This Islamorada resort offers a prime location in the Village of Islands, approximately 160 kilometres south of Miami, known for its upscale, small-town atmosphere and natural beauty. The accommodation provides a 2-bedroom, 1-bathroom unit for up to 4 guests, featuring air conditioning, free Wi-Fi, a swimming pool, complimentary breakfast and parking, and welcomes pets for an additional nightly charge under the "Islamorada Stay! Free Breakfast | Pool & Parking!" offer.
8.4 5 reviews
Islamorada, FL
09/08 – 14/08
NZ$384/nighttotal: NZ$1920 (5 )
Swim With Dolphins In The Florida Keys! Free Breakfast & Parking, Marina, Pool!
1 2
apartment , Islamorada, Village of Islands
This Islamorada apartment hotel boasts a central location, offering easy access to attractions such as Indian Key Historic State Park and the San Pedro Underwater Archaeological Preserve State Park. The 28-square-metre (301 sq ft) self-catering apartment features one bedroom, one bathroom, sleeps four guests, and includes a balcony with partial ocean views, a kitchenette with dishwasher, and complimentary continental breakfast; on-site amenities include a heated pool, private beach access, and kayak/paddleboard hire.
9.6 40 reviews
Islamorada, FL
09/07 – 12/07
NZ$448/nighttotal: NZ$1344 (3 )
Floating 2 Bd, 1 Bath Private Villa Pirates Lair
1 5
apartment , Islamorada, Village of Islands
This charming cottage is located in Islamorada, just a short distance from the village centre and within easy reach of the best fishing spots. The property has received excellent ratings for its location, cleanliness and overall experience, making it a popular choice for travellers. The cottage is a one-bedroom property with one bathroom and can accommodate up to six guests. Guests can enjoy the privacy and tranquility of the cottage while taking advantage of amenities such as private boat rentals, discounted boat rental rates, and breathtaking sunset views.
10 2 reviews
Islamorada, FL
28/06 – 01/07
NZ$728/nighttotal: NZ$2184 (3 )
Proximity Ats Its Best! 2 Convenient Units, Pool
2 5
resort , Islamorada, Village of Islands
This Islamorada apartment rental is situated on a private beach, within walking distance of the Theatre of the Sea and close to Windley Key Fossil Reef and Lignum Vitae Key Botanical State Parks. The 606 sq ft property comprises two bedrooms, two bathrooms, sleeps eight guests, and offers amenities including a heated pool, kayaks, paddleboards, bicycles, and complimentary continental breakfast.
9.4 7 reviews
Islamorada, FL
17/10 – 26/10
NZ$1000/nighttotal: NZ$9000 (9 )
Isla Acai: Free Boat Dockage Sep-oct Only!
1 6
house , Islamorada, Village of Islands
Isla Acai Villa #8, situated in Islamorada's Art District, offers easy walking access to local shops and restaurants, and is within 1.6km of Robbie's Marina and the Theater of the Sea. This three-bedroom, three-bathroom luxury villa sleeps six, boasting a private heated pool, modern kitchen, and a deck with partial water views, plus optional baby equipment and is pet-friendly.
10 65 reviews
Islamorada, FL
20/06 – 27/06
NZ$670/nighttotal: NZ$4690 (7 )
Just A Few Friends - Ocean View And Bring Your Boat!
2 2
apartment , Islamorada, Village of Islands
This two-bedroom apartment is situated in the peaceful, gated community of Bay Harbour in Islamorada, just a short drive from the village centre and its shops and restaurants. The property has received excellent ratings for location, cleanliness and user experience. The apartment offers 137 square metres of living space, comfortably accommodating up to four guests. Enjoy a range of amenities including a swimming pool, Jacuzzi, fitness centre, and a private boat slip, perfect for exploring the waters of the Florida Keys.
