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Islamorada, FL apartments
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1210 Holiday apartments 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

Sunrise Breeze On The Marina [Ocean Pointe 5302] - Islamorada, FL
9.8 176 reviews

Sunrise Breeze On The Marina [Ocean Pointe 5302]

apartment, Tavernier
This Tavernier beach apartment is conveniently located within a 10-minute walk of Baker's Cay Resort Beach and Harry Harris Park, offering easy access to the area's attractions. The property consistently receives excellent ratings for location, cleanliness, and overall user experience.
The apartment offers 85 square metres of space, comfortably accommodating up to 6 guests in its two bedrooms and two bathrooms. This family-friendly apartment includes a range of amenities such as a swimming pool, Jacuzzi, tennis court, and a garden, ensuring a comfortable and enjoyable stay.
Condo ∙ 2 Bedrooms ∙ 4 Guests - Islamorada, FL
10 3 reviews

Condo ∙ 2 Bedrooms ∙ 4 Guests

apartment, Islamorada, Village of Islands
This exceptional top-floor, ocean-view flat is situated on the ocean side in Islamorada, Village of Islands, at Mile Marker 83.2, offering direct access to a sandy beach and proximity to restaurants, fishing charters, diving, snorkelling, and the Dolphin Research Centre.
This family-friendly condominium sleeps four guests across two bedrooms and two bathrooms, boasting a fully remodelled kitchen with granite counters and stainless steel appliances, a king bed in the master suite, two full beds in the second bedroom, air conditioning, a swimming pool, jacuzzi, spa, fitness centre, terrace, garden, and covered parking with trailer space, all within the Beacon Reef complex.
Deluxe Oceanfront 1/1 Sleeps 4. Cafe & Pool Bar. - Islamorada, FL
9.7 131 reviews

Deluxe Oceanfront 1/1 Sleeps 4. Cafe & Pool Bar.

apartment, Tavernier
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.
Key Largo-islamorada Area-1 Br, 1 Bath -Privately Owned Condo -Fab Reviews! - Islamorada, FL
10 201 reviews

Key Largo-islamorada Area-1 Br, 1 Bath -Privately Owned Condo -Fab Reviews!

apartment, Tavernier
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.

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

Chic Coastal Retreat With Pool, Marina, Beach Access & Resort-style Amenities - Islamorada, FL
9.8 101 reviews

Chic Coastal Retreat With Pool, Marina, Beach Access & Resort-style Amenities

apartment, Tavernier
This Tavernier waterfront apartment, located 1 kilometre from Harry Harris Park and within 5 kilometres of Mariners Hospital and the Florida Keys Dive Centre, offers stunning views.
The two-bedroom, two-bathroom condo sleeps six guests and boasts a fully equipped kitchen, private balcony, jetted tub, swimming pool, Jacuzzi, free Wi-Fi, and parking.
Island Escape In Islamorada | Breakfast, Pool & Pet-friendly Stay! - Islamorada, FL
No reviews

Island Escape In Islamorada | Breakfast, Pool & Pet-friendly Stay!

apartment, Islamorada, Village of Islands
This two-bedroom flat is located by the sea in the Matecumbe district of Islamorada, within walking distance of the History of Diving Museum and Keys History & Discovery Centre, and a short drive from Windley Key Fossil Reef Geological State Park and Indian Key Historic State Park.
This 52 square metre apartment accommodates up to four guests, offers daily cleaning, complimentary toiletries, air conditioning, Wi-Fi, a swimming pool, and pet-friendly accommodation for two dogs under 22.7 kilograms, with one parking space per unit.
Islamorada Oceanfront Luxury Living - Islamorada, FL
No reviews

Islamorada Oceanfront Luxury Living

apartment, Islamorada, Village of Islands
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.
Boat Slip Included August-november 2026! - Islamorada, FL
9.9 112 reviews

Boat Slip Included August-november 2026!

apartment, Islamorada, Village of Islands
This waterfront property is located just 0.6 km from Windley Key Fossil Reef Geological State Park and within 5 km of Founders Park and Islamorada County Park, offering easy access to popular attractions. This property boasts excellent ratings for location, cleanliness, and overall user experience.
This house has two bedrooms and can accommodate up to six guests. The property features a fully equipped kitchen, a private pool, a balcony, a garden, and free Wi-Fi, making it a perfect choice for a relaxing and enjoyable holiday.

