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Vacation Rentals near Founders Park

87000 Overseas Hwy, Islamorada, Florida 33036-3110
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    Travelers to Islamorada are booking August dates now. Secure your vacation rental today, and have the perfect trip.
    All 116 Rentals in Islamorada
    Newly refinished  condo open water views very nice1 / 22
    (7)Excellent
    1.1 miles from Founders Park
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Bayside Condo, marina, pool and beach1 / 35
    (18)Very good
    1.1 miles from Founders Park
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    3 bedrooms at Ocean Harbour Apartment, Islamorada, Florida Keys.1 / 32
    (3)Excellent
    0.6 miles 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
    0.8 miles from Founders Park
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Waterfront
    • Washer
    • Cable/satellite TV
    • Wi-Fi
    • Ocean Views
    • Children's Pool
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 10, 2017
    Everything was perfect. Weather was great, the unit was clean and fully furnished with everything we needed. The other vacationers and full-time residents were friendly and...
    Reviewed May 5, 2016
    This condo was to die for. The decor was fabulous and the location was perfect and close to many restaurants. The sunset from the balcony was breathtaking. The owner was a...
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    About this property
    Beautiful / tropical decorated one bedroom, one bath water front condo in Summer Sea Condominiums located at Mile Marker 88.5 Bayside Islamorada, FL. Bayside means amazing open water views & world famous Florida Keys sunsets from your own private balcony overlooking the Florida Bay. You can also...
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    Islamorada, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    Blue Dolphin  Private Oceanfront 1.8 acre Estate on Millionaire's Row with Pool1 / 38
    (3)Excellent
    0.5 miles from Founders Park
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Air Conditioning
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    • Private Outdoor Pool (Heated)
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    • Waterfront
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    Pet friendly
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    Reviewed July 15, 2020
    Perfect vacation house on the ocean, close to everything. The spacious house was immaculate when we checked in. The owner was extremely friendly and responsive. It was perfect...
    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...
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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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    Islamorada, Florida Keys
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 12
    LYONS LANDING1 / 25
    (1)Excellent
    1.2 miles from Founders Park
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Private Outdoor Pool (Heated)
    • Patio
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    Pet friendly
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    Reviewed June 27, 2017
    Every room is comfortable,charming and the property managed to make you feel comfortable and at home..with every amenity..including an ice maker..so nice to have here in The...
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    About this property
    Minimum Rental: 28 Days 'Lyons Landing' is an exceptional VENETIAN SHORES single family home with pool, dock, boat lift and outdoor living area! Everything you need for a spectacular holiday awaits you in this extraordinary home. 3 bedrooms and two baths on the upper level plus a bedroom and...
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    Islamorada, Florida Keys
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    1.1 miles from Founders Park
    1 Bedroom, 1 Bathroom, Sleeps 5 Quick View
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    • Central Heating
    • Terrace
    • DVD Player
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    • Sauna
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ****Recently updated paint, furniture and a Beauty Rest Mattress!!**** Looking to escape reality? Look no further! Spacious 1 bedroom/1 bathroom condo located in the newly renovated Summer Seas Condominiums. Sit back and relax at the pool, go swimming at the private beach. Feeling adventurous?...
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    Islamorada, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 5
    Lazy Daze Beach House 5 Star Modern Oceanfront Islamorada Townhome on the Beach!1 / 34
    (1)Excellent
    1.2 miles from Founders Park
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    • Waterfront
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    Pet friendly
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    Smoking allowed
    Reviewed January 31, 2020
    Our first visit to the Florida keys and we wanted explore! But, I like to have my conveniences (ok, I hate sleeping in a tent!) This condo was quiet-Loved that! Islamorada is...
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    About this property
    Lazy Daze Beach House is a piece of paradise literally on the Beach! Gorgeous and all new! One King plus set of Full/Twin bunk beds, spacious gourmet kitchen with glass atrium dining. Completely renovated, designer finished, all new gorgeous home, no expense spared! Private oceanfront townhouse...
