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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

Spacious Unit W/ Kitchenette & Balcony! Marina, Pets Allowed, Free Breakfast - Islamorada, FL
No reviews

Spacious Unit W/ Kitchenette & Balcony! Marina, Pets Allowed, Free Breakfast

apartment, Islamorada, Village of Islands
This Islamorada apartment hotel boasts a central location, offering direct beach access and proximity to the History of Diving Museum and Keys History & Discovery Centre.
The 37 square metre self-catering apartment sleeps four, featuring a bedroom, bathroom, fully equipped kitchenette, and a terrace with ocean views, plus access to a heated pool, kayaks, and paddleboards.
Premium Units W/ Ocean Views & Balcony! Marina, Pets Allowed, Free Breakfast - Islamorada, FL
No reviews

Premium Units W/ Ocean Views & Balcony! Marina, Pets Allowed, Free Breakfast

apartment, Islamorada, Village of Islands
This one-bedroom flat is located in the centre of Islamorada, Village of Islands, directly on the beach, offering ocean views and convenient access to the History of Diving Museum and Keys History & Discovery Centre.
This pet-friendly accommodation for up to four guests provides air conditioning, Wi-Fi, a swimming pool, and parking, with complimentary continental breakfast and on-site kayaks and paddleboards available for exploring the surrounding waters.
Leisure Inn Villa, Islamorada - Islamorada, FL
No reviews

Leisure Inn Villa, Islamorada

apartment, Islamorada, Village of Islands
The Leisure Inn Villa, Islamorada, is a three-bedroom, canal-front property on Lower Matecumbe Key, approximately 5km from the Angler House private club.
This Islamorada holiday home sleeps six guests and boasts two bathrooms, a swimming pool, and parking, plus membership access to the Angler House's pool and tiki bar.
House ∙ 8 Bedrooms ∙ 16 Guests - Islamorada, FL
No reviews

House ∙ 8 Bedrooms ∙ 16 Guests

house, Islamorada, Village of Islands
This oceanfront residence in Islamorada, Village of Islands, is located near the Arts and Culture District and is approximately a 145-kilometre drive from Miami, with seaplane access available on the bay.
This spacious villa offers direct oceanfront access with private beach steps, an 86-foot lagoon-style pool, a heated jacuzzi, two full kitchens, outdoor kitchens, and accommodation for 16 guests, alongside an optional 32-foot boat slip.

Best family friendly Islamorada, FL lodging

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

Marlin House @ Tarpon Point - Islamorada, FL
10 6 reviews

Marlin House @ Tarpon Point

apartment, Islamorada, Village of Islands
Marlin House, an oceanfront property in the exclusive Tarpon Point community of Islamorada, offers direct access to the beach and is conveniently located near local attractions.
This four-bedroom, four-bathroom dwelling boasts a chef's kitchen, private pool access, smart TVs, and sleeps up to eight guests, perfect for families seeking a luxurious Islamorada getaway.
Stay & Play; Enjoy Scenic Views  Ocean Pointe 5312 - Islamorada, FL
9.8 53 reviews

Stay & Play; Enjoy Scenic Views Ocean Pointe 5312

apartment, Tavernier
This waterfront apartment is situated in Tavernier, within easy walking distance of Baker's Cay Resort Beach and Harry Harris Park, and just a short drive from Mariners Hospital and Florida Keys Dive Center. It enjoys a peaceful location, perfect for a relaxing getaway. The apartment has received excellent guest reviews and is rated highly for its amenities and service.
The apartment has two bedrooms, two bathrooms, and can comfortably accommodate up to six guests. It has a fully equipped kitchen, a terrace or balcony, a swimming pool, a spa, a tennis court, and free parking, providing everything you need for a comfortable and enjoyable stay.
139 M² House ∙ 3 Bedrooms ∙ 8 Guests - Islamorada, FL
No reviews

139 M² House ∙ 3 Bedrooms ∙ 8 Guests

house, Islamorada, Village of Islands
Vacation house to rent for 8 guests. You will stay in Islamorada, Village of Islands.
Facilities and services include a garden, a freeze and air conditioning. Enjoy free parking with this accommodation in Islamorada, Village of Islands!
Isla Kiwi: Waterfront Boutique Resort, Free Boat Dockage Sept-oct Only - Islamorada, FL
10 2 reviews

Isla Kiwi: Waterfront Boutique Resort, Free Boat Dockage Sept-oct Only

house, Islamorada, Village of Islands
Isla Kiwi: Waterfront Boutique Resort in Matecumbe, Islamorada, offers a 3-bedroom villa, a short walk from the Islamorada Brewery & Distillery and Keys History & Discovery Centre, and within a 2.4km radius of the History of Diving Museum and Matecumbe United Methodist Church.
This smoke-free property boasts a 156 square metre floor area, accommodating up to six guests, and features a fully equipped kitchen, private balcony, swimming pool, spa, and free Wi-Fi; barbecue facilities are also available on-site.

