58,368 properties available

Located in Islamorada, Florida, United States. Newly Renovated - 2-bedroom state of the art condo Islamorada. Perfect Location! The Palms - IslamoradaBrand New - Ripped down to the studs and just completed a $150k remodel with state of the art everything. The location of the Palms is absolutely perfect for all of your Keys adventures. Right next to Lazy Days, Bud & Mary’s, and Papa Joes opening later this month. The unit has an amazing view of the Pool, Jacuzzi, and Alligator Reef. Everything inside is brand new including Too go the line LG appliances, Cutco knives, CusinArt Mixer, Espresso and Coffee Machines, a Chefs kitchen any chef would be proud of. Google Homes’ in every room, 2 brand new King Size, high end Beds with Cool Memory Foam and Cotton Sheets. Each room has a brand new smart TV (55” in each bedroom)and the living room has an 75” 8k Neo QLED TV which makes you feel like you are in the game. Pull out high end sofa with Queen size bed, and leather recliner for those lazy days in the Keys. Bathrooms include two walk in

Located in Islamorada, Florida, United States. Marlin House @ Tarpon Point Summary:Stunning ocean views from all living levels & a waterfront pool!The Space:Welcome to the captivating Marlin House, an extraordinary 4-bedroom, 4-bath retreat nestled in the scenic paradise of Islamorada. Prepare to be enthralled by its exquisite design, unparalleled amenities, and sweeping ocean vistas that grace every level of this remarkable abode. Your journey begins as you pass through the gates of Tarpon Point, an exclusive enclave comprised of just twelve oceanfront residences. Within this private sanctuary lies Marlin House, waiting to envelop you in a world of sheer luxury.As you step foot inside Marlin House and ascend to the main living level, a symphony of awe-inspiring ocean views unfolds before your eyes. The sheer beauty of the surrounding turquoise waters will leave you breathless. Adjacent to the living area, an elegant dining room and a chef's kitchen beckon, promising unforgettable culinary experiences and convivial gatherings. This

Located in Islamorada, Florida, United States. Harbor house 2 Bedrooms, 2 Baths, Partial Ocean View Partial Ocean View 1 King Bed, 1 Queen Bed, 1 Pull OutResort guests stay in warm and inviting Caribbean-style homes. Rich mahoganies, teaks and Tommy Bahama furnishings all provide a unique experience.Many of the homes are named after one of the specimen palm trees on the property. Each home enjoys privacy among native gardens.Guests enjoy the beautiful Caribbean decor and high, open ceilings. Solid wood Anderson doors and windows, chiseled stone or tile flooring, open living and dining area all add to your tropical experience. Wrap-around outdoor verandas and comfortable lounging chairs create a seamless transition to outdoor living where you are just steps away from our one-of-a-kind tropical garden beach-entry pool.This home includes a full washer-dryer, Weber BBQ gas grill, wireless Internet, and cable TV.

Located in Islamorada, Florida, United States. Island pool home awaits in Islamorada's Port Antigua Your island pool home awaits in Islamorada's Port Antigua! 3,500 square foot, 3 bedroom, additional 2nd floor loft that serves as 4th bedroom with daybed, 3 bath, 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.

Located in Islamorada, Florida, United States. Custom-Built Oceanfront Caribbean Home w/ Gorgeous Ocean & Sunrise Views Custom designed and built from the ground up by resort owner Phil Sena – with nothing compromised – this luxurious Caribbean home is on the ocean’s edge with 180 degrees of unobstructed ocean views and sunrises. With complete privacy, this site is home to famous movie shoots, celebrity weddings and family reunions.About The Caribbean ResortOur Caribbean homes are named in honor of Hemingway, the beautiful Canary Island Jamaican Malayan Princess and Royal Palm trees that grace our resort. These homes rest on white-sand grounds among luxuriant tropical flower gardens and arching palms that sway in the gentle ocean breezes. Just steps away from the emerald-green oceans edge. Endless piers and a beach-entry pool awaits your arrival. Coconut palms arching gracefully over the pool. Fresh water lapping at your toes as you enter the beach. Our one-of-a-kind pool is a natural oasis that gives life to gardens of tropical fl