Islamorada, FL
19/07 – 26/07
NZ$2099/nighttotal: NZ$14693 (7 )
One Bedroom Suite W/2 Queen Beds, Kitchenette, Pool, Free Parking & Pet Friendly
2 9
resort , Islamorada, Village of Islands
This pet-friendly resort, offering the 'One Bedroom Suite W/2 Queen Beds, Kitchenette, Pool, Free Parking & Pet Friendly' package, is located in Islamorada's Matecumbe district, directly on the beach and within easy reach of Indian Key Historic State Park and the Hurricane Monument. The self-catering suite features two bedrooms, two bathrooms, sleeps up to twelve guests, and includes a kitchenette, balcony, free Wi-Fi, and access to on-site and nearby water sports.
8.4 5 reviews
Islamorada, FL
18/07 – 22/07
NZ$487/nighttotal: NZ$1948 (4 )
Discover Florida Keys! Seaside Villa W/ Patio! Marina, Pool, Parking, Breakfast
1 4
apartment , Islamorada, Village of Islands
This house is located in the heart of Islamorada, directly on the beach, offering easy access to the area's attractions. The surrounding area is vibrant and offers a range of shops, restaurants, and bars. This one-bedroom house is 27 square metres and can accommodate up to four guests. It includes a range of amenities, including a private beach, a heated pool with ocean views, and a continental breakfast.
Islamorada, FL
25/07 – 01/08
NZ$1204/nighttotal: NZ$8428 (7 )
Condo ∙ 3 Bedrooms ∙ 6 Guests
3 5
apartment , Islamorada, Village of Islands
This Islamorada condo, situated bayside at MM 77.5, offers direct ocean views and is located within 1.6 kilometres of Anne's Beach, with a beach accessible for watersports just across the street. This family-friendly three-bedroom accommodation for six features a screened terrace, a gourmet kitchen with stainless steel appliances, a private 9.45-metre deep water dock with a lift, and access to a communal swimming pool and spa.
9.2 10 reviews
Islamorada, FL
09/10 – 12/10
NZ$670/nighttotal: NZ$2010 (3 )
Islamorada Paradise Overlooking The Fabulous Florida Bay.
3 2
apartment , Islamorada, Village of Islands
This Islamorada apartment, near Florida Bay, is conveniently located 5.1 km from Windley Key and 10.5 km from Upper Matecumbe Key. The 93 square metre property boasts three bedrooms, two bathrooms, sleeping six guests, and features an equipped kitchen, terrace, swimming pool, tennis court, and free Wi-Fi.
10 27 reviews
Islamorada, FL
02/07 – 05/07
NZ$2388/nighttotal: NZ$7164 (3 )
Islamorada Reef Canal & Pool Home Off Tav Creek-
1 5
apartment , Islamorada, Village of Islands
This Islamorada canal-front property, moments from Tavernier Creek Marina and restaurants, offers direct bay and ocean access, with the reef approximately 1.6 kilometres away. This two-bathroom apartment sleeps five, boasting a private pool, patio, boat dockage, large loft with Netflix, outdoor shower, bait freezer, BBQ, and full kitchen including dishwasher, fridge, freezer and microwave.
9.6 4 reviews
Islamorada, FL
03/07 – 05/07
NZ$983/nighttotal: NZ$1966 (2 )
2br Condo W/ Ocean View, Pool & Tropical Setting
2 5
apartment , Tavernier
This Tavernier oceanfront apartment, near Key Largo and Islamorada, offers private beach access and is conveniently located for exploring John Pennekamp Coral Reef State Park and Jacob's Aquatic Centre. The 79 square metre (850 square foot) property sleeps six guests in two bedrooms and two bathrooms, boasting a fully equipped kitchen, swimming pool, parking, and internet access; kayaking and motor boating opportunities are also nearby.
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
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.
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.
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.
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
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.
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.
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.
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?
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?
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?
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?
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?
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
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.
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.
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.
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
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.
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.
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.
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.