Vacation Rentals in Islamorada, FL

This holiday home in Islamorada is located just 1.6 kilometres from both Sunset Drive Beach and Anne's Beach, offering easy access to the beautiful Florida Keys coastline. The property has received excellent ratings from previous guests, highlighting its comfortable and convenient features.
The three-bedroom house spans 125 square metres and can comfortably accommodate up to 10 guests. Amenities include a private pool, a fenced yard, a barbecue grill, concierge services, and a fully equipped kitchen, ensuring a relaxing and enjoyable stay.

Ocean Oasis at Ocean Pointe is situated in Tavernier, a short walk from Harry Harris Park Beach and a short drive from Pigeon Key, offering a tranquil escape in a beautiful location. The property has received very good ratings for its location, cleanliness and overall experience.
This holiday home features a well-equipped kitchen, a private balcony with sea views and a private beach for your enjoyment. Guests can also relax in the hot tub, swim in the pool, or enjoy the garden and outdoor play equipment.

This pet-friendly, family-friendly townhome in Islamorada, Village of Islands, offers oceanfront living within the gated Peaceful Palms community, featuring direct ocean access and proximity to local dining and the Islamorada Sandbar, with a private dock for boats up to 27 feet (advance reservation required) and a sandy entry ideal for watersports.
This spacious 156-square-meter accommodation boasts 3 bedrooms and 3 bathrooms for up to 7 guests, complete with air conditioning, a fully equipped kitchen including a dishwasher, a resort-style oceanfront swimming pool, a private balcony with panoramic sunrise views, and a garden, all within walking distance of Starbucks.

This Islamorada canal-front property, moments from Tavernier Creek Marina and restaurants, offers direct bay and ocean access, with the reef approximately 1.6 kilometres away.
This two-bathroom apartment sleeps five, boasting a private pool, patio, boat dockage, large loft with Netflix, outdoor shower, bait freezer, BBQ, and full kitchen including dishwasher, fridge, freezer and microwave.

This oceanfront villa in the Mirage community of Islamorada offers direct sea views and is conveniently located near the popular Sandbar, 4.66 kilometres from Upper Matecumbe Key.
This property boasts a 156 square metre floor area, accommodates up to 9 guests across 2 bedrooms and 3 bathrooms, and features a swimming pool, fitness centre, and a well-equipped kitchen with a dishwasher and microwave, with free private parking and Wi-Fi included.

This two-bedroom apartment is situated in Islamorada, directly overlooking the Atlantic Ocean, within walking distance of fishing, snorkeling, diving, and kayak/paddleboard rentals. Local charters for these activities are about 1.6 kilometres away. The apartment has received excellent ratings for location, cleanliness, and overall user experience.
This comfortable property can sleep up to four adults and features a fully equipped kitchen with a fridge, microwave oven, and dishwasher, as well as air conditioning, a swimming pool, a garden, a fitness centre, and parking. Guests can enjoy stunning ocean views from the spacious porch, relax by the pool, or barbecue on the beach.

Ragged Edge Resort & Marina is located in Islamorada, just a short drive from Windley Key and Upper Matecumbe Key, offering easy access to the area's natural beauty. The resort has consistently received excellent ratings for location, cleanliness, and overall experience.
The accommodation features a mix of rooms and suites, some with balconies offering sea views. Guests can enjoy amenities such as a swimming pool, terrace, free bikes, a communal grill, and free Wi-Fi.

Angler's Reef Resort is conveniently located in Islamorada, a short walk from Anne's Beach and within easy reach of other attractions like Upper Matecumbe Key and the Florida Keys Aquarium. This resort has excellent ratings for location, cleanliness, and overall user experience.
The resort offers a range of accommodation options, including rooms with kitchens for those who prefer to self-cater. Guests can enjoy a variety of amenities, including a swimming pool, BBQ facilities, a garden, and a fitness centre.

Anglers Reef Vacation Rental is situated just a 5-minute walk from Windley Key and 1.6 kilometres from Windley Key Fossil Reef Geological State Park, offering easy access to some of Islamorada's most popular attractions. This property has received excellent ratings for its location, cleanliness, and overall user experience.
The 2-bedroom villa spans 121 square metres and comfortably accommodates up to 6 guests. Amenities include a private pool, a fully equipped kitchen, a washing machine, a cable flat-screen TV, free Wi-Fi, a terrace, barbecue facilities, and access to a private beach area and water sports facilities.

This Tavernier apartment is situated just a short walk from the end of the pier, offering stunning views of the Atlantic Ocean and Florida Keys mangroves. It has received excellent ratings for location, cleanliness, and user experience.
The two-bedroom, two-bathroom apartment spans 91 square metres and can comfortably accommodate up to six guests. Amenities include a swimming pool, jacuzzi, tennis courts, a marina, a cafe, and a beach area, providing a range of activities and features for a relaxing getaway.

This boat is situated in the Village of Islamorada, Florida Keys, at Mile Marker 85, within a gated community overlooking the Atlantic Ocean, just a short distance from the Florida Keys Brewing Co. and Florida Keys Dive Center. The property has excellent user ratings and offers a private dock for a 31' boat, easy access to the water and the beautiful Florida Keys waters.
This 109 square metre boat has two bedrooms and three bathrooms, and can accommodate up to six guests. Enjoy the private balconies, the ocean views, the heated/cooled pool, the 52' beachfront, the well-equipped kitchen, the spacious living room and the convenient amenities including a stacked washer and dryer.

This beachfront cottage in Islamorada's Matecumbe district is situated less than 2.4km from Indian Key Historic State Park and Bud n' Mary's Dive Center, and under 1.6km from the Hurricane Monument and Florida Keys Brewing Company.
This 42 square metre self-catering property sleeps four, featuring a bedroom, bathroom, private balcony with potential ocean views, and amenities including air conditioning, Wi-Fi, a swimming pool, and parking.

This solar and wind-powered houseboat is located in Islamorada, half a mile from the shore and a short distance from restaurants, bars, and music venues. The houseboat has received excellent ratings for location, cleanliness, and user experience.
The houseboat offers one bedroom and one bathroom, sleeping up to two guests. You can enjoy a fully equipped kitchen, a bathroom with a compost toilet and shower, a queen-sized bed, and a roof deck for enjoying cocktails. The houseboat also comes with a 12-foot skiff, a kayak, a stand-up paddleboard, and snorkeling gear, encouraging guests to explore the surrounding waters.

This Islamorada studio apartment is located in the Matecumbe district, offering convenient access to Long Key State Park and Windley Key Fossil Reef Geological State Park, although precise distances are not specified.
The 37-square-metre (approximately 398 square feet) self-catering unit sleeps three, featuring a queen-size bed, a twin sleeper sofa, a fully equipped kitchenette (including fridge, microwave, and dishwasher), and a private balcony; guests also benefit from access to Caloosa Cove Resort and Marina amenities, including a heated swimming pool and beach access.

This one-bedroom apartment, located in the Matecumbe district of Islamorada, is just a short walk from Anne's Beach and Sunset Drive Beach, and within a 3.2 km drive of San Pedro Underwater Archaeological Preserve State Park and Robbie's of Islamorada. The 46 square metre property features a fully equipped kitchen, a balcony, a swimming pool, a Jacuzzi, and a tennis court, and can accommodate up to five guests.

This Key Largo coastal home, offering convenient access to the restaurants of Key Largo and Islamorada, boasts a private beach, pool and dock.
This six-bedroom, four-bathroom property, spanning 279 square metres, provides ample space for large families or corporate retreats, featuring a fully equipped kitchen, spa, and gated entrance for ultimate privacy.