Search Islamorada, FL accommodations

1677 available accommodation offers

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

1677 Best accommodations in Islamorada, FL

Best Islamorada, FL accommodations with a pool

Among the 1677 accommodations in the area, here is the list of the 4 best ones with a pool

Look No Further! 4 Relaxing Units, Onsite Pool - Islamorada, FL
Islamorada, FL
16/10 – 18/10
NZ$1692/nighttotal: NZ$3384 (2 )

Look No Further! 4 Relaxing Units, Onsite Pool

4 12
resort , Islamorada, Village of Islands
This Islamorada resort, situated on a private beach within walking distance of the Theatre of the Sea and close to Windley Key Fossil Reef Geological State Park and Lignumvitae Key Botanical State Park, offers direct beach access.
This four-bedroom, four-bathroom property provides 120 square metres of space, sleeping up to 16 guests across four separate rooms, each with a balcony and amenities including a private fridge and Keurig coffee machine; on-site facilities comprise a heated pool, complimentary continental breakfast, and kayak and paddleboard rentals.
Snorkeling & Kayaking Beach Resort! Seaside Villa W/patio! Marina, Parking - Islamorada, FL
Islamorada, FL
16/10 – 18/10
NZ$2159/nighttotal: NZ$4318 (2 )

Snorkeling & Kayaking Beach Resort! Seaside Villa W/patio! Marina, Parking

4 12
apartment , Islamorada, Village of Islands
This resort is located in the heart of Islamorada, Village of Islands, directly on the beach, just a short walk from Florida Keys Brewing Co. and Bud n' Mary's Dive Center. The surrounding area is known for its beautiful beaches, excellent fishing, and relaxed atmosphere.
The "Snorkeling & Kayaking Beach Resort! Seaside Villa W\/patio! Marina, Parking" offers spacious villas with 4 bedrooms, 4 bathrooms, and a floor area of 108 square meters, accommodating up to 16 guests. Amenities include a private beach, a heated pool, free parking, bike rentals, kayaks, stand-up paddleboards, and outdoor barbecue facilities.
Anglers Reef Islamorada Vacation Rental 2/2.5 Updated 131 Anglers Way - Islamorada, FL
9.8 73 reviews
Islamorada, FL
25/07 – 01/08
NZ$1016/nighttotal: NZ$7112 (7 )

Anglers Reef Islamorada Vacation Rental 2/2.5 Updated 131 Anglers Way

2 5
apartment , Islamorada, Village of Islands
This oceanfront villa is situated on Anglers Way in Islamorada, just a short distance from the vibrant downtown area, with its shops, restaurants, and bars. The property has consistently received excellent ratings for user experience, location, and cleanliness.
The spacious two-bedroom villa, spanning 109 square metres, comfortably accommodates up to six guests. It boasts a range of amenities, including a fully equipped kitchen, air conditioning, a private balcony, a swimming pool, and a garden, as well as free access to kayaks and bikes for exploring the surrounding area.
Oceanfront Islamorada Townhome With Pool & Dock - Islamorada, FL
10 8 reviews
Islamorada, FL
20/06 – 27/06
NZ$1113/nighttotal: NZ$7791 (7 )

Oceanfront Islamorada Townhome With Pool & Dock

1 6
house , Islamorada, Village of Islands
This three-bedroom, three-bathroom house in Islamorada, Village of Islands, offers comfortable accommodation for up to eight guests and includes a swimming pool, garden, and parking.
The property boasts a fully equipped kitchen, air conditioning, and internet access, providing a relaxing base for exploring the Florida Keys, although precise distances to local attractions require further clarification.

Best family friendly Islamorada, FL accommodations

Among the 1677 accommodations in the area, here is the list of the 4 best family friendly ones

Sunrise Sanctuary - Top Floor Ocean Pointe 2415 - Islamorada, FL
9.8 17 reviews
Islamorada, FL
09/07 – 12/07
NZ$655/nighttotal: NZ$1965 (3 )

Sunrise Sanctuary - Top Floor Ocean Pointe 2415

2 5
apartment , Tavernier
This Tavernier waterfront apartment, situated 1.1 kilometres from Harry Harris Park and within 4.8 kilometres of Mariners Hospital and the Florida Keys Dive Centre, offers stunning views.
The 84-square-metre property features three bedrooms, two bathrooms, sleeps six guests, and includes a fully equipped kitchen, private balcony, swimming pool, and on-site barbecue facilities.
House ∙ 2 Bedrooms ∙ 4 Guests - Islamorada, FL
Islamorada, FL
01/07 – 08/07
NZ$688/nighttotal: NZ$4816 (7 )

House ∙ 2 Bedrooms ∙ 4 Guests

2 2
house , Islamorada, Village of Islands
This oceanfront dwelling is located within the secure Anglers Reef community in Islamorada, offering direct access to the Florida Keys' celebrated sport-fishing and marine life, with world-class snorkelling, scuba diving, dining, and shopping opportunities approximately 1.6 kilometres away.
This family-friendly villa accommodates up to four guests, featuring two bedrooms and two bathrooms, a well-equipped kitchen with modern appliances, air conditioning, a swimming pool, a terrace, garden, and parking, with optional dock space available for rent for vessels up to 9.45 metres.
Sunshine Paradise Key Largo Ocean Pointe 4402 - Islamorada, FL
10 8 reviews
Islamorada, FL
02/07 – 05/07
NZ$1014/nighttotal: NZ$3042 (3 )

