Villas and Holiday homes in Islamorada, FL

Isla Key Acai: Waterfront Boutique Resort in Matecumbe, Islamorada, offers easy access to the Islamorada Brewery & Distillery and Keys History & Discovery Centre, both within 1.6km, and the History of Diving Museum and Matecumbe United Methodist Church within 2.4km.
This smoke-free villa boasts 156 square metres of space, sleeping up to six guests in three bedrooms and four bathrooms, and features a fully equipped kitchen, private balcony, on-site fitness centre, swimming pool, and free Wi-Fi.

Little Bay Cottage, a two-bedroom house in Islamorada, offers convenient access to Upper Matecumbe Key, Windley Key (4.3km), and Pigeon Key (21km), with John Pennekamp Coral Reef State Park a further 32km away.
This self-catering property sleeps seven, boasting a fully equipped kitchen with dishwasher, air conditioning, a spa, fitness centre, free Wi-Fi, in-unit laundry, and on-site parking.

This Islamorada holiday home, Sunshine Place, is conveniently located a short walk (less than 2km) from Windley Key Fossil Reef Geological State Park and within a few kilometres of other attractions such as the History of Diving Museum.
The one-bedroom, one-bathroom property sleeps five guests and boasts a fully equipped kitchen, free Wi-Fi, on-site parking, and access to a spa and fitness centre; nearby activities include exploring Pigeon Key (17.7km) and John Pennekamp Coral Reef State Park (30.6km).

This newly built, three-storey villa in the exclusive Peaceful Palms gated community offers direct oceanfront access with panoramic views of the Islamorada Sandbar and Alligator Reef Lighthouse, just a 5-minute walk to dining, the marina, and Starbucks.
This 186 square metre holiday home accommodates up to 8 guests with 3 bedrooms and 3 bathrooms, featuring a third-floor oceanfront balcony, a boat slip for vessels up to 7.3 metres, complimentary paddleboards and kayaks, an air-conditioned entertainment retreat with a ping pong table, and access to a communal oceanfront swimming pool.

Isla Kiwi: Waterfront Boutique Resort in Matecumbe, Islamorada, offers a 3-bedroom villa, a short walk from the Islamorada Brewery & Distillery and Keys History & Discovery Centre, and within a 2.4km radius of the History of Diving Museum and Matecumbe United Methodist Church.
This smoke-free property boasts a 156 square metre floor area, accommodating up to six guests, and features a fully equipped kitchen, private balcony, swimming pool, spa, and free Wi-Fi; barbecue facilities are also available on-site.

Coral Penthouse Key Largo Ocean Pointe 4216, situated in Key Largo, offers stunning ocean views and is a short drive (approximately 2.4km) from Harry Harris Park Beach.
This two-bedroom, two-bathroom apartment boasts 77 square metres of floor space, sleeps seven guests, and includes a private patio, swimming pool, Jacuzzi, and fully equipped kitchen with dishwasher; free Wi-Fi and cable TV are also provided.

Isla Key Lime: Waterfront Boutique Resort, a three-bedroom villa in Matecumbe, Islamorada, is located within 1.6km of the Islamorada Brewery & Distillery and Keys History & Discovery Centre, and under 2.4km from the History of Diving Museum.
This smoke-free property boasts 156 square metres of living space, sleeping up to six guests and featuring a fully equipped kitchen, private balcony, access to a garden, and free Wi-Fi; outdoor barbecues are also available.

This Key Largo holiday home is conveniently located near Pigeon Key (1 km), John Pennekamp Coral Reef State Park (13.5 km), and Dolphin Cove (13.7 km), offering easy access to Key Largo's attractions.
The 98-square-metre property boasts three bedrooms, three bathrooms, sleeps up to 15 guests, and includes a private pool, hot tub, fully equipped kitchen, free Wi-Fi, and an elevator; canoeing is available nearby.

This Islamorada waterfront villa offers spectacular ocean views and direct beach access within the Village of Islands, conveniently located near local attractions.
The four-bedroom, four-bathroom property sleeps eight guests and boasts a private marina (size restrictions apply), a swimming pool, jacuzzi, fitness centre, and access to on-site activities including yoga, aqua aerobics, pickleball, and bocce ball, plus the Ocean House Bar and Spa.

This Islamorada villa, situated in the Matecumbe neighbourhood, is conveniently located near the Hurricane Monument and Indian Key Historic State Park.
Sleeping eight guests, this three-bedroom property boasts a private plunge pool, access to a community pool, and private boat dockage, alongside a fully equipped kitchen, four bathrooms, and a terrace; nearby attractions include the Florida Keys Brewing Co. and Islamorada Brewery & Distillery.

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 three-bedroom, three-bathroom townhome is located within the exclusive gated Executive Bay Club in Islamorada, Florida, directly adjacent to Founder's Park, offering privacy and security with stunning ocean views.
Spanning 153 square meters, this family-friendly residence accommodates up to six guests and features a newly remodelled interior, a private on-site beach, a freshwater swimming pool, tennis and pickleball courts, and marina access for daytime use.