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Islamorada, FL place to stay
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2091 Lodgings in Islamorada, FL

Best Islamorada, FL lodging with a pool

Among the 2091 accommodations in Islamorada, FL, here are the 4 best ones with a pool

Sportfishing In Florida Keys! Free Parking! Breakfast, Pool, Bike Rentals! - Islamorada, FL
9.4 3 reviews

Sportfishing In Florida Keys! Free Parking! Breakfast, Pool, Bike Rentals!

apartment, Islamorada, Village of Islands
This Islamorada beachfront apartment, part of a pet-friendly resort, offers direct beach access and is within easy reach of the Islamorada Brewery & Distillery and Florida Keys Brewing Co., both a short drive or walk away.
The 27-square-metre (290 sq ft) self-catering flat features two queen beds, sleeping up to four guests, and includes a refrigerator, microwave, and Keurig coffee maker; on-site amenities comprise a heated pool, kayak and paddleboard rentals, plus a daily continental breakfast.
Seaside Villas W/ Ocean Views & Front Porch! Marina, Pets Allowed, Breakfast! - Islamorada, FL
No reviews

Seaside Villas W/ Ocean Views & Front Porch! Marina, Pets Allowed, Breakfast!

apartment, Islamorada, Village of Islands
This one-bedroom flat is located in Islamorada's city centre, directly on the beach, offering direct access to a private beach and proximity to Islamorada Brewery & Distillery and Florida Keys Brewing Co., approximately 2 kilometres away.
Guests can enjoy a heated swimming pool with ocean views, complimentary continental breakfast, and free Wi-Fi, alongside the convenience of pet-friendly accommodation for up to two dogs, with bike rentals, kayaks, and paddleboards available for exploring the surrounding waters and nearby Windley Key Fossil Reef Geological State Park and Indian Key Historic State Park.
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.
77 M² Condo ∙ 1 Bedroom ∙ 3 Guests - Islamorada, FL
10 2 reviews

77 M² Condo ∙ 1 Bedroom ∙ 3 Guests

apartment, Islamorada, Village of Islands
This oceanfront apartment in the Palms of Islamorada condo complex, located at Mile Marker 79.9 on the Overseas Highway, offers direct beach access and is close to Islamorada's attractions.
The 76-square-metre (820 sq ft) property features one bedroom, one bathroom, sleeps three, and includes a king bed, queen sleeper sofa, updated kitchen, and access to a swimming pool, jacuzzi, spa, and fitness centre.

Best family friendly Islamorada, FL lodging

Among the 2091 accommodations in Islamorada, FL, here are the 4 best for families

Cheeca Lodge & Spa - Islamorada, FL
8.8 219 reviews

Cheeca Lodge & Spa

resort, Islamorada, Village of Islands
Cheeca Lodge & Spa, a resort in Islamorada, Village of Islands, offers direct access to a nearby beach, ideal for exploring the coastal beauty of the Florida Keys.
This establishment provides a comprehensive range of amenities including an on-site spa, swimming pool with a poolside bar, fitness centre, and convenient parking, with express check-in/check-out services available.
Ocean Pointe 2309 - Islamorada, FL
8.9 10 reviews

Ocean Pointe 2309

house, Tavernier
Ocean Pointe 2309, a beachfront property in Tavernier, Florida, offers ocean views and is a 14-minute walk from Harry Harris Park Beach and 4.8km from Pigeon Key.
This two-bedroom, two-bathroom house boasts 85 square metres of floor space, sleeps up to 11 guests, and includes a private pool, bar, free Wi-Fi, and parking.
Isla Mirabelle: Boutique Resort, Free Boat Dockage Sep-oct Only! - Islamorada, FL
10 8 reviews

Isla Mirabelle: Boutique Resort, Free Boat Dockage Sep-oct Only!

house, Islamorada, Village of Islands
Isla Mirabelle, a three-bedroom waterfront villa in Matecumbe, Islamorada, is located within a 1.6km walk of the Islamorada Brewery & Distillery and Keys History & Discovery Centre, and within a 2.4km radius of the History of Diving Museum.
This 156 square metre smoke-free property offers a private balcony, garden access, a fully equipped kitchen, and accommodates up to six guests, boasting four bathrooms and convenient on-site parking.
Deja Blue Suite  [Ocean Pointe 1409] - Islamorada, FL
9.8 177 reviews

Deja Blue Suite [Ocean Pointe 1409]

apartment, Tavernier
This waterfront apartment in Tavernier is conveniently located just a short walk from Baker's Cay Resort Beach and Harry Harris Park, offering easy access to the beautiful beaches of the Florida Keys. The property has consistently received excellent ratings for its location, cleanliness, and overall experience.
The apartment features two bedrooms and two bathrooms, spanning 91 square metres and comfortably accommodating up to six guests. Enjoy a range of amenities including a swimming pool, jacuzzi, tennis court, barbecue grills, and a fully equipped kitchen, all set within a beautiful garden area.

Frequently asked questions about accommodations in Islamorada, FL

  • What outdoor activities can visitors enjoy in and around Islamorada, FL?

    Islamorada is a paradise for outdoor enthusiasts. You can go fishing, kayaking, paddleboarding, diving, and snorkeling. There are also several parks and nature trails to explore, like the Anne's Beach Park and the Indian Key Historic State Park.
  • When is the ideal time to plan a trip to Islamorada, FL?

    The best time to visit Islamorada is during the winter months, from December to April, when the weather is warm and sunny. The summer months can be hot and humid, but it's still a great time to visit if you don't mind the heat. The hurricane season runs from June to November, so it's best to avoid travelling during this time.
  • What are the best walking or cycling routes in Islamorada, FL?