Sunshine Paradise Key Largo Ocean Pointe 4402

2 5
apartment , Tavernier
This two-bedroom apartment is situated in Tavernier, Florida, approximately 0.8 kilometres from the Circle K convenience store and Dairy Queen on Route 1, offering a convenient location for exploring the surrounding area.
The apartment provides comfortable accommodation for up to five guests, boasting a king-size bed in the master bedroom, two twin beds in the guest bedroom, and a pull-out sofa, as well as access to Ocean Pointe's amenities including a swimming pool, hot tub, and private beach.
Apartment ∙ 2 Bedrooms ∙ 6 Guests - Islamorada, FL
Islamorada, FL
25/07 – 01/08
NZ$1072/nighttotal: NZ$7504 (7 )

Apartment ∙ 2 Bedrooms ∙ 6 Guests

2 5
apartment , Islamorada, Village of Islands
This Islamorada, Florida Keys apartment, located at mile marker 82.2 on Florida Bay, offers direct bayfront access and is a short drive from John Pennekamp Coral Reef State Park, Theatre of the Sea, and Robbie's Marina.
The two-bedroom, two-bathroom duplex sleeps six, features a private balcony with Florida Bay views, a fully equipped kitchen, and access to a spa, fitness centre, and parking within a gated one-acre tropical compound.

Frequently asked questions about accommodations in Islamorada, FL

  • What are the must-see sites in or near Islamorada, FL?

    Islamorada is known for its beautiful beaches and watersports, but you should also check out the Theater of the Sea, a marine park with dolphin shows and sea lion encounters. If you're into fishing, the Islamorada Fishing Museum is a must-visit. For a taste of local history, head to the History of Islamorada Museum.
  • What are the best accommodations in Islamorada, FL?

    Among the accommodations in Islamorada, FL, Sunset Inn, La Jolla Resort and Conch Villa 4 are the most popular ones.

  • How can travelers reach Islamorada, FL?

    The easiest way to get to Islamorada is by car, as it's located on the Overseas Highway (US-1), which connects the Florida Keys. You can also fly into Key West International Airport (EYW) and drive about 100 km north. If you're arriving by boat, there are several marinas in Islamorada.
  • What are the best accommodations with a pool in Islamorada, FL?

    Sunset Inn, La Jolla Resort and Conch Villa 4 are the best accommodations with a pool in Islamorada, FL.

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

    Islamorada is a paradise for water sports enthusiasts! You can go diving, snorkeling, fishing, kayaking, paddleboarding, and even jet skiing. If you prefer to stay on land, there are plenty of hiking trails and biking paths, including the scenic Overseas Highway itself.
  • What are the best accommodations with a jacuzzi in Islamorada, FL?

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

    The best time to visit Islamorada is during the shoulder seasons, from April to May or September to October, when the weather is still pleasant and the crowds are smaller. You can expect average temperatures between 21-27 degrees Celsius. The summer months are hot and humid, while winter can bring cooler temperatures and the occasional cold front.
  • 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 are the best walking or cycling routes in Islamorada, FL?

    For a leisurely stroll, try the Anne's Beach Walk, a paved path that runs along the beach. If you're up for a longer ride, the Overseas Highway is a great option for cycling, offering stunning views of the ocean. You can also explore the many backroads and trails in the surrounding areas.
  • What are the best pet friendly accommodations in Islamorada, FL?

    The best pet friendly accommodations in Islamorada, FL are Sunset Inn, Conch Villa 4 and Sands Of Islamorada.

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

    From Islamorada, you can easily visit the charming town of Marathon, located about 20 km to the south. It's known for its historic district and the Seven Mile Bridge, a scenic drive that connects Marathon to the rest of the Keys. If you're looking for a bigger city, Key West is about 100 km south, offering vibrant nightlife and cultural attractions.
  • What are the best accommodations with parking in Islamorada, FL?

    Sunset Inn, La Jolla Resort and Conch Villa 4 are the best accommodations with parking in Islamorada, FL.

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

    Accommodation options in Islamorada range from budget-friendly motels to luxurious resorts. Most places offer amenities like swimming pools, restaurants, and bars. Some also have private beaches, fishing docks, and boat rentals. You can find accommodation options to suit every taste and budget.

Destinations nearby

Best Islamorada, FL accommodations with a balcony

Beautiful Island Home In Anglers Reef! Ocean Front Community. Pool & Boat Slip. - Islamorada, FL
10 148 reviews
Islamorada, FL
17/10 – 26/10
NZ$625/nighttotal: NZ$5625 (9 )

Beautiful Island Home In Anglers Reef! Ocean Front Community. Pool & Boat Slip.

