking ocean views especially from the master bed and...
    4 of 5 stars Reviewed 17 April 2015
    Great location. As described. A multimillion dollar view from back porch. Well maintained grounds and a private master suite upstairs. There are dogs next door that might be an...
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    1 / 34
    4.5 of 5 stars (38) Very good
    6 Bedrooms, 3 Bathrooms, Sleeps 14 | Quick View
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    • DVD Player
    • Patio
    • Hot Tub
    • Washer
    • Satellite TV
    • Private Outdoor...
    • Air Conditioning
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
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    • Elder access
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    About this property
    White Ibis Inn away from the hustle of Key West activities, but close enough to the excitement when you want it and the Atlantic Ocean’s spectacular sunrises, sunsets and endless views of the starry nights. A private Caribbean-style accommodation with adjacent guest house with panoramic view of... View all property information
    Location Information
    Cudjoe Key, Florida Keys 33042
    4 of 5 stars Reviewed 31 December 2015
    We came with a very large group of family for our daughters wedding. While making reservations we decided we didn't want to be in all the noise and rat race of bust Key West...
    5 of 5 stars Reviewed 12 November 2015
    I was in vacation with my family (4 children) for the wedding of my oldest daughter. I am satisfied with everything. The house is comfortable, convenient, wonderful. The pool is...
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    1 / 22
    5 of 5 stars (2) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    • Washer
    • Waterfront
    • Internet Access
    • Private Outdoor...
    • Grill
    • Porch
    • Hot Tub
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
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    • Smoking allowed
    • Elder access
    • ?
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    About this property
    Beautiful four thousand plus square foot home located on Cudjoe Key. Private beach and 30 foot swimming pool with 10 foot waterfall hot tub. Huge master suite overlooking the ocean. The house comes with BBQ grill and single and double kayaks. Spectacular views can be enjoyed from the screened... View all property information
    Location Information
    Cudjoe Key, Florida Keys 33042
    5 of 5 stars Reviewed 1 week ago
    We had a great time, the house has everything, it is very relaxing. We had no problem with the WIfi and we had multiple devices. The large master bedroom upstairs is awesome...
    5 of 5 stars Reviewed 6 January 2014
    We are 3 families, 5 adults and 3 teenagers. The 4 bedrooms are each very private and quiet. There are 2 master bedrooms each with ensuite bathrooms; 1 upstairs and 1 downstairs...
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    1 / 22
    5 of 5 stars (6) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Private Outdoor...
    • Internet Access
    • DVD Player
    • Waterfront
    • Satellite TV
    • Washer
    • Air Conditioning
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • ?
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    About this property
    2 Bedroom+/2 Bath+ Tropical Paradise Home with floating dock, small beach, heated dipping pool and hot tub. 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... View all property information
    Location Information
    Cudjoe Key, Florida Keys 33042
    5 of 5 stars Reviewed 15 January 2015
    A lovely waterfront home facing south on Cudjoe Bay. Outside you have palms, a dock, hot tub, pool, hammock, bikes, kayaks, adirondack chairs, deck, umbrella table, flowers...
    5 of 5 stars Reviewed 10 January 2015
    In October I contacted owner of this property and I was glad it's was available! We were absolute in love with place from the moment we saw it! It has everything you've ever need...
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    1 / 24
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    Amenities & Details
    • Washer
    • Hot Tub
    • Satellite TV
    • Air Conditioning
    • Waterfront
    • Internet Access
    • Private Outdoor...
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This 5 bedroom 3 bath house with pool on ocean front property on Highway, located just 20 miles away from the famous Key west complete with WiFi. This lovely home has it's own huge pool area with full lounge chairs all the way around pool area, the pool is heated. Downstairs grill, upstairs grill,... View all property information
    Location Information
    Cudjoe Key, Florida Keys 33042