Best Vacation rentals and Airbnb offers in Islamorada, FL
9.7 127 reviews
Islamorada, FL
06/28 – 07/01
$367/nighttotal: $1101 (3 )
Fish, Dive, Snorkel & Unwind-coral Reefs, Pool, Pickleball & Onsite Bar
2 5
apartment , Tavernier
This waterfront condo in Tavernier offers stunning views and is within a 15-minute walk of Baker's Cay Resort Beach and Harry Harris Park. With excellent user, location, and cleanliness ratings, this apartment is a great choice for travelers. The apartment has two bedrooms, two bathrooms, and a floor area of 940 square feet, accommodating up to six guests. It features a kitchen with a fridge, microwave oven, and dishwasher, as well as air conditioning, a swimming pool, a jacuzzi, a terrace or balcony, a garden, a spa, a tennis court, and parking.
8.7 83 reviews
Islamorada, FL
07/30 – 08/06
$437/nighttotal: $3059 (7 )
Three Waters Resort And Marina, Islamorada, A Tribute Portfolio Resort
1 2
resort , Islamorada, Village of Islands
Three Waters Resort And Marina, a Tribute Portfolio Resort, is located in Islamorada, Florida, on fifteen waterfront acres offering easy access to the village's attractions and the Sport Fishing Capital of the World. This Islamorada resort boasts various accommodations including guest rooms and cottages, plus The Cove, an adults-only area with a private beach lagoon, nine dining options ranging from casual to upscale, a full-service marina, a fitness center, and a swimming pool.
9.8 176 reviews
Islamorada, FL
06/20 – 06/27
$395/nighttotal: $2765 (7 )
Seagulls Oceanfront End Unit, Wifi, Pool, Gym, Panoramic Ocean Views!
2 2
apartment , Islamorada, Village of Islands
This Tavernier condo is directly on the beach, just a short distance from the Florida Keys Dive Center and Mariners Hospital, with parks and other attractions within easy reach. This Islamorada apartment has received excellent user ratings and is perfect for travelers seeking a relaxing and enjoyable Florida Keys getaway. This 2-bedroom, 2-bathroom apartment offers 1170 square feet of space and comfortably accommodates up to 4 guests. Amenities include a private pool, a fitness center, a tennis court, and a fully equipped kitchen, ensuring a comfortable and enjoyable stay.
9.6 4 reviews
Islamorada, FL
07/02 – 07/05
$455/nighttotal: $1365 (3 )
2br Condo W/ Ocean View, Pool & Tropical Setting
2 5
apartment , Tavernier
This oceanfront condo rental in Tavernier, Florida, offers direct beach access and is near John Pennekamp Coral Reef State Park and Jacob's Aquatic Center. The 850-square-foot unit features two bedrooms, two bathrooms, sleeps six guests, and includes a full kitchen with a fridge, microwave, and dishwasher, plus resort amenities like a swimming pool, hot tub, and tennis courts.
9.6 66 reviews
Islamorada, FL
07/03 – 07/05
$530/nighttotal: $1060 (2 )
Oceanfront Condo Ocean Pointe Suites. Swimming Pool, Beach.
2 5
apartment , Tavernier
This recently remodeled 830 sq ft waterfront condo in Tavernier, located at Mile Marker 91 on the ocean side within the gated Ocean Pointe complex, offers direct access to Bldg 5 and is conveniently situated near John Pennekamp Coral Reef State Park and Windley Key Fossil Reef Geological State Park. Accommodating up to 4 guests with two king beds, this family-friendly apartment features oceanfront views from the living room and master bedroom, a fully equipped kitchen, in-unit laundry, air conditioning, a swimming pool, jacuzzi, and a terrace, with on-site resort amenities including jet skiing and scuba diving.
9.2 14 reviews
Islamorada, FL
07/09 – 07/12
$353/nighttotal: $1059 (3 )
Sunrise Sanctuary - Top Floor Ocean Pointe 2415
2 5
apartment , Tavernier
Ocean Pointe 2415 in Key Largo, Florida, offers this two-bedroom, two-bathroom condo with stunning ocean views, a 15-minute walk from Harry Harris Park Beach and within an 11-mile radius of other Key Largo attractions. This 830-square-foot top-floor unit features a fully equipped kitchen, private patio, in-unit laundry, free Wi-Fi, and sleeps up to eight guests, making it ideal for families or groups visiting Tavernier.