Located in Islamorada, Florida, United States. Ocean Front 4 Bedroom Estate with Private Beach Enjoy all the beauty of Islamorada's clear blue waters from your private beachfront estate. Turtle Nest Estate features an exotic wood deck surrounding a custom pool overlooking a private sugar sand beach on the Atlantic Ocean. Newly built-in outdoor shower! This home features an inviting living room with a sliding glass wall and a stunning 180-degree ocean view. You'll love to call Turtle Nest "your home away from home". Key Features of Turtle Nest: -The kitchen includes all your usual appliances and tableware to feel at home – Cinema media room- TVs in the living room and bedrooms- 150' Private beach- Viewing dock- Pool and spa- 2 kayaks onsite for guest use- Enough parking for several vehicles and/or boat trailers- Minimum 7-day rental- No PetsVR LICENSE #24-0363** Sargassum seaweed affects the coasts of the Florida Keys. Islamorada has its share, which ebbs and flows based on winds and tides, collecting on the shoreline at different t

Located in Islamorada, Florida, United States. Luxurious Caribbean 2 Bedroom 2 Bath Home Guests enjoy the beautiful Caribbean decor and high, open ceilings. Solid wood Anderson doors and windows, chiseled stone or tile flooring, open living and dining area all add to your tropical experience. Wrap-around outdoor verandas and comfortable lounging chairs create a seamless transition to outdoor living where you are just steps away from our one-of-a-kind tropical garden beach-entry pool.This home includes a full washer-dryer, Weber BBQ gas grill, wireless Internet, and cable TV.2 Bedrooms, 2 baths. Caribbean homes with 450-foot fishing pier and beach entry pool keep guest coming back. Its the off-shore fishing and diving that makes it so hard to leave. Located on a deep-water channel with protected dockage. 1 King Bed, 2 Full Beds, 1 Pull Out

Located in Islamorada, Florida, United States. Charming cottage on the Florida Bay in the heart of Islamorada with pool, dockage, beach + more The Bay View Cottage is one of three private homes located at Mermaid's Bay Boutique Estate. Located in the heart of Islamorada, just moments away from top attractions and restaurants, this secluded estate is situated directly on the bay. Secured by a gated entrance, the property sprawls over 3.5 meticulously maintained acres, with over 300 feet of bay frontage, protected dockage, and a resort-style pool and hot tub.Nestled within one captivating property, our collection of vacation rentals at Mermaid's Bay includes three individual homes, each with their own allure and privacy. The homes may be rented individually or collectively and are available for weekly or longer rentals. (Note: This listing is for booking JUST the Bay View Cottage.)The original Florida Keys charm has been preserved and tastefully updated throughout this romantic 2/1 '60s era cottage. Two sets of French doors off the o

Located in Islamorada, Florida, United States. Your Ultimate Keys Getaway Awaits! Welcome to your dream getaway at Coastal Cove Villa! Nestled in the heart of downtown Islamorada, this spacious 4-bedroom, 4-and-a-half-bathroom abode offers the perfect blend of comfort and luxury for your vacation retreat.As you step through the front door, you'll be greeted by a warm and inviting atmosphere, where relaxation meets style. The open-concept living area boasts plush sofas and modern decor, providing an ideal space for lounging and catching up with loved ones. Whip up your favorite meals in the fully equipped kitchen, complete with stainless steel appliances and ample counter space, perfect for preparing delicious feasts.When it's time to unwind, retreat to one of the four cozy bedrooms, each thoughtfully appointed with comfortable furnishings and soft linens to ensure a restful night's sleep. With 4 and a half bathrooms, there's no need to worry about sharing space – everyone can enjoy their own private oasis.Step outside to the privat

