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 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 events:No events allowed.

Tucked away in the vibrant Florida Keys, is our pristine Bungalow paradise. We are located in the heart of Islamorada, where the weather is always gorgeous, the fishing never disappoints, and the sunsets are mesmerizing. If you are seeking a relaxing getaway, look no further. Relax with the family in this cozy Island retreat. Completely remodeled! Come enjoy the community heated pool and a morning bike run. Enjoy the Florida Keys with your own private backyard and private parking.About pets:No pets allowed.About checkOut:Check out before 10:00 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: 21.About events:No events allowed.

Waterfront Islamorada 4/3 Deep Water Canal w direct easy access to ocean and bay with Amazing heated Pool and Hottub. Bring your boat or rent one locally and spend your keys vacation in paradise. Spacious Dock area .This home has it all ! Pool/hottub, pool table, King size beds, Wifi, Electronic Gated yard, Flat-screen Tvs, BBQ, screened porch , washer and dryer. More info /photos on insta under keyshouses Located near the best restaurants and shops in the Village of Islamorada Plantation Key Neighborhood.. Free access to Founders park and beach , Plenty of parking.Boat Dock-If you are bringing a boat please note on our dock there is a 28 ft area where you can tie up to during your stay. If your boat is bigger there are many marinas nearby where you can arrange to dock.Bus Tax ID #138028Tourism Tax Acct Active About pets:No pets allowed, service animals permitted.About checkOut:Check out before 10:30 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: 30.About events:No events allowed.

Islamorada Rental License: VR - 065 *** SATURDAY TO SATURDAY RENTALS ONLY!If your preferred dates are not available, check our other home, The Last Resort Too - VRBO #4357870, MM 77, or contact us with an inquiry here, SPECIFYING The Last Resort TooCHECK OUT A FEW WORDS FROM THE OWNERS BELOW THE INITIAL INFORMATION...4 bed/5 bath beachfront on over 1 acre with a private beach, heated pool & dockSeparate upstairs Den area sleeps up to 6 kids.* 7 Day minimum rental - Saturday to Saturday *SORRY, NO WEDDINGS OR LARGE EVENTS ALLOWED Max 8 adults + 4 childrenYou must be 25 years+ to rent this home and must be staying for the duration of the rental.Our house is one of the most highly sought-after vacation homes in Islamorada that regularly books years in advance. The Last Resort is a firm favorite of multi-generational families and friends looking to create memorable moments that last a lifetime in a lush, private, and tropical setting.As owners, we have spent 24+ years providing the best possible Keys experience for guests. Michele handles the day-to-day operations of the property and ensures guests have everything they need for a stress-free vacation. We believe that guests should not have to worry about 'extra or hidden' charges, so our rates INCLUDE many of the things other vacation rentals charge for, such as pool heat, BBQ gas, kayaks, and baby equipment. Though the property is self-catering, we supply many household items so you don't have to worry about purchasing them, such as laundry detergent, dishwasher detergent, garbage bags, kitchen paper, cleaning fluids, etc.We also don't charge a security deposit or pet fee. We operate on an honor & integrity system, giving our guests an authentic Keys experience that keeps them returning year after year as repeat guests.From years of international travel with our kids, one of my pet peeves was the amount of equipment that I had to pack just to go on vacation. Another was arriving at houses that were sparsely stocked or having to rent additional equipment. Greg and I made the commitment to provide as many supplies and equipment for our guests, from all kitchen equipment to baby equipment, from hairdryers & straighteners to lifejackets and water shoes, all to alleviate the need for guests to stuff their suitcases and truly make it a 'pack your shorts, flip-flops & toothbrush' kind of house.The Last Resort is truly in a beautiful setting, and we look forward to the opportunity to host you, your family, and your friends someday.Michele & Greg.... AND NOW THE HOUSE...Built in 1922, this historic Conch Style oceanfront executive retreat boasts overwhelming views of the Atlantic, large open verandas, 165 feet of private sandy beach, a 15 x 30 seaside heated swimming pool, 37 ft. concrete protected dockage on the canal adjacent to the house, and a gated entrance. Quiet seclusion awaits you at this unique destination.This 4-bedroom, 5-bath home with 4,000 square feet of living area is situated on over an acre in a private, tropical setting. Located in an upscale neighborhood in famed Islamorada, this fine home offers you the ability to relax, entertain, and enjoy the many recreational activities found only in the Florida Keys! Recognized by international publications as a preferred location for resort and swimwear photo sessions, the interior is casually furnished, tropically decorated, and offers every imaginable convenience.* Ralph Lauren* Victoria's Secret* Abercrombie & Fitch* Michael Kors* Opening shot Bloodlines* Promo shot HGTV Dream Home* Variety of European magazinesYou'll find an abundance of great island shops, full-service marinas, and popular local restaurants nearby! Ideal home for extended families, as most of the living space is on the ground level. Also, wide-covered front and back porches are ideal for outdoor entertaining/relaxing. The rear veranda overlooks breathtaking ocean views, palm trees, and a private sand beach. The front veranda overlooks a beautiful, tropical landscaped yard. Our home also has a rooftop deck overlooking the palm-lined sand beach and brilliant shades of the tropical ocean.Amenities: Two-story home with front and back covered porches, a 15x30 heated in-ground pool, a 165-wide private sand beach, and beautiful landscaping. House includes phone, high-speed wireless Internet/DSL line, dual-zone central air conditioning, ceiling fans in all rooms, 3 cable/smart TVs (both Masters & Living room)(2 smart TVs in the kids' Den, DVD player, and Bluetooth speakerFull kitchen includes a microwave, dishwasher, refrigerator, beverage fridge, coffee maker & Keurig 2.0, toaster, cooking utensils, and linens provided. 2 washers, 2 dryers, and 2nd fridge in the Laundry room. Jacuzzi tub in the downstairs Master bath. Gas grill (BBQ). Pets are allowed with advanced permission. 37-foot concrete private dockage with mains water and direct ocean access is available on our canal lot adjacent to the oceanfront home, with plenty of room for a boat trailer.There is one exterior camera on the front porch pointing towards the driveway. and a 2nd camera on the exterior of the laundry room door. There are no other cameras anywhere on or on the property.Feel free to send us an inquiry for any further information before making a booking decision. We are always happy to help.MicheleAbout pets:Pets allowed: dogs less than 50 lbs per pet (limit 2 pets total).Prior permission required..About children:Children allowed: ages 0-17.About customRules:Pro-rated refunds given in the event of a hurricane evacuation. For cancellations, refund given once replacement renter books property..IMPORTANT: Saturday to Saturday bookings ONLY..About smoking:Smoking is not permitted.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.