9.4 34 reviews
Islamorada, FL
07/02 – 07/05
$520/nighttotal: $1560 (3 )
Sunshine & Sandbars 2 Br Suite
2 5
apartment , Tavernier
This family-friendly condo building is located in Tavernier, a short 15-minute walk from Baker's Cay Resort Beach and Harry Harris Park, with Mariners Hospital and Florida Keys Dive Center within a 3-mile radius. It receives excellent user ratings for its comfortable accommodations and convenient location. This two-bedroom, two-bathroom apartment offers 1000 square feet of space and can comfortably sleep up to six guests. Enjoy access to a swimming pool, Jacuzzi, spa, tennis court, barbecue grills, and a bar/lounge, in addition to free WiFi and a private balcony.
9.1 74 reviews
Islamorada, FL
07/09 – 07/12
$387/nighttotal: $1161 (3 )
Tavernier Oceanfront Resort Condo-pool, Dockage, Kayaks, Onsite Restaurant & Bar
2 5
apartment , Tavernier
This apartment in Tavernier is a 15-minute walk from Baker's Cay Resort Beach and Harry Harris Park. It is highly rated for its location, cleanliness, and user experience. The apartment has two bedrooms, two bathrooms, a sofa bed, and a floor area of 830 square feet. It can accommodate up to six guests. Amenities include a private pool, concierge services, barbecue grills, a washing machine, and a smoke-free environment.
9.7 6 reviews
Islamorada, FL
09/08 – 10/06
$196/nighttotal: $5488 (28 )
Gated Community Townhome With Private Beach, Pool, And Tennis Courts!
3 4
apartment , Islamorada, Village of Islands
This Islamorada vacation home, located a 10-minute walk from Founders Park and Islamorada County Park and within two miles of Rain Barrel Village and Old Road Gallery, offers easy access to local attractions. This 1,500-square-foot property features three bedrooms sleeping six, a private pool, Jacuzzi, fitness center, tennis court, and a fully equipped kitchen; barbecue grills and a DVD player are also available.
Best Islamorada, FL vacation rentals with a balcony
9.0 96 reviews
Islamorada, FL
07/18 – 07/22
$363/nighttotal: $1452 (4 )
Luxurious 2br Beachfront Condo | Steps To Pool & Ocean | Ocean Pointe Resort
2 4
apartment , Tavernier
This Tavernier apartment is a 15-minute walk from Baker's Cay Resort Beach and Harry Harris Park, offering easy access to beautiful beaches and waterfront activities. The apartment has received excellent user and location ratings, and a very good cleanliness rating. The apartment features two bedrooms and two bathrooms and can comfortably accommodate up to six guests. It offers a fully equipped kitchen, a swimming pool, a jacuzzi, a terrace, parking, and internet access, ensuring a comfortable and enjoyable stay.
This waterfront apartment is located in Lower Matecumbe, Islamorada, at mile marker 76.5, just a short distance from Robbie's Marina, Bud & Mary's Marina, and World Wide Sportsman. The property enjoys an excellent user rating, indicating a high level of satisfaction among previous guests. This three-bedroom, three-bathroom vacation rental spans 1400 square feet and comfortably accommodates up to six guests. The apartment features a fully equipped kitchen, a private terrace or balcony, a garden, a spa, and a large dock with plenty of space for boat owners.
9.4 8 reviews
Islamorada, FL
07/03 – 07/05
$571/nighttotal: $1142 (2 )
2br - Ocean View, Pool & Near Founders Park
2 5
apartment , Tavernier
This Tavernier, Florida Keys oceanfront condo offers direct beach access and proximity to John Pennekamp Coral Reef State Park and Indian Key Historic State Park, with convenient access to the Florida Keys Dive Center and Bluefin Rock Harbor Marina. This 850-square-foot rental features two bedrooms (one with a king or queen bed, the other with two twin or a queen bed), two bathrooms, a pull-out sofa accommodating up to six guests, a full kitchen with a fridge, microwave, and dishwasher, plus resort amenities including a Jr. Olympic pool, hot tub, and tennis courts.
