58,368 properties available

Located in Islamorada, Florida, United States. Sunset Views and Serenity! Outdoor Pool, Free Parking, Near Hurricane Monument Step into our thoughtfully designed and spacious accommodations, featuring modern furnishings and luxurious amenities. Our well-maintained rooms offer comfort and tranquility, providing a peaceful haven to rest and rejuvenate after a day filled with adventure. Each room boasts a cozy ambiance, complete with plush bedding, elegant decor, and all the essentials you need to feel at home. With a private beach just steps away from your doorstep, you can enjoy the soothing sound of waves and the warm kiss of the sun, making your stay truly unforgettable. Whether you're lounging by the pool, exploring the nearby coral reefs, or indulging in fresh seafood at our waterfront restaurant, our property creates an idyllic retreat for an unforgettable escape in the heart of Islamorada's enchanting landscape.Please Note:- The resort fee is not included in the daily rate. A mandatory resort fee of $49/night per accommodation

Located in Islamorada, Florida, United States. Keys Villa Two bedroom "gem" in the Florida Keys!! Enjoy our sand beach, beautiful sunsets, fish from our docks, swim in our pool, relax in our hot tub or explore in our kayaks. Private boat ramp and boat slip!!

Located in Islamorada, Florida, United States. Lush Tropical Waterfront Oasis With Heated Pool, Dock And WiFi This tropical oasis includes a heated pool and dock that reaches out onto a protected lagoon that opens into the Florida Bay.There are 3 bedrooms and two bathrooms upstairs, and a downstairs bedroom suite with private bathroom that opens onto the pool deck. The upstairs bedrooms are furnished with two king sized beds and one queen sized bed. Downstairs the bedroom suite is furnished with a king sized bed. The house comfortably sleeps 8. The oversized lot is lushly landscaped for privacy. There are local 4-star restaurants nearby but the property also includes a well appointed kitchen and outside grille for the chefs at heart. For those who enjoy boating, there is immediate access to the Florida Bay, with the Atlantic Ocean minutes away. Local marinas with boat, kayaks, and jetski rentals are within minutes.The house amenities include free wifi, laundry room, as well as flat-screen televisions in great-room, master bedroom a

Located in Islamorada, Florida, United States. The Beach House-Luxury Oceanfront Home, Views, Pool, Sandy Beach ‘The Beach House’ at Tarpon Point in Islamorada-OWNER DIRECT RENTAL WITH NO ADDITIONAL FEESThis end home offers privacy and beautiful ocean views including of Indian Key Historic State Park. Enjoy morning coffee and a phenomenal sunrise on the tip of the observation pier or from your covered deck. Afternoons lounge around the heated (and chilled) waterfront pool taking in the ocean views or launch your kayak from the private beach area and paddle over to Indian Key Island.On the main level is the Great Room which offers more amazing ocean views with plenty of room for everyone to gather, do puzzles or just lounge on the deck and take in the vista. On cooler nights (yes, even in The Keys there is some cooler weather) enjoy the fireplace in the Living Room. An Osprey Nest is in your front yard for the nature lover.The Gourmet Kitchen offers a Wolf 6 burner gas stove, microwave draw and warming oven. Bosch Silence dishwasher

Located in Islamorada, Florida, United States. Hidden Gem Islamorada | 2nd Floor Summary:This newly renovated unit is truly is a Hidden Gem in the heart of Islamorada! This duplex is nestled in the trees just a few steps from one of the most amazing sunsets in the Upper Keys. Walking distance to all the wonderful shops, restaurants and breweries that Islamorada has to offer. Bikes and Kayaks can be rented steps away from the front door of this unit. Want to find a place that you'll want to return year after year? Look no further!This unique property was originally built as motel in the 1950's. We have taken it upon ourselves to give it a facelift! Expects new bathrooms, flooring, beds, windows, and new split AC units in every room! Cool down when you get inside from that Florida heat! BrrrrrThe Space:This unit is 620 sq. ft. located on the second floor. Its two bedroom/two bath with a small kitchen and living room. The master bedroom has a King memory foam mattress with an en suite bathroom. The guest bedroom has a King memory fo

