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.
9.8 25 reviews
Islamorada, FL
17/07 – 24/07
452 €/nighttotal: 3164 € (7 )
Keezy Dream House+beach, Pool & Kayaks At Anglers
2 3
apartment , Islamorada, Village of Islands
This oceanfront property in Islamorada, Florida Keys, offers a gated community setting with convenient access to local attractions. The two-bedroom, two-and-a-half-bathroom house sleeps five, boasting a well-equipped kitchen, swimming pool, garden, and access to community kayaks; on-site boat slips are available to rent (subject to size restrictions: 9-foot bridge height, 31-foot length, 3.5-foot draught).
Islamorada, FL
01/01 – 31/05
129 €/nighttotal: 19350 € (150 )
Beautiful Islamorada Keys Home
1 2
apartment , Islamorada, Village of Islands
This Islamorada apartment, situated in the Matecumbe district, offers private canal/oceanside access and is within 0.16 km of two beaches, and a short walk from Robbie's Marina, Morada Bay Beach Restaurant, and the Florida Keys Brewery. This one-bedroom, one-bathroom dwelling sleeps up to 20 guests and features a private entrance, parking, kayak and boat access, a private bath with TV and internet, and a refrigerator and microwave; nearby attractions include the Theatre of the Sea and the Keys History & Discovery Center.
9.8 128 reviews
Islamorada, FL
01/01 – 31/05
231 €/nighttotal: 34650 € (150 )
Superhost Waterfront Paradise Home- Dock32 Ft Boat
1 2
apartment , Islamorada, Village of Islands
This apartment is situated in Islamorada, Village of Islands, offering picturesque water views and sunsets. The property has been highly rated by guests, receiving excellent scores for location, cleanliness, and overall user experience. The two-bedroom flat can comfortably accommodate up to four guests. It features a modern interior, a shared backyard area, and a private dock offering direct access to the water for fishing, kayaking, or simply enjoying the views.
This Islamorada ocean view condominium offers direct Atlantic access from its prime location in the Village of Islands, placing you moments from notable restaurants, bars, and fishing charters. This two-bedroom, one-bathroom property accommodates up to six guests and features a private balcony with ocean vistas, a fully equipped kitchen, on-site swimming pool, fitness centre, and private parking.
10 64 reviews
Islamorada, FL
26/06 – 30/06
341 €/nighttotal: 1364 € (4 )
Charming Cabana-condo In Picturesque Tavernier
2 3
apartment , Tavernier
This two-bedroom apartment is located in Tavernier, Florida, within a 2.4 kilometre walk of Baker's Cay Resort Beach and Harry Harris Park, making it ideal for exploring the area's natural beauty. The property has received excellent user ratings and is perfect for families or groups of friends. The 85 square metre apartment can comfortably accommodate up to six guests and boasts a fully equipped kitchen, air conditioning, and a private garden. Guests can enjoy the on-site swimming pool, Jacuzzi, and tennis court, as well as the nearby beach and other attractions.
9.8 45 reviews
Islamorada, FL
02/07 – 12/07
477 €/nighttotal: 4770 € (10 )
Keezy Dream House + Beach, Pool & Kayaks - Anglers Reef 119
2 3
apartment , Islamorada, Village of Islands
This waterfront property in Islamorada is located just 0.4 miles from Windley Key Fossil Reef Geological State Park and within 3 miles of Founders Park and Islamorada County Park. Guests consistently rate this property as excellent. The house has two bedrooms and can accommodate up to six guests. This family-friendly property offers a range of amenities, including a private pool, spa, a fully equipped kitchen, and a balcony with stunning views.
10 1 review
Islamorada, FL
06/08 – 09/08
291 €/nighttotal: 873 € (3 )
A Slice Of Islamorada Paradise With Ocean Views
1 2
apartment , Islamorada, Village of Islands
This studio apartment is located in Islamorada, Village of Islands, offering ocean views and convenient access to downtown restaurants via a complimentary app, with Founders Park and its sandy beaches just a short distance away. Guests can enjoy direct access to Founders Park amenities including beaches and swimming areas, alongside full use of Caloosa Cove Resort and Marina facilities such as a heated pool, beach, Safari Lounge, and General Store, with an on-site marina providing charter boat and boat slip rentals for sport fishing and aquatic activities.
