Islamorada Hotels with Private Pools

Welcome to Cheeca Lodge & SpaTurquoise water. Towering palms. Calm breezes. Imagine yourself whisked away to a tropical paradise where you indulge in mind, body, and spirit, as you rediscover an oasis called Cheeca Lodge & Spa. Romantic, serene, and dynamic, our Florida Keys Islamorada resort is a standard of excellence achieved by few. Be swept away by the casual elegance emanating from every detail and settle into the laid-back lifestyle of Islamorada.Stay in the Sportfishing Capital of the WorldLocated in the Sportfishing Capital of the World, Cheeca Lodge is a premier destination for serious anglers. Charter a boat and find over 500 species of fish within minutes from shore. The casual fisherman can cast a line from the end of our 525-foot pier – the longest in the Keys. A host of other activities can be found at our Islamorada luxury resort, including snorkeling, sea kayaking, bicycling, and scuba diving. Between activities, enjoy first-class dining at one of our three restaurants: Atlantic’s Edge, Mia Cucina, or Nikai Sushi.

Your island pool home awaits in Islamorada's Port Antigua! 3,500 square foot, 4 bedroom, 3 bathroom, high ceilings, tile & hardwood floors, state of the art kitchen w/ concrete counters & top of the line stainless appliances. Open, spacious and perfect for entertaining is how this home was designed. Walk out the great room french doors into an intimate pool setting with custom chickee & lounge area decorated with a vibe of Gilligan's Island meets The Ritz Carlton. Out back is 65ft of yacht dockage w/ shore power & water for water toys. Rare 2 car garage with golf cart, fishing rods, ping pong table/ game room, and bicycles provided. Private beach 1 minute by golf cart & ramp for owners in this golf cart approved community on Lower Matecumbe in Islamorada, the Village of Islands.About pets:No pets allowed.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 25.About events:No events allowed.

Gorgeous 30’ oceanfront heated pool. House on an exceptionally private, natural beach and oceanfront seawall in Islamorada - observation dock for paddle boarding, fishing and kayaking. Property is flanked by natural preserve on one side and has wide open expansive ocean views. The private beach is located along a wildlife protected turtle nesting beach that left natural for turtle nesting season. There is an incredible 180 degree water view from almost every room in the house. Spectacular sunrises flood the rooms with golden light reflected off the ocean. The sun rises over the water every morning within your view. The sunsets are equally stunning over the peninsula leaving the view with purple and pink clouds. Constant onshore breeze drifts through the house with pure, invigorating ocean scents. 2 Paddle boards and 2 kayaks are included with rental as the waters off the house are perfect for exploring by kayak. 2 cabanas for rest and relaxation - one by the pool and one the dock. The wildlife is stunning and you are bound to see amazing creatures during each outing! There is also an amazing State Park (an island) just a paddle away. Alligator Reef Lighthouse is on the horizon and the ocean views from the end of the observation dock are simply incredible. The oceanfront pool is heated to 86 degrees.The house is a 100% non-smoking property. The observation dock is for non-motorized vessels only as the tides can get very low during full moons.THIS PROPERTY RENTS SATURDAY TO SATURDAY Robbie's of Islamorada is down the street from the property a half mile and offering an outdoor restaurant, jet ski rentals, tarpon feeding, shops, fishing charters, snorkeling trips & sunset cruises to the Lighthouse.About the owner: Islamorada is absolute paradise - we love the island and happy to share the vacation house with guests looking to escape to a patch of paradise in the Keys. The is property is exclusively offered as a vacation rental so it is similar to staying at a hotel and is exceptionally clean and easy to enjoy.We privately own a total of 5 boutique vacation rentals in Islamorada:VRBO listing #1576833 (5 bedroom)VRBO listing #1054019 (5 bedroom)VRBO listing #1977457 (7 bedroom)VRBO listing #689629 (5 bedroom) (no boat dockage due to tides)LICENSE #: 26-0279 - IslamoradaAbout pets:No pets allowed.About checkOut:Check out before 10:00 AM.About children:Children allowed: ages 0-17.About customRules:Absolutely no smoking, no access to the rooftop..About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 24.About events:No events allowed.

Village of Islamorada - Vacation Rental License No. 24-0248This home is remodeled every year in some way or form...We try to make it interesting and fun particularly for our repeat customers. Our objective is to provide the most rewarding and awesome experience possible. From the most comfortable beds you can find, to the various cooking options and outdoor eating choices. You can pretty much live outside with all the amenities for outdoor living provided at this vacation rental. This property is NOT AVAILABLE for any special events including WEDDINGSAbout pets:Pets allowed: dogs less than 20 lbs per pet (limit 2 pets total).No more than 15 pounds; ask about pet policy..About checkOut:Check out before 10:00 AM.About children:Children allowed: ages 0-17.About customRules:No modifying TV connections to add on ancillary equipment to audio visual systems..Cancellations are up to 60- days before checkin to receive a full refund. If there is a medical emergency 100% full refunds granted before check in.,.About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.No where on the property is smoking allowed.About minBookingAge:Minimum age to rent: 21.About events:No events allowed.

Absolutely comfortable keys Home , great location to restaurants and activities, two bedroom and two full bath upstairs with lower level bedroom and 1/2 bath. Laundry lower level, outside shower on lower level, dock for up to a 60' boat. Internet/cable in living room. Local attractions include Founders Park marina, beach, recreation area, all types of fishing, Everglades National Park, World Wide Sportsman, snorkeling/diving, kayak, Islander, Diving Museum, lots of great restaurants.and supermarket closed by.About pets:Pets allowed.Small pets 25lbs Max.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.Can smoke outside.About minBookingAge:Minimum age to rent: 21.About events:No events allowed.