Holiday Rentals in Islamorada, FL

This Tavernier apartment is conveniently located just a 15-minute walk from Baker's Cay Resort Beach and Harry Harris Park, offering easy access to both relaxation and exploration. The apartment has received excellent ratings for user experience, location, and cleanliness, ensuring a comfortable and enjoyable stay.
The 81 square metre apartment comfortably accommodates up to 4 guests in its two bedrooms and two bathrooms. Enjoy a range of amenities including a private pool, a fully equipped kitchen, a DVD player, and a balcony, perfect for relaxing and enjoying the Florida sunshine.

This Islamorada waterfront villa, offering direct beach access, is situated in the Village of Islands and is conveniently located near various attractions within Islamorada (precise distances unspecified).
The four-bedroom, four-bathroom property sleeps eight guests and boasts a private marina (size restrictions apply, no boat ramp or jet ski/trailer parking), multiple pools, a jacuzzi, fitness pavilion, watersports equipment rentals, and on-site spa services.

This family-friendly holiday home is located in Islamorada, just a short drive from the San Pedro Underwater Archaeological Preserve State Park, Robbie’s of Islamorada, and Indian Key Historic State Park, all within a 3 km radius. This property has consistently received excellent ratings for its location, cleanliness, and overall user experience.
This two-bedroom dwelling can comfortably accommodate up to five guests. The property offers a range of amenities, including a swimming pool, a Jacuzzi, a terrace, a garden, a spa, and concierge services, as well as a tennis court and free parking.

Cheeca Lodge & Spa is situated on a 27-acre stretch of waterfront in Islamorada, just a 20-minute drive from downtown Key Largo and 13.7 miles from Long Key State Park. The resort has received very good user ratings, with excellent scores for location and cleanliness.
The property features spacious rooms with balconies and resort views. Guests can enjoy a range of amenities, including a 9-hole golf course, spa, fishing pier, swimming pools, fitness centre, tennis courts, and watersports facilities.

This Islamorada holiday flat is located within a resort community, offering convenient access to cultural sites such as the Old Road Gallery and the History of Diving Museum, and is situated near attractions including John Pennekamp Coral Reef State Park and Jacob's Aquatic Centre.
This two-bedroom, two-bathroom apartment features a second-floor patio with sunrise views, air conditioning, a fully equipped kitchen with a microwave oven and dishwasher, internet access, and on-site parking, with complimentary use of paddle boards and kayaks for exploring the waters and access to two swimming pools and gym facilities, subject to a minimum 28-day stay.

This Tavernier oceanfront condo offers direct beach access and is conveniently located near Key Largo and Islamorada attractions, including John Pennekamp Coral Reef State Park and Indian Key Historic State Park.
The 79 square metre apartment sleeps six guests, boasting two bedrooms, two bathrooms, a fully equipped kitchen (including fridge, microwave, and dishwasher), air conditioning, and access to a swimming pool, parking, and resort amenities such as a junior Olympic-sized swimming pool, hot tub, and tennis courts.

This four-bedroom, three-bathroom villa offers prime waterfront living in an upscale neighbourhood of Islamorada, Village of Islands, located 1.5 hours' drive from Miami and Key West, and 1 kilometre from the Holiday Isles Tiki Bar.
This spacious property, covering 223 square metres, accommodates up to eight guests and features a heated swimming pool, jacuzzi, and an independent one-bedroom apartment, with modern furnishings and internet access, providing an excellent base for exploring local attractions such as swimming with dolphins and stingrays, just 1 minute away.

This charming cottage is situated in Islamorada at mile marker 76.7, just a short drive from Caloosa Cove Marina at mile marker 73.5 and Robbie's Marina, offering a peaceful retreat in the Shady Palms community. The cottage boasts excellent user, location and cleanliness ratings, ensuring a comfortable and enjoyable stay.
The property features two bedrooms, making it ideal for families or groups of up to four. Guests can enjoy amenities such as a communal heated pool, a fully equipped kitchen, a private garden, a spa, and a starter pack with essential supplies.

Isla Key Lychee, a waterfront villa in Islamorada, offers easy access to Upper Matecumbe Key (a 2km walk) and Windley Key (4km), with Pigeon Key and John Pennekamp Coral Reef State Park further away.
This three-bedroom, three-bathroom property boasts 156 square metres of living space, comfortably accommodating nine guests and featuring a fully equipped kitchen, private balcony, swimming pool, fitness centre, free Wi-Fi, and on-site parking.

This penthouse apartment is located in Islamorada, approximately 13 kilometres from the town centre and within walking distance of Sunset Drive Beach and Anne's Beach, offering a peaceful retreat near the beautiful coastline. The property enjoys an excellent user rating, indicating its high standard of accommodation and amenities.
The apartment is spacious, with 138 square metres of floor area, comfortably accommodating a large group of travellers. It features a fully equipped kitchen, air conditioning, a swimming pool, a terrace, a fitness centre, a tennis court, and parking, providing a wide range of amenities for a relaxing and enjoyable stay.

This waterfront villa in Islamorada, Village of Islands, is within walking distance of Windley Key Fossil Reef Geological State Park and a 15-minute walk to Hog Heaven.
This 156 square meter holiday home accommodates up to 8 guests with 4 bedrooms and 3 bathrooms, featuring a fully equipped kitchen, air conditioning, a shared swimming pool, a terrace, a spa, a tennis court, and on-site parking.

This beachfront apartment, part of the Ocean Pointe Suites resort in Tavernier, Florida Keys, offers easy access to John Pennekamp Coral Reef State Park and Jacob's Aquatic Centre, though precise distances are not specified.
The 79-square-metre (850-square-foot) self-catering property sleeps six, boasting two bedrooms, two bathrooms, a fully equipped kitchen including an American coffee maker and blender, a terrace, and resort amenities such as a heated pool, jacuzzi, BBQ area, tennis/pickleball courts, and a private beach, plus complimentary parking for two cars.

This apartment is located in Blue Waters, a 15-minute walk from Baker's Cay Resort Beach and Harry Harris Park, with Mariners Hospital and Florida Keys Dive Center within 5 kilometres. The accommodation has received excellent ratings for location, cleanliness and overall user experience.
The apartment has a floor area of 77 square metres and can accommodate up to 6 guests. It comes with a private pool, a spa tub, barbecue grills, a washing machine, a sofa bed, and a fully equipped kitchen, ensuring a comfortable stay for families and groups.

This Islamorada bungalow, ideally situated near pristine beaches and world-class fishing opportunities in the Village of Islands, offers easy access to various attractions.
The two-bedroom, one-bathroom house sleeps four, boasting a fully equipped kitchen, in-unit laundry, a private porch, and access to a community heated swimming pool; on-site bicycles are available for exploring the area.

This Islamorada beachfront apartment, part of a pet-friendly resort, offers direct beach access and partial ocean views from its 28-square-metre (301 sq ft) balcony, conveniently located near the Islamorada Brewery & Distillery and Indian Key Historic State Park.
The self-catering flat features two queen beds sleeping four, a fully equipped kitchenette including a fridge, microwave, and dishwasher, plus daily housekeeping and continental breakfast; on-site amenities include a heated pool, kayaks, paddleboards, and bike rentals.

Ocean Pointe 2309, a beachfront property in Tavernier, Florida, offers ocean views and is a 14-minute walk from Harry Harris Park Beach and 4.8km from Pigeon Key.
This two-bedroom, two-bathroom house boasts 85 square metres of floor space, sleeps up to 11 guests, and includes a private pool, bar, free Wi-Fi, and parking.