Located in Islamorada, Florida, United States. Blue Haven ~ Modern Downtown Islamorada Home with Pool! Welcome to Blue Haven! This immaculate 3 bedroom / 2.5 bathroom home provides the perfect home base for your next Florida Keys vacation! Tucked away from the main highway you will experience peace and quiet while still being in the heart of Islamorada. Sitting on a large corner lot, this home is surrounded by acres of protected hardwood hammocks which provides extra privacy that other homes can’t offer. Step inside and enjoy this beautiful newly constructed home that features high ceilings, an open floor plan, and one level living. The large kitchen features stainless steel appliances and is fully appointed and ready for you to prepare your favorite home cooked meals. The primary bedroom features a gorgeous ensuite bathroom with double sinks and custom tile, a convenient walk-in closet, and direct access to the backyard. The separate dedicated office space and whole house Wi-Fi makes it easy to stay connected and work from home. H

Located in Islamorada, Florida, United States. Sensational Ocean Front Villa | Kayak+PBs+Cinema+Fire Pit+Pool Summary:This is a truly unique and spectacular Villa thanks to its breathtaking view of the sea and its warm sandy beach.On the beautiful beach you will find paddle boards and kayaks (both for rent) and comfortable sun loungers while you sunbathe and enjoy the dreamy sunsets.Get ready for a private saltwater pool with lush tropical landscaping, plus a cozy cabana with a dining table, a cinema (projector) and a lovely fire pit!The interior has 4 bedrooms, 4 bathrooms, a dining area, a living room and a fully equipped kitchen.The Space:1. Master Bedroom with a KING SIZE BED with excellent quality linens. A balcony with an amazing view of the beach and access to a full private bathroom with a hot tub.2. Bedroom with a QUEEN SIZE BED and access to a full private bathroom.3. Bedroom with THREE QUEEN SIZE BEDS and access to a full private bathroom.4. Bedroom with TWO FULL SIZE BEDS and access to a full private bathroom.*Two extra

Located in Islamorada, Florida, United States. Caribbean-Style Family Home w/ Kitchen, WiFi, Outdoor Veranda, & Washer-Dryer 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 Caribbe

Located in Islamorada, Florida, United States. Oceanfront, Pool, Dock... Checks all the boxes! 141 LeSerra Lane - Freewheeler Vacations newest weekly rental is now available for your next Islamorada Vacation! Located at mile marker 76, LeSerra Lane is a three-bedroom, two and a half bath oceanfront home that checks all the boxes needed to make your upcoming vacation the best yet! Enjoy your morning coffee watching the sun rise over the Atlantic Ocean. Jump in your boat and head out to some of the best fishing Islamorada has to offer or simply hang out by the private pool with a cocktail in hand and grill up your catch! We dare you to not have a good time at this property! VACATION RENTAL LICENSE: 24-0020Per Islamorada's vacation rental ordinances for weekly rentals 2 people per bedroom are allowed, and 2 additional guests if under the age of 6.If booking more than a year in advance current prices may not reflect the annual cost of living increase. Many of our guests' re-book the same property on an annual basis. No reservation is c

Located in Islamorada, Florida, United States. Welcome to Our Beautiful 3 BR Home in the Heart of Islamorada, Florida Experience the perfect getaway in our stunning 3-bedroom home located in the vibrant heart of Islamorada, Florida. Nestled amidst lush tropical surroundings, this beautiful property offers the ultimate blend of comfort, luxury, and adventure. Whether you’re looking to relax by the pool, explore the nearby waters, or enjoy the local dining and shopping, our home provides the ideal base for your vacation.If you're a boater- this is your spot. Centrally located and close to all the amenities in Islamorada from the spectacular lighthouse and sandbars which is only minutes away to all the best restaurants!PLEASE NOTE: we are only allowed per the city of Islamorada to allow for 30 days rentals. Please contact with any questions prior to booking.