Located in Islamorada, Florida, United States. Caribbean-Style Family Home w/ Full Kitchen, WiFi, Grill, & Outdoor Veranda Resort guests stay in warm and inviting Caribbean-style homes. Rich mahoganies, teaks and Tommy Bahama furnishings all provide a unique experience.Many of the homes are named after one of the specimen palm trees on the property. Each home enjoys privacy among native gardens.Guests enjoy the beautiful Caribbean décor and high, open ceilings. Solid wood Anderson doors and windows, chiseled stone or tile flooring, open living and dining area all add to your tropical experience. Wrap-around outdoor verandas and comfortable lounging chairs create a seamless transition to outdoor living where you are just steps away from our one-of-a-kind tropical garden beach-entry pool.This home includes a full washer-dryer, Weber BBQ gas grill, wireless Internet, and cable TV.About The Caribbean ResortOur Caribbean homes are named in honor of Hemingway, the beautiful Canary Island Jamaican Malayan Princess and Royal Palm trees th

Located in Islamorada, Florida, United States. Royal Palm South 3 Bedrooms, 3 Baths, Ocean Front, Marina King, Queen, 2 twins, 1 pullout. Custom designed and built from the ground up by resort owner Phil Sena with nothing compromised this luxurious Caribbean home is on the oceansedge with 180 degrees of unobstructed ocean views and sunrises. Withcomplete privacy, this site is home to famous movie shoots, celebrityweddings and family reunions.Caribbean homes with 450-foot fishing pier and beach entry pool keep guestcoming back. Its the off-shore fishing and diving that makes it so hard toleave. Located on a deep-water channel with protected dockage

Located in Islamorada, Florida, United States. BRAND NEW Island-design home located in Islamorada fishing capital of the world! The Pink Sands House is located in the beautiful Lower Matecumbe island in close proximity to all your Class-A shopping, dining, and fishing needs. The Island-Design House is located in a quiet, private community with your own private gated sandy beach area with sunset views and crystal clear warm waters. For area info call or text Alexis at (305) 345-7217. Also, per month COMPLIMENTARY HOUSE CLEANING will be occur for rentals 2 or more months. Please note prices are subject to change based on season, holidays, occupancy, and weekly rates.

Located in Islamorada, Florida, United States. Large bay-front home with dockage, pool and beach in the heart of Islamorada The Dock View House is one of three homes at Mermaid's Bay Boutique Estate. This private waterfront oasis sprawls 3.5 acres in the heart of Islamorada, just moments away from all of the top attractions and restaurants. The estate features over 300 feet of open-water views, a large boat basin and a resort-style pool and spa. This estate-style home was originally built in the 1940s and has been preserved and tastefully updated to maintain the Florida Keys charm. Large windows offer waterfront views out of almost every room. In the heart of the house is a double-sided fireplace (non-working), with a chef-style kitchen and dining room on one side, and a vaulted-ceiling living room and solarium on the other. To the left of the house are two ensuites, one downstairs with two queen size beds and one upstairs with a king bed. There is also a half-bath located in the stairwell hallway. The right side of the house mirro

Located in Islamorada, Florida, United States. Experience Life in Islamorada: 1BR Condo Immerse yourself in our spacious 1-bedroom, 2-bathroom suite, offering a delightful haven for guests. Relax in the bedroom with two queen beds, an ensuite bathroom, and a private balcony. The living area features a snug queen sofa bed, a functional kitchen with a dining table for four, a second bathroom, and an additional balcony. While our property boasts an oceanfront location, not all units guarantee direct ocean views.At Caloosa Cove Resort, enjoy breathtaking vistas, a heated swimming pool, a serene beachfront, a convenient General Store, boat slips, and invigorating boat charters. With plenty of activities nearby, it's the perfect destination to unwind and fully immerse yourself in the captivating ambiance of Islamorada. Room assignments are based on availability at check-in, and specific views or locations cannot be guaranteed. Thank you for your understanding.