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    Islamorada, Florida Keys
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    1.2 miles from Founders Park
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
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    • Private Outdoor Pool (Heated)
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    Pet friendly
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    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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    Islamorada, Florida Keys
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 10
    1.0 miles 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
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    Islamorada cottage on deep water canal1 / 15
    (2)Excellent
    1.2 miles from Founders Park
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Waterfront
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    • Cable/satellite TV
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 12, 2020
    My husband and I thoroughly enjoyed our stay. The apartment was very clean and most comfortable. Well-stocked kitchen, included dishwasher & wine cooler. Screened-in porch...
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    About this property
    Our cottage is located in a quaint and quiet neighborhood on a deep water canal, Bayside at Mile Marker 89. A concrete boat dock is available for a 30 foot boat and a fish cleaning station. There is easy ocean access through Snake Creek or Tavernier Creek. The fenced private back garden has a...
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    Islamorada, Florida Keys
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    0.6 miles from Founders Park
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Waterfront
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    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
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    PARADISE AWAITS YOU IN ISLAMORADA, FLORIDA!1 / 42
    (8)Very good
    0.1 miles from Founders Park
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Lower Matecumbe Key, Islamorada
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    0.1 miles 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
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 8
    0.1 miles 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
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Islamorada Keys Home In Anglers Reef With Ocean View, Dock,  Pool & Beach1 / 35
    (136)Excellent
    1.8 miles from Founders Park
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    Islamorada, Florida Keys
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 4
    Brand New / Totally Renovated Luxurious Home New To Rental Market.1 / 46
    (40)Excellent
    10.6 miles from Founders Park
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Islamorada, Florida Keys
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Welcome to Paradise 'Sandbar Bungalow Villa' * Anglers Reef1 / 31
    (114)Excellent
    1.8 miles from Founders Park
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Islamorada, Florida Keys
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Beautiful Water Front in Angler's Reef with View of Sand Bar with Boat Slip1 / 31
    (104)Excellent
    2.0 miles from Founders Park
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Islamorada, Florida Keys
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Mitchell's Bayview Villa - Islamorada House on the Bay1 / 26
    (22)Excellent
    4.6 miles from Founders Park
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Islamorada, Florida Keys
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Amazing Islamorada Sunsets, 2 Sandy Beaches, Pier Fishing, Pool, WiFi, Cable1 / 50
    (33)Excellent
    0.1 miles from Founders Park
    4 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Islamorada, Florida Keys
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 6
    Mitchell's Keys Villa - Private, Secluded House on the Bay1 / 24
    (51)Excellent
    4.6 miles from Founders Park
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Islamorada, Florida Keys
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
    0.3 miles from Founders Park
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Lower Matecumbe Key, Islamorada
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    This is Paradise! Beautiful 2 Acre Oceanfront Beach, A MUST SEE. 3/2  Sleeps 61 / 34
    (55)Excellent
    3.6 miles from Founders Park
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Islamorada, Florida Keys
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Beautiful Maison #3071 / 44
    (7)Excellent
    6.2 miles 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
    Beautiful 3 Bedroom Condo with Ocean Views Located in Lower Matecumbe - Bay Harb1 / 30
    (5)Very good
    12.4 miles from Founders Park
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Balcony
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    Lower Matecumbe Key, Islamorada
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    0.5 miles from Founders Park
    7 Bedrooms, 7 Bathrooms, Sleeps 16 Quick View
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    Lower Matecumbe Key, Islamorada
    Rental Home - 7 Bedrooms, 7 Bathrooms, Sleeps 16
    Beautiful Anglers Reef # 1361 / 41
    (10)Excellent
    2.1 miles from Founders Park
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    Lower Matecumbe Key, Islamorada
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 4
    Wonderful 1 Bedroom Condo with Pool & Bay Views - Summer Seas #4201 / 29
    (2)Excellent
