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Islamorada, FL apartments
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1210 Best apartments in Islamorada, FL

Best family friendly Islamorada, FL Holiday Apartments and Self Catering Accommodations

Among the 1210 accommodations in Islamorada, FL, here are the 4 best family friendly holiday apartments

Fabulous Ocean View @ Ocean Pointe Heated Pool Beach & More - Islamorada, FL
No reviews

Fabulous Ocean View @ Ocean Pointe Heated Pool Beach & More

apartment, Tavernier
This Ocean Pointe Suites apartment in Tavernier offers direct Atlantic Ocean access, situated within a protected mangrove forest and 2.9 kilometres from Jimmy Johnson's Big Chill and Mangrove Marina, with John Pennekamp Coral Reef State Park and Jacob's Aquatic Centre nearby.
This 79 square metre flat accommodates up to six guests across two bedrooms and a living area, featuring a fully equipped kitchen, air conditioning, a swimming pool, jacuzzi, private beach, tennis/pickleball courts, and inclusive parking for two vehicles.
Reel Key Largo Escape Ocean Pointe 5209 - Islamorada, FL
9.6 10 reviews

Reel Key Largo Escape Ocean Pointe 5209

apartment, Tavernier
This Tavernier waterfront apartment is situated a 2.4km walk from Baker's Cay Resort Beach and Harry Harris Park, and within 5km of Mariners Hospital and the Florida Keys Dive Centre.
The 79-square-metre property offers two bedrooms, two bathrooms, a sofa bed, and sleeps four, boasting a private pool, balcony, fully equipped kitchen, and access to shared amenities including an indoor pool and barbecue grills.
Outstanding Ocean View W/heated Pool Beach Marina - Islamorada, FL
No reviews

Outstanding Ocean View W/heated Pool Beach Marina

apartment, Tavernier
This waterfront apartment in Tavernier, located within Ocean Pointe Suites on the Atlantic Ocean, offers direct access to a protected mangrove forest and is minutes from fine restaurants, the History of Diving Museum, and Old Road Gallery.
This 79 square meter flat, ideal for up to six guests, features two bedrooms and two bathrooms, a fully equipped kitchen, in-unit laundry, free WiFi, and access to resort amenities including a heated swimming pool, jacuzzi, and private beach, with complimentary parking for two cars.
Heated Pool And Tennis Court - Exquisite Coastal Retreat - Islamorada, FL
10 1 review

Heated Pool And Tennis Court - Exquisite Coastal Retreat

apartment, Islamorada, Village of Islands
This expansive duplex penthouse offers panoramic ocean views from a high-end, quiet neighbourhood in Islamorada, Village of Islands, with direct access to waterfront dining.
This five-bedroom, three-bathroom apartment sleeps ten and features a grand open-concept layout, a rooftop terrace, a gourmet kitchen, Gigabit Wi-Fi, a heated swimming pool, jacuzzi, tennis court, gym, and provided beach gear for exploring the coast.

Best Holiday Apartments and Self Catering Accommodations in Islamorada, FL with a pool

Among the 1210 accommodations in Islamorada, FL, here are the 4 best apartments with a pool

Islamorada Retreat "Bungalow Blue" W/ Heated Pool, Bikes, Bbq, Amenities Galore! - Islamorada, FL
10 26 reviews

Islamorada Retreat "Bungalow Blue" W/ Heated Pool, Bikes, Bbq, Amenities Galore!

apartment, Islamorada, Village of Islands
This Matecumbe holiday home in Islamorada, Village of Islands, is situated within 3.2km of San Pedro Underwater Archaeological Preserve State Park, Robbie's of Islamorada, and Indian Key Historic State Park, and 3.7km from Sunset Drive Beach.
The 49-square-metre property offers two bedrooms, one bathroom, sleeps four guests, and boasts a private pool, jacuzzi, spa, and fully equipped kitchen including a dishwasher; concierge services are also available.
Amazing Ocean View At Ocean Pointe W/heated Pool - Islamorada, FL
9.6 57 reviews

