Vacation Rentals in Islamorada, FL

This waterfront property in Tavernier is located within a short walk of Baker's Cay Resort Beach and Harry Harris Park, offering easy access to the area's natural beauty. The apartment has received excellent ratings for its location, cleanliness, and overall user experience.
The spacious two-bedroom flat, covering 85 square metres, comfortably accommodates up to six guests. Enjoy a range of amenities including a fully equipped kitchen, a swimming pool, a Jacuzzi, a tennis court, and a spa, making it ideal for a relaxing and enjoyable stay.

Blue Palm Oasis, a substantial residence in Islamorada, Village of Islands, is located on Plantation Key, offering direct bay access and a swift 3-kilometre journey to ocean access via Snake and Tavernier Creek, with popular spots like Old Tavernier Restaurant a mere 1.6 kilometres away.
This 291-square-metre property accommodates up to eight guests with four bedrooms and three bathrooms, featuring a heated and chilled swimming pool, over 51 metres of dockage with two boat lifts, an air-conditioned tackle garage, and an open-concept living area with floor-to-ceiling windows.

This canal-front flat in Islamorada, Village of Islands, offers direct water access and ocean views, ideal for boating enthusiasts and those seeking a coastal escape within the Florida Keys.
This family-friendly accommodation sleeps six and features two bedrooms and two bathrooms, complete with air conditioning, internet, and a kitchen fitted with a fridge, microwave, and dishwasher, whilst being a short drive from local restaurants and shops.

This tropically furnished condominium in the gated Futura Yacht Club offers direct Gulf of Mexico views from a 5th-floor balcony, located centrally within the Village of Islamorada, providing easy access to local restaurants, shops, and recreational activities.
This 93 square meter apartment, ideal for up to 4 guests, features 2 bedrooms and 2 bathrooms, a newly renovated kitchen with quartz countertops, air conditioning, and on-site amenities including a heated swimming pool, tennis and pickleball courts, and a beach area with picnic tables and a firepit.

This two-bedroom villa is located in the gated community of Angler's Reef in Islamorada, just a short drive from the best restaurants and attractions in the Keys. The property has received excellent user ratings, reflecting its desirable location and amenities.
The villa offers 128 square metres of living space, accommodating up to six guests comfortably. Guests can enjoy a private boat slip, a heated pool, two private beaches, and a range of water activities, including kayaking, paddleboarding, fishing, and boating.

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 charming bungalow is situated just a short distance from the lively downtown area of Islamorada, offering easy access to the renowned fishing piers and the scenic Overseas Highway. The property has consistently received excellent ratings for location, cleanliness, and overall guest experience.
The cottage comfortably accommodates up to four guests across two bedrooms and one bathroom, spanning 88 square metres. Guests can enjoy a private backyard and porch, a community heated pool, a fully equipped kitchen with modern appliances, a washer and dryer, complimentary bicycles, and a security camera for added peace of mind.

This apartment in Tavernier is located within an oceanfront resort, offering views of the sea and convenient access to attractions such as John Pennekamp Coral Reef State Park, situated 2.8 kilometres away, and the Hurricane Monument and Caribbean Club Bar are nearby landmarks.
This 56 square metre flat accommodates up to six guests, featuring two bedrooms, one bathroom, air conditioning, a kitchen equipped with a fridge, microwave oven, and dishwasher, and access to a communal swimming pool and parking, with the resort also providing tennis courts and an on-site café.

This beachfront flat in central Islamorada offers direct access to the coast and is situated within 1.5 kilometres of the Hurricane Monument and Indian Key Historic State Park, with Windley Key Fossil Reef Geological State Park and San Pedro Underwater Archaeological Preserve State Park nearby for exploration.
This three-bedroom, three-bathroom residence accommodates up to twelve guests and features a swimming pool, terrace, air conditioning, Wi-Fi, and is conveniently located near popular dining and entertainment venues, with opportunities for kayaking, sailing, hiking, biking, and mountain climbing in the vicinity.

This Islamorada holiday flat offers direct beachfront access and ocean views, situated 4.3 kilometres from Windley Key and 5 kilometres from the Theatre of the Sea Islamorada.
This spacious three-bedroom, two-bathroom property accommodates up to eleven guests and features a fully equipped kitchen, air conditioning, a private balcony, and on-site spa facilities including a hot tub and fitness room, with complimentary private parking available.

This houseboat resort is situated on the waterfront in Tavernier, within a 15-minute walk of Baker's Cay Resort Beach and Mariners Hospital, and within 3 miles of Florida Keys Dive Center and Harry Harris Park. The resort has received excellent ratings for its location, cleanliness and overall experience.
The houseboat offers a rooftop deck for stunning views of the sunrise and sunset, with a spacious 84 square metre layout and four bedrooms. Guests can enjoy a range of amenities, including a swimming pool, restaurant, bar, and free Wi-Fi in public areas, making it the perfect base for exploring the area.

This studio apartment is located in the Matecumbe district of Islamorada, Village of Islands, directly on the beach and close to Indian Key Historic State Park and the Hurricane Monument.
This pet-friendly, air-conditioned accommodation offers Wi-Fi, a balcony, and concierge service for up to four guests, with direct access to water sports and nearby cycling opportunities.

This Tavernier apartment is directly on the beach, a 15-minute walk from Baker's Cay Resort Beach and Harry Harris Park, with Mariners Hospital and Florida Keys Dive Center within 3 miles. This property has received excellent ratings for location, cleanliness and user experience.
The one-bedroom apartment offers 56 square metres of space and can accommodate up to four guests. The apartment includes a fully equipped kitchen, air conditioning, a swimming pool, a jacuzzi, a terrace, a garden, a bar, a fitness centre, a tennis court, and parking.

This Tavernier oceanfront condo, near Key Largo and Islamorada, offers direct beach access and proximity to John Pennekamp Coral Reef State Park and Indian Key Historic State Park, though precise distances aren't specified.
This 79 square metre (850 square foot) apartment sleeps six, boasting two bedrooms with flexible bedding, two bathrooms, a fully equipped kitchen including a dishwasher, air conditioning, a swimming pool, parking, and internet access; on-site resort amenities include a junior Olympic-sized swimming pool, hot tub, and tennis courts.

This waterfront apartment is situated in Islamorada's Matecumbe district, just a short distance from Bud n' Mary's Dive Center and Florida Keys Brewing Co., offering stunning views of the ocean and marina. The apartment has received excellent user ratings, indicating a high level of satisfaction among previous guests.
The apartment is spacious, measuring 158 square metres and accommodating up to 6 guests. It features a range of amenities and activities, including a private dock, a heated pool, a hot tub, a fitness centre, lighted tennis courts, a clubhouse, and a well-equipped equipment closet.

This apartment is situated in Tavernier, a village in the Florida Keys, just 8 kilometres from John Pennekamp Coral Reef State Park and Jacob's Aquatic Center. It is rated excellent by previous guests and offers direct access to the beach.
This three-bedroom property spans 110 square metres and can accommodate up to six guests. The apartment has a fully equipped kitchen, a balcony, and a swimming pool, as well as access to tennis courts and kayaking rentals.