Vacation Rentals in Islamorada, FL

This Tavernier apartment is situated just a short walk from the end of the pier, offering stunning views of the Atlantic Ocean and Florida Keys mangroves. It has received excellent ratings for location, cleanliness, and user experience.
The two-bedroom, two-bathroom apartment spans 91 square metres and can comfortably accommodate up to six guests. Amenities include a swimming pool, jacuzzi, tennis courts, a marina, a cafe, and a beach area, providing a range of activities and features for a relaxing getaway.

This charming cottage is located just a short distance from the main attractions of Islamorada, offering a peaceful escape from the hustle and bustle of the Village of Islands. The cottage consistently receives excellent ratings for location, cleanliness, and overall guest experience.
The cottage features one bedroom and one bathroom, comfortably accommodating up to three guests. Amenities include air conditioning, a fully equipped kitchen, a private garden, parking, and internet access, along with the added benefit of discounted boat rentals, allowing you to explore the beautiful waters of Islamorada at your leisure.

This waterfront houseboat resort in Tavernier is conveniently located within a 15-minute walk of Baker's Cay Resort Beach and Mariners Hospital, offering easy access to both relaxation and healthcare. The resort boasts excellent user ratings and very good scores for location and cleanliness, ensuring a pleasant stay.
The 46 square metre houseboat features a comfortable layout with one bathroom, perfect for a couple or small family. Guests can enjoy a range of amenities, including a swimming pool, barbecue grills, and a tranquil garden, making it ideal for a relaxing getaway.

This Islamorada ocean view condominium offers direct Atlantic access from its prime location in the Village of Islands, placing you moments from notable restaurants, bars, and fishing charters.
This two-bedroom, one-bathroom property accommodates up to six guests and features a private balcony with ocean vistas, a fully equipped kitchen, on-site swimming pool, fitness centre, and private parking.

This Islamorada apartment, ideally located in the Village of Islands, offers easy access to local restaurants and attractions; precise distances are not provided.
Sleeping up to eight guests, this recently remodelled two-bedroom, three-bathroom dwelling boasts a full kitchen, a patio with BBQ, a swimming pool, fitness centre, and parking; high-speed fibre optic internet and a new washer/dryer are also included.

This four-bedroom, four-bathroom house in Islamorada, Village of Islands, offers a relaxing retreat, although precise location and proximity to specific landmarks requires further clarification.
Sleeping up to ten guests, the property boasts a swimming pool, jacuzzi, and ample parking, alongside a fully equipped kitchen and air conditioning; further details regarding the property's size and additional amenities are unavailable.

This two-bedroom townhouse is situated in a gated community of just ten homes, a short distance from Islamorada's restaurants, beaches and parks.
The property boasts a private swimming pool, a boat dock, and four terraces, perfect for enjoying the Florida sunshine and stunning sunsets, and can accommodate up to six guests.

This one-bedroom apartment, located in the Matecumbe district of Islamorada, is just a short walk from Anne's Beach and Sunset Drive Beach, and within a 3.2 km drive of San Pedro Underwater Archaeological Preserve State Park and Robbie's of Islamorada. The 46 square metre property features a fully equipped kitchen, a balcony, a swimming pool, a Jacuzzi, and a tennis court, and can accommodate up to five guests.

This waterfront apartment is located in Tavernier, within a 15-minute walk of Baker's Cay Resort Beach and Harry Harris Park, offering easy access to the area's natural beauty. Guests have consistently rated this property as excellent for location, cleanliness, and overall experience.
The apartment features two bedrooms and two bathrooms spread across 85 square metres. Enjoy the convenience of a fully equipped kitchen, a private fenced yard, a swimming pool, a jacuzzi, and a tennis court, making this a perfect choice for families and groups seeking a comfortable and relaxing stay.

This Islamorada apartment, situated on a private beach within walking distance of the Theatre of the Sea and close to Windley Key Fossil Reef and Lignum Vitae Key Botanical State Parks, offers convenient access to local attractions.
The 301 sq ft (28 sq m) self-catering flat features two queen beds, a balcony, and accommodates up to four guests, with amenities including a heated pool, kayaks, paddleboards, bike rentals, daily continental breakfast, and daily housekeeping.

This studio apartment is situated within Caloosa Cove Marina & Resort in Islamorada, Village of Islands, offering direct access to an on-site marina and restaurant, with Founders Park, featuring a saltwater swimming area and sandy beaches, located 500 meters away.
This accommodation for up to three guests provides air conditioning, Wi-Fi, a kitchenette with a fridge and microwave, and full access to resort amenities including recreational facilities and an oceanfront heated swimming pool.

This Islamorada resort offers direct access to a private beach and is situated within 600 metres of the History of Diving Museum and the Theater of the Sea, with easy access to Windley Key Fossil Reef Geological State Park and Lignumvitae Key Botanical State Park.
The "3 Relaxing Units, Free Parking, Breakfast, Pool" offer at this Islamorada accommodation provides 3 bedrooms and 3 bathrooms for up to 12 guests, featuring air conditioning, internet, a heated outdoor swimming pool, a garden, and allows pets for an additional charge.

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 Tavernier apartment is conveniently located just 2.4 kilometres from Baker's Cay Resort Beach and Harry Harris Park, offering easy access to the area's attractions. The property has received excellent ratings for user experience, location, and cleanliness.
The two-bedroom apartment spans 79 square metres and comfortably accommodates up to four guests. It features a fully equipped kitchen, air conditioning, a swimming pool, a Jacuzzi, a terrace, a garden, a spa, a tennis court, and parking.