Amazing Ocean View At Ocean Pointe W/heated Pool

apartment, Tavernier
This oceanfront apartment is located in Tavernier, just a short distance from the Florida Keys Dive Center and Bluefin Rock Harbor Marina, offering easy access to the area's attractions and activities. It has received excellent ratings from previous guests, highlighting its comfortable and convenient features.
The two-bedroom, two-bathroom apartment spans 78 square metres and comfortably accommodates up to six guests. It offers a range of amenities, including a swimming pool, a jacuzzi, a terrace, and a garden, as well as a fully equipped kitchen and air conditioning.
Second Floor Den Suite  Sunny Islamorada Escape, Pool, Beach, Marina, Sleeps 6 - Islamorada, FL
No reviews

Second Floor Den Suite Sunny Islamorada Escape, Pool, Beach, Marina, Sleeps 6

apartment, Islamorada, Village of Islands
This waterfront apartment in Matecumbe, Islamorada, offers easy access to San Pedro Underwater Archaeological Preserve State Park and Indian Key Historic State Park, both within a short driving distance.
The 74-square-metre (797 sq ft) one-bedroom suite sleeps five, featuring a queen bed, queen sleeper sofa, full sleeper sofa, a kitchen with fridge, microwave, and dishwasher, plus a swimming pool, terrace, and parking.
Condo ∙ 2 Bedrooms ∙ 6 Guests - Islamorada, FL
9.0 1 review

Condo ∙ 2 Bedrooms ∙ 6 Guests

apartment, Islamorada, Village of Islands
This Islamorada condo, part of the Topsider Resort, offers oceanfront private beach access and is situated 2km from Lazy Days South, 8.7km from Alligator Reef Lighthouse, and 6.6km from Robbie's of Islamorada.
The two-bedroom, two-bathroom apartment sleeps six, features a fully equipped kitchen, private balcony with tropical views, and access to resort amenities including a heated pool, Jacuzzi, and tennis courts, plus complimentary boat docking (up to 7m).

Frequently asked questions about apartment rentals in Islamorada, FL

  • What is Islamorada, FL best known for?

    Islamorada is often called the 'Sportfishing Capital of the World', so it's no surprise that fishing is a big draw. It's also a great place to enjoy the beautiful Florida Keys, with its stunning beaches, clear waters, and diverse marine life.
  • What are the best ways to relax in Islamorada, FL?

    Islamorada is all about slowing down and enjoying the laid-back atmosphere. Spend some time lounging on the beach, take a dip in the ocean, or enjoy a sunset cruise. You can also treat yourself to a massage at one of the many spas in the area.
  • What are the advantages of choosing an apartment for your stay in Islamorada, FL?

    Apartments offer more space and privacy than a hotel room, and you can often find great deals, especially if you're travelling with a family or group. Many apartments also come with kitchens, so you can save money by cooking some of your own meals.

Popular destinations

Best Islamorada, FL holiday apartments with air conditioning

2br/2.5ba Angler's Reef Conch Villa 103 With Private Beach And Pool Access - Islamorada, FL
9.4 3 reviews

2br/2.5ba Angler's Reef Conch Villa 103 With Private Beach And Pool Access

apartment, Islamorada, Village of Islands
This Islamorada holiday home is situated within 3km of Windley Key Fossil Reef Geological State Park, Rain Barrel Village, and Islamorada County Park, offering easy access to local attractions.
The three-bedroom property sleeps six guests and boasts a private pool, fully equipped kitchen including a dishwasher, and free on-site parking, alongside in-house entertainment options.
Relax And Unwind Near Robbie's Of Islamorada! Free Parking & Breakfast, Pool! - Islamorada, FL
No reviews

Relax And Unwind Near Robbie's Of Islamorada! Free Parking & Breakfast, Pool!

apartment, Islamorada, Village of Islands
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.
2405 Ocean Pointe Suites - Islamorada, FL
9.6 50 reviews

