You’re missing a lot if you’ve never been to the Florida Keys before! It’s a string of tropical islands that are going to amaze you. With a laid-back atmosphere, many visit the Florida Keys to enjoy its stunning beaches and gin-clear waters and to experience its local culture. It’s also the perfect destination for those who love outdoor watersports. It’s truly a place like no other! And to make your trip even better, you should consider spending your nights at one of the top luxury vacation rentals in Florida Keys. The luxury Florida Keys rentals will provide you with all the amenities you need and some extra that you’ll appreciate. And to save your precious, we’re here to show you some of the top Florida Keys luxury rentals you can consider! Keep scrolling to learn more about them!
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Islamorada Waterfront Suite 2
6
Kicking off our list of the best luxury vacation rentals in Florida Keys is Islamorada Waterfront Suite 2. This is the perfect option for those who are seeking a romantic, intimate getaway. Perfect for lovebirds, this gorgeous waterfront suite offers a huge, comfy king-sized bedroom. Of course, it’s also fitted with standard in-room amenities for your convenience. Aside from that, you can also spot a bright, modern living space, which allows you to enjoy the outdoor views through the huge glass doors. And as one of the best Florida Keys luxury rentals, it also features an outdoor waterfront lounge area!
Moreover, this pet-friendly property also boasts an elevator so you can easily access your suite and other floors! As if that’s not enough, it’s also wheelchair accessible. You can also expect daily housekeeping service, free kayaks, and paddleboards. Speaking of which, there are plenty of activities centered around the water that you can enjoy. There’s a private marina, direct access to the beach, a waterfront bar, pampering spa services, and communal pools! For more romantic accommodations, check out these most romantic hotels in the Florida Keys!
Key features:
- 656 Square Feet
- Wheelchair accessible
- King Bedroom
- Living Area
- Queen Pull-Out Sofa
- Waterfront Balcony
- Exterior parking
- Elevator
- Complimentary daily housekeeping service
- Complimentary watersports equipment (kayaks, paddleboards, Hobie cat)
Included amenities:
- Complimentary Wi-Fi
- Wheelchair accessible
- Air conditioning
- Pet-friendly
- Private parking
- Elevator
- Direct beach access
- Access to the boat dock
- Modern living space
Islamorada Waterfront Villa 2
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The top luxury vacation rentals in Florida Keys are nothing short of amazing. But what makes the Islamorada Waterfront Villa 2 different from the others is that it’s wheelchair accessible. Designed to accommodate a group of eight, this waterfront villa has plenty of space to lounge. Actually, there are there outdoor waterfront lounge areas, which are distributed on each floor. This means no matter where you are; you can always kick back and enjoy the views of the ocean. Aside from that, we also love how homey the living area is. It boasts modern but homey furnishings, making the villa feels like your home away from home.
Considered one of the top luxury Florida Keys rentals, it also boasts a fully equipped kitchen that has literally every appliance you need. Whether you’re planning to make a toast or spaghetti, preparing the meal will always be convenient. Plus, there’s a dining area and a breakfast bar as well! When the weather is nice, feel free to bask in the warmth of the sun in the pool area, or you can also float on the pool! But if lifting weights sounds better for you, there’s also a 24-hour gym and other outdoor fitness activities for you to try out.
Key features:
- 4,067 Square Feet
- Wheelchair accessible
- 3 King Bedrooms with en-suite bathrooms
- Bunk room or twin room with adjacent bathroom
- Powder room
- 3 Waterfront balconies
- Ground floor waterfront loggia
- 2-car garage with storage
- Electric car charging
- Laundry room
- Transitional Island Architecture
- Complimentary daily housekeeping service
- Complimentary watersports equipment (kayaks, paddleboards, Hobie cat)
Included amenities:
- Complimentary Wi-Fi
- Air conditioning
- Private parking
- Wheelchair accessible
- Pet-friendly
- Open-plan living area
- Fully equipped kitchen
- Breakfast bar
- Indoor dining area
- Multiple lounge areas
Islamorada Waterfront Villa 1
4
Among all Florida Keys luxury rentals, the Islamorada Waterfront Villa 1 is one of the best. Featuring three stories, there’s more than enough space for a group of eight to spread out! One of the biggest perks of staying at this vacation rental is that guests have full access to the resort amenities. You can access the sandy beach easily, make a splash in one of the communal pools, rejuvenate your body with spa services, and even lift weights in the state-of-the-art gym! As one of the best luxury vacation rentals in Florida Keys, it also offers complimentary watersports equipment, including kayaks and paddleboards!
The amenities inside the villa aren’t less impressive. There are four bright bedrooms on the property, and each of them is extremely homey. There are also two waterfront balconies, which are our favorite spots to unwind. Moreover, the living area is cozy, and we love how well-equipped the kitchen is. And if you arrive by car, you can park your vehicle in the two-car garage. Better yet, electric car charging is also available! Best of all, there’s a complimentary daily housekeeping service as well, promising the best holiday experience! No wonder it’s named one of the best luxury Florida Keys rentals!