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Best Islamorada, FL holiday apartments with air conditioning

Coral Cove Resort - A Fishermans Dream - Islamorada, FL
10 31 reviews

Coral Cove Resort - A Fishermans Dream

apartment, Islamorada, Village of Islands
Coral Cove Resort - A Fishermans Dream is located in Matecumbe, Islamorada, just a short drive from Florida Keys Brewing Co. and Bud n' Mary's Dive Center. The resort has received excellent reviews from previous guests.
The three-bedroom house is perfect for families or groups of up to six people. The resort offers a range of amenities, including a private pool, a deep-water boat slip, and easy access to the beach, making it ideal for a relaxing and enjoyable stay.
Sea View And Sunrise Ocean Pointe 2412 2ba/2br - Islamorada, FL
9.6 89 reviews

Sea View And Sunrise Ocean Pointe 2412 2ba/2br

apartment, Tavernier
This two-bedroom apartment is located in Ocean Pointe Suites, Tavernier, Florida, halfway between Key Largo and Islamorada, about 800 metres from the Circle K convenience store and Dairy Queen. The property has received excellent user ratings and offers a comfortable and convenient stay for travellers.
The 84 square metre apartment can accommodate up to six guests and features a fully equipped kitchen, two bathrooms, and a spacious living area. Guests can enjoy a range of amenities including a swimming pool, hot tub, tennis courts, and a private beach, as well as direct access to the resort's marina and boat ramp.
New Caribbean Home.  Resort Access To Pool - Islamorada, FL
9.8 29 reviews

New Caribbean Home. Resort Access To Pool

apartment, Islamorada, Village of Islands
This smoke-free holiday home is located in Matecumbe, a quieter area of Islamorada, within walking distance of the Matecumbe United Methodist Church, Florida Keys Brewing Co., and the Hurricane Monument. It has received excellent user ratings.
The two-bedroom, two-bathroom property provides guests with a comfortable living space that includes a microwave, stovetop, TV, coffee/tea maker, and dishwasher. You can also enjoy parking, internet access, and the convenience of being close to historical attractions like the History of Diving Museum and Indian Key Historic State Park.
180 Degrees Of Ocean Views, Lagoon And Florida Bay - Islamorada, FL
9.3 3 reviews

180 Degrees Of Ocean Views, Lagoon And Florida Bay

apartment, Islamorada, Village of Islands
This five-bedroom, three-bathroom townhouse in Islamorada's Lower Matecumbe area offers direct lagoon access to Florida Bay and boasts uninterrupted 180-degree ocean views, with proximity to attractions such as the Theatre of the Sea and Robbie's Marina (distances unspecified).
Sleeping up to twelve guests, the two-storey property features a fully equipped kitchen including a fridge, microwave, and dishwasher, plus air conditioning, parking, and internet access; kayaking and paddleboarding are readily available from the property's private lagoon access.

Best pet-friendly Islamorada, FL holiday apartments

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

Key Escape Dock & Ocean Access - Islamorada, FL
No reviews

Key Escape Dock & Ocean Access

apartment, Tavernier
This two-bedroom flat is situated in Tavernier's Blue Waters district, 200 metres from the Hurricane Monument and Caribbean Club Bar, and a short drive from John Pennekamp Coral Reef State Park.
This pet-friendly accommodation for four offers air conditioning, internet, and a terrace, with parking available, and is close to Jacob's Aquatic Centre for water activities.
2 Balcony Rooms Near Marina With Daily Breakfast | Pet Friendly - Islamorada, FL
No reviews

2 Balcony Rooms Near Marina With Daily Breakfast | Pet Friendly

apartment, Islamorada, Village of Islands
This beachfront apartment in Islamorada, Village of Islands, is situated 300 metres from Windley Key Fossil Reef Geological State Park and 720 metres from Hog Heaven, offering convenient access to coastal activities.
This two-bedroom, two-bathroom flat accommodates up to eight guests and features air conditioning, Wi-Fi, a shared swimming pool, and a private balcony, with concierge and parking services also available.
Islamorada Waterfront Home, Spectacular View-great Dockage-wifi-contact Owner - Islamorada, FL
10 57 reviews

Islamorada Waterfront Home, Spectacular View-great Dockage-wifi-contact Owner

apartment, Islamorada, Village of Islands
This secluded waterfront house is located on a private peninsula in Matecumbe, Islamorada, just across from Sea Oats Beach and a short walk from wholesale stone crab and lobster vendors, offering a peaceful escape in a prime location. The property is highly rated, receiving excellent reviews from previous guests.
The three-bedroom, two-bathroom house spans 172 square metres and comfortably accommodates up to eight guests. Enjoy the spacious kitchen, open dining and living area, screened porch, private balcony, jetted Jacuzzi tub, and a range of amenities including a garden, spa, and parking.
Sunrise Haven - Maison 306 - Beach, Pool, Hot Tub, Kayaks, Sups & Day Dock - Islamorada, FL
10 76 reviews

Sunrise Haven - Maison 306 - Beach, Pool, Hot Tub, Kayaks, Sups & Day Dock

apartment, Islamorada, Village of Islands
This apartment is situated in the Matecumbe district of Islamorada, just off Old Federal Highway at Mile Marker 80.6, a short walk from restaurants, the arts district, and marinas. It is located 145 kilometres from Key West and 137 kilometres from Miami International Airport. It has received excellent user ratings.
The apartment offers 209 square metres of living space, with three bedrooms, three bathrooms, and a capacity for six guests. It boasts a range of amenities, including a swimming pool, jacuzzi, terrace, garden, spa, and private water sports equipment.
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