Holiday Rentals in Islamorada, FL

This Tavernier waterfront apartment, located 1 kilometre from Harry Harris Park and within 5 kilometres of Mariners Hospital and the Florida Keys Dive Centre, offers stunning views.
The two-bedroom, two-bathroom condo sleeps six guests and boasts a fully equipped kitchen, private balcony, jetted tub, swimming pool, Jacuzzi, free Wi-Fi, and parking.

This Tavernier beach apartment is conveniently located within a 10-minute walk of Baker's Cay Resort Beach and Harry Harris Park, offering easy access to the area's attractions. The property consistently receives excellent ratings for location, cleanliness, and overall user experience.
The apartment offers 85 square metres of space, comfortably accommodating up to 6 guests in its two bedrooms and two bathrooms. This family-friendly apartment includes a range of amenities such as a swimming pool, Jacuzzi, tennis court, and a garden, ensuring a comfortable and enjoyable stay.

This Islamorada holiday home, situated in the Peaceful Palms community, is minutes from the Islamorada Sandbar and within walking distance of restaurants and shops, offering easy access to attractions such as the History of Diving Museum (approximately 0.8km away).
The 163 square metre property boasts three bedrooms, three bathrooms, sleeping up to six guests, and features a private boat dock (dockage fee applies), a heated community pool, a game room, and a modern kitchen; electric vehicle charging is also available.

This waterfront property is situated in Indian Waterways, a neighbourhood in Tavernier, just a short distance from Founders Park and the beach. The area offers a peaceful and relaxing atmosphere, perfect for enjoying the natural beauty of the Florida Keys.
The house is ideal for families or groups of up to four people, with two bedrooms and two bathrooms. Enjoy the convenience of a fully equipped kitchen, a screened-in porch, and a large enclosed garage, as well as the option to bring your own boat or rent one on-site.

This one-bedroom flat is located in the centre of Islamorada, directly on a private beach with ocean views and within 1.5 kilometres of Islamorada Brewery & Distillery and Florida Keys Brewing Co.
This pet-friendly accommodation offers a heated outdoor swimming pool, complimentary Wi-Fi, and on-site bike, kayak, and paddleboard rentals, with a capacity for four guests.

This waterfront apartment is situated in Tavernier, Florida, just 2.4 kilometres from Baker's Cay Resort Beach and Harry Harris Park, offering easy access to the beautiful beaches and natural surroundings of the Florida Keys. The apartment has received excellent ratings for its location, cleanliness, and overall user experience, making it a popular choice for travellers.
The apartment offers 54 square metres of space, with one bedroom and one bathroom, comfortably accommodating up to three guests. This bright and comfortable apartment comes equipped with a range of amenities, including a fully equipped kitchen, a fireplace, a terrace, a swimming pool, a spa, a tennis court, and free Wi-Fi, ensuring a relaxing and enjoyable stay.

This waterfront apartment in Matecumbe, Islamorada, is situated 2.4km south of Anne's Beach and its boardwalk, and conveniently located 8km north of Robbie's Marina and 16km north of Islamorada's town centre.
The 188 square metre property boasts three bedrooms, three bathrooms, sleeping up to six guests, and features a private dock, a fully equipped kitchen including an air fryer oven and coffee bar, plus resort amenities including a swimming pool, jacuzzi, and spa.

Isla Guava: Waterfront Boutique Resort in Matecumbe, Islamorada, offers convenient access to the Islamorada Brewery & Distillery and Keys History & Discovery Centre (both within 1.6km), and the History of Diving Museum (within 2.4km).
This smoke-free villa boasts a 156 square metre floor area, sleeping up to six guests in three bedrooms and four bathrooms, and features a private balcony, fully equipped kitchen, swimming pool, spa, and free Wi-Fi.

This two-bedroom flat is located in Angler's Reef, a secure oceanfront community in Islamorada, offering direct beach access and a heated oceanfront swimming pool.
This family-friendly accommodation sleeps up to six guests and features a kitchen with a fridge, microwave, and dishwasher, along with air conditioning, a terrace/balcony, garden, and parking.

This Islamorada apartment complex offers direct beach access in the centre of Islamorada, conveniently located near the History of Diving Museum and Keys History & Discovery Centre.
The self-catering property boasts two bedrooms, two bathrooms, and sleeps up to eight guests across a 54 square metre floor area, featuring a heated pool, barbecue facilities, and kayak/paddleboard hire.

This two-bedroom apartment is located in the Matecumbe district of Islamorada, just a short distance from mile marker 75, offering easy access to fishing, diving, and other water activities. It has been rated excellent by previous guests.
The apartment is 139 square metres in size and comfortably sleeps up to 6 guests. It features a fully equipped kitchen, two master bedrooms with private bathrooms, a private boat slip, a heated swimming pool, a hot tub, a clubhouse, a fitness centre, tennis courts, gas barbeque grills, tennis equipment, beach chairs, and coolers.

This waterfront property is located just two miles from Windley Key Fossil Reef Geological State Park, Rain Barrel Village, and Founders Park, offering easy access to the area's top attractions. With a user rating of 'excellent', this house is a great choice for travellers seeking a comfortable and convenient stay. This two-bedroom house can accommodate up to six guests, offering a comfortable and spacious living area. You can enjoy a private pool, garden, and a terrace, perfect for relaxing and enjoying the Florida sunshine.

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.

Islander Resort is situated directly on the beach in Islamorada, offering easy access to the beautiful waters of the Florida Keys and the area's attractions. The resort has received very good ratings for its overall experience, with excellent marks for its location and cleanliness.
The resort provides spacious rooms with private porches or lanais, perfect for enjoying the tropical ambiance. Guests can enjoy a range of amenities including swimming pools, a bar and restaurant, a spa, a fitness centre, and a concierge service.

This one-bedroom flat offers a prime beachfront setting in downtown Islamorada, a mere 3-minute walk from Windley Key Fossil Reef Geological State Park and 9 minutes from Hog Heaven.
This pet-friendly apartment accommodates two guests and features air conditioning, Wi-Fi, a swimming pool, and concierge services, with on-site parking facilitating exploration of nearby attractions such as Hurricane Monument and Indian Key Historic State Park.

This Islamorada holiday rental is located in the Executive Bay Club, a short walk from the marina, beach, and community facilities, and near John Pennekamp Coral Reef State Park.
This four-bedroom, two-bathroom apartment accommodates up to eight guests and features a large private garden, a swimming pool, and offers easy access to boating, fishing, snorkelling, diving, and paddleboarding.