Located in Islamorada, Florida, United States. ☀️Luxury 3 BR Remodeled! Ocean View PoolSpa, MarinaBikes Boat Slip Tennis/Pickle Boat Slip is available for a small weekly fee of $150Come enjoy relaxing or being active at luxurious Bay Harbour - a small and quiet gated community...perfect for a much needed get away! Bay Harbour is a small, quiet, private gated community with many amenities including large heated/cooled pool, hot tub/spa, tennis courts, pickle ball, clubhouse with large fitness center and gas grills located at the pool and clubhouse. Boat slip available for $150/week rent upon request. This beautiful newly remodeled home is located in Islamorada on Lower Matecumbe Key and brings you back to old Florida. Our home is a 3 bedroom, 2.5 bath that sleeps 6 people comfortably with a large living area and beautiful balcony with breath-taking views of the ocean and bay. Our home has been completely updated with new flooring, remodeled bathrooms, kitchen, plantation shutters, furniture, lighting, linens, and beautiful coastal

Located in Islamorada, Florida, United States. Gorgeous Keys Vacation Home in Prestigious Neighborhood of Port Antigua Beautiful Port Antigua waterfront home with a 60 foot concrete dock on a wide, clear-water canal. Access to Port Antigua homeowners' boat ramp and private white sandy beach on the Florida Bay. Meticulously maintained residence with third floor suite, with two walk-in closets, spacious spa-style bathroom featuring double sinks, and large balcony with water views. Office/loft space with trundle bed to accommodate 2 extra guests. Main level offers two bedrooms, one bath, custom kitchen, and dining and living room with vaulted Cypress plank ceilings. Substantial waterside screened patio that wraps around the entire 2nd floor. Additional rooms on ground floor which includes 2 bedrooms and one full bath. Featuring a brand new in-ground spa-style saltwater pool with putting green on the side. Also features metal roof, small barbeque and covered patio. A lovely home dubbed 'Banana Republic'.

Located in Islamorada, Florida, United States. Isla Guava: Waterfront Boutique Resort, Htd Pool, Dock, Walkable Short Description🏡 Community amenities: heated pool, boat dock, BBQ📍Walk to shops, grocery store, parks, restaurants🛏️ All bedrooms feature ensuite bathroom 🤝 24/7 Guest supportIsla Key Guava (Villa #4) is part of Little Basin Villas upscale community of nine luxury vacation villas, located in the heart of the Art District of Islamorada. Boasting a bayside boat dock and private community pool, our villa offers the perfect blend of relaxation and adventure. Enjoy breathtaking sunsets, waterfront views and island décor & foliage. It uniquely offers three bedrooms complete with their own ensuite bathroom, plus a half bath. It is fully furnished, and offers a private deck, and a top balcony with partial water view. This home is fully stocked with everything you need, including pickleball equipment (courts very close by at Gib Reese Park) and a full time Guest Experience Team to assist in making the most of your stay. We welc

Located in Islamorada, Florida, United States. By The Sea ~ Islamorada Home with Ocean Views! Summary:Canal front 2/2 with ocean views and relaxing breezes!The Space:This canal front two bedroom two bathroom home offers a large open living area with kitchen and dining rooms opening to a large screened patio with ocean breezes - just a couple of homes away from the open ocean with unobstructed ocean views.As you walk up the exterior steps you enter the main floor patio which is screened in and overlooks the Atlantic ocean. The main living area features a full kitchen, dining area, living space with a pull out couch and television. The main floor also has the guest bedroom with two twin beds. As you go up the spiral staircase you will enter the master suite which has direct ocean views, king size bed, and ensuite bathroom. You also have your own private balcony. The views will leave you awestruck!This home has covered parking for two vehicles and exposed parking for up to two more. The dock has space for up to a 25' boat directly beh

