This second-floor flat in Islamorada, Village of Islands, offers tranquil marina views and is situated close to beaches and resort amenities. This apartment sleeps up to six guests and features a full-sized kitchen, two private balconies, and access to a heated resort pool, alongside on-site recreational facilities and complimentary resort transport.
9.9 101 reviews
Islamorada, FL
07/08 – 23/08
A$624/nighttotal: A$9984 (16 )
Islamorada Bungalow 2 Bed & Pool
1 4
apartment , Islamorada, Village of Islands
Bungalow Blue is located in the Shady Palms community of Islamorada, at mile marker 76, just a short walk from the community pool and a short bike ride from Robbie's Marina. The cottage has consistently received excellent ratings for its location, cleanliness, and overall experience. This charming two-bedroom property can comfortably accommodate up to four guests. The cottage offers a private backyard, a fully equipped kitchen with modern appliances, air conditioning, and a private heated pool, making it ideal for a relaxing and enjoyable stay in the Florida Keys.
9.7 127 reviews
Islamorada, FL
07/07 – 11/07
A$436/nighttotal: A$1744 (4 )
Keys Deal W/cafe & Pool Bar! Up To 20% Off Beachfront 1bd Sleeps 4.
1 4
apartment , Tavernier
This Tavernier apartment is located just 2.4 kilometres from Baker's Cay Resort Beach and Harry Harris Park, both offering a relaxed beach atmosphere, and is within 5 kilometres of Mariners Hospital and Florida Keys Dive Center. It has received excellent ratings for location, cleanliness, and overall user experience. The one-bedroom apartment spans 60 square metres and comfortably accommodates up to four guests. It offers a range of amenities including a fully equipped kitchen, a private balcony, a swimming pool, a jacuzzi, a tennis court, and a garden, ensuring a relaxing and enjoyable stay.
Isla Guava: Waterfront Boutique Resort in Matecumbe, Islamorada, offers convenient access to the Islamorada Brewery & Distillery and Keys History & Discovery Centre (both within 1.6km), and the History of Diving Museum (within 2.4km). This smoke-free villa boasts a 156 square metre floor area, sleeping up to six guests in three bedrooms and four bathrooms, and features a private balcony, fully equipped kitchen, swimming pool, spa, and free Wi-Fi.
9.6 155 reviews
Islamorada, FL
30/07 – 06/08
A$536/nighttotal: A$3752 (7 )
2br/1ba Serene Cozy Cottage Of Shady Palms In Islamorada With Heated Pool
1 2
cottage , Islamorada, Village of Islands
This charming cottage is situated in Islamorada at mile marker 76.7, just a short drive from Caloosa Cove Marina at mile marker 73.5 and Robbie's Marina, offering a peaceful retreat in the Shady Palms community. The cottage boasts excellent user, location and cleanliness ratings, ensuring a comfortable and enjoyable stay. The property features two bedrooms, making it ideal for families or groups of up to four. Guests can enjoy amenities such as a communal heated pool, a fully equipped kitchen, a private garden, a spa, and a starter pack with essential supplies.
Islamorada, FL
08/09 – 06/10
A$334/nighttotal: A$9352 (28 )
Beacon Reef 406
2 2
house , Islamorada, Village of Islands
Beacon Reef 406, a beachfront property in Islamorada, Village of Islands, offers direct sea views and is a short walk (approximately 0.4km) from the History of Diving Museum, with Windley Key Fossil Reef Geological State Park a 2km drive away. This two-bedroom, two-bathroom holiday home sleeps seven, boasting a fully equipped kitchen, Jacuzzi, spa, fitness centre, and free Wi-Fi; on-site parking and a 24-hour front desk add to guest convenience.
