The Best Airbnb's in the Florida Keys for a Group Getaway (May 2021)

Vacation Rentals in Key West, Islamorada, and Key Largo for Spring Break, Friends Reunions, Girls' Getaways, and Fishing Trips

The Florida Keys are a popular vacation spot for groups of friends, spring breakers, and anyone looking to have a fun getaway. The Keys have a large number of vacation rental properties which are perfect for groups. There are a variety of options to choose from including homes, villas, condos, and more. Many properties have great amenities like pools, kayaks, paddle boards, docks, and nice kitchens. Choosing the Key to stay on can be as challenging as choosing a property! But don't worry, we've got you covered. From south to north, here are some of the best places to stay in the Keys.

Jump to: Key West | Lower Keys | Marathon Key | Islamorada | Key-Largo

Key West, Florida Airbnbs for Groups

Whether you're in town for spring break or simply a fun getaway with your friends, Key West offers a vibrant setting with great restaurants, lively bars, festive boat trips and more. Key West is the most popular and infamous destination in the Florida Keys. It's also the place to stay if you're looking for a party, but there's so much more to the town. It offers visitors a unique historical setting with plenty of outdoor activities and fine dining at its best.

Key West Airport makes the town very accessible, but it's generally more expensive than Miami International Airport. It will save you the time of driving the 3.5 hours from Miami. Granted, it's a pretty spectacular drive, and you’ll likely want to get a rental car anyway (check car rental prices here).

There is no limit to the number of activities you can enjoy in Key West. Kayaking, snorkeling, diving, and fishing trips are all great. If your group is interested in fishing, this area is better than northern Key Largo, where much of the water is protected from fishing. Also make sure you experience the quintessential sunset cruise. The drinks and festivities set against a beautiful ocean backdrop can't be beat.

For land lovers, there are a number of famous sights around Key West. Popular sights include The Oldest House, which dates back to the 1820’s, Higgs Beach African Graves, which has a tragic but poignant story, and the Harry S. Truman Little White House. Also make sure you visit the Southernmost Point as well as the Ernest Hemingway Home and Museum.

A truly unique Key West experience is a visit to Mallory Square at sunset. The fun starts as the sun begins to drop, but the parties can last late into the night. During sunset, street performers and musicians gather to make this the place to be every night as the sun dips below the horizon.

Key West is the most pedestrian friendly town in the Florida Keys. Even so, you'll want a car to explore everything that the islands have to offer (check car rental prices here).

Key West is the place to stay for the best nightlife and the most action in the Florida Keys, but it's also the most expensive area. There are less houses available for rent and more single rooms or small apartments. You also won't find all of the amenities you get at rental properties further north. Even so, there are a number of nice options to choose from and for many groups, it's worth the price to be near everything.

Mango Margarita - Key West Vacation Rental

Uptown - Upper Duval, Key West, Florida
This beautiful house is a popular option in Key West, as it has 2 bedrooms and 2 bathrooms. There's plenty of space here for the whole family or group to hang out. With Duval Street located just 0.3 miles away and Southernmost Point only 0.6 miles away, you'll find this to be a very convenient place to stay, as you're right in the heart of old town Key West with all of it's bars, restaurants, and shops within walking distance. Places like this get booked up quickly.



Casa Margarita

Historic Seaport, Key West, Florida
For anyone that wants a fun-filled vacation in Key West, this 3-bedroom, 3-bathroom house is a great vacation rental as it can accommodate 8 people. There's plenty of space here for the whole family or group to hang out. Couples appreciate the large king-sized bed in one of the bedrooms. One of the bedrooms also has a queen-sized bed. And with the dining area and living room, everyone will be able to spread out and relax. Included with this property is laundry, television, and parking. Also, this rental allows pets, so you can bring the dog.

The gorgeous private swimming pool is a great area to hang out with your group. You can also enjoy the nearby activities such as fishing, boating, and kayaking. Duval Street, Southernmost Point, Smathers Beach, Mallory Square, South Beach, and Higgs Beach are within five miles of this place. If you're looking for comfort and convenience, this is a great house.



Casa De Cuba a Beach House - Old Key West

Uptown - Upper Duval, Key West, Florida
This is a great spot to enjoy your next trip to Key West. This 3-bedroom, 2-bathroom beach house can fit up to 6 people. This is a family-friendly place with enough room for everyone. Or, it could be good for a group of friends. You can lounge by the pool, or take a dip in the water to cool off. You'll be able to relax at this rental as you're right by the beach.

