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Holiday Rentals near Founders Park

87000 Overseas Hwy, Islamorada, Florida 33036-3110
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    Travellers to Islamorada are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    All 274 Rentals in Islamorada
    3 bedrooms at Ocean Harbour Apartment, Islamorada, Florida Keys.1 / 32
    (3)Excellent
    1.0 kilometres from Founders Park
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Bay Front Beauty/ Summer Sea Must See!!!!1 / 19
    (4)Excellent
    1.4 kilometres from Founders Park
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Blue Dolphin  Private Oceanfront 1.8 acre Estate on Millionaire's Row with Pool1 / 38
    (4)Excellent
    0.8 kilometres from Founders Park
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    1.6 kilometres from Founders Park
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Terrace
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    About this property
    Welcome to Modern Keys Living with Bay Views! New from top to bottom!!! Newly remodeled and beautifully decorated 1st floor corner unit with a private entrance. Enjoy the mix of vintage and new furniture and the most comfortable sofas, beds, linens and more! This home is equipped with everything...
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    Islamorada, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    1.1 kilometres from Founders Park
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Waterfront
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    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
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    SPECTACULAR SUNSETS AND FRESH OCEAN BREEZE AWAIT YOU IN ISLAMORADA, FLORIDA!1 / 42
    (8)Very good
    0.2 kilometres from Founders Park
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Lower Matecumbe Key, Islamorada
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    0.2 kilometres from Founders Park
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    About this property
    Sleeps 8, 2 Story Townhome On The Bayside, Mile Marker 87 Our Islamorada beach modern decorated townhome is waiting for you. It’s a two story unit and third level loft; 2 Bedroom/2 Bath - sleeps 8. Next door is Founders Park & Plantation Yacht Harbor. A private gated community with 24hr...
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    Islamorada, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
    0.2 kilometres from Founders Park
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    About this property
    Come to Paradise and Enjoy it with Comfort! Located on Mile Marker 87 in Islamorada ( Fishing Capital of the World ), part of the Wonderful Florida Keys. Executive Bay Club is a Private Gated Community with 24 Hr Security, Heated Pool and Club House, Tennis Courts, Private Beach, Fishing off your...
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    Islamorada, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Islamorada Keys Home In Anglers Reef With Ocean View, Dock,  Pool & Beach1 / 35
    (140)Excellent
    3.0 kilometres from Founders Park
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    Islamorada, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
    Brand New / Totally Renovated Luxurious Home New To Rental Market.1 / 46
    (40)Excellent
    17.0 kilometres from Founders Park
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Islamorada, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Welcome to Paradise 'Sandbar Bungalow Villa' * Anglers Reef1 / 31
    (117)Excellent
    3.0 kilometres from Founders Park
    3 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    Islamorada, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 4
    Mitchell's Bayview Villa - Islamorada House on the Bay1 / 26
    (22)Excellent
    7.4 kilometres from Founders Park
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Islamorada, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Amazing Islamorada Sunsets, 2 Sandy Beaches, Pier Fishing, Pool, WiFi, Cable1 / 51
    (33)Excellent
    0.2 kilometres from Founders Park
    4 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Islamorada, Florida Keys
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 6
    Mitchell's Keys Villa - Private, Secluded House on the Bay1 / 24
    (51)Excellent
    7.4 kilometres from Founders Park
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Islamorada, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    16.6 kilometres from Founders Park
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Lower Matecumbe Key, Islamorada
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
    This is Paradise! Beautiful 2 Acre Oceanfront Beach, A MUST SEE. 3/2  Sleeps 61 / 34
    (55)Excellent
    5.9 kilometres from Founders Park
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Islamorada, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Beautiful Maison #3071 / 44
    (7)Excellent
    10.0 kilometres from Founders Park
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Lower Matecumbe Key, Islamorada
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    20.0 kilometres from Founders Park
    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    Lower Matecumbe Key, Islamorada
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 10
    20.0 kilometres from Founders Park
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Lower Matecumbe Key, Islamorada
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    1.0 kilometres from Founders Park
    3 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Lower Matecumbe Key, Islamorada
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 4
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    10.1 kilometres from Founders Park
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    Lower Matecumbe Key, Islamorada
    Condo/Apartment - 3 Bedrooms, 4 Bathrooms, Sleeps 6
    Wonderful 1 Bedroom Condo with Pool & Bay Views - Summer Seas #4201 / 29
    (2)Excellent
    1.7 kilometres from Founders Park
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Lower Matecumbe Key, Islamorada
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
    4.2 kilometres from Founders Park
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Lower Matecumbe Key, Islamorada
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    Stunning 3 Bedroom Bayfront Home - 194 Airstream Lane1 / 35
    (2)Excellent
    1.4 kilometres from Founders Park
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Lower Matecumbe Key, Islamorada
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    1.9 kilometres from Founders Park
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Lower Matecumbe Key, Islamorada
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    8.1 kilometres from Founders Park