2405 Ocean Pointe Suites

apartment, Tavernier
This two-bedroom apartment is located in Tavernier, just 2.4 kilometres from Baker's Cay Resort Beach and Harry Harris Park, offering easy access to the beautiful beaches and local attractions. It has received excellent reviews from previous guests.
The apartment is 84 square metres in size and can comfortably accommodate up to six guests. It features a fully equipped kitchen, a private balcony, a spa tub, barbecue grills, and access to a swimming pool and Jacuzzi.
Gulf View Retreat @ Bay Harbor - Islamorada, FL
9.8 17 reviews

Gulf View Retreat @ Bay Harbor

apartment, Islamorada, Village of Islands
This two-bedroom apartment is situated in Matecumbe, just 3.5 kilometres from Sunset Drive Beach and Anne's Beach, and 3.5 kilometres from San Pedro Underwater Archaeological Preserve State Park. This highly rated property offers a comfortable and convenient stay for travellers seeking a relaxing getaway in the Florida Keys.
The apartment can accommodate up to four guests and features a fully equipped kitchen, a washing machine, a terrace, a garden, a swimming pool, a jacuzzi and a fitness centre. Guests can enjoy a range of amenities and activities, including relaxing by the pool, exploring the nearby beaches, and enjoying the beautiful surroundings.

Best pet-friendly Islamorada, FL holiday apartments

Among the 1210 accommodations in Islamorada, FL, here are the 4 best pet friendly holiday apartments

Best Place To Stay In Florida! 3 Pet-friendly Units, Free Breakfast, Parking - Islamorada, FL
10 1 review

Best Place To Stay In Florida! 3 Pet-friendly Units, Free Breakfast, Parking

apartment, Islamorada, Village of Islands
This Islamorada beachfront apartment, part of a pet-friendly resort, offers direct beach access and is centrally located, providing easy access to local breweries and proximity to Indian Key Historic State Park and San Pedro Underwater Archaeological Preserve State Park (distances unspecified).
The 75 square metre property comprises three uniquely decorated bedrooms, each with two queen-size beds, accommodating up to twelve guests, and includes a private kitchen, three bathrooms, a swimming pool, concierge service, parking, and daily continental breakfast.
Isla Santorini | Islamorada Waterfront Condo, Pool - Islamorada, FL
10 1 review

Isla Santorini | Islamorada Waterfront Condo, Pool

apartment, Islamorada, Village of Islands
This Islamorada flat offers direct water views and a screened balcony, located just a 5-minute drive from Anne's Beach and a 10-minute drive from Robbie's of Islamorada.
This two-bedroom, two-bathroom apartment for four guests features an open-plan living area, ensuite bedrooms, a fully equipped kitchen, air conditioning, communal swimming pool, hot tub, gym, tennis courts, and barbecue grills, with a washer and dryer provided for convenience.
Venetian Shores Escape! Heated Pool, 3br, 70ft Dock, Dog-friendly! - Islamorada, FL
9.6 67 reviews

Venetian Shores Escape! Heated Pool, 3br, 70ft Dock, Dog-friendly!

apartment, Islamorada, Village of Islands
This Venetian Shores holiday home is situated just off the beach, within 1.6km of Founders Park and Islamorada County Park, and a short drive from Windley Key Fossil Reef Geological State Park. The property has received excellent user ratings, making it a popular choice for travellers seeking a comfortable and enjoyable stay.
The spacious 279 square metre property has three bedrooms and four bathrooms, comfortably accommodating up to eight guests. It offers a range of amenities, including a private pool, a fully equipped kitchen, air conditioning, a terrace, a garden, and free Wi-Fi, ensuring a relaxing and enjoyable stay.
3 Relaxing Units! Free Breakfast, Free Parking, Onsite Pool, Pets Allowed! - Islamorada, FL
No reviews

3 Relaxing Units! Free Breakfast, Free Parking, Onsite Pool, Pets Allowed!

apartment, Islamorada, Village of Islands
This Islamorada, Florida aparthotel enjoys a central location, offering easy access to beaches and attractions such as Indian Key Historic State Park and San Pedro Underwater Archaeological Preserve State Park.
The self-catering property boasts 84 square metres of space, sleeping up to 12 guests in three bedrooms and three bathrooms, and includes a private balcony, swimming pool, and complimentary continental breakfast.
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