8.4 11 reviews
Islamorada, FL
07/03 – 07/05
$527/nighttotal: $1054 (2 )
Op-2 Ocean View W/heated Pool Beach Marina
1 5
apartment , Tavernier
This beachfront condo in Tavernier, Florida, offers direct access to the Atlantic Ocean and is minutes from John Pennekamp Coral Reef State Park and local restaurants. This 850-square-foot rental boasts two bedrooms, two bathrooms, sleeps six, and includes a fully equipped kitchen, in-unit laundry, weekly housekeeping, resort amenities (heated pool, jacuzzi, BBQ, tennis/pickleball courts), and complimentary parking for two vehicles.
Our Favorite Family-Friendly Vacation Rentals in Islamorada, FL
Find the perfect family vacation rental or Airbnb in Islamorada, FL with plenty of room to spread out near local beaches.
10 148 reviews
Islamorada, FL
10/17 – 10/26
$364/nighttotal: $3276 (9 )
Beautiful Island Home In Anglers Reef! Ocean Front Community. Pool & Boat Slip.
2 6
apartment , Islamorada, Village of Islands
This 2-bedroom, 3-bathroom boat is docked in Anglers Reef, an exclusive gated community in Islamorada, Village of Islands. The boat has an excellent user rating and is located within walking distance of shops and restaurants. It features a private dock, access to complimentary paddle boards and kayaks, a temperature-controlled pool with ocean views, and modern amenities such as granite countertops, stainless steel appliances, and a gas BBQ. The boat can accommodate up to 6 guests and is pet-friendly.
This oceanfront Tavernier condo, located 0.6 miles from Harry Harris Park and within 3 miles of Mariners Hospital and the Florida Keys Dive Center, offers stunning ocean views and easy beach access. The 830-square-foot rental boasts three bedrooms, two bathrooms, sleeps five, and includes a fully equipped kitchen, private balcony, swimming pool, jacuzzi, and on-site barbecue grills.
Isla Lychee: Little Basin Villas, a waterfront boutique resort in Matecumbe, Islamorada, offers easy walking access to the Islamorada Brewery & Distillery and Keys History & Discovery Center, with the History of Diving Museum and Matecumbe United Methodist Church within a 15-minute drive. This smoke-free, 3-bedroom villa boasts 1680 square feet of space, accommodating up to 6 guests and featuring a fully equipped kitchen, private balcony, free Wi-Fi, and access to barbecue grills; a swimming pool is also available on the property.
10 2 reviews
Islamorada, FL
07/19 – 07/26
$2125/nighttotal: $14875 (7 )
Private Beach / Private Overwater Dock / Heated Pool / Mahi Key
3 9
apartment , Islamorada, Village of Islands
This Islamorada beachfront condo in Matecumbe offers direct beach access and is conveniently located near Robbie's of Islamorada and Bud n' Mary's Dive Center. This 1,320-square-foot rental boasts three bedrooms, three bathrooms, sleeps up to ten guests, and includes a heated pool, private dock, and beach gear.
Frequently Asked Questions about vacation rentals in Islamorada, FL
What sports or outdoor activites can visitors enjoy in and around Islamorada, FL?
Islamorada is a great place for fishing, boating, and diving. You can also go kayaking, paddleboarding, or snorkeling. If you're looking for something more adventurous, try kitesurfing or windsurfing. For those who prefer to stay on land, there are plenty of hiking and biking trails.
What are the best Airbnb and vacation rentals in Islamorada, FL?
What other towns or cities can be easily accessed from Islamorada, FL?
You can easily get to Key Largo, Marathon, and Big Pine Key from Islamorada. If you want to head north, you can drive to Miami, which is about a 2-hour drive. You can also access the mainland via the Overseas Highway.
What are the most popular Airbnbs in Islamorada, FL?
What amenities are commonly available in vacation rentals in Islamorada, FL?
Vacation rentals in Islamorada typically include amenities like a kitchen, laundry facilities, and a private balcony or patio. Many rentals also have a pool, hot tub, or access to a private beach. You can often find rentals with boat docks or kayak rentals.
