Search Islamorada, FL accommodations

2091 available accommodation offers

7 nights
2
1
  • airbnb
  • booking
  • stayz
  • expedia
  • hotelscom
  • tripadvisor
  • tripcom
  • agoda
  • homestay
  • tuivillas
  • hostelworld
  • hotelopia
Islamorada, FL accommodation
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

2091 Best accommodations in Islamorada, FL

Find Accommodations by the Sea in Islamorada, FL, United States

Step straight out of your front door directly onto the powdery white sand at seashore accommodation in Islamorada, FL, United States.

Updated Ocean-view Condo With 2 Balconies, Pool, Hot Tub, W/d, & Ac - Islamorada, FL
9.8 47 reviews

Updated Ocean-view Condo With 2 Balconies, Pool, Hot Tub, W/d, & Ac

apartment, Tavernier
This oceanfront condominium in Tavernier offers direct sea views from two private balconies and is a short walk to Ocean Point's private beach, with John Pennekamp Coral Reef State Park located 16 kilometres away.
This 78 square metre apartment, accommodating up to six guests, features a well-equipped kitchen, air conditioning, a private washer/dryer, and access to resort amenities including a swimming pool and hot tub, with nearby activities such as deep-sea fishing and water sports.

Find City Centre Accommodations in Islamorada, FL, United States

Stay right where the coastal dining meets the local nightlife strips at accommodation in the heart of Islamorada, FL, United States.

93 M² Condo ∙ 2 Bedrooms ∙ 4 Guests - Islamorada, FL
9.0 6 reviews

93 M² Condo ∙ 2 Bedrooms ∙ 4 Guests

apartment, Islamorada, Village of Islands
This tropically furnished condominium in the gated Futura Yacht Club offers direct Gulf of Mexico views from a 5th-floor balcony, located centrally within the Village of Islamorada, providing easy access to local restaurants, shops, and recreational activities.
This 93 square meter apartment, ideal for up to 4 guests, features 2 bedrooms and 2 bathrooms, a newly renovated kitchen with quartz countertops, air conditioning, and on-site amenities including a heated swimming pool, tennis and pickleball courts, and a beach area with picnic tables and a firepit.
The Nest Villa & Marina In The Heart Of Islamorada - Islamorada, FL
9.8 18 reviews

The Nest Villa & Marina In The Heart Of Islamorada

house, Islamorada, Village of Islands
This Islamorada waterfront villa offers easy walking access to local shops, restaurants, and a brewery, enjoying a central location within the Village of Islands.
The two-bedroom, two-bathroom property sleeps four guests and boasts a private rooftop sun terrace with Florida Bay views, a private jetty for swimming and snorkelling, and on-site parking for two cars, including space for a boat trailer (maximum boat size 26ft, launch up to 18ft).
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.
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.

Frequently asked questions about accommodations in Islamorada, FL

  • How can travelers reach Islamorada, FL?

    The most convenient way to get to Islamorada is by car, as it's located on US-1, the Overseas Highway. You can also fly into Key West International Airport (EYW) and drive about 100km north. If you are looking for a more scenic option, you can take the Florida Keys Scenic Highway, which runs along the coast.
  • What are the best accommodations in Islamorada, FL?

    Among the accommodations in Islamorada, FL, Sunset Inn, La Jolla Resort and Sands Of Islamorada are the most popular ones.

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

    Islamorada is a paradise for water sports enthusiasts! You can go fishing, diving, snorkelling, kayaking, paddleboarding, or simply relax on the beach. If you prefer something a little more adventurous, you can try kiteboarding or windsurfing. For a unique experience, take a boat trip to the nearby Alligator Reef Lighthouse.
  • What are the best accommodations with a pool in Islamorada, FL?

    Sunset Inn, La Jolla Resort and Sands Of Islamorada are the best accommodations with a pool in Islamorada, FL.

  • When is the ideal time to plan a trip to Islamorada, FL?

    The best time to visit Islamorada is during the spring (March to May) and autumn (September to November) when the weather is pleasant and there are fewer crowds. However, if you're looking for warm weather and sunshine, you can visit during the summer (June to August), but be prepared for some humidity and potential thunderstorms.
  • What are the best accommodations with a jacuzzi in Islamorada, FL?

  • What are the best walking or cycling routes in Islamorada, FL?