For those who enjoy cooking, there's a full kitchen with a dishwasher, refrigerator, stove, oven, and microwave. And with the dining area, everyone will be able to spread out and relax. Laundry, television, parking, internet, and a grill are also on the list of amenities.

By staying here you'll be very close to Duval Street, Southernmost Point, Mallory Square, South Beach, and Higgs Beach. You'll be close to a number of fun things including fishing, golf, boating, and kayaking. Add this one to your list of favorites!



Renovated Key West Vacation Rental

Key West, Florida
Visitors love this condo and it makes a great place to stay for your vacation in Key West. The 2-bedroom, 2-bathroom vacation rental has room for 6 people. There's plenty of space here for the whole family or group to hang out. With a large king bed, you'll sleep very comfortably. And the other bedroom has a nice queen sized bed, too. The kitchen in this condo is very nice, and with a dishwasher, refrigerator, and stove you'll be able to cook for everyone. Everyone can also relax in the dining area and living room.

With a view of the water, it's hard to beat this location, too. Stroll out to the balcony and enjoy the views. Also on the list for this condo is laundry, television, and parking. Guests can also use the community's sauna, communal pool, fitness center, and tennis. If you're looking for comfort and convenience, this is a great condo. Also nearby is fishing, golf, and tennis. Located less than three miles away you'll find Duval Street, Smathers Beach, Southernmost Point, Mallory Square, South Beach, and Higgs Beach.



Downtown Duval Street Penthouse in Key West

Downtown Key West, Key West, Florida
This roomy 3-bedroom, 2-bathroom villa is beautiful, and has room for up to 8 people. This is a comfortable option for anyone headed to Key West. With a private pool, you can relax, swim, and enjoy everything the area has to offer. Relax on the balcony and enjoy the views. This is a great option for a family as there's room for everyone.

You'll be able to cook all of your meals in the fully-equipped kitchen with a dishwasher, refrigerator, microwave, and coffee maker. Enjoy meals or relaxing in this property's dining area.

Laundry, television, and parking are also on the list of amenities. Fishing, golf, boating, kayaking, and shopping are all nearby, too, making this location very convenient. The location is very convenient because Duval Street, Southernmost Point, Mallory Square, and South Beach is less than one mile from here.



Direct Ocean View Condo in Key West

Key West, Florida
This is a 2-bedroom, 2-bathroom beach condo that is large and gorgeous. It can accommodate up to 6 guests. There's plenty of space here for the whole family or group to hang out. The master bedroom has a king-sized bed and nice furnishings, so you'll be able to relax in style. There's even more space to hang out in the dining area and living room. The dishwasher, refrigerator, and stove in the full kitchen will let you cook all of your meals if you like. There's even more space to hang out in the dining area and living room.

There's also a fitness center, communal pool, and tennis that guests can use. The property is in a great spot near the beach. Wake up and enjoy your morning coffee and breakfast from the balcony. Located less than three miles away you'll find Duval Street, Smathers Beach, Southernmost Point, Mallory Square, South Beach, and Higgs Beach. Fishing, skiing, golf, and boating are all nearby, too, making this location very convenient. This one is a good find for anyone headed to Key West.



Casa Loca

Downtown Key West, Key West, Florida
If you're looking for a vacation rental in Key West, this 3-bedroom, 2-bathroom house is a great option. For the price and everything that's included, this rental is a great option. This is a family-friendly place with enough room for everyone. Or, it could be good for a group of friends. This house has a terrific private pool which is great for adults and kids alike. The bedrooms are very well furnished, as you'll find more than one bedroom with a king-sized bed. A fully equipped kitchen with a dishwasher, refrigerator, stove, and oven lets guests prepare their own meals. And with the nice dining room and living room where you can spread out, this house will let you relax and unwind.

The house also includes laundry, television, internet, a grill, and a coffee maker. The location is very convenient because Duval Street, Southernmost Point, Mallory Square, South Beach, and Higgs Beach is less than one mile from here. This is a pet-friendly property.



Lady Admiral

Uptown - Upper Duval, Key West, Florida
There's plenty of space here for the whole family or group to hang out. The 3-bedroom, 2-bathroom house has a great location. You'll also find Duval Street, Southernmost Point, Smathers Beach, Mallory Square, South Beach, and Higgs Beach less than 5 miles away. Places like this get booked up quickly.