9.7 152 reviews
Islamorada, FL
26/06 – 30/06
A$611/nighttotal: A$2444 (4 )
Experience Unparalleled Atlantic Ocean Views 4215
2 3
apartment , Tavernier
This waterfront apartment is located in Tavernier, within a 15-minute walk of Baker's Cay Resort Beach and Harry Harris Park, offering easy access to the area's natural beauty. Guests have consistently rated this property as excellent for location, cleanliness, and overall experience. The apartment features two bedrooms and two bathrooms spread across 85 square metres. Enjoy the convenience of a fully equipped kitchen, a private fenced yard, a swimming pool, a jacuzzi, and a tennis court, making this a perfect choice for families and groups seeking a comfortable and relaxing stay.
Islamorada, FL
08/09 – 06/10
A$388/nighttotal: A$10864 (28 )
Villa Riolo
2 2
house , Islamorada, Village of Islands
Villa Riolo is a two-bedroom, two-bathroom house in Islamorada, Florida Keys, situated 2.6km from Sea Oats Beach and within easy driving distance of Windley Key (14km) and Pigeon Key (31km). This self-catering property sleeps up to 11 guests and boasts a fully equipped kitchen, free Wi-Fi, on-site parking, a spa, and a fitness centre; nearby attractions include Florida Keys Aquarium Encounters (39km) and John Pennekamp Coral Reef State Park (43km).
9.8 45 reviews
Islamorada, FL
27/06 – 04/07
A$382/nighttotal: A$2674 (7 )
Casa Seagulls
2 2
apartment , Islamorada, Village of Islands
This two-bedroom apartment is situated in Islamorada, directly overlooking the Atlantic Ocean, within walking distance of fishing, snorkeling, diving, and kayak/paddleboard rentals. Local charters for these activities are about 1.6 kilometres away. The apartment has received excellent ratings for location, cleanliness, and overall user experience. This comfortable property can sleep up to four adults and features a fully equipped kitchen with a fridge, microwave oven, and dishwasher, as well as air conditioning, a swimming pool, a garden, a fitness centre, and parking. Guests can enjoy stunning ocean views from the spacious porch, relax by the pool, or barbecue on the beach.
Islamorada, FL
30/07 – 06/08
A$490/nighttotal: A$3430 (7 )
Convenient Stay, Superb Location, Free Breakfast
1 2
resort , Islamorada, Village of Islands
This Islamorada resort offers a "Convenient Stay, Superb Location, Free Breakfast" package, situated on a private beach just 200 metres from the History of Diving Museum and within easy reach of Windley Key Fossil Reef Geological State Park and Lignumvitae Key Botanical State Park. This family-friendly accommodation, suitable for up to four guests, features air conditioning, Wi-Fi, an outdoor heated swimming pool, and allows pets for an additional fee, with complimentary parking available.
9.1 74 reviews
Islamorada, FL
28/06 – 01/07
A$536/nighttotal: A$1608 (3 )
Tavernier Oceanfront Resort Condo-pool, Dockage, Kayaks, Onsite Restaurant & Bar
2 5
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.
9.7 228 reviews
Islamorada, FL
26/06 – 30/06
A$526/nighttotal: A$2104 (4 )
Keys Waterfront Condo: Beach, Pool & Sunset Views!
2 3
apartment , Tavernier
This waterfront apartment in Tavernier is located a short 2.4 km walk from Baker's Cay Resort Beach and Harry Harris Park, offering easy access to the beautiful waters and the local area. It has received excellent ratings for its location, cleanliness, and overall experience. The apartment spans 84 square metres and comfortably accommodates up to 6 guests, with 2 bedrooms and 2 bathrooms. You'll enjoy a range of amenities including a swimming pool, jacuzzi, terrace, garden, spa, tennis court, and parking, as well as a fully equipped kitchen and air conditioning.