    2 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    Lower Matecumbe Key, Islamorada
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 8
    4.2 kilometres from Founders Park
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Lower Matecumbe Key, Islamorada
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    Beautiful Oceanfront Property with Pool -- Alligator Reef - Conch & Lobster1 / 49
    (6)Very good
    3.8 kilometres from Founders Park
    5 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    Lower Matecumbe Key, Islamorada
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 14
    Private Tropical Oceanfront Estate with Pool and Beach1 / 50
    (31)Excellent
    16.1 kilometres from Founders Park
    6 Bedrooms, 7 Bathrooms, Sleeps 14 Quick View
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    Lower Matecumbe Key, Islamorada
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 14
    Unique 2 Bedroom Bay Front Home with Roof Top Terrace - 75130 Overseas Hwy.1 / 19
    (15)Excellent
    19.1 kilometres from Founders Park
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Lower Matecumbe Key, Islamorada
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    20.2 kilometres from Founders Park
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Lower Matecumbe Key, Islamorada
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    3.4 kilometres from Founders Park
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Lower Matecumbe Key, Islamorada
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
    Charming 2 Bedroom Canalfront Home in Islamorada1 / 22
    (1)Average
    16.8 kilometres from Founders Park
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Lower Matecumbe Key, Islamorada
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Charming 2 Bedroom Oceanfront Cottage with Pool and Dockage1 / 36
    (9)Excellent
    1.0 kilometres from Founders Park
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Lower Matecumbe Key, Islamorada
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    Wonderful 3 Bedroom Oceanfront Townhome with Pool - Windy Cove #11 / 19
    (6)Very good
    4.4 kilometres from Founders Park
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Lower Matecumbe Key, Islamorada
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    1.8 kilometres from Founders Park
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Lower Matecumbe Key, Islamorada
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
    *Searenity Beach House*  - Ocean Front Home with Views of the Atlantic Ocean1 / 24
    (5)Excellent
    18.2 kilometres from Founders Park
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Lower Matecumbe Key, Islamorada
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
    Gorgeous Anglers Reef Islamorada Florida Keys Oceanfront Pool1 / 50
    (94)Excellent
    3.0 kilometres from Founders Park
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Islamorada, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    2.3 kilometres from Founders Park
    4 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    Lower Matecumbe Key, Islamorada
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 9
    Beautiful Oceanfront Oasis with Pool - 83003 Old Hwy.1 / 50
    (1)Excellent
    6.3 kilometres from Founders Park
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Lower Matecumbe Key, Islamorada
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
    10.5 kilometres from Founders Park
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Lower Matecumbe Key, Islamorada
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    Great 4 Bedroom Home with Breathtaking Bay Views - 76004 Overseas Highway1 / 35
    (5)Average
    17.7 kilometres from Founders Park
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
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    Lower Matecumbe Key, Islamorada
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    1.7 kilometres from Founders Park
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Balcony
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    • Shared Outdoor Pool (Unheated)
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    • Terrace
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    Lower Matecumbe Key, Islamorada
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Oceanfront, Pool, Dock... Checks all the boxes!1 / 50
    (3)Very good
    17.0 kilometres from Founders Park
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Location Information
    Lower Matecumbe Key, Islamorada
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    20.9 kilometres from Founders Park
    7 Bedrooms, 5 Bathrooms, Sleeps 15 Quick View
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    • Air Conditioning
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    Location Information
    Lower Matecumbe Key, Islamorada
    Holiday Rental House - 7 Bedrooms, 5 Bathrooms, Sleeps 15
    15.3 kilometres from Founders Park
    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Parking
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    Pet friendly
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    Location Information
    Lower Matecumbe Key, Islamorada
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
    19.8 kilometres from Founders Park
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
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    Location Information
    Lower Matecumbe Key, Islamorada
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    19.7 kilometres from Founders Park
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Balcony
    • Terrace
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    • Cable/satellite TV
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    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Lower Matecumbe Key, Islamorada
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    19.5 kilometres from Founders Park
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Parking
    • Balcony
    • Patio
    • Air Conditioning
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    • Washer
    • Private Outdoor Pool (Unheated)
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Lower Matecumbe Key, Islamorada
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
    5.9 kilometres from Founders Park
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
    stayz logo
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    Amenities & Details
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Parking
    • Internet Access
    • Terrace
    • Balcony
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
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    Location Information
    Lower Matecumbe Key, Islamorada
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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