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.

Popular destinations

Best Islamorada, FL accommodations with a balcony

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).
Private Beach  / Heated Pool / Private Dock / Dolphin Key - Islamorada, FL
No reviews

Private Beach / Heated Pool / Private Dock / Dolphin Key

house, Islamorada, Village of Islands
This beachfront villa is located in Islamorada's Matecumbe district, a 3.22 kilometre drive from Robbie's of Islamorada and 6.44 kilometres from Anne's Beach, placing you close to the Keys History & Discovery Center and the History of Diving Museum.
This family-friendly property accommodates up to 8 guests across 4 bedrooms and 4 bathrooms, featuring a heated swimming pool, a balcony, a barbecue grill, and on-site parking, with free Wi-Fi, air conditioning, and a concierge service for your comfort.
3212 Across From Pool * King & Queen/twin Bunk Bed - Islamorada, FL
9.8 158 reviews

3212 Across From Pool * King & Queen/twin Bunk Bed

apartment, Tavernier
This Ocean Pointe Suites condo is located in Tavernier, Florida, just a short distance from Harry Harris Park, offering stunning ocean views and easy access to the park's playground, walking trails, and beautiful scenery. The property has received excellent user ratings, making it a popular choice for travellers seeking a comfortable and enjoyable stay.
This two-bedroom, two-bathroom apartment comfortably accommodates six guests. Guests have access to a range of amenities, including a heated swimming pool, a hot tub, a tropical beach, a marina, a pool bar, a lounge, tennis and pickleball courts, and parking for two cars.
Aqua Vista Ocean Pointe 3307 - Islamorada, FL
9.6 4 reviews

Aqua Vista Ocean Pointe 3307

apartment, Tavernier
This Tavernier seaside apartment, located 1.1 km from Harry Harris Park and within 5 km of Mariners Hospital and the Florida Keys Dive Centre, offers stunning ocean views.
The 77 square metre property features two bedrooms, two bathrooms, a sofa bed sleeping up to five guests, a fully equipped kitchen, private balcony, swimming pool, hot tub, and on-site barbecue facilities.

Best Islamorada, FL accommodations with a kitchen

Sunbeam Dream Oasis [Ocean Pointe 4211] - Islamorada, FL
9.8 1796 reviews

Sunbeam Dream Oasis [Ocean Pointe 4211]

apartment, Tavernier
This beachside apartment building is located in Tavernier, Florida, just a 15-minute walk from Baker's Cay Resort Beach and Harry Harris Park, offering a tranquil setting within easy reach of local attractions. The resort consistently receives excellent ratings for its location, cleanliness and overall experience.
The Keys Life At Ocean Pointe apartment offers two bedrooms, a sofa bed and a balcony, providing ample space for families or groups. Guests can enjoy a range of amenities including a swimming pool, Jacuzzi, tennis court, and a bar, as well as direct access to the beach.
The Salty Suite Islamorada House Boat - Islamorada, FL
No reviews

The Salty Suite Islamorada House Boat

barge, Islamorada, Village of Islands
The Salty Suite, a unique floating accommodation, is moored in a protected, shallow basin (1.2-2.4 metres deep) behind the World Wide Sportsman in Islamorada, Village of Islands, with land-based amenities and restaurants less than 400 metres away.
This one-bedroom, one-bathroom houseboat accommodates up to three guests, offering solar-powered amenities, air conditioning, a kayak, a paddleboard, and a $50 discount for excursions with Key King Charters.
By The Sea ~ Islamorada Home With Ocean Views! - Islamorada, FL
9.4 10 reviews

By The Sea ~ Islamorada Home With Ocean Views!

apartment, Islamorada, Village of Islands
This holiday home is located in Matecumbe, a district of Islamorada, just 1.6 kilometres from Sunset Drive Beach and San Pedro Underwater Archaeological Preserve State Park. The property has received excellent reviews from previous guests.
The accommodation is a two-bedroom, two-bathroom house with a capacity of six guests. It features a fully equipped kitchen, air conditioning, a terrace, a garden, and internet access.
Islamorada Spectacular Executive Bay Club 87200 - Islamorada, FL
No reviews

Islamorada Spectacular Executive Bay Club 87200

apartment, Islamorada, Village of Islands
This Islamorada townhouse, situated within a gated community offering 24-hour security and direct beach access, provides convenient access to the village's amenities.
The two-bedroom, three-bathroom property sleeps six, boasting a king-size bed in the master suite, two queen beds in the second bedroom, a full kitchen, in-unit laundry, a living room with a large-screen TV, and access to a heated pool, activity courts, and clubhouse.
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