Architect's Personal Residence in Key West with Pool

Downtown Key West, Key West, Florida
With room for up to 6 people, this is a 2-bedroom beach house that makes for a perfect Key West vacation rental. The private swimming pool is a great area to hang out with your group. The location is nice, not far from the beach.

As for the interior, this house has all of the comforts you need. Enjoy cooking your meals in the kitchen, which has modern appliances including a dishwasher, refrigerator, stove, and oven. There's even more space to hang out in the porch and living room. With space for the whole group, this is a great vacation rental for the entire family. Also on the list for this house is laundry, television, and parking.

Duval Street, Southernmost Point, Smathers Beach, Mallory Square, and South Beach are also very close by. There are a number of things to do nearby including fishing, golf, boating, kayaking, and shopping. Pets are welcome, too. This one is a good find for anyone headed to Key West.



The Lower Keys - Airbnb Beach Houses

If your group is looking for a more natural setting, then the Lower Keys can be the perfect option. The Lower Keys start at the infamous Seven Mile Bridge and include popular places such as Big Pine Key, Little Duck Key, Summerland Key, Big Torch and Little Torch Keys, Cudjoe Key, Sugarloaf Key, Big Coppitt Key, and Stock Island. The area also includes two national wildlife refuges, a national marine sanctuary, and a state park. These islands are the most common area for the famous key deer so if you're lucky, you might have a sighting. The area has RV parks and camping, as well as lodging and vacation rentals. There are also a number of snorkeling and dive spots as well as beaches where you can enjoy the beautiful blue Florida Keys water.

Stock Island offers a nice, unique spot for groups visiting the Florida Keys. It's an artist's haven and there are plenty of art studios, festivals, and a waterfront area with lots of bars and restaurants. The area is also known for its commercial fishing industry, so there are vibrant marinas and delicious fresh seafood.

There are a range of rental properties available in this area. If you're traveling with a small group that doesn't need much space, then there are RV's for rent for around $150 to $200 a night. Small homes and bungalows are available for about $350 and luxury homes, often with pools, will cost about $800 a night.

Private Waterfront Luxury Retreat

Geiger Key, Key West, Florida
Visitors love this house and it makes a great place to stay for your vacation in Key West. The 4-bedroom, 3-bathroom vacation rental has room for 10 people. This property would be an amazing option for a large group with all of its extra space. There's a king-sized bed in one of the bedrooms. One of the bedrooms also has a queen-sized bed.

If you're looking for comfort and convenience, this is a great house. You'll also be very close to Duval Street, Smathers Beach, Key West Harbour, Saddlebunch Keys, Southernmost Point, and South Beach.



Lower Keys Retreat

Eden Pines, Big Pine Key, Florida
This is a 2-bedroom, 3-bathroom house that is roomy and stunning. It can accommodate up to 8 guests. This is a great option for a family as there's room for everyone. You'll find more than one bedroom with a queen sized bed, too. Everyone can also relax in the dining area and porch. If you just want to eat in, the fully-equipped kitchen with its refrigerator, stove, oven, microwave, and coffee maker will let you cook all of your meals. Everyone can also relax in the dining area and porch. And you can bring the furry members of the family, as this place is pet-friendly.

The private swimming pool is a great place for families or groups to relax. Relax on the balcony and enjoy the views. You'll be close to plenty of things to do because within a few miles you'll find Bahia Honda State Park, Looe Key National Marine Sanctuary, National Key Deer Refuge Visitor Center, and Key West Visitors Center. Check out the photos!



4-Bedroom on Big Pine Key

Big Pine Key, Florida
With so much space, everyone can relax, hang out, plan the day's activities, and have a memorable vacation together. The 4-bedroom, 3-bathroom house has a great location. Bahia Honda State Park and Beach, Bahia Honda State Park, Looe Key National Marine Sanctuary, and National Key Deer Refuge Visitor Center are also very close by. Check out the photos!



Magnificent Home on a Private Beach with Pool

Big Coppitt Key, Key West, Florida
This house is a great place to base yourself during your time in Key West. With Duval Street located just 10.2 miles away and Smathers Beach only 8.6 miles away, you'll find this to be a very convenient place to stay.

Featuring 5 bedrooms and 4 bathrooms, there's plenty of room for up to 12 people here, so add it to your must-see list. This is a large space and would be perfect for a big family, or multiple families on vacation together.

It's hard to find a place like this, so check it out before it's booked up.