8.8 8 reviews
Islamorada, FL
22/09 – 28/09
208 €/nighttotal: 1248 € (6 )
Snorkeling & Kayaking Beach Resort! Seaside Villa W/patio! Marina, Pool, Parking
1 2
apartment , Islamorada, Village of Islands
This 'Snorkeling & Kayaking Beach Resort! Seaside Villa W\/patio! Marina, Pool, Parking' is located in Islamorada, just a short walk from Florida Keys Brewing Co. and Bud n' Mary's Dive Center, offering a convenient location to explore the area. The resort is situated right on the beach, giving guests direct access to the beautiful Florida Keys waters. The one-bedroom villa offers a comfortable 28 square metres of space and can accommodate up to four guests. The resort provides a range of amenities, including a heated pool with ocean views, a private beach, access to kayaks and paddleboards, and a continental breakfast each morning.
8.4 5 reviews
Islamorada, FL
06/08 – 09/08
266 €/nighttotal: 798 € (3 )
Discover Florida Keys! Seaside Villa W/ Patio! Marina, Pool, Parking, Breakfast
1 2
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.
9.3 50 reviews
Islamorada, FL
06/08 – 09/08
241 €/nighttotal: 723 € (3 )
Peaceful Island Getaway In Islamorada! Parking!
1 2
resort , Islamorada, Village of Islands
This apartment is located in Islamorada, a charming seaside village known for its stunning coral reefs, and is just a short walk from the Theater of the Sea and nearby tropical forests like Windley Key Fossil Reef Geological State Park and Lignumvitae Key Botanical State Park. This property has received excellent ratings for its location, cleanliness, and overall experience. The apartment has one bedroom and one bathroom, comfortably accommodating up to four guests. Guests can enjoy a range of amenities, including a private beach, a heated pool with ocean views, a private boat ramp, kayaks, stand-up paddleboards, bicycles, and a daily continental breakfast.
9.6 157 reviews
Islamorada, FL
07/08 – 23/08
235 €/nighttotal: 3760 € (16 )
2br/1ba Serene Cozy Cottage Of Shady Palms In Islamorada With Heated Pool
1 4
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.
Best family friendly Islamorada, FL holiday rentals
Among the 1414 accommodations in Islamorada, FL, here are the 4 best family friendly rentals
9.4 3 reviews
Islamorada, FL
01/01 – 31/05
121 €/nighttotal: 18150 € (150 )
Starfish -1 Bedroom 1 Bath Apartment With Full Kitchen In Islamorada, Florida.
1 2
apartment , Islamorada, Village of Islands
This one-bedroom apartment is located in Plantation Key Colony, a neighbourhood in Tavernier, just 160 kilometres from Miami International Airport and a short distance from the attractions of the Upper Keys. It has received excellent user ratings, making it a popular choice for travellers. The apartment has a modern and comfortable interior, ideal for families of up to four people. It offers a range of amenities including internet access, a kitchen with a fridge and microwave, air conditioning, a terrace or balcony, and a spa. Guests can enjoy a peaceful retreat while having easy access to a variety of activities such as fishing, diving, exploring museums, shopping, and beaches.
9.8 100 reviews
Islamorada, FL
27/06 – 04/07
385 €/nighttotal: 2695 € (7 )
Single Family Home In Angler's Reef Gated Community, Beaches,marina,heated Pool
2 2
apartment , Islamorada, Village of Islands
This beachfront property is located in Islamorada, just under 5 kilometres from Windley Key Fossil Reef Geological State Park, Founders Park, and Islamorada County Park, and 3.5 kilometres from the History of Diving Museum. The home has received excellent ratings for location, cleanliness and user experience. The house is spread over 149 square metres and can accommodate up to 6 guests. It features 2 bedrooms, 3 bathrooms, a fully equipped kitchen, a spacious balcony, a swimming pool, a jacuzzi, a garden, a spa and parking.
This Tavernier apartment is situated just 3 kilometres from Mariners Hospital and Florida Keys Dive Center, with Baker's Cay Resort Beach and Harry Harris Park within a 1.5 kilometre walk. It has received excellent user ratings and is perfect for those looking for a comfortable and convenient base to explore Tavernier. This one-bedroom, one-bathroom apartment is 56 square metres in size and can comfortably accommodate up to four guests. The apartment offers a range of amenities including a fully equipped kitchen, a private balcony, a swimming pool, a jacuzzi, a tennis court, and free Wi-Fi, all within a smoke-free environment.
Islamorada, FL
27/06 – 04/07
346 €/nighttotal: 2422 € (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.