This waterfront apartment is located in Tavernier, a 15-minute walk from Baker's Cay Resort Beach and Harry Harris Park, offering easy access to the area's beautiful beaches and attractions. The property has received excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay.
The apartment features two bedrooms and two bathrooms, spanning 85 square metres and comfortably accommodating up to six guests. Enjoy a range of amenities including a swimming pool, jacuzzi, terrace, garden, spa, tennis court, and parking, as well as a fully equipped kitchen and free Wi-Fi.

This waterfront apartment is located in Tavernier, a short walk from Baker's Cay Resort Beach and Harry Harris Park, offering a peaceful setting close to attractions. The property has received excellent ratings for its location, cleanliness, and overall experience.
The two-bedroom apartment can comfortably accommodate up to four guests. It offers a range of amenities, including a swimming pool, jacuzzi, tennis court, and a fully equipped kitchen, ensuring a comfortable and enjoyable stay.

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 one-bedroom, one-bathroom condominium is located bayside on Plantation Key at Mile Marker 88.5 in Islamorada, Village of Islands, offering direct access to outdoor activities and stunning open water bay views, with Marker 88 Restaurant and four other eateries within walking distance.
Guests can enjoy the Summer Sea Condominium complex's amenities, including two swimming pools (one heated), a beach area, an updated fitness centre, two game rooms, community rooms, and a lending library, all within a safe and secure gated community.

This canal-front apartment is located in Islamorada, just a 5-minute boat ride from the famous tiki sandbar, offering a peaceful retreat away from the main tourist areas. This property has received excellent ratings for user experience, location and cleanliness.
The apartment has three bedrooms and two bathrooms, accommodating up to six guests. It features a fully equipped kitchen, air conditioning, a swimming pool, a jacuzzi, a garden, parking, and direct canal access with 32 feet of dockage.

This studio apartment is situated in Islamorada, Village of Islands, offering direct access to oceanfront resort amenities and a 25-acre Founders Park with a saltwater swimming area, accessible via the Caloosa KeyCard.
Accommodating up to three guests, this first-floor unit features a queen bed and a twin sofa sleeper, a compact kitchen for light meal preparation, and offers full access to resort facilities including a heated swimming pool with ocean views, along with nearby recreational activities such as shuffleboard, pickleball, and tennis.

This Tavernier apartment is situated just 3 kilometres from Mariners Hospital and Florida Keys Dive Center, with Baker's Cay Resort Beach and Harry Harris Park within a 1.5 kilometre walk. It has received excellent user ratings and is perfect for those looking for a comfortable and convenient base to explore Tavernier.
This one-bedroom, one-bathroom apartment is 56 square metres in size and can comfortably accommodate up to four guests. The apartment offers a range of amenities including a fully equipped kitchen, a private balcony, a swimming pool, a jacuzzi, a tennis court, and free Wi-Fi, all within a smoke-free environment.

This Tavernier waterfront apartment, a short 1km stroll from Harry Harris Park and within 5km of Mariners Hospital and Pigeon Key, offers stunning views.
The two-bedroom, two-bathroom condo sleeps four, boasting a fully equipped kitchen, free Wi-Fi, a swimming pool, Jacuzzi, tennis court, and private terrace – perfect for families seeking a relaxing Tavernier getaway.

This pet-friendly, family-friendly townhome in Islamorada, Village of Islands, offers oceanfront living within the gated Peaceful Palms community, featuring direct ocean access and proximity to local dining and the Islamorada Sandbar, with a private dock for boats up to 27 feet (advance reservation required) and a sandy entry ideal for watersports.
This spacious 156-square-meter accommodation boasts 3 bedrooms and 3 bathrooms for up to 7 guests, complete with air conditioning, a fully equipped kitchen including a dishwasher, a resort-style oceanfront swimming pool, a private balcony with panoramic sunrise views, and a garden, all within walking distance of Starbucks.

Brand New! 2-bedroom House In Resort is situated in Seabreeze Trailer Park, Islamorada, directly opposite Founders Park, offering beach access and conveniently located a short drive from Islamorada's restaurants and fishing attractions.
This two-bedroom, two-bathroom house sleeps six, boasting full access to Sun Outdoors Islamorada resort amenities including a heated pool, clubhouse, and oceanfront boardwalk, plus proximity to John Pennekamp Coral Reef State Park.

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 two-bedroom duplex is located in the Upper Keys of Islamorada, just a short walk from shops, restaurants, and breweries, and within a two-minute walk of the boat basin with its stunning sunset views. The property has excellent user, location, and cleanliness ratings.
The apartment has two bedrooms and two bathrooms, accommodating up to four guests. Amenities include a fully equipped kitchen, air conditioning, a terrace, a garden, parking, and shared laundry facilities, as well as access to kayak and bike rentals nearby.

This waterfront apartment in Tavernier is conveniently situated just a short walk from Baker's Cay Resort Beach and Harry Harris Park, offering easy access to beautiful beaches and natural attractions. The apartment has received excellent ratings for its location, cleanliness, and overall user experience, ensuring a comfortable and enjoyable stay.
The two-bedroom, two-bathroom apartment spans 87 square metres and comfortably accommodates up to six guests. The property is fully equipped with modern amenities, including a swimming pool, Jacuzzi, tennis court, and a fully equipped kitchen, making it ideal for families or groups seeking a relaxing and active holiday.

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.