What are the best vacation rentals with a pool 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 winter months, from December to April. The weather is warm and sunny, and there are fewer crowds. However, prices are higher during this time. If you're looking for a more affordable trip, consider visiting during the shoulder season, from May to June or September to November.
What are the best rentals for families and kids in Islamorada, FL?
This Islamorada condo is located bayside at MM 77.5 within the gated Bay Harbour community, offering direct beach access across the street and is approximately one mile from Anne's Beach. This spacious three-bedroom condominium accommodates up to six guests and features a gourmet kitchen, a private screened terrace with ocean views, and a private 31-foot dock with a lift, along with access to a communal pool and spa.
9.8 483 reviews
Islamorada, FL
07/18 – 07/22
$487/nighttotal: $1948 (4 )
Fla Keys Luxury Houseboat, Prime Location-steps To Fun, Food & Water Adventures
2 4
houseboat , Islamorada, Village of Islands
This houseboat is located at Mile Marker 90, at the northern edge of Islamorada, offering easy access to both the ocean and bay. The property has received excellent ratings for user experience, location, and cleanliness. This floating home is 1190 square feet and comfortably accommodates up to four guests. The houseboat offers a fully equipped kitchen, a spacious living area, a triple upper deck, a pet-friendly environment, and a relaxing atmosphere.
10 172 reviews
Islamorada, FL
07/09 – 07/12
$949/nighttotal: $2847 (3 )
Tikibar With Tv &Stereo, Privatespa, Heated Pool, Hammock,sups, Kayaks,bikes,fp
2 5
apartment , Islamorada, Village of Islands
This house is situated by the sea in Islamorada, Village of Islands, within 2 miles of San Pedro Underwater Archaeological Preserve State Park and Indian Key Historic State Park. It has excellent user, location and cleanliness ratings. The house is suitable for families and groups, with 2 bedrooms and a guest capacity of 5. It includes a cozy interior with a fireplace, a fully equipped kitchen with a refrigerator and an oven, and a balcony. Guests can also enjoy amenities such as a water park, outdoor pool, spa tub, concierge services, a garden, and barbecue grills.
9.2 10 reviews
Islamorada, FL
07/01 – 07/08
$317/nighttotal: $2219 (7 )
Islamorada Paradise Overlooking The Fabulous Florida Bay.
3 2
apartment , Islamorada, Village of Islands
This Islamorada, Florida Keys rental is conveniently located near Florida Bay, 3.2 miles from Windley Key and 6.5 miles from Upper Matecumbe Key, offering easy access to local attractions. This 1000-square-foot apartment features three bedrooms, two bathrooms, and sleeps six, boasting a balcony with direct Florida Bay views, a fully equipped kitchen, and access to a swimming pool, tennis court, and barbecue facilities.
Search Vacation Rentals with Swimming Pool in Islamorada, FL
Choose a vacation rental with a pool in Islamorada, FL to perfectly complement your day of adventures.
Islamorada, FL
09/08 – 10/06
$179/nighttotal: $5012 (28 )
Palms 301
2 4
house , Islamorada, Village of Islands
Palms 301, a two-bedroom Islamorada vacation home, is conveniently located 2.1 miles from Upper Matecumbe Key and 5.2 miles from Windley Key, offering easy access to nearby attractions like Pigeon Key (15 miles) and John Pennekamp Coral Reef State Park (23 miles). This Islamorada rental boasts a fully equipped kitchen, a private pool, jacuzzi, spa, and fitness center, comfortably accommodating up to 11 guests with free Wi-Fi and on-site parking.
9.8 241 reviews
Islamorada, FL
07/09 – 07/12
$529/nighttotal: $1587 (3 )
Luxurious Suite+open Ocean Views+pool & Cabana Bar
2 5
apartment , Tavernier
This Tavernier apartment is located just a 15-minute walk from Baker's Cay Resort Beach and Harry Harris Park, providing easy access to the beautiful Florida Keys beaches. The apartment has received excellent ratings for location, cleanliness, and user experience. The 2-bedroom, 2-bathroom apartment comfortably accommodates up to 6 guests in its 910 square feet of space. Enjoy the convenience of a fully equipped kitchen, in-unit laundry, a private balcony, and access to a swimming pool, spa, tennis court, and BBQ grills.