Located in Islamorada, Florida, United States. Ideal Mix of Comfort and Value! Pool, Free Parking, Near Anne's Beach & Sea Oats Discover island adventures with us! Explore Islamorada’s beachfront, soak in Alligator Reef Lighthouse views, or dive into water sports. Enjoy nearby attractions like Anne's Beach, Theater of the Sea, and the History of Diving Museum.Experience a slice of paradise in this authentic room at our boutique beachfront resort! We offer a private lounge on the beach where you can relish the authentic island life experience. Enjoy a bike tour through the island, an outdoor pool, and a sun terrace with breathtaking views of Alligator Reef Lighthouse. Embark on boating excursions and dine at our delightful American restaurant. Relax, rejuvenate, and explore the serene beauty that awaits.PLEASE NOTE:This listing is specifically for a hotel room located within a hotel, distinguishing it from typical residential or apartment accommodations.- The property requires a damage deposit of $100/night/unit on the credit/debit

Located in Islamorada, Florida, United States. Cozy Caribbean-Style Home w/ Outdoor Veranda - Steps to Beach-Entry Pool Resort guests stay in warm and inviting Caribbean-style homes. Rich mahoganies, teaks and Tommy Bahama furnishings all provide a unique experience.Many of the homes are named after one of the specimen palm trees on the property. Each home enjoys privacy among native gardens.Guests enjoy the beautiful Caribbean décor and high, open ceilings. Solid wood Anderson doors and windows, chiseled stone or tile flooring, open living and dining area all add to your tropical experience. Wrap-around outdoor verandas and comfortable lounging chairs create a seamless transition to outdoor living where you are just steps away from our one-of-a-kind tropical garden beach-entry pool.This home includes a full washer-dryer, Weber BBQ gas grill, wireless Internet, and cable TV.The Malayan Palm has the option of opening a locked interior door, combining the space into a 3 bedroom, 2 bath home.About The Caribbean ResortOur Caribbean ho

Located in Islamorada, Florida, United States. Water Front 3/3 Family and Boat Friendly Home, Great Views This beautiful well-kept and spacious two story bay-side waterfront home is a perfect rental home for you and your family. The home has three bedrooms and three baths, 2/2 upstairs and 1/1 down. The expansive great room (22 ft. X 38ft.), which includes the kitchen, dining, sitting and living rooms with 60 inch hd tv overlooks the wide open views of hurricane creek, making entertaining or just chilling something to remember. The front of home has a balcony with chairs overlooking the park and partial view of the bay. . From the 96 ft. Dock you have a view of the bay and are able to fish, swim and tie up at least two boats. It is located at mile marker 73.5, on lower matecumbe key, making it close to islamorada restaurants and shopping. Within one mile of the home, you will find a convenient store, gas station, restaurant, lounge, hard ware store, bait and tackle store and ann’s beach. By boat, channel 2 and 5 are less than t

Located in Islamorada, Florida, United States. Updated Unit with Beautiful Florida Bay Sunsets PROPERTY NAME: The Palms #41779901 Overseas Highway, Islamorada, FLLOCATION: Oceanside Condominium MINIMUM STAY: 28 Days, All stays must be the whole month(s), No Partial Months AllowedMILE MARKER: 79.9DETAILS: The Palms of Islamorada is a condo complex consisting of 84 units and is located directly on the Atlantic Ocean. The complex features separate his and hers mini-gyms, heated pool, hot tub, tiki for gatherings and lots of lounge chairs so soaking up the wonderful sunshine. This one bedroom unit has partial views of the ocean and a good view of the Florida Bay. It is perfectly proportioned - large living area and large bedroom and dressing area with separate linen closet and walk-in closet. The kitchen and baths have been updated. You'll be glad you chose this unit for your holiday in the Keys. Bedding is king. This property is professionally managed by Keys Holiday Rentals.Sleeping Arrangements: Sleeps 2-3 comfortably

Located in Islamorada, Florida, United States. Gorgeous 2 bedroom condo with panoramic views of the Atlantic Ocean. PROPERTY NAME: Beacon Reef #30683201 Old Highway, Islamorada, FloridaLOCATION: Ocean Side CondoMINIMUM STAY: 28 Days, All stays must be the whole month(s), No Partial Months AllowedMILE MARKER: 83.2DETAILS: Enjoy a relaxing stay here in the Keys at this immaculate and charming two bedroom and two bath condo. While the owners attend to their other property "up north" you can relish all the delightful amenities of their condo. This unit is beautifully appointed and offers comfortable accommodations - fully equipped kitchen, full size washer and dryer, king size bed in the master and two full size beds for your guests. Located in the heart of Islamorada, you'll love the charm of an ocean front complex with the large freeform pool, hot tub, sandy beach and dock privileges. There's even a well-equipped gym for exercise enthusiasts. You'll find this location exceptionally convenient to fabulous dining and recreati