    For a leisurely stroll, try the Islamorada Founders Park, which offers a beautiful waterfront path. If you're looking for a more challenging ride, you can cycle the Overseas Highway, which offers stunning views of the ocean. There are also several bike paths along the coast, offering opportunities to explore the local shops and restaurants.
  • What are the best accommodations for families and kids in Islamorada, FL?

    The best accommodations for families and kids in Islamorada, FL are La Jolla Resort, Sands Of Islamorada and Amara Cay Resort.

  • What nearby towns or cities can be explored from Islamorada, FL?

    From Islamorada, you can easily explore the surrounding Keys, such as Key Largo, Marathon, and Key West. Each town has its unique charm and attractions. Key Largo is known for its diving and snorkeling, while Marathon offers a variety of restaurants and shops. Key West is a vibrant city with a rich history and a lively nightlife.
  • What are the best pet friendly accommodations in Islamorada, FL?

    The best pet friendly accommodations in Islamorada, FL are Sunset Inn, Sands Of Islamorada and Amara Cay Resort.

  • What amenities can travelers expect from accommodations in Islamorada, FL?

    You can find a wide range of accommodation options in Islamorada, from budget-friendly motels to luxurious resorts. Most accommodations offer amenities like swimming pools, hot tubs, and restaurants. Some also have private beaches, boat docks, and water sports rentals.
  • What are the best accommodations with parking in Islamorada, FL?

    Sunset Inn, La Jolla Resort and Sands Of Islamorada are the best accommodations with parking in Islamorada, FL.

Popular destinations

Your Guide to the Finest High-End Stays in Islamorada, FL, United States

Find luxury beach accommodation in Islamorada, FL, United States for an indulgent tropical escape.

2402 Ocean Pointe - 2 Bedroom Condo Upgraded With Clean Lines And Coastal Colors - Islamorada, FL
9.2 30 reviews

2402 Ocean Pointe - 2 Bedroom Condo Upgraded With Clean Lines And Coastal Colors

apartment, Tavernier
This Tavernier apartment is situated near Harry Harris Park (0.97 km), Mariners Hospital (under 5 km), and Pigeon Key (5 km), offering easy access to local amenities and attractions.
The 79-square-metre property boasts two bedrooms, two bathrooms, sleeps six, and includes a fully equipped kitchen, swimming pool, jacuzzi, terrace, parking, and free Wi-Fi; barbecue facilities are also available on-site.

Find the Best Accommodations with a Swimming Pool in Islamorada, FL, United States

Swim lines in total seclusion surrounded by coastal beauty at beach accommodation with a pool in Islamorada, FL, United States.

Tavernier Oceanfront Resort Condo-pool, Dockage, Kayaks, Onsite Restaurant & Bar - Islamorada, FL
9.0 78 reviews

Tavernier Oceanfront Resort Condo-pool, Dockage, Kayaks, Onsite Restaurant & Bar

apartment, Tavernier
This two-bedroom apartment is situated in Tavernier, just 2.4 kilometres from Baker's Cay Resort Beach and Harry Harris Park, offering easy access to the beautiful beaches of the Florida Keys. The property has received excellent ratings for location, cleanliness, and user experience.
The 77 square metre apartment can comfortably accommodate up to six guests and features a well-equipped kitchen, two bathrooms, and a private pool. Guests can enjoy a range of amenities including a washing machine, air conditioning, and a garden.
Santorini- Islamorada Waterfront Condo, Ensuites, Pool, Hot Tub - Islamorada, FL
No reviews

Santorini- Islamorada Waterfront Condo, Ensuites, Pool, Hot Tub

apartment, Islamorada, Village of Islands
This two-bedroom, two-bathroom holiday flat is located in Islamorada, Village of Islands, a minute's walk from Sea Oats Beach and 12.2 kilometres from Upper Matecumbe Key.
This 137 square metre condo accommodates up to five guests and offers a waterfront balcony with sea views, a well-equipped kitchen, a communal swimming pool, hot tub, fitness centre, and a children's playground, with free WiFi and parking available.
King Room W/ Balcony, Daily Breakfast & Heated Pool Access - Islamorada, FL
No reviews

King Room W/ Balcony, Daily Breakfast & Heated Pool Access

apartment, Islamorada, Village of Islands
This one-bedroom flat is located in Islamorada's city centre, directly on a private beach, placing you within 1 kilometre of the History of Diving Museum and the Keys History & Discovery Centre.
This pet-friendly accommodation for two guests features air conditioning, Wi-Fi, a swimming pool, and direct beach access with water sports including kayaking and paddleboarding, alongside complimentary continental breakfast and on-site bike rentals.
Steps To Windley Key! Pet-friendly Villa! Marina, Free Parking, Breakfast, Pool! - Islamorada, FL
No reviews