South Point Sunset

Sugarloaf Shores, Sugarloaf Key, Florida
A popular vacation rental in Sugarloaf Key is this spacious 3-bedroom, 3-bathroom house that has room for up to 8 people. There's plenty of space here for the whole family or group to hang out. Staying here will make your trip to Sugarloaf Key fun and convenient. The location is very convenient because Florida Keys Beaches, Key West Fly Fishing, and Upper Sugarloaf Key is less than three miles from here.



Ocean's Edge Retreat Waterfront Home

Bay Point, Key West, Florida
This roomy 2-bedroom, 2-bathroom house is delightful, and has room for up to 6 people. It's hard to find a place like this, so check it out before it's booked up. There's plenty of space here for the whole family or group to hang out.



Luxurious Oceanfront 5-Bedroom with Pool

Bay Point, Key West, Florida
For anyone that wants a fun-filled vacation in Key West, this 5-bedroom, 4-bathroom oceanfront house is a great vacation rental as it can accommodate 12 people. With space for the whole group, this is a great vacation rental for the entire family. You'll really feel like you're on vacation with this property's ocean view. Cook all of your meals in the kitchen, as the dishwasher, refrigerator, stove, and oven are provided. This is a great way to save money and let everyone enjoy their time together. And with the dining area and living room, everyone will be able to spread out and relax. Also on the list for this house is laundry, television, parking, internet, a grill, and a coffee maker. This property is pet-friendly.

One of the highlights of this place is the private pool. You'll be able to relax and swim in your own space. With a nice balcony, you can relax and enjoy the weather.

You can also enjoy the nearby activities such as fishing, golf, and boating. Florida Keys Beaches, Saddlebunch Keys, and Key West Fly Fishing are within three miles of this place. Places like this get booked up quickly.



Bayside Beauty

Sugarloaf Shores, Sugarloaf Key, Florida
Need a oceanfront house in Sugarloaf Key? Add this one to your bucket list, because it has plenty of great features. There's plenty of space here for the whole family or group to hang out. For the price and everything that's included, this rental is a great option. This house has a relaxing private pool which is great for adults and kids alike. The extra space of this 3-bedroom house is an added bonus. Everyone can also relax in the dining area and living room.

Enjoy cooking your meals in the kitchen, which has modern appliances including a dishwasher, refrigerator, stove, and oven. Not too far away you'll find Florida Keys Beaches, Saddlebunch Keys, Key West Fly Fishing, and Upper Sugarloaf Key. This place also has a great balcony where you can relax and enjoy the nice views. This location is also close to fishing, golf, boating, and kayaking. For the price and everything that's included, this rental is a great option.



Canalfront Home

Sugarloaf Shores, Sugarloaf Key, Florida
This is a great spot to enjoy your next trip to Sugarloaf Key. This 3-bedroom, 2-bathroom house can fit up to 9 people. This is a family-friendly place with enough room for everyone, or it could be good for a group of friends.

The comfortable king-sized bed in one bedroom is perfect for couples. With queen-sized beds in several bedrooms, no one will have to fight over which room to stay in.

Florida Keys Beaches, Key West Fly Fishing, and Upper Sugarloaf Key are within three miles of this place. Add this one to your must-see list!



Little Torch Key Vacation Rental

Little Torch Key, Florida
This house is a popular option in Little Torch Key, as it has 5 bedrooms and 2 bathrooms. Ideal for a larger group of friends or a big family, this spacious house has plenty of room to spread out. Multiple bedrooms in this house have king sized beds, which is a nice luxurious touch that is hard to find elsewhere.

You'll also be very close to Bahia Honda State Park and Beach, Bahia Honda State Park, and Looe Key National Marine Sanctuary. This amazing house has everything you need, and provides it all with style, too.



Plumeria Paradise with Pool

Raccoon Key, Florida
With room for up to 8 people, this is a 3-bedroom waterfront house that makes for a perfect Raccoon Key vacation rental. The private swimming pool is a nice spot to relax and unwind, and is one of the highlights of this property.

As for the interior, this house has all of the comforts you need. Guests appreciate the convenience of this property's full kitchen which has a dishwasher, refrigerator, stove, oven, microwave, and coffee maker. Everyone can spread out in the dining area and living room, too. This is a family-friendly place with enough room for everyone. Or, it could be good for a group of friends. Laundry, television, parking, internet, and a grill are also on the list of amenities.

Duval Street, Smathers Beach, Southernmost Point, and Mallory Square are also very close by. This location is also close to fishing, golf, boating, and kayaking. For the price and everything that's included, this rental is a great option.