    1.1 miles 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
    Alligator Reef - Conch Home1 / 29
    (3)Very good
    2.2 miles from Founders Park
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Lower Matecumbe Key, Islamorada
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Beautiful Oceanfront Property with Pool -- Alligator Reef - Conch & Lobster1 / 49
    (6)Very good
    2.3 miles from Founders Park
    5 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    Lower Matecumbe Key, Islamorada
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 14
    Two acre oceanfront estate home in Islamorada - Southern Comfort1 / 50
    (28)Excellent
    10.0 miles from Founders Park
    6 Bedrooms, 7 Bathrooms, Sleeps 14 Quick View
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    Lower Matecumbe Key, Islamorada
    Rental Home - 6 Bedrooms, 7 Bathrooms, Sleeps 14
    Tastefully Renovated Townhome with Great Community Amenities - Executive Bay G51 / 35
    (2)Very good
    0.1 miles from Founders Park
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Lower Matecumbe Key, Islamorada
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    Unique 2 Bedroom Bay Front Home with Roof Top Terrace - 75130 Overseas Hwy.1 / 19
    (13)Excellent
    11.9 miles from Founders Park
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Lower Matecumbe Key, Islamorada
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Charming 2 Bedroom Canalfront Home in Islamorada - 102 Columbus Dr.1 / 22
    (1)Average
    10.4 miles from Founders Park
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Lower Matecumbe Key, Islamorada
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Leatherback Cottage - Charming 2 Bedroom Oceanfront Cottage1 / 36
    (9)Excellent
    0.6 miles from Founders Park
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Lower Matecumbe Key, Islamorada
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    Wonderful 3 Bedroom Oceanfront Townhome with Pool - Windy Cove #11 / 19
    (6)Very good
    2.7 miles from Founders Park
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Lower Matecumbe Key, Islamorada
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    *Searenity Beach House*  - Ocean Front Home with Views of the Atlantic Ocean1 / 24
    (5)Excellent
    11.3 miles from Founders Park
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Lower Matecumbe Key, Islamorada
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 10
    Gorgeous Anglers Reef Islamorada Florida Keys Oceanfront Pool1 / 49
    (94)Excellent
    1.8 miles from Founders Park
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Islamorada, Florida Keys
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    Beautiful Oceanfront Oasis with Pool - 83003 Old Hwy.1 / 50
    (1)Excellent
    3.9 miles from Founders Park
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Lower Matecumbe Key, Islamorada
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 12
    Stunning 3 Bedroom Condo with Basin & Ocean Views Located in Lower Matecumbe - B1 / 34
    (16)Excellent
    12.6 miles 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
    Maison Matecumbe #303 - 3 Bedroom Oceanfront Townhome in Premier Gated Complex1 / 50
    (6)Excellent
    6.3 miles from Founders Park
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Lower Matecumbe Key, Islamorada
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Great 4 Bedroom Home with Breathtaking Bay Views - 76004 Overseas Highway1 / 35
    (5)Average
    11.0 miles from Founders Park
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Lower Matecumbe Key, Islamorada
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    4.1 miles from Founders Park
    6 Bedrooms, 11 Bathrooms, Sleeps 14 Quick View
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    Lower Matecumbe Key, Islamorada
    Rental Home - 6 Bedrooms, 11 Bathrooms, Sleeps 14
    Port of Call C2 - Townhome with Oceanview1 / 45
    (1)Excellent
    1.3 miles from Founders Park
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    Lower Matecumbe Key, Islamorada
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 4
    Oceanview Maison Matecumbe #306 - Beachy 3 Bedroom Condo with Ocean Views1 / 21
    (5)Very good
    6.3 miles 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
    1.0 miles from Founders Park
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Experience high-end coastal luxury while staying at “Sea Breeze 41” in the highly sought-after Coral Harbour Club Condominium (CHC). A 30' Boat Slip is available in the CHC Marina. Your spacious 3 Bedroom / 2 Bathroom island getaway exudes luxury tropical vibes and is professionally decorated in...
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    Islamorada, Florida Keys
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Islamorada Oceanfront Home In Anglers Reef Ocean Views, Dock, Comm Pool & Beach1 / 50
    (65)Excellent
    1.9 miles from Founders Park
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Islamorada, Florida Keys
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    Canalfront 2 bedroom up and 1 bedroom down in Venetian Shores - 107 San Remo1 / 36
    (3)Excellent
    0.9 miles from Founders Park
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Location Information
    Lower Matecumbe Key, Islamorada
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Stunning 3 Bedroom Condo with Oceanviews Located in Lower Matecumbe - Bay Harbou1 / 26
    (7)Very good
    12.7 miles from Founders Park
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Lower Matecumbe Key, Islamorada
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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