Key features:
- 4,067 Square Feet
- 3 King Bedrooms with en-suite bathrooms
- Bunk room or twin room with adjacent bathroom
- Powder room
- 2 Waterfront balconies
- Ground floor waterfront loggia
- 2-car garage with storage
- Electric car charging
- Laundry room
- Transitional Island Architecture
- Complimentary daily housekeeping service
- Complimentary watersports equipment (kayaks, paddleboards, Hobie cat)
Included amenities:
- Complimentary Wi-Fi
- Air conditioning
- Children welcome
- Private parking
- Pets considered
- Open-plan living area
- Fully equipped kitchen
- Indoor dining area
Islamorada Premium Villa 1
3
Up next is Islamorada Premium Villa 1, one of the top luxury vacation rentals in Florida Keys that welcomes everyone in the family, including your four-legged companion! Perhaps the villa’s biggest perk is that it allows guests to take in the fantastic ocean views without leaving the villa! There are two comfy balconies on-site, each with two loungers and a small table. Trust us; there’s nothing better than feeling the ocean breeze on the balcony as you take in the views and enjoy your lemonade! It’s not surprising that it’s called one of the top luxury Florida Keys rentals.
Furthermore, this villa is conveniently set on Islamorada’s Upper Matecumbe Key. You can arrive either by car, boat, or even seaplane! Because of its location, you can rest assured that the beach is within easy reach. On top of that, the open-plan living area is worth two thumbs up! The living room has ample seating for eight, and the kitchen is equipped with modern appliances, including a microwave and coffee maker. And when you’re in the mood to venture out, make sure to explore all of the resort amenities like the spa center, boat dock, marina, and more.
Key features:
- 4,067 Square Feet
- 3 King Bedrooms with en-suite bathrooms
- Bunk room or twin room with adjacent bathroom
- Powder room
- 2 Waterfront balconies
- Ground floor waterfront loggia
- 2-car garage with storage
- Electric car charging
- Laundry room
- Transitional Island Architecture
- Complimentary daily housekeeping service
- Complimentary watersports equipment (kayaks, paddleboards, Hobie cat)
Included amenities:
- Complimentary Wi-Fi
- Air conditioning
- Private parking
- Pet-friendly
- Children welcome
- Open-plan living area
- Fully equipped kitchen
- Indoor dining area
Islamorada Waterfront Villa 3
2
Another awesome option for those searching for luxury vacation rentals in Florida Keys is the Islamorada Waterfront Villa 3. For two small families, this accommodation is the perfect option! It can accommodate up to 10 family members and have 4 bedrooms. Three of them are king-sized bedrooms, and the last one features two bunk beds for kids. As one of the best luxury Florida Keys rentals, this three-story waterfront villa has everything you need and more. What’s amazing about this villa is that it boasts three waterfront lounge areas, which are amazing. That way, you can enjoy the views of the sea whenever you want.
When it’s time to gather with your family, the open-plan living area is the place to be! Plenty of seating space, a flat-screen TV, and glass doors let you enjoy the outside views. Right beside it is a modern kitchen where you can whip up everyone’s comfort food. Of course, there’s also a tropical dining area that we love. Best of all, you can also access the top-notch resort amenities! You can have fun on the beach, pamper yourself in the spa center, work up a sweat in the 24/7 gym, and more! By the way, make sure also to check out these family hotels in the Florida Keys!
Key features:
- 4,067 Square Feet
- Sleeps 8 Adults, 2 Children
- 3 King Bedrooms with en-suite bathrooms
- Bunk room or twin room with adjacent bathroom
- Powder room
- 2 Waterfront balconies
- Ground floor waterfront loggia
- 2-car garage with storage
- Electric car charging
- Laundry room
- Transitional Island Architecture
- Complimentary daily housekeeping service
- Complimentary watersports equipment (kayaks, paddleboards, Hobie cat)
Included amenities:
- Complimentary Wi-Fi
- Pet-friendly
- Air conditioning
- Balcony
- Open-plan living area
- Fully equipped kitchen
- Dining area
Islamorada Premium Villa 2
1
A little big bigger than the rest, it’s safe to say that the Islamorada Premium Villa 2 is the best option on this list. If other Florida Keys luxury rentals here can only accommodate 8 people, this one can sleep up to 10 comfortably. There are four airy bedrooms on-site. Three of them feature premium king-sized beds, and the last one boasts two bunk beds, making it the perfect room for little ones. Apart from that, there are 4.5 bathrooms, so you don’t have to spend too much time waiting for your turn to shower or do your business! As one of the top luxury vacation rentals in Florida Keys, its main living area is spacious and offers you a direct view of the sea.
This villa also offers many complimentary amenities to make your stay even better. Aside from the free Wi-Fi, complimentary daily housekeeping service and water sports equipment are also available. No more renting a Hobie cat! Additionally, it offers direct beach access as well! But if it’s too crowded, you can always take a dip and have fun in the communal pool area. After that, don’t forget to take a sip at the waterfront bar. Then, whip up some delicious food in the villa’s fully-equipped kitchen!
Key features:
- 4,067 Square Feet
- Sleeps 8 Adults, 2 Children
- 3 King Bedrooms with en-suite bathrooms
- Bunk room or twin room with adjacent bathroom
- Powder room
- 2 Waterfront balconies
- Ground floor waterfront loggia
- 2-car garage with storage
- Electric car charging
- Laundry room
- Complimentary daily housekeeping service
- Complimentary watersports equipment
Included amenities:
- Complimentary Wi-Fi
- Direct beach access
- Air conditioning
- Children welcome
- Private parking
- Pet-friendly
- Open-plan living area
- Fully equipped kitchen
- Indoor dining area
- Access to the boat dock
Things You May Need During Your Stay
- Top Villas Sun Lounger – Need a portable sun lounger you can take to the pool or the beach? We’ve got you covered! The sun loungers from Top Villas will be sent fully sanitized!
- Beach towel – Since you’re probably going to the beach, you should bring your best beach towel with you. That way, you’ll have something that can dry your body effectively!
- Swimming pool lounge float – Make the most of the pool by bringing your pool lounge float! Bring one, and you’ll be able to relax and float on the water for as long as you want!