Marathon Key Airbnbs for Groups

Marathon makes a great base for exploring the entire Florida Keys. Located right in the middle of the Keys, it's just over an hour from both Key West and Key Largo.

If your group is looking for a quiet beach where you can relax, head to either Bahia Honda State Park or Sombrero Beach. They both have nature trails and Bahia Honda also has camping. Reservations are recommended well in advance as space fills up quickly.

There are also a number of famous attractions nearby. The Dolphin Research Center is an excellent place to visit if you love marine life. It's a nonprofit organization, not a marine theme park, so you can feel good about the price of admission benefiting the animals. It's also a great place to swim with dolphins. The Turtle Hospital is another popular place to visit for animal lovers, as is Crane Point Nature Museum.

Prices for vacation rentals in Marathon Key range from about $150 for a small bungalow or apartment rental to $900 for luxury villas with private pools.

Waterfront House with Pool

Marathon, Florida
Need a waterfront house in Marathon? Add this one to your must-see list, because it has plenty of great features. This is a great option for a family as there's room for everyone. If you're looking for comfort and convenience, this is a great house. One of the highlights of this place is the private pool. You'll be able to relax and swim in your own space. The extra space of this 3-bedroom house is an added bonus. You'll find a king sized bed in the master bedroom, too. With a nice queen sized bed, you'll be sleeping soundly. You'll be able to spread out through the living room here, too.

Enjoy cooking your meals in the kitchen, which has modern appliances including a dishwasher, refrigerator, stove, oven, and microwave. Sombrero Beach, Seven Mile Bridge, and Dolphin Research Center are also very close by. Stroll out to the balcony and enjoy the views. If you're looking for comfort and convenience, this is a great house.



3-Bedroom Conch House

Marathon, Florida
If you're looking for a oceanfront vacation rental in Marathon, this 3-bedroom, 1-bathroom house is a great option. It's hard to find a place like this, so check it out before it's booked up. There's plenty of space here for the whole family or group to hang out. The kitchen in this house is very nice, and with a dishwasher, refrigerator, and stove you'll be able to cook for everyone. With a dining area, porch, and living room, there is enough space for guests to relax and hang out.

Included with this property is laundry, television, parking, internet, a grill, and a coffee maker. Not too far away you'll find Sombrero Beach, Seven Mile Bridge, Dolphin Research Center, The Turtle Hospital, Vaca Key, and Florida Keys Country Club. Also nearby is fishing, surfing, and boating.



Luxury Oceanfront with Pool

Marathon, Florida
For anyone that wants a fun-filled vacation in Marathon, this 3-bedroom, 3-bathroom house is a great vacation rental as it can accommodate 8 people. With space for the whole group, this is a great vacation rental for the entire family. You can either go out to eat or just stay in and cook all of your meals in the kitchen. It's equipped with everything you need with a dishwasher, microwave, and coffee maker. Laundry, television, and parking are also included. Pets are welcome, too.



Fishermans Paradise

Marathon, Florida
With room for up to 8 people, this is a 3-bedroom ski in/ski out house that makes for a perfect Marathon vacation rental. Have a drink by the terrific pool which you'll have all to yourself. You can take in the fresh air from the balcony and enjoy some time to unwind.

As for the interior, this house has all of the comforts you need. For those who enjoy cooking, there's a full kitchen with a dishwasher, refrigerator, stove, oven, microwave, and coffee maker. There's also plenty of space in the dining area, porch, and living room, too. Everyone will enjoy the game room in the evenings, too. This is a great option for a family as there's room for everyone. Included with this property is laundry, television, parking, and internet.

Sombrero Beach, Dolphin Research Center, Seven Mile Bridge, The Turtle Hospital, Vaca Key, and Florida Keys Country Club are also very close by. This location is also close to fishing, skiing, golf, and surfing. This amazing house has everything you need, and provides it all with style, too.



Marathon Vacation Rental

Marathon, Florida
This is a comfortable option for anyone headed to Marathon. This 3-bedroom, 3-bathroom waterfront house can fit up to 8 people. This is a great option for a family as there's room for everyone. With a view of the water, it's hard to beat this location, too. You can take in the fresh air from the balcony and enjoy some time to unwind.

With queen-sized beds in several bedrooms, no one will have to fight over which room to stay in. Guests appreciate the convenience of this property's full kitchen which has a dishwasher, refrigerator, and stove. There's also plenty of space in the dining area and living room, too. Laundry, television, parking, internet, a grill, and a coffee maker are also on the list of amenities.