Best family friendly Islamorada, FL holiday rentals
Among the 1414 accommodations in Islamorada, FL, here are the 4 best family friendly rentals
9.8 57 reviews
Islamorada, FL
07/08 – 23/08
A$825/nighttotal: A$13200 (16 )
Pristine Pool Front Home W/ocean Views Anglers 148
2 4
apartment , Islamorada, Village of Islands
This beachside home is located in Islamorada, within 3 kilometres of Windley Key Fossil Reef Geological State Park, Founders Park, and Islamorada County Park, offering a relaxing and convenient base for exploring the area. This property has received excellent guest reviews, indicating a high level of satisfaction. The 157 square metre house has two bedrooms and can accommodate up to six guests. Enjoy the private outdoor pool, garden, barbecue grills, and direct beach access, plus a fully equipped kitchen, air conditioning, and free Wi-Fi.
9.6 48 reviews
Islamorada, FL
07/07 – 11/07
A$395/nighttotal: A$1580 (4 )
Amazing Ocean View Condo
1 4
apartment , Tavernier
This apartment is located in Tavernier, just a short walk from Baker's Cay Resort Beach and Harry Harris Park and within a 5km radius of Mariners Hospital and Florida Keys Dive Center. This property has received excellent user ratings, making it a popular choice for travellers. The apartment has one bedroom and one bathroom, comfortably accommodating up to four guests. It boasts a fully equipped kitchen, a washing machine, a sofa bed, and a balcony, with a private pool, a tennis court, and a Jacuzzi on-site.
8.4 28 reviews
Islamorada, FL
07/08 – 23/08
A$431/nighttotal: A$6896 (16 )
Anglers Reef Paradise
1 4
house , Islamorada, Village of Islands
Angler's Reef Resort is conveniently located in Islamorada, a short walk from Anne's Beach and within easy reach of other attractions like Upper Matecumbe Key and the Florida Keys Aquarium. This resort has excellent ratings for location, cleanliness, and overall user experience. The resort offers a range of accommodation options, including rooms with kitchens for those who prefer to self-cater. Guests can enjoy a variety of amenities, including a swimming pool, BBQ facilities, a garden, and a fitness centre.
9.6 76 reviews
Islamorada, FL
09/10 – 12/10
A$390/nighttotal: A$1170 (3 )
Relax In Your One Bedroom Oceanfront Suite In Tavernier Fl. Florida Keys.
1 2
apartment , Tavernier
This Tavernier condo is conveniently located near Harry Harris Park (approx. 1km), Mariners Hospital (under 5km), and other attractions within a 10km radius, offering easy access to waterfront activities and medical facilities. The one-bedroom, one-bathroom apartment sleeps four guests and boasts a fully equipped kitchen, private balcony, free Wi-Fi, on-site pool, hot tub, and tennis court; perfect for exploring Tavernier and its surroundings.
Best Islamorada, FL holiday rentals with a pool
Among the 1414 accommodations in Islamorada, FL, here are the 4 best rentals with a pool
9.8 111 reviews
Islamorada, FL
07/08 – 23/08
A$672/nighttotal: A$10752 (16 )
Anglers Reef Islamorada, Bikes,kayak,paddle Boards Dock Available-pool
2 4
apartment , Islamorada, Village of Islands
This two-bedroom apartment is located in the Anglers Reef community in Islamorada, just a short distance from local shops, bars, and restaurants, and within easy reach of the famous Islamorada "sandbar" and Alligator Reef. The apartment has received excellent ratings from previous guests and offers a peaceful, gated oasis with minimal traffic and stunning ocean views. The 128 square metre apartment can accommodate up to six guests and features a spacious open layout, granite countertops, updated appliances, and a comfortable king-size bed in the master bedroom. Guests can enjoy a range of amenities, including a private swimming pool, boat docks, private beaches, three flat-screen TVs with Hulu and Netflix, complimentary wireless internet, a Keurig coffee pot, a full-size washer and dryer, and a fully equipped kitchen.
This private beachfront villa in Islamorada's Matecumbe neighbourhood offers direct ocean views and is a short drive to the Keys History & Discovery Center and History of Diving Museum, with Indian Key Historic State Park and Windley Key Fossil Reef Geological State Park nearby. Spanning 418 square meters, this expansive property accommodates up to 12 guests across a central villa, a primary suite villa, and a guest suite wing, featuring a heated infinity pool, hot tub, a 100-meter ocean dock, and on-site water sports like kayaking and paddleboarding.