Located in Islamorada, Florida, United States. 2 houses located on a private peninsula. PROPERTY NAME: Martin Family Fish Camp106 Madeira Rd., Islamorada, FloridaLOCATION: 2 Houses Located on a private peninsulaMINIMUM STAY: WeeklyMILE MARKER: 81.9DETAILS: The Martin Family Fish Camp is located on a private peninsula and offers two houses named Bonefish and Tarpon. Each home offers two private bedrooms. Between the two homes the bedding is: King, Queen/Queen in Tarpon and Queen, Twin/Twin in Bonefish. There's a large Tiki for relaxing or dining, onsite parking - covered and open plus room for a boat trailer, a tropical outdoor shower and 100' of open dock space! The houses are one story concrete buildings with easy access and water views. Tarpon House is the larger of the two and offers a front porch with bay views, a sandy area by the water and a fire pit. Bonefish House is the smaller and is located by the boat basin. It makes a perfect sleeping cottage with a mini-kitchen and a small living area. Built in the early 19

Located in Islamorada, Florida, United States. Caribbean-Style Family Home w/ Full Kitchen, WiFi, Veranda, & Washer-Dryer 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 tha

Located in Islamorada, Florida, United States. Islamorada Bungalows Suite 1 Bottom Floor Summary:Location is key! This beautiful and zen getaway is just minutes away from the Heart of Islamorada! The city's Art and Cultural District is not even 1 miles north of the property and local attractions are within 1.5 mile radius - It does not get any more local than that.The property offers 4 individual, beautifully designed 1 bedroom suites with fully stocked kitchens. Housekeeping service with linen refresh is offered twice a week. Enjoy, Relax and Recharge!The Space:The quaint backyard features outdoor games, fire pit surrounded by adirondack chairs and a charcoal grill!Guest Access:Come anytime - You will receive a unique door code prior to your arrival.The Neighborhood:Explore the neighborhood with the free bicycles which are provided.Getting Around:Don't forget to check out Freebee Electric Vehicle Ridesharing Service. Freebee picks up customers right at their home, hotel or a business within Islamorada. Request a ride and jump on b

Located in Islamorada, Florida, United States. 180 Degrees of Ocean Views, Sitting on a Large Lagoon that Opens to Florida Bay PROPERTY NAME: Sandglass 474980 Overseas Highway #4, Islamorada, FLLOCATION: Bayside Town House Located in Lower MatecumbeMINIMUM STAY: 7 Days MILE MARKER: 74.9DETAILS: ONE OF A KIND!!! Magnificent two story townhouse with 5 bedrooms and 3 baths located on Lower Matecumbe in Islamorada. Sandglass is a four-unit condo complex. This unit offers 180 degree ocean views and is situated on a large lagoon which opens to the Florida Bay. Bring your boat and water toys. Swim, paddleboard or kayak right from the property. There's a private boat ramp on site, fish cleaning table, designated boat slip and room to park your trailer. Inside you will love the spacious air-conditioned living area with plenty of room for everyone in your party to gather. Sliding glass doors disappear into the wall opening the area to an enormous screened balcony overlooking the cove. There is an exceptional amount of seating - inside

Located in Islamorada, Florida, United States. Islamorada Paradise! Luxury Townhouse! Sleeps 4-6 Boat Slip And Pool This Modern Upscale duplex Home Has All The Amenities For A Wonderful And Special Vacation. King Size Master Bedroom And Queen Size Second Bedroom,sofa Bed In Living Room,extra folding bed, 4 Balconies, Gas BBQ, Satellite TV and WiFi. Carport For Two Cars. Pool, Tiki Hut. End Unit Provides Extra Sunlight And More Privacy. Boat slip .Boat rental available Washer Dryer in unit. Storage shed.Bike path at our door.Security front gate

Located in Islamorada, Florida, United States. Bay Harbour Islamorada Oceanfront Views 3/2.5 UPDATED condo DOCK Beautiful views from this condo dock 32 available-Unit C109 License Number: VR-194Bay Harbour is a gated community located at MM 77.5 bayside in Islamorada, FL.We are new owners of this condo that has never been in the rental pool. (that is why few reviews)Complete remodel with no expense spared! The location is quiet with the most beautiful blues and greens to make you feel like you have arrived in paradise, without actually leaving the country.This Immaculate and spacious three bedroom condominium has plenty of room to spread out with gourmet kitchen and exquisite ocean views!The Great room has expansive glass doors overlooking the ocean, queen sleeper sofa and large flat panel tv.Fully equipped gourmet kitchen has stainless appliances and Quartz counters. There is a full-size washer and dryer right in the condo. , Wi-Fi, scanner, printer, just bring your laptop.Watch the sunrise in the morning and manatees in the af