Located in Islamorada, Florida, United States. Tropical Paradise Beautiful bayside villa in Islamorada. Sandy beach, fishing dock, pool, tennis court and boat slip for up to 25 ft boat included. Bicycles available. Close to many restaurants, bars and places of interest.

Located in Islamorada, Florida, United States. Exceptional condo with panoramic views of the Atlantic Ocean. PROPERTY NAME: The Palms #30979901 Overseas Highway, Islamorada, FLLOCATION: Bayside Condominium MINIMUM STAY: 28 Days, All stays must be the whole month(s), No Partial Months AllowedMILE MARKER: 79.9DETAILS: an exceptional condo with panoramic views of the Atlantic Ocean. This condo is in one of the most popular condo complexes in Islamorada - The Palms of Islamorada. Comfortably furnished and ready for your arrival this unit offers an updated kitchen with Corian counters, updated cabinetry and a little breakfast nook. All kitchen appliances are newer and the kitchen is complete with pots, pans, dishes, glasses and flatware. The two bathrooms have been updated - one features a tub and shower combination and the other a walk-in shower. The master suite has small office area with a desk, monitor and keyboard. Bring your computer there's even a printer. There is a queen size bed, walk-in closet, and a dressing area.

Located in Islamorada, Florida, United States. Leisure Inn Islamorada - 3/2 canal home on a double lot, bring all of the toys! This charming Florida home is situated on a double lot with a full sea basin on an ocean side, deep water canal...seconds from the Atlantic Ocean and a straight shot to Alligator Reef. This one story home has 3 bedrooms, 2 baths, a spacious kitchen and living area. Sleeps 6 guests comfortably, 8 guests if using the living room sleeper sofa. Access to an exclusive, nearby club is included in your stay. The club offers free access to the pool, boat ramp, and fuel at cost for guests.

Located in Islamorada, Florida, United States. Waves of Luxury: Access to Bayside Pool and Boat Slips. FREE Parking Onsite! Nestled along the stunning coastline, our newly renovated resort offers a tranquil escape from the everyday hustle and bustle. Step outside your door and be greeted by the breathtaking beauty of our private beach. Feel the soft sand between your toes as you stroll along the shoreline or soak up the sun on a beach lounger. For those seeking adventure, indulge in various water sports activities nearby, such as kayaking or paddle boarding, Our newly renovated resort boasts an array of amenities to enhance your experience. Take a dip in our sparkling outdoor pool, surrounded by lush tropical gardens. Our friendly staff is always ready to provide recommendations and assist you in planning memorable excursions. Experience the epitome of coastal elegance and create timeless memories at our exclusive retreat. PLEASE NOTE:This listing is specifically for a hotel room located within a hotel, distinguishing it from typic

Located in Islamorada, Florida, United States. Ocean Front Villa, 3/4's acre of private beach! Serenity, Retreat, Island Life! Come enjoy the beautiful Florida Keys in this new build stylish villa located in Islamorada close to shopping & restaurants but private and secluded perfect for a short term retreat to live a real island life! Welcoming seasonal snowbirds as well as short term group trips. Entire home completely stocked with all linens/supplies for ease, comfort and finished with immaculate decor. 5 bedrooms, 3 full bathrooms, private outdoor shower and private outdoor bath tub, 2 family private setup with each floor boasting its own living room, kitchen, coffee bars, ocean front master on each as well as private entrances per floor. Upstairs kitchen decked w/ Italian Bertazzoni appliances, 4 seat island with bar sink & wine fridge. Each bedroom equipped with smart TV's, balconies with outdoor furniture to sip sunset cocktails or enjoy nespresso watching the phenomenal sunrise each morning. Each bedroom has a walk-in or ex