Vacation Rentals in Islamorada, FL

This Islamorada condominium is located in Tavernier, at mile marker 88.5 on the bay side, offering waterfront views and convenient access to the Florida Keys Dive Center, Mangrove Marina, John Pennekamp Coral Reef State Park, and Windley Key Fossil Reef Geological State Park.
This fully furnished 2-bedroom condo spans 79 square metres, accommodates up to six guests, and features en-suite bathrooms, a balcony overlooking tennis courts, on-site WiFi, central air conditioning, and laundry facilities, with available dockage, a boat ramp, and trailer parking for boating enthusiasts.

This Islamorada canal-front property, moments from Tavernier Creek Marina and restaurants, offers direct bay and ocean access, with the reef approximately 1.6 kilometres away.
This two-bathroom apartment sleeps five, boasting a private pool, patio, boat dockage, large loft with Netflix, outdoor shower, bait freezer, BBQ, and full kitchen including dishwasher, fridge, freezer and microwave.

This canal-front holiday home in Islamorada, Village of Islands, is situated at mile marker 90, offering 40 feet of private dockage and convenient access to local attractions.
Accommodating up to six guests, this property features two bedrooms and two bathrooms, along with a swimming pool, hot tub, and an outdoor kitchen, making it ideal for boaters and families seeking a Keys ambiance.

This Tavernier apartment is located just 2.4 kilometres from Baker's Cay Resort Beach and Harry Harris Park, offering a peaceful and relaxing setting. The property has received excellent user ratings, indicating a high level of satisfaction from previous guests.
The apartment has two bedrooms, two bathrooms, and a floor area of 84 square metres, comfortably accommodating up to six guests. It boasts a range of amenities including a swimming pool, a jacuzzi, a tennis court, and a garden, along with direct beach access and a fully equipped kitchen.

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.

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.

This one-bedroom condo is located in Lower Matecumbe Beach, a short 10-minute walk from Sunset Drive Beach and Anne's Beach, and a 4.3 km drive from the San Pedro Underwater Archaeological Preserve State Park. The property has received excellent user ratings and is a popular choice for travellers seeking a relaxing and convenient stay.
The 74 square metre apartment comfortably accommodates up to 6 guests and features a fully equipped kitchen, two bathrooms, a washing machine, free Wi-Fi, a balcony, games, and books. Guests can enjoy the convenience of self-catering, relax in the private outdoor space, and explore the nearby beaches and attractions.

This waterside holiday let in Plantation Key Colony, Tavernier, offers a 5-minute journey to both Florida Bay and the Atlantic Ocean, close to John Pennekamp Coral Reef State Park.
This four-bedroom holiday home sleeps eight, featuring a third-floor primary suite, a first-floor guest suite, a heated swimming pool, a waterfront tiki hut, a gas grill, and dockage for boats up to 10.67 meters with a fish-cleaning station and bait freezer.

This Tavernier oceanfront condo, near Key Largo and Islamorada, offers direct beach access and proximity to John Pennekamp Coral Reef State Park and Jacob's Aquatic Centre.
The 79 square metre (850 square foot) apartment sleeps six, featuring two bedrooms, two bathrooms, a fully equipped kitchen (fridge, microwave, dishwasher), air conditioning, a swimming pool, parking, and internet access; resort amenities include a junior Olympic-sized swimming pool, hot tub, and tennis courts.

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.

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 two-bedroom flat in Islamorada, Village of Islands, boasts an exceptional beachfront position within the village, offering direct access to the coast and situated just 270 metres from Windley Key Fossil Reef Geological State Park and 810 metres from Hog Heaven.
This accommodation for up to eight guests features air conditioning, Wi-Fi, a shared swimming pool, and a private balcony, with concierge services available and proximity to sailing, kayaking, mountain climbing, and hiking activities.

This beachfront flat is centrally located in Islamorada, Village of Islands, offering direct access to the private beach resort and proximity to the History of Diving Museum and Keys History & Discovery Centre.
This one-bedroom, one-bathroom holiday let accommodates up to four guests and includes a heated swimming pool with ocean views, complimentary Wi-Fi, air conditioning, and on-site activities such as kayak and paddleboard rentals, with pets welcome.

This five-bedroom house is situated in Tavernier, just a short walk from Baker's Cay Resort Beach and Florida Keys Dive Center, and within a 2km drive of Mariners Hospital. The property has received excellent ratings for location, cleanliness, and user experience.
This spacious holiday home offers 260 square metres of living space and can comfortably accommodate up to 12 guests. The property features a private pool, spa tub, fully equipped kitchen, washing machine, terrace, bar, and parking.

This pet-friendly apartment in Islamorada, centrally located in the Village of Islands, offers easy access to attractions such as the History of Diving Museum and Keys History & Discovery Centre.
The 35-square-metre (377-square-foot) self-catering flat features one bedroom, one bathroom, sleeps four guests, and includes a kitchenette, swimming pool access, and complimentary continental breakfast.

Ocean Pointe 5209, Key Largo, offers a two-bedroom house in Tavernier, a 2.4km walk from Harry Harris Park Beach and 4.5km from Pigeon Key.
This 77 square metre property sleeps six, boasting a private patio with ocean views, a swimming pool, jacuzzi, and fully equipped kitchen including a dishwasher; free Wi-Fi and on-site parking are also provided.