Located in Islamorada, Florida, United States. Beautifully Renovated Home w/ Custom Furnishings, Chef's Kitchen, & Veranda Welcome to the Jamaican Palm. Our most recently renovated home is a sight to behold. Every detail and fixture was handpicked and custom crafted from the finest materials and builders.Inspired by the Caribbean lifestyle and design from Ocean Gardens Showroom. The Jamaican Palm is an expansive 3 bedroom, two-bathroom single home with a large great room, chef’s kitchen and outdoor wrap-around veranda. Chisel stone flooring, granite countertops, Keys Stone Coral wall and custom cabinets are just a few of the high quality features the home holds. The chef’s commercial kitchen features a Wolf stove, Subzero refrigeration and a separate built-in wine cooler.Nautical décor includes one of a kind Marine Antiques and ship lighting throughout the home. Like all our other homes, The Jamaican Palm also comes with a washer-dryer, Weber BBQ gas grill, wireless Internet and cable TV.This home includes a full washer-dryer, Webe

Located in Islamorada, Florida, United States. All the feels... tranquility and relaxation 75731 Overseas Highway - You are overcome with tranquility and relaxation as you pass through the gates of this oceanfront estate. You are greeted with ocean breezes and luscious landscaping making you feel like you've entered your own little oasis. This French Caribbean home has a large infinity pool, a private oceanfront beach, incredible porches to sit and watch the sunrise, and a salt-water pond. The main house has three bedrooms, three full baths, den, and a gourmet kitchen. The second floor has the master bedroom, with a king size bed, and the guest bedroom, which has a king size bed. The third floor has a small bedroom with a queen bed, and a loft with two twins. There is a charming, beachfront, guest cottage which has one bedroom and a full-size bath. The beach cottage has a queen size bed. Some great amenities include Wi-Fi, TVs, a printer, BBQ grill and beach chairs. Islamorada is the Spiritual Center of the Keys, the Sportfishing C

Located in Islamorada, Florida, United States. Breezy Beach Waterfront home in Port Antigua Relax in this beautiful and comfortably updated bayside home in Port Antigua. Port Antigua is the Lower Keys best kept secret. A mile-long private beach shared only with Port Antigua residents. It's crystal clear waters, Tiki huts, picnic tables, and BBQ will provide all the relaxation you need. Relax in this designer waterfront cul de sac home with 4 bedrooms, 3.5 bathrooms, and 95' of dockage. The home is fully equipped with everything you need from fast WIFI, linens, towels, cooking, large capacity washer/dryer, BBQ, ice chest, etc. Take pleasure in all the amenities this home has to offer with breathtaking sunset views, this home is one you must enjoy for your families vacation. Copy and Paste video on YouTube: https://www.youtube.com/watch?v=-HVPkMfAJpg

Located in Islamorada, Florida, United States. Sunrise Haven - Maison 306 - Beach, Pool, Hot Tub, Kayaks, SUPs & Day Dock COVID-19 Update: Sunrise Haven is professionally cleaned including all linens and towels. The owners or property manager do not do the cleaning and laundry. Islamorada, Florida, is known as the Sports Fishing Capital of the Florida Keys. The Maison resort property in Islamorada is half way between Key West and mainland Florida. "Sunrise Haven," our Atlantic Ocean beach front condo is located near the heart of Islamorada at Mile Marker 80.6 on the quiet, less traveled, Old Federal Highway, not on the busy US-1 Overseas Highway. Walk to great restaurants, the arts district and marinas in Islamorada. The Maison resort property includes 21 condos, in 4 buildings in a U shape around a very large, 86' x 25', resort style pool and hot tub. Enjoy 350 feet of white sand beach. We provide 2 double kayaks and 2 stand-up paddle boards for our guests private usage. The Overseas Highway, US-1, follows Henry Flagler’