Hotels with pools in Islamorada

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.

With a stay at Pines & Palms Resort in Islamorada (Matecumbe), you'll be a 5-minute walk from Indian Key Historic State Park and 12 minutes by foot from Bud n' Mary's Dive Center. This beach hotel is 1 mi (1.6 km) from Hurricane Monument and 1.2 mi (1.9 km) from Florida Keys Brewing Co.. Relax on the private beach or enjoy other recreational amenities such as an outdoor pool and bicycles to rent. Additional features at this hotel include complimentary wireless internet access, concierge services, and wedding services. Take advantage of the hotel's room service. Need to unwind? Take a break at the bar/lounge, the beach bar, or the poolside bar for a tasty beverage. Featured amenities include limo/town car service, multilingual staff, and luggage storage. Free self parking is available onsite. Make yourself at home in one of the 26 individually decorated guestrooms, featuring kitchens with full-sized refrigerators/freezers and ovens. Flat-screen televisions with cable programming provide entertainment, while complimentary wireless internet access keeps you connected. Conveniences include separate sitting areas and microwaves, and housekeeping is provided daily.

Located in Islamorada (Matecumbe), Matecumbe Resort is within a 5-minute drive of Robbie’s of Islamorada and Indian Key Historic State Park. This beach resort is 1.9 mi (3 km) from Sunset Drive Beach and 2.9 mi (4.6 km) from Anne's Beach. Relax on the private beach or enjoy other recreational amenities such as an outdoor pool. Additional amenities at this resort include complimentary wireless internet access, a picnic area, and charcoal grills. The front desk is staffed during limited hours. Free self parking is available onsite. Make yourself at home in one of the 36 guestrooms, featuring kitchens with full-sized refrigerators/freezers and ovens. Rooms have private patios. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Conveniences include separate sitting areas and microwaves, and housekeeping is provided on request.

With a stay at La Siesta Resort & Villas in Islamorada (Matecumbe), you'll be within a 15-minute walk of Indian Key Historic State Park and Bud n' Mary's Dive Center. This beach resort is 1 mi (1.7 km) from Hurricane Monument and 1.3 mi (2.1 km) from Florida Keys Brewing Co.. Head down to the water and enjoy a day at the private beach, or take advantage of other recreational amenities including an outdoor pool and bicycles to rent. Additional amenities at this resort include wedding services and a picnic area. Guests can catch a ride to nearby destinations on the complimentary area shuttle. Take advantage of the resort's room service (during limited hours). Wrap up your day with a drink at the poolside bar. Cooked-to-order breakfasts are available daily from 7:00 AM to 11:00 AM for a fee. Guests will find features like a car charging station and an area shuttle. Make yourself at home in one of the 55 individually decorated guestrooms, featuring kitchenettes with refrigerators and microwaves. Your pillowtop bed comes with Egyptian cotton sheets. Cable television is provided for your entertainment. Conveniences include phones, as well as safes and desks.

With a stay at Sunset Inn in Islamorada (Matecumbe), you'll be a 5-minute walk from Islamorada Brewery & Distillery and 8 minutes by foot from Keys History & Discovery Center. This hotel is 0.5 mi (0.9 km) from Matecumbe United Methodist Church and 0.8 mi (1.3 km) from History of Diving Museum. Enjoy recreation amenities such as an outdoor pool or take in the view from a garden. Additional features at this hotel include complimentary wireless internet access, a picnic area, and barbecue grills. Featured amenities include luggage storage and a safe deposit box at the front desk. Free self parking is available onsite. Make yourself at home in one of the 30 air-conditioned rooms featuring refrigerators and flat-screen televisions. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Private bathrooms with showers feature complimentary toiletries and bidets. Conveniences include laptop-compatible safes and coffee/tea makers, and housekeeping is provided daily.

With a stay at La Jolla Resort in Islamorada (Matecumbe), you'll be steps from Islamorada Brewery & Distillery and 10 minutes by foot from Keys History & Discovery Center. This hotel is 0.6 mi (1 km) from Matecumbe United Methodist Church and 0.7 mi (1.1 km) from History of Diving Museum. Head down to the water and enjoy a day at the private beach, or take advantage of other recreational amenities, which include an outdoor pool. Additional amenities at this hotel include complimentary wireless internet access, concierge services, and a picnic area. The front desk is staffed during limited hours. Limited parking is available onsite. Make yourself at home in one of the 20 air-conditioned rooms featuring flat-screen televisions. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Bathrooms with showers are provided. Conveniences include coffee/tea makers and ceiling fans, and housekeeping is provided daily.

Beautiful 4-bedroom, 3.5 bath home in Angler's Reef. Located at MM85, this tastefully decorated, open floor plan features a newly renovated gourmet kitchen including all of the amenities you’ll need for a perfect stay – updated appliances, quartz countertops and breakfast bar. Enjoy viewing some of the local artwork as you stroll throughout the home. We pride our home for hosting large groups and the newly added large sectional pulls out as additional sleeping space. A queen bedroom with en-suite bathroom is conveniently located on the first floor. There is also a stylish powder bathroom on the first floor off the kitchen and living area. The 8-person dining table is a perfect space to play cards and enjoy meals with your friends and family, while the kitchen island seats 5 people. A console table off the kitchen offers all the essential openers, koozies, martini shaker and plenty of games for a fun vacation! The porch off the family room offers ocean views, 2 comfortable chairs w/side table, an outdoor dining table seating 4-people and a grill. The second floor includes 3 bedrooms. Upstairs, the master bedroom features a four-poster king bed, en-suite bathroom with double sinks and an updated shower with bench. The master bedroom opens up to its own private covered porch with spectacular views of the ocean, 2 sofa lounge and 3 club chairs. The two upstairs bedrooms offer queen beds with a partial ocean view. There’s a full bathroom located between these two rooms. You’ll conveniently find a laundry closet with washer and dryer in the upstairs hallway that also offers a steamer and iron. All bedrooms include TV’s and wireless internet service provided. This rental includes boat slip #14, which can accommodate boats up to 31 feet in length. Angler’s Reef is a wonderfully maintained and gated community in Islamorada, the fishing capital of the world. In Islamorada you can swim with dolphins, go dive the reefs, sport fish or just simply enjoy the salt-water life and great restaurants.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.