Steps To Windley Key! Pet-friendly Villa! Marina, Free Parking, Breakfast, Pool!

apartment, Islamorada, Village of Islands
This beachfront flat offers direct access to a private beach and is located in the city centre of Islamorada, Village of Islands, placing it within 2 kilometres of Islamorada Brewery & Distillery, Florida Keys Brewing Co., Windley Key Fossil Reef Geological State Park, and Indian Key Historic State Park.
This pet-friendly one-bedroom apartment accommodates up to four guests and features air conditioning, Wi-Fi, a swimming pool with ocean views, and on-site activities including bike, kayak, and paddleboard rentals.

The Best Family-Rated Stays in Islamorada, FL, United States

Browse family beach accommodation in Islamorada, FL, United States with space and facilities for all ages.

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |Bbq - Islamorada, FL
9.9 335 reviews

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |Bbq

apartment, Tavernier
Isla Lychee: Free Boat Dockage Sep-oct Only! - Islamorada, FL
10 7 reviews

Isla Lychee: Free Boat Dockage Sep-oct Only!

house, Islamorada, Village of Islands
Tropical Getaway W/private Beach 1 Bd Condo - Islamorada, FL
8.0 12 reviews

Tropical Getaway W/private Beach 1 Bd Condo

apartment, Tavernier
Ocean Views With Secret Speakeasy Bbq Patio Dock Pool 3br With Private Bathrooms - Islamorada, FL
10 3 reviews

Ocean Views With Secret Speakeasy Bbq Patio Dock Pool 3br With Private Bathrooms

house, Islamorada, Village of Islands

Leading Dog-Friendly Accommodations in Islamorada, FL, United States

Let your dog run wild through the sand and surf at these pet-friendly beach accommodations in Islamorada, FL, United States.

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
Islamorada Fishing Getaway: Dock, Pool & Sunrise - Islamorada, FL
10 9 reviews

Islamorada Fishing Getaway: Dock, Pool & Sunrise

apartment, Islamorada, Village of Islands
Get Ready For Blissful Getaway! 2 Relaxing Units, Onsite Pool, Free Breakfast - Islamorada, FL
No reviews

Get Ready For Blissful Getaway! 2 Relaxing Units, Onsite Pool, Free Breakfast

apartment, Islamorada, Village of Islands
Islander Resort - Islamorada, FL
9.1 3918 reviews

Islander Resort

resort, Islamorada, Village of Islands

Find the Best Accommodations with Balconies in Islamorada, FL, United States

Take in breathtaking, uninterrupted ocean sunsets directly from your personal balcony at beach accommodation in Islamorada, FL, United States.

Ocean View 2br - Pool, Beach & Tropical Landscaping - Islamorada, FL
No reviews

Ocean View 2br - Pool, Beach & Tropical Landscaping

apartment, Tavernier
Tarpon Palms - 4 Bedroom Waterfront Home With Dock & Heated Pool In Islamorada - Islamorada, FL
No reviews

Tarpon Palms - 4 Bedroom Waterfront Home With Dock & Heated Pool In Islamorada

apartment, Islamorada, Village of Islands
Bayside Villas By Islander Resort - Islamorada, FL
8.9 899 reviews

Bayside Villas By Islander Resort

resort, Islamorada, Village of Islands
Bright 2br Condo With Breathtaking Ocean View - Islamorada, FL
9.4 10 reviews

Bright 2br Condo With Breathtaking Ocean View

apartment, Tavernier

Best Islamorada, FL accommodations with a kitchen

Houseboat 2bd, 1 Bath Private Keys Cottage Mullet - Islamorada, FL
9.7 420 reviews

Houseboat 2bd, 1 Bath Private Keys Cottage Mullet

boat, Islamorada, Village of Islands
Paradise In The Heart Of Islamorada.come Relax And Have The Time Of Your Life! - Islamorada, FL
No reviews

Paradise In The Heart Of Islamorada.come Relax And Have The Time Of Your Life!

apartment, Islamorada, Village of Islands
Ocean Breeze Den Suite | Island Vibes - Islamorada, FL
10 2 reviews

Ocean Breeze Den Suite | Island Vibes

apartment, Islamorada, Village of Islands
Little Bay Cottage - Islamorada, FL
No reviews

Little Bay Cottage

house, Islamorada, Village of Islands
©2026 cozycozy.com