Holiday Rentals in Islamorada, FL

This upscale villa is located in the Art District of Islamorada, just a short walk from shops, restaurants, and parks, including the Islamorada Library Beach Park and the Morada Way Arts & Cultural District. The villa is part of a luxury community with a private heated pool, bayside boat dock, and BBQ area.
This three-bedroom, three-bathroom property can accommodate up to six guests and offers a range of amenities, including a fully equipped kitchen, air conditioning, a swimming pool, a garden, and parking. Enjoy breathtaking sunsets and waterfront views from the private deck and top balcony, and take advantage of the villa's close proximity to numerous activities like paddleboarding, kayaking, snorkeling, fishing, biking, running, and walking along the beautiful Islamorada paths.

This Key Largo oceanfront property, located 1 kilometre from Pigeon Key and 13.5 kilometres from John Pennekamp Coral Reef State Park, offers direct water access.
The 250-square-metre house boasts three bedrooms, three bathrooms, sleeps seventeen guests, and includes a private pool, hot tub, fully equipped kitchen, free Wi-Fi, and an elevator; canoeing is readily available nearby.

Isla Mirabelle, a three-bedroom waterfront villa in Matecumbe, Islamorada, is located within a 1.6km walk of the Islamorada Brewery & Distillery and Keys History & Discovery Centre, and within a 2.4km radius of the History of Diving Museum.
This 156 square metre smoke-free property offers a private balcony, garden access, a fully equipped kitchen, and accommodates up to six guests, boasting four bathrooms and convenient on-site parking.

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 two-bedroom apartment is situated in Tavernier, just 2.4 kilometres from Baker's Cay Resort Beach and Harry Harris Park, offering easy access to the beautiful beaches of the Florida Keys. The property has received excellent ratings for location, cleanliness, and user experience.
The 77 square metre apartment can comfortably accommodate up to six guests and features a well-equipped kitchen, two bathrooms, and a private pool. Guests can enjoy a range of amenities including a washing machine, air conditioning, and a garden.

This apartment is located in Islamorada, a charming seaside village known for its stunning coral reefs, and is just a short walk from the Theater of the Sea and nearby tropical forests like Windley Key Fossil Reef Geological State Park and Lignumvitae Key Botanical State Park. This property has received excellent ratings for its location, cleanliness, and overall experience.
The apartment has one bedroom and one bathroom, comfortably accommodating up to four guests. Guests can enjoy a range of amenities, including a private beach, a heated pool with ocean views, a private boat ramp, kayaks, stand-up paddleboards, bicycles, and a daily continental breakfast.

This Tavernier condo is conveniently located near Harry Harris Park (approx. 1km), Mariners Hospital (under 5km), and other attractions within a 10km radius, offering easy access to waterfront activities and medical facilities.
The one-bedroom, one-bathroom apartment sleeps four guests and boasts a fully equipped kitchen, private balcony, free Wi-Fi, on-site pool, hot tub, and tennis court; perfect for exploring Tavernier and its surroundings.

This Islamorada condo, offering direct bay access with sunset views and a sandy beach, is located within walking distance of Islamorada's restaurants.
The three-bedroom, two-bathroom apartment sleeps six, features a fully equipped kitchen, a large balcony, and access to on-site amenities including a marina, tennis courts, and a heated swimming pool.

This 3-bedroom, 2-bathroom flat offers direct Florida Bay views from its 5th-floor balcony within the private, gated Futura Yacht Club in Islamorada, Village of Islands.
This family-friendly condominium sleeps six and boasts a heated swimming pool, BBQ grills, tennis courts, and marina access for boats up to 36 feet, with easy ocean access via Snake Creek or Tavernier Creek.

Isla Lychee: Little Basin Villas, a waterfront boutique resort in Matecumbe, Islamorada, is within walking distance of the Islamorada Brewery & Distillery and Keys History & Discovery Centre, and less than 2.4km from the History of Diving Museum.
This 156 square metre, three-bedroom villa sleeps six, offering four bathrooms, a fully equipped kitchen, free Wi-Fi, a private balcony, and access to on-site barbecue grills.

This oceanfront dwelling is located within the secure Anglers Reef community in Islamorada, offering direct access to the Florida Keys' celebrated sport-fishing and marine life, with world-class snorkelling, scuba diving, dining, and shopping opportunities approximately 1.6 kilometres away.
This family-friendly villa accommodates up to four guests, featuring two bedrooms and two bathrooms, a well-equipped kitchen with modern appliances, air conditioning, a swimming pool, a terrace, garden, and parking, with optional dock space available for rent for vessels up to 9.45 metres.

Isla Key Acai, a waterfront holiday home in Islamorada, Village of Islands, is a short walk (less than 2km) from Upper Matecumbe Key and within 4km of Windley Key, offering easy access to Pigeon Key (21km) and John Pennekamp Coral Reef State Park (34km).
This 156 square metre property boasts three bedrooms and three bathrooms, sleeping up to nine guests, and includes a fully equipped kitchen, spa, fitness centre, parking, and a terrace; free Wi-Fi and a children’s playground are also available.

This waterfront holiday home, part of the Waterfront / Ocean Access Canal / Kamp Key / Homes offer, is located in Matecumbe, Islamorada, offering easy access to the Morada Way Arts & Cultural District and Keys History & Discovery Centre.
The three-bedroom, three-bathroom property sleeps up to ten guests and boasts a private dock, heated pool, spacious open-plan living area, fully equipped kitchen, and outdoor terrace with access to beach gear including chairs, a cooler, and a cart.

This Islamorada apartment offers direct access to a private, pet-friendly beach with ocean views, situated in the city centre and within 1 kilometre of the History of Diving Museum and Keys History & Discovery Centre.
This three-bedroom, three-bathroom flat accommodates up to twelve guests, featuring air conditioning, Wi-Fi, a heated outdoor pool, and complimentary daily continental breakfast, with on-site bike, kayak, and paddleboard rentals available.

This beachfront flat is located in Islamorada's city centre, 200 metres from Hurricane Monument and Indian Key Historic State Park.
This one-bedroom, one-bathroom residence accommodates up to four guests and offers direct beach access, a heated pool with ocean views, complimentary continental breakfast, on-site water sports equipment hire including kayaks and paddleboards, and pet-friendly facilities, with nearby attractions such as Windley Key Fossil Reef Geological State Park and local nightlife at Hog Heaven.

This charming cottage is located in Islamorada, just a short distance from the village centre and within easy reach of the best fishing spots. The property has received excellent ratings for its location, cleanliness and overall experience, making it a popular choice for travellers.
The cottage is a one-bedroom property with one bathroom and can accommodate up to six guests. Guests can enjoy the privacy and tranquility of the cottage while taking advantage of amenities such as private boat rentals, discounted boat rental rates, and breathtaking sunset views.