9.8 27 reviews
Islamorada, FL
27/06 – 04/07
A$434/nighttotal: A$3038 (7 )
Idyllic Tropical Paradise Overlooking The Fabulous Florida Bay.
2 2
apartment , Islamorada, Village of Islands
This two-bedroom apartment is situated in the Futura Yacht Club in Tavernier, Islamorada, just a short distance from Indian Key Historic State Park and San Pedro Underwater Archaeological Preserve State Park. The apartment has received excellent user ratings and offers a peaceful and secluded escape. The apartment can accommodate up to six guests and comes equipped with a fully equipped kitchen, laundry facilities, cable TV, and internet access. Guests can enjoy a variety of amenities, including a swimming pool, tennis courts, a basketball court, a fish cleaning station, and direct waterfront views from the balcony.
9.8 25 reviews
Islamorada, FL
07/07 – 11/07
A$431/nighttotal: A$1724 (4 )
Key Largo Baha Penthouse Ocean Pointe 1416
2 4
apartment , Tavernier
This Tavernier waterfront apartment, situated 1.1 kilometres from Harry Harris Park and within 5 kilometres of Mariners Hospital and the Florida Keys Dive Centre, offers stunning views. The 77 square metre property features three bedrooms, two bathrooms, sleeps five guests, and includes a fully equipped kitchen, private balcony, swimming pool, jacuzzi, and on-site barbecue grills.
Frequently asked questions about holiday rentals in Islamorada, FL
What sports or outdoor activites can visitors enjoy in and around Islamorada, FL?
Islamorada is a water sports paradise. You can go fishing, kayaking, paddleboarding, diving, snorkeling, or even take a boat tour to see dolphins and manatees. If you prefer something on land, you can try hiking, birdwatching, or exploring the Florida Keys National Marine Sanctuary.
What are the best Airbnb and holiday rentals in Islamorada, FL?
What amenities are commonly available in vacation rentals in Islamorada, FL?
Vacation rentals in Islamorada typically offer a range of amenities, including private pools, hot tubs, WiFi, cable TV, and fully equipped kitchens. Some rentals also have boat docks, private beaches, and outdoor grills. You can find rentals that suit different budgets and preferences.
What are the most popular Airbnbs in Islamorada, FL?
What time of year is best to rent a vacation rental Islamorada, FL?
The best time to visit Islamorada is during the shoulder season, from April to May or September to October, when the weather is still pleasant but the crowds are smaller. You can find better deals on vacation rentals during these months.
What are the best holiday rentals with a pool in Islamorada, FL?
Best Islamorada, FL holiday rentals with a balcony
Islamorada, FL
08/09 – 06/10
A$602/nighttotal: A$16856 (28 )
Waterfront Ocean Access Canal Kamp Key Homes
3 2
house , Islamorada, Village of Islands
This Islamorada waterfront property, 2.3km from Sea Oats Beach and 8.8km from Upper Matecumbe Key, offers direct ocean access via a private canal. The one-bedroom house sleeps fourteen guests, boasts three bathrooms, a fully equipped kitchen including a dishwasher, and features a terrace, air conditioning, free parking, and is conveniently located near Theater of the Sea and Windley Key.
9.8 173 reviews
Islamorada, FL
26/06 – 30/06
A$591/nighttotal: A$2364 (4 )
Sunrise Breeze On The Marina [Ocean Pointe 5302]
2 3
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.
9.6 10 reviews
Islamorada, FL
27/06 – 04/07
A$493/nighttotal: A$3451 (7 )
Charming Bayside 2 Bed, 2 Bath Condo At Futura In Islamorada Wifi, Pool, Dockage
2 2
apartment , Islamorada, Village of Islands
This Islamorada condominium is located in Tavernier, at mile marker 88.5 on the bay side, offering waterfront views and convenient access to the Florida Keys Dive Center, Mangrove Marina, John Pennekamp Coral Reef State Park, and Windley Key Fossil Reef Geological State Park. This fully furnished 2-bedroom condo spans 79 square metres, accommodates up to six guests, and features en-suite bathrooms, a balcony overlooking tennis courts, on-site WiFi, central air conditioning, and laundry facilities, with available dockage, a boat ramp, and trailer parking for boating enthusiasts.