9.9 172 reviews
Islamorada, FL
07/18 – 07/22
$383/nighttotal: $1532 (4 )
Snorkel & Dive Legendary Coral Reefs - Then Relax Poolside With A Drink!
2 4
apartment , Tavernier
This waterfront condo in Tavernier is located just a 15-minute walk from Baker's Cay Resort Beach and Harry Harris Park, offering easy access to the beautiful Florida Keys. This rental has earned excellent ratings for its cleanliness, location, and overall user experience. The 950-square-foot apartment comfortably sleeps four guests in its two bedrooms and two bathrooms. Enjoy swimming, relaxing in the Jacuzzi, grilling outdoors, and taking advantage of the tennis court, all while taking in the stunning waterfront views from your private balcony.
9.0 4 reviews
Islamorada, FL
07/02 – 07/05
$455/nighttotal: $1365 (3 )
2br Ocean View Condo, Pool, Near Marine Park
2 5
apartment , Tavernier
This Tavernier oceanfront condo, near Key Largo and Islamorada, provides private beach access and proximity to John Pennekamp Coral Reef State Park and Indian Key Historic State Park. This 850-square-foot vacation rental boasts three bedrooms, two bathrooms, sleeps six, and includes a kitchen with a fridge, microwave, and dishwasher, plus resort amenities such as a pool and tennis courts; a daily resort fee applies.
Search Coastal Vacation Rentals near Islamorada, FL
These seaside vacation rentals in Islamorada, FL provide an excellent base for exploring the coast. Browse top local properties and plan your beach-town trip.
9.3 66 reviews
Islamorada, FL
07/18 – 07/22
$230/nighttotal: $920 (4 )
Aqua Lodge In The Florida Keys!
1 4
barge , Islamorada, Village of Islands
10 2 reviews
Islamorada, FL
07/02 – 07/05
$846/nighttotal: $2538 (3 )
Studio W/2 Queen Beds, Kitchenette, Pool, Free Parking & Pet Friendly
1 5
studio , Islamorada, Village of Islands
Islamorada, FL
06/28 – 07/01
$410/nighttotal: $1230 (3 )
2 Pet-friendly Units, Free Breakfast, Pool
2 5
resort , Islamorada, Village of Islands
9.3 124 reviews
Islamorada, FL
06/28 – 07/01
$383/nighttotal: $1149 (3 )
Oceanfront Views At Ocean Pointe + Pool + Beach & Marina Access, Updated 2br
2 5
apartment , Tavernier
Browse Luxury Vacation Rentals in Islamorada, FL
Premium waterfront rentals in Islamorada, FL combine upscale design with refined service for a truly superior getaway.
10 4 reviews
Islamorada, FL
07/23 – 07/26
$333/nighttotal: $999 (3 )
Perfect For Family Beach Vacation! Free Breakfast
1 2
resort , Islamorada, Village of Islands
Choose the Right Vacation Rentals with a Steam Room in Islamorada, FL
Relax with an on-site sauna at these vacation rentals in Islamorada, FL, perfect for a steam session after a day by the water.
9.1 3678 reviews
Islamorada, FL
07/18 – 07/22
$1159/nighttotal: $4636 (4 )
Cheeca Lodge & Spa
2 4
resort , Islamorada, Village of Islands
10 1 review
Islamorada, FL
07/30 – 08/06
$383/nighttotal: $2681 (7 )
Ocean Front Townhouse With Breathtaking Views!
1 2
apartment , Islamorada, Village of Islands
Islamorada, FL
09/08 – 10/06
$261/nighttotal: $7308 (28 )
Paradise In The Heart Of Islamorada.come Relax And Have The Time Of Your Life!
2 4
apartment , Islamorada, Village of Islands
9.6 224 reviews
Islamorada, FL
07/23 – 07/26
$376/nighttotal: $1128 (3 )
Two Spectacular Ocean Views From The Living Room And Master Bedroom Of The Condo