    The Overseas Highway is a great place to go for a walk or bike ride. It's a scenic route that runs along the coast, and you can stop at various points to enjoy the views. There's also a dedicated bike path that runs along the Overseas Highway, which is a great option for families with young children.
  • What nearby towns or cities can be explored from Islamorada, FL?

    Islamorada is a great base to explore the rest of the Florida Keys. You can easily drive to Key Largo, Marathon, and Key West. If you're looking for something a bit further afield, you can drive up to Miami, which is about a 2-hour drive.
  • What amenities can travelers expect from accommodations in Islamorada, FL?

    Islamorada has a wide range of accommodation options, from budget-friendly motels to luxury resorts. Most accommodations offer swimming pools, restaurants, and bars. You can also find accommodations with private beaches, marinas, and other amenities.

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Best Islamorada, FL accommodations with a balcony

Your Happy Place - Gorgeous 2 Bed/2 Bath Oceanfront Suite With Full Kitchen - Islamorada, FL
9.8 25 reviews

Your Happy Place - Gorgeous 2 Bed/2 Bath Oceanfront Suite With Full Kitchen

apartment, Tavernier
This Tavernier condo is situated within 5km of Harry Harris Park and Mariners Hospital, and within 10km of the Old Road Gallery and Bluefin Rock Harbour Marina, offering convenient access to local amenities and attractions.
This two-bedroom, two-bathroom apartment sleeps seven, boasting a fully equipped kitchen, swimming pool, jacuzzi, spa, fitness centre, tennis court, and parking, alongside family-friendly features such as a terrace and garden.
Bayberry Key - Waterfront Boutique Resort, Dock, Direct Water Views! - Islamorada, FL
10 3 reviews

Bayberry Key - Waterfront Boutique Resort, Dock, Direct Water Views!

house, Islamorada, Village of Islands
This Islamorada waterfront property, situated on Bayberry Key, offers direct dock access and is a 2km walk from Upper Matecumbe Key, 4.3km from Windley Key, and a short drive from Pigeon Key and John Pennekamp Coral Reef State Park.
The 156 square metre house features three bedrooms and three bathrooms, accommodating up to nine guests, and includes a fully equipped kitchen, swimming pool, fitness centre, and free Wi-Fi.
Matecumbe Resort - Islamorada, FL
8.7 551 reviews

Matecumbe Resort

aparthotel, Islamorada, Village of Islands
The Matecumbe Resort is situated in Islamorada, a short distance from Sea Oats Beach, Upper Matecumbe Key, and Windley Key, offering a convenient base to explore the beautiful Florida Keys. This 2-star aparthotel consistently receives very good user ratings for its cleanliness, location, and overall experience.
Each self-catering apartment comes equipped with a kitchen, including a fridge, microwave, and other essentials. Guests can enjoy a range of amenities, including a swimming pool, a terrace, a garden, free parking, and Wi-Fi, as well as access to a private beach.
Ocean's Fourteen:direct Ocean View-balconies-dock-htd Pool - Islamorada, FL
10 4 reviews

Ocean's Fourteen:direct Ocean View-balconies-dock-htd Pool

house, Islamorada, Village of Islands
This villa in Islamorada, Village of Islands, is located in the private Peaceful Palms community, offering oceanfront views and direct access, with the History of Diving Museum just 800 metres and Theater of the Sea 640 metres away.
This 156 square metre home accommodates six guests across three bedrooms and three bathrooms, featuring a private game room with a pool table, a community heated pool, an oceanfront boat dock, and included paddleboards and bicycles for exploring the area.

Best Islamorada, FL accommodations with a kitchen

Fully Renovated With Bay View Available Jan 27 - Islamorada, FL
No reviews

Fully Renovated With Bay View Available Jan 27

house, Islamorada, Village of Islands
This fully renovated 3-bedroom, 3-bathroom townhome is located within Executive Bay Club in Islamorada, Village of Islands, offering direct bay views from its prime position.
This Islamorada accommodation sleeps up to six guests, featuring two King beds and one Queen bed, and includes amenities such as air conditioning, internet, a swimming pool, and parking, making it an ideal escape to the Florida Keys.
Aqua Vista Ocean Pointe 3307 - Islamorada, FL
9.8 11 reviews

Aqua Vista Ocean Pointe 3307

house, Tavernier
Aqua Vista Ocean Pointe 3307, a Key Largo property, is situated a short walk (approximately 1.5km) from Harry Harris Park Beach and within a few kilometres of Pigeon Key and other attractions including Upper Matecumbe Key and Windley Key Fossil Reef Geological State Park.
This 77 square metre house boasts two bedrooms, two bathrooms, sleeps seven guests, and includes a fully equipped kitchen, private patio, swimming pool, Jacuzzi, garden, parking, and in-unit laundry facilities, alongside free Wi-Fi and cable TV.
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.
Flamingo Flats Ocean Pointe 5306 - Islamorada, FL
9.8 6 reviews

Flamingo Flats Ocean Pointe 5306

house, Tavernier
Flamingo Flats Ocean Pointe 5306, situated in Key Largo, offers convenient access to Harry Harris Park Beach (a 2.4km walk), Pigeon Key (4.5km), and Windley Key Fossil Reef Geological State Park (14.3km).
This two-bedroom, two-bathroom property boasts 77 square metres of living space, sleeps six guests, and includes a private patio with ocean views, a swimming pool, Jacuzzi, and fully equipped kitchen with dishwasher.
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