Islamorada, FL
08/09 – 06/10
A$362/nighttotal: A$10136 (28 )
Beacon Reef 222
2 2
house , Islamorada, Village of Islands
Beacon Reef 222, a two-bedroom house in Islamorada, is conveniently located near Upper Matecumbe Key and Windley Key, with Pigeon Key 19km and John Pennekamp Coral Reef State Park 32km away. This 119 square metre property offers a swimming pool, fitness centre, and terrace with sea views, accommodating up to seven guests and including a fully equipped kitchen, free Wi-Fi, and on-site parking.
Best Islamorada, FL holiday rentals with parking
9.7 287 reviews
Islamorada, FL
26/06 – 30/06
A$552/nighttotal: A$2208 (4 )
Keys Deal W/cafe & Pool Bar! Up To 20% Off Oceanfront 2/2 With Private Beach
2 3
apartment , Tavernier
This Tavernier apartment is conveniently located just 2.4 kilometres from Baker's Cay Resort Beach and Harry Harris Park, offering easy access to the area's attractions. The property has received excellent ratings for user experience, location, and cleanliness. The two-bedroom apartment spans 79 square metres and comfortably accommodates up to four guests. It features a fully equipped kitchen, air conditioning, a swimming pool, a Jacuzzi, a terrace, a garden, a spa, a tennis court, and parking.
10 173 reviews
Islamorada, FL
07/08 – 23/08
A$845/nighttotal: A$13520 (16 )
Tikibar With Tv &Stereo, Privatespa, Heated Pool, Hammock,sups, Kayaks,bikes,fp
2 4
apartment , Islamorada, Village of Islands
This family-friendly holiday home is located in Islamorada, just a short drive from the San Pedro Underwater Archaeological Preserve State Park, Robbie’s of Islamorada, and Indian Key Historic State Park, all within a 3 km radius. This property has consistently received excellent ratings for its location, cleanliness, and overall user experience. This two-bedroom dwelling can comfortably accommodate up to five guests. The property offers a range of amenities, including a swimming pool, a Jacuzzi, a terrace, a garden, a spa, and concierge services, as well as a tennis court and free parking.
Islamorada, FL
04/08 – 09/08
A$812/nighttotal: A$4060 (5 )
Vacation At Its Finest! 2 Convenient Units, Free Parking, Breakfast, Onsite Pool
2 5
apartment , Islamorada, Village of Islands
This Islamorada apartment, centrally located in the Village of Islands, offers convenient access to the History of Diving Museum and Keys History & Discovery Centre, with the precise distance unspecified. The 54-square-metre (581-square-foot) self-catering property features two bedrooms, two bathrooms, and sleeps eight guests, boasting amenities including a swimming pool, terrace, and parking, plus nearby access to water sports and breweries.
9.7 92 reviews
Islamorada, FL
30/07 – 06/08
A$509/nighttotal: A$3563 (7 )
Oceanfront, 2 Bedroom Unit At Ocean Pointe Condominium
2 2
apartment , Tavernier
This waterfront apartment in Tavernier is ideally located within a 15-minute walk of Baker's Cay Resort Beach and Harry Harris Park, offering easy access to the area's main attractions. The property consistently receives excellent ratings for its cleanliness, location, and overall experience, ensuring a comfortable and enjoyable stay. The two-bedroom apartment spans 79 square metres and comfortably accommodates up to four guests. Enjoy a range of amenities including a private pool, fenced yard, and a fully equipped kitchen, as well as access to a shared swimming pool, jacuzzi, garden, tennis court, and parking.