Find short term rentals in Islamorada, FL at the best prices

Little Bay Cottage is located directly on Florida Bay in Islamorada, just off Overseas Highway at Mile Marker 82.2, within easy reach of attractions like John Pennekamp Coral Reef State Park and Robbie's Marina. The cottage is part of a gated compound offering privacy and security, and has a unique floor plan with a spacious living area, two bedrooms and two bathrooms, comfortably sleeping up to four guests.
The cottage features a modern kitchen with new appliances and granite countertops, as well as a full-size washer and dryer, central air conditioning, and WiFi. Guests can also enjoy a variety of outdoor spaces for relaxation, including a sunning area with lounge chairs, hammocks, a pergola and a tiki hut, as well as a protected dock for boats up to 10 metres long.

This oceanfront apartment is situated in Tavernier, Florida Keys, at mile marker 92, offering easy access to the Tavernier Creek for both bay and ocean activities. It has received excellent user ratings, indicating a comfortable and enjoyable stay for guests.
The apartment spans 78 square metres and comfortably accommodates up to 6 guests in its two bedrooms and two bathrooms. Guests can enjoy a range of amenities within the gated resort community, including a heated pool, jacuzzi, BBQ picnic area, tennis courts, a private beach, a dock and marina, a boat ramp, boat and trailer parking, and a waterfront café.

This Islamorada holiday home is situated near Sunset Drive Beach (0.6 km), Anne's Beach (4.8 km), and Robbie's of Islamorada (9.7 km), offering easy access to local attractions.
The three-bedroom, three-bathroom property sleeps eight guests and boasts a fully equipped kitchen, Wi-Fi, a private garden, spa, and barbecue facilities; pets are welcome.

This two-bedroom flat is located in Angler's Reef, a secure oceanfront community in Islamorada, offering direct beach access and a heated oceanfront swimming pool.
This family-friendly accommodation sleeps up to six guests and features a kitchen with a fridge, microwave, and dishwasher, along with air conditioning, a terrace/balcony, garden, and parking.

This Tavernier oceanfront condo, near Key Largo and Islamorada, offers direct beach access and proximity to attractions such as John Pennekamp Coral Reef State Park.
The 79-square-metre (850-square-foot) apartment sleeps six, featuring two bedrooms, two bathrooms, a fully equipped kitchen including a dishwasher, and access to a swimming pool, parking, and on-site resort amenities.

This waterside condominium is located in the gated Bay Harbour community at mile marker 77.5 bayside in Matecumbe, Islamorada, within 1.6 kilometres of Anne's Beach and the San Pedro Underwater Archaeological Preserve State Park.
This three-bedroom holiday flat, accommodating up to six guests, offers a private screened terrace with ocean views, a gourmet kitchen, a private 9.45-metre protected dock with a boat lift, and on-site access to a swimming pool and spa.

This Tavernier waterfront apartment, situated 1.3 km from Harry Harris Park and within 5 km of Mariners Hospital and the Florida Keys Dive Centre, offers stunning views.
The 76-square-metre property boasts two bedrooms, two bathrooms, sleeps seven guests, and includes a fully equipped kitchen, private balcony, swimming pool, jacuzzi, tennis court, and free Wi-Fi.

This two-bedroom apartment is located just 3 kilometres from Baker's Cay Resort Beach and Harry Harris Park in Tavernier, offering easy access to the area's attractions. The property has received excellent user ratings, making it a popular choice for travellers.
The apartment comfortably accommodates up to six guests and features a fully equipped kitchen, a balcony, and a swimming pool. Guests can enjoy free Wi-Fi in public areas, parking for larger vehicles, and the convenience of being located in a smoke-free environment.

This Tavernier apartment is located just 2.4 kilometres from Baker's Cay Resort Beach and Harry Harris Park, both offering a relaxed beach atmosphere, and is within 5 kilometres of Mariners Hospital and Florida Keys Dive Center. It has received excellent ratings for location, cleanliness, and overall user experience.
The one-bedroom apartment spans 60 square metres and comfortably accommodates up to four guests. It offers a range of amenities including a fully equipped kitchen, a private balcony, a swimming pool, a jacuzzi, a tennis court, and a garden, ensuring a relaxing and enjoyable stay.

This charming bed and breakfast is situated on the beautiful coastline of Islamorada, just a few kilometers from the History of Diving Museum and Theater of the Sea. The surrounding area offers a relaxed, tropical atmosphere, perfect for those seeking a peaceful escape.
The property features spacious villa suites, each accommodating up to six guests, providing ample space for families or groups. Guests can enjoy a range of amenities, including a swimming pool, fitness centre, and on-site water sports activities, making it an ideal choice for a relaxing and active holiday.

This two-bedroom apartment is situated in the Executive Bay Club community in Islamorada, just a short distance from the village's centre and close to the beaches and fishing spots of the Florida Keys. It has received excellent ratings for location, cleanliness, and overall user experience.
The apartment is ideal for families or groups of friends, offering space for up to four guests. It benefits from a shared heated pool, clubhouse, tennis court, beach, fishing dock, and a private backyard with a barbecue.

This oceanfront property in Islamorada, Florida Keys, offers a gated community setting with convenient access to local attractions.
The two-bedroom, two-and-a-half-bathroom house sleeps five, boasting a well-equipped kitchen, swimming pool, garden, and access to community kayaks; on-site boat slips are available to rent (subject to size restrictions: 9-foot bridge height, 31-foot length, 3.5-foot draught).

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 holiday home, part of the Sun Outdoors resort in the Seabreeze Trailer Park neighbourhood, offers convenient access to the Old Road Gallery and History of Diving Museum, within walking distance depending on location.
The 'Charming 2-bedroom House In Gorgeous Resort' sleeps six, featuring two bedrooms (one king, one double), two bathrooms with bidets, Wi-Fi, air conditioning, and access to resort amenities including two heated pools, a clubhouse, and a games lawn; John Pennekamp Coral Reef State Park and Jacob's Aquatic Centre are a short drive away.

This oceanfront apartment in Islamorada, Village of Islands, offers direct sea access and is located within 500 meters of the oceanfront beach.
This two-bedroom, three-bathroom property accommodates four guests and features a private rooftop deck, a new 10-meter boat dock, a heated community pool, and on-site peacock viewing.

This waterfront condominium in Tavernier, Ocean Pointe, is situated at Mile Marker 91 on the ocean side, offering convenient access to John Pennekamp Coral Reef State Park and Windley Key Fossil Reef Geological State Park, just a short drive away.
This recently remodelled two-bedroom, two-bathroom apartment, covering 77 square metres and accommodating up to five guests, features oceanfront views, a fully equipped kitchen, in-unit laundry, complimentary Wi-Fi, and access to a shared swimming pool and jacuzzi within a gated resort complex.