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 operation of the property and ensures that guests have everything needed 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 the honor & integrity system, giving our guests an authentic Keys experience that keeps them returning year after year as repeats.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, 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 as a preferred location by international publications for resort and swimwear photo sessions, the interior is casually furnished, tropically decorated, and provides 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 due to the majority of living space being 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 which includes front and back covered porches, 15x30 heated in-ground pool, 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 kid's 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 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.

Introducing the "Bonefish House," at Tarpon Point!This opulent, luxury, home is equipped to accommodate eight adults with 4 bedrooms & 4 full bathrooms. The open living space offers easy entertaining and direct panoramic views of the community pool and Atlantic Ocean. The well-appointed and fully equipped chef’s kitchen offers the finest high-end appliances to satisfy everyone’s culinary needs. Whether you are cooking for two or eight, there is plenty of room for everyone to have a seat at the table. Or, eat al fresco right off the main level balcony and enjoy the balmy ocean breeze. The integrated Sonos system offers the ultimate wireless home sound system that streams off the house WiFi network and fills the home with brilliant sound.  This sought after gated community boasts beautifully landscaped grounds, oceanfront pool with heater and chiller, 420 feet of ocean frontage, an observation dock you can fish from, and a beach area where you can launch your paddle boards, kayaks or canoes. Indian Key State Park is just a paddle away! Wake up to exquisite sunrises and ocean views right from the master bedroom, which offers its own private balcony for a birds eye view, a king size bed, a private en suite bath with double vanities, a separate shower and a soaking tub. There are two additional bedrooms upstairs, each equipped with king beds and en suites. There is an additional queen bedroom on the main level with a neighboring bathroom. Each bedroom has it's own flat screen smart TV with streaming service capabilities.  Located at mile marker 77.5, at the northern tip of Lower Matecumbe Key and conveniently located across the street is the world famous Robbies which offers fishing charters, snorkel charters, restaurants, shops, parasailing, kayaks / paddle board rentals. You can even hand feed the enormous tarpon! Downtown Islamorada is just 4 miles north which offers endless restaurants, breweries, shopping, activities and grocery. Love The Bonefish House at Tarpon Point but need dockage? Robbies of Islamorada is located directly across the street from Tarpon Point and offers transient boat slip rentals. There is also Safe Harbor Islamorada Marina which is approximately 3.3 miles north and Caloosa Cove Marina which is approximately 3.7 miles south. Both offer transient boat slip rentals. With our Coastal Concierge Service we can have your groceries and adult beverages chilling in the fridge prior to your arrival so you can settle straight into vacation mode. Just send us a list and we will take care of the rest! Yes, it’s that easy!  BOOK TODAY before it's too late! Have any questions? Feel free to ask away! Coastal Vacation Rentals of the Florida Keys is located in the heart of Islamorada and has a full office staff to ensure you have the best vacation possible.Cancellation Policy: A one-half (50%) deposit is required at the time of booking. This deposit is fully refundable, minus any non-refundable fees, if the reservation is cancelled at least 180 days before check-in. If the cancellation occurs within 180 days of the occupancy date, the one-half (50%) reservation deposit shall be non-refundable. The remaining balance is due 60 days prior to arrival, at which point the full reservation becomes non-refundable. However, if we are able to rebook the property for the same dates and rate, a full or partial refund may be issued based on the new booking.Instant quote prices and calendar availability are subject to change without notice and are not guaranteed. Please contact Coastal Vacation Rentals of the Florida Keys to speak to one of our associates to confirm pricing and availability.Islamorada Vacation Rental License #: 25-0093About pets:No pets allowed.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About customRules:Tarpon Point Homeowners Association Rules for Rentals (Separate Document).Coastal Vacation Rentals of the Florida Keys Vacation and Short-Term Rental Agreement (Separate Document).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.

We are proud to announce- Castaway Island has been named for KW people’s choice awards as a FINALIST for Best Vacation Rental in the Florida Keys. . Being named top three of over 6,000 vacation rentals is the honor of a lifetime. Experience the ultimate tropical getaway in our enchanting bungalow, boasting 82 consecutive 10/10 guest reviews! Our hosts' lifetime in hospitality shines through in the meticulous restoration and thoughtful amenities, ensuring an unparalleled vacation experience. Discover your home away from home, where every detail is designed to exceed your expectations.About pets:Pets allowed: dogs less than 20 lbs per pet (limit 2 pets total).About checkOut:Check out before 10:00 AM.About children:Children allowed: ages 0-17.About customRules:1 boat and trailer allowed.No More than 4 visitors. Visitors may not use the community pool.,Quite time is 10pm. pool hours are 8am to dusk.About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 23.About events:No events allowed.