2 6
apartment , Islamorada, Village of Islands
This boat is situated in the exclusive gated community of Anglers Reef, located at Mile Marker 85 in Islamorada, just a short distance from the beach, Florida Keys Brewing Co., and Florida Keys Dive Center. The boat has been rated excellent by previous guests and offers a private and secure environment for travellers.
The boat features two bedrooms and three bathrooms, comfortably accommodating up to six guests. It includes a range of amenities, such as a fully equipped kitchen, air conditioning, a swimming pool, a terrace, a garden, a spa, parking, and complimentary paddleboards and kayaks for exploring the nearby sandbar, fishing, or investigating the mangrove shoreline.
Ocean View 2br - Pool, Beach & Tropical Landscaping - Islamorada, FL
Islamorada, FL
03/07 – 05/07
NZ$983/nighttotal: NZ$1966 (2 )

Ocean View 2br - Pool, Beach & Tropical Landscaping

2 5
apartment , Tavernier
This Tavernier oceanfront condo, near Key Largo and Islamorada, offers direct access to a private sandy beach and is close to John Pennekamp Coral Reef State Park and Jacob's Aquatic Centre.
This 79 square metre apartment sleeps six, featuring two bedrooms (one with a king or queen bed, the other with twin beds or a queen), a pull-out sofa, two bathrooms, a fully equipped kitchen, and resort amenities including a swimming pool, hot tub, and tennis courts.
Sunrise Breeze On The Marina [Ocean Pointe 5302] - Islamorada, FL
9.8 173 reviews
Islamorada, FL
23/07 – 26/07
NZ$736/nighttotal: NZ$2208 (3 )

Sunrise Breeze On The Marina [Ocean Pointe 5302]

2 2
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.
Beacon Reef 501 - Islamorada, FL
Islamorada, FL
08/09 – 06/10
NZ$395/nighttotal: NZ$11060 (28 )

Beacon Reef 501

2 4
house , Islamorada, Village of Islands
Beacon Reef 501 is a beachfront villa in Islamorada, Village of Islands, situated 2.1 kilometres from the Theater of the Sea and 2.4 kilometres from Upper Matecumbe Key.
This two-bedroom villa accommodates up to seven guests and features a jacuzzi, spa, fitness centre, water park access, and complimentary WiFi, with sea views from the terrace.

Best Islamorada, FL accommodations with a kitchen

2br 1.5bath Condo In Islamorada - Islamorada, FL
Islamorada, FL
20/06 – 27/06
NZ$435/nighttotal: NZ$3045 (7 )

2br 1.5bath Condo In Islamorada

1 2
apartment , Islamorada, Village of Islands
This Islamorada condo, registered as Village of Islamorada Vacation rental #25-0235, is conveniently located 0.8 kilometres from Founders Park, offering easy access to local restaurants and the beach.
The two-bedroom, one-and-a-half-bathroom apartment sleeps six, includes a kitchen, swimming pool, fitness centre, parking and private marina access for observing marine life, plus numerous other amenities.
Gated Community Townhome With Private Beach, Pool, And Tennis Courts! - Islamorada, FL
9.7 6 reviews
Islamorada, FL
08/09 – 06/10
NZ$337/nighttotal: NZ$9436 (28 )

Gated Community Townhome With Private Beach, Pool, And Tennis Courts!

3 4
house , Islamorada, Village of Islands
This Islamorada holiday home is conveniently located within a 1.6km walk of Founders Park and Islamorada County Park, and within 3.2km of Rain Barrel Village and Old Road Gallery.
This 139 square metre property sleeps six guests in three bedrooms and boasts a private pool, Jacuzzi, tennis court, fitness centre, and fully equipped kitchen; barbecue grills and free Wi-Fi are also available.
Ocean Oasis At Ocean Pointe - Islamorada, FL
8.3 5759 reviews
Islamorada, FL
03/07 – 05/07
NZ$906/nighttotal: NZ$1812 (2 )

Ocean Oasis At Ocean Pointe

2 5
house , Tavernier
Ocean Oasis at Ocean Pointe is situated in Tavernier, a short walk from Harry Harris Park Beach and a short drive from Pigeon Key, offering a tranquil escape in a beautiful location. The property has received very good ratings for its location, cleanliness and overall experience.
This holiday home features a well-equipped kitchen, a private balcony with sea views and a private beach for your enjoyment. Guests can also relax in the hot tub, swim in the pool, or enjoy the garden and outdoor play equipment.
Two-story Townhome With Community Pool & Tennis - Islamorada, FL
Islamorada, FL
08/09 – 06/10
NZ$295/nighttotal: NZ$8260 (28 )

Two-story Townhome With Community Pool & Tennis

1 4
house , Islamorada, Village of Islands
This Islamorada townhouse, situated at mile marker 87.2, offers easy access to Founders Park and numerous restaurants and shops.
Sleeping up to six guests, this fully renovated two-bedroom, two-bathroom property boasts a king bed, two queen beds, and two single beds in a loft, a private patio with BBQ, in-unit laundry, and access to Executive Bay Club amenities including a swimming pool and private beach.
©2026 cozycozy.com