With Sombrero Beach located just 4.7 miles away and Dolphin Research Center only 5.5 miles away, you'll find this to be a very convenient place to stay. You can also enjoy the nearby activities such as fishing, golf, and boating. Add this one to your wish list!



Seaside Pool Home on Vaca Cut

Marathon, Florida
There's plenty of space here for the whole family or group to hang out. The 3-bedroom, 2-bathroom waterfront house has a great location. You'll also find Sombrero Beach, The Turtle Hospital, Sunset Park Beach, and Florida Keys Country Club less than 5 miles away. There are a number of things to do nearby including fishing, golf, and boating. Places like this get booked up quickly. The private swimming pool is a great place for families or groups to relax.

Stroll out to the balcony and enjoy the views. For those who enjoy cooking, there's a full kitchen with a dishwasher, refrigerator, stove, microwave, and coffee maker. There's also the dining area, porch, and living room offering more space to guests. Laundry, television, parking, internet, and a grill are also on the list of amenities.



Spectacular Gulf Front Home with Pool & Dock

Marathon, Florida
This is a 3-bedroom, 1-bathroom waterfront house that is roomy and beautiful. It can accommodate up to 8 guests. With space for the whole group, this is a great vacation rental for the entire family. There's even more space to hang out in the dining area. You can either go out to eat or just stay in and cook all of your meals in the kitchen. It's equipped with everything you need with a dishwasher, refrigerator, and stove. There's even more space to hang out in the dining area.

The pool is a fantastic addition to the house that everyone will enjoy. Enjoy the beautiful ocean view. Relax on the balcony and enjoy the views. The Turtle Hospital and Vaca Key are all less than a mile away. There's also fishing, golf, boating, and kayaking in the area. Places like this get booked up quickly.



Waterfront home with Tiki Hut in Marathon

Marathon, Florida
A popular vacation rental in Marathon is this roomy 4-bedroom, 3-bathroom house that has room for up to 10 people. This property would be an amazing option for a large group with all of its extra space. Places like this get booked up quickly. Relax on the balcony and enjoy the views. Wake up every morning and enjoy the ocean view. Sombrero Beach, Dolphin Research Center, and Seven Mile Bridge are also very close by.

Enjoy cooking your meals in the kitchen, which has modern appliances including a dishwasher, refrigerator, stove, oven, microwave, and coffee maker. There's also plenty of space in the dining room and living room, too. Also on the list for this house is laundry, television, parking, and internet. You'll be close to a number of fun things including fishing, boating, and kayaking.



Islamorada, Florida Airbnbs for Groups

Islamorada also makes a nice base for exploring the Florida Keys in its entirety. It's part of the middle keys and is about 1.5 to 2 hours from Key West and just half an hour to 45 minutes from Key Largo. Islamorada is a village made up of five keys including Tea Table Key, Lower Matecumbe Key, Upper Matecumbe Key, Windley Key and Plantation Key.

This village offers a number of peaceful places to relax. It has a little less commercialization than some of the other keys and because of that, you'll likely have to drive to Marathon to find restaurants to accommodate your group.

There are a number of great activities for groups around Islamorada. Head to the ICE Amphitheater at Founders Park if you want to enjoy some live music. They host a number of concerts and live performances. You could also head to Theater of the Sea for a classic Florida Keys experience. They have dolphin and sea lion shows that are fun for all ages. There are also a number of state parks in the area including Indian Key Historic State Park, Long Key State Park, and Indian Key Historic State Park. Islamorada is also the home of the only production brewery in the Florida Keys. The Florida Keys Brewing Company is a small micro brewery with an eclectic style that feels like a quintessential part of the Florida Keys.

Like elsewhere in the Florida Keys, you'll find plenty of vacation rentals in Islamorada. Prices are a bit more expensive than Key Largo and you can expect to pay anywhere from $250 a night for a simple bungalow to upwards of $1000 a night for a luxurious beachfront villa.

Relaxing, Waterfront Retreat

Islamorada, Florida
For anyone that wants a fun-filled vacation in Islamorada, this 3-bedroom, 3-bathroom beachfront house is a great vacation rental as it can accommodate 8 people. This is a great option for a family as there's room for everyone. You'll love the view from this house, as you can see the ocean. You can either go out to eat or just stay in and cook all of your meals in the kitchen. It's equipped with everything you need with a dishwasher, refrigerator, stove, oven, microwave