Best Islamorada, FL holiday rentals with a pool
Among the 1414 accommodations in Islamorada, FL, here are the 4 best rentals with a pool
8.3 5658 reviews
Islamorada, FL
19/08 – 21/08
211 €/nighttotal: 422 € (2 )
Ocean Oasis At Ocean Pointe
1 4
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
03/08 – 05/08
431 €/nighttotal: 862 € (2 )
Get Ready For Blissful Getaway! 2 Relaxing Units, Onsite Pool, Free Breakfast
2 5
apartment , Islamorada, Village of Islands
This Islamorada apartment complex offers direct beach access in the centre of Islamorada, conveniently located near the History of Diving Museum and Keys History & Discovery Centre. The self-catering property boasts two bedrooms, two bathrooms, and sleeps up to eight guests across a 54 square metre floor area, featuring a heated pool, barbecue facilities, and kayak/paddleboard hire.
Islamorada, FL
19/08 – 21/08
211 €/nighttotal: 422 € (2 )
1br Condo W/ Pool, Beach, Near Coral Reef Park
1 4
apartment , Tavernier
This two-bedroom holiday flat is situated in Tavernier, offering direct oceanfront access and being just a short drive to attractions in Key Largo and Islamorada, including the renowned John Pennekamp Coral Reef State Park. This 56 square meter residence accommodates up to four guests, featuring a kitchen with a fridge, microwave oven, and dishwasher, air conditioning, a swimming pool, and on-site parking, with access to resort amenities such as a Jr. Olympic pool, hot tub, and tennis courts.
8.8 10 reviews
Islamorada, FL
03/08 – 05/08
317 €/nighttotal: 634 € (2 )
Ocean Pointe 2309
2 5
house , Tavernier
Ocean Pointe 2309, a beachfront property in Tavernier, Florida, offers ocean views and is a 14-minute walk from Harry Harris Park Beach and 4.8km from Pigeon Key. This two-bedroom, two-bathroom house boasts 85 square metres of floor space, sleeps up to 11 guests, and includes a private pool, bar, free Wi-Fi, and parking.
Frequently asked questions about holiday rentals in Islamorada, FL
What are some interesting places to visit in or near Islamorada, FL?
Islamorada is known for its beautiful beaches and laid-back atmosphere. You should definitely check out the Florida Keys Aquarium Encounters for a close-up look at marine life. If you're interested in history, the History of Islamorada Museum is a great place to learn about the area's past. And for a unique experience, visit the Theatre of the Sea, where you can see dolphins, sea lions, and other marine animals.
What are the best Airbnb and holiday rentals in Islamorada, FL?
Which walking or cycling routes are the best in Islamorada, FL?
The Islamorada Footbridge is a great spot for a leisurely stroll, offering stunning views of the water. For a longer bike ride, the Overseas Highway is a scenic route that takes you through the heart of the Florida Keys. You can also check out the Anne's Beach trail for a peaceful walk along the shore.
What are the most popular Airbnbs in Islamorada, FL?
What sports or outdoor activites can visitors enjoy in and around Islamorada, FL?
Islamorada is a paradise for water sports enthusiasts. You can go fishing, snorkelling, diving, kayaking, paddleboarding, and boating. There are also plenty of opportunities for hiking and birdwatching in the area.
What are the best holiday rentals with a pool in Islamorada, FL?
What other towns or cities can be easily accessed from Islamorada, FL?
Islamorada is a great base for exploring the Florida Keys. You can easily drive to Key Largo to the north, which is known for its diving and snorkeling. To the south, Marathon is a charming town with a historic district and a vibrant fishing scene. You can also take a day trip to Key West, the southernmost point of the United States.
What are the best rentals for families and kids 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, fully equipped kitchens, laundry facilities, and balconies or patios with stunning views of the ocean. Many rentals also have boat docks for those who want to bring their own boat.
What are the best rentals or Airbnbs with a jacuzzi 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 seasons, from April to May and September to October. The weather is still pleasant during these months, but the crowds are smaller and prices are typically lower.
Destinations nearby
Best Islamorada, FL holiday rentals with a balcony
9.8 46 reviews
Islamorada, FL
03/08 – 05/08
322 €/nighttotal: 644 € (2 )
Updated Ocean-view Condo With 2 Balconies, Pool, Hot Tub, W/d, & Ac
2 5
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.
Islamorada, FL
01/01 – 28/02
288 €/nighttotal: 16704 € (58 )
Spacious Newly Renovated 3 Bedroom, 2 Bath Home On The Canal In Islamorada, Fl
3 2
apartment , Islamorada, Village of Islands
This three-bedroom property in Tavernier, Islamorada, Village of Islands, is situated within 1 kilometre of the Florida Keys Dive Centre and Mangrove Marina, with John Pennekamp Coral Reef State Park and the Morada Way Arts & Cultural District also close by. This apartment accommodates six guests and features air conditioning, a terrace, parking, and two bathrooms, offering comfortable sleeping arrangements with a king, queen, and full bed for your stay.
10 81 reviews
Islamorada, FL
26/06 – 30/06
397 €/nighttotal: 1588 € (4 )
Charming & Tranquil Condo At Ocean Pointe-sleeps 6
2 3
apartment , Tavernier
This family-friendly apartment is located in Tavernier, a 15-minute walk from Baker's Cay Resort Beach and Harry Harris Park, offering easy access to the area's attractions. It has received excellent user ratings, making it a popular choice for travellers. This 88 square metre apartment comfortably accommodates up to six guests in its two bedrooms and two bathrooms. You can enjoy a range of amenities, including a private pool, a tennis court, a garden, and a terrace, perfect for relaxing and enjoying the Florida sunshine.
9.0 98 reviews
Islamorada, FL
17/07 – 24/07
257 €/nighttotal: 1799 € (7 )
Island Time | Ocean Pointe 1207 | Oceanfront 2br Condo In Key Largo
2 3
apartment , Tavernier
This two-bedroom apartment in Tavernier is conveniently located within a 15-minute walk of Baker's Cay Resort Beach and Harry Harris Park, offering easy access to Tavernier's laid-back charm. The apartment has received excellent user and location ratings and a very good cleanliness rating. The apartment comfortably accommodates up to six guests and features a fully equipped kitchen, two bathrooms, a washing machine, and a coffee/tea maker. Enjoy relaxing amenities like a TV, internet access, and a terrace/balcony, as well as the convenience of parking and an elevator.
Best Islamorada, FL holiday rentals with parking
10 1 review
Islamorada, FL
01/01 – 28/02
162 €/nighttotal: 9396 € (58 )
Clean, Comfortable, & Centrally Located 1/1
1 2
apartment , Islamorada, Village of Islands
This canal-side flat in Tavernier, Islamorada, is less than 500 metres from waterfront dining, shops, and attractions such as the Florida Keys Wild Bird Centre. This one-bedroom, one-bathroom flat accommodates up to four guests and features a king-size bed, a large shower, a terrace, a garden with a grill and sunset views, a 50-foot dock, a dockside Tiki Hut, and an eight-person hot tub.
Islamorada, FL
19/08 – 21/08
257 €/nighttotal: 514 € (2 )
Friends' Getaway 2br W/ Ocean View, Pool & Beach
2 4
apartment , Tavernier
This Tavernier oceanfront apartment, near Key Largo and Islamorada, offers private beach access and proximity to attractions such as Jimmy Johnson's Big Chill. The 79-square-metre (850 sq ft) property sleeps six, featuring three bedrooms, two bathrooms, a fully equipped kitchen (fridge, microwave, dishwasher), a terrace, swimming pool access, and parking; resort amenities include a junior Olympic-sized pool, hot tub, and tennis courts.
9.7 127 reviews
Islamorada, FL
03/08 – 05/08
358 €/nighttotal: 716 € (2 )
Fish, Dive, Snorkel & Unwind-coral Reefs, Pool, Pickleball & Onsite Bar
2 5
apartment , Tavernier
This waterfront apartment is situated in Tavernier, just a 2.4km walk from Baker's Cay Resort Beach and Harry Harris Park, offering a peaceful and scenic location close to the area's attractions. The property has consistently received excellent ratings for its cleanliness, location, and overall experience. The apartment spans 87 square metres and comfortably accommodates up to six guests in its two bedrooms and two bathrooms. It features a range of amenities, including a swimming pool, jacuzzi, tennis court, and a fully equipped kitchen, making it ideal for families or groups seeking a relaxing and enjoyable stay.
Islamorada, FL
01/01 – 31/05
319 €/nighttotal: 47850 € (150 )
Lovely 2-bedroom House In Ocean Front Resort.
2 2
apartment , Islamorada, Village of Islands
This Islamorada holiday home, part of the Sun Outdoors resort in the Seabreeze Trailer Park neighbourhood, offers convenient access to the Old Road Gallery and History of Diving Museum, within walking distance depending on location. The 'Charming 2-bedroom House In Gorgeous Resort' sleeps six, featuring two bedrooms (one king, one double), two bathrooms with bidets, Wi-Fi, air conditioning, and access to resort amenities including two heated pools, a clubhouse, and a games lawn; John Pennekamp Coral Reef State Park and Jacob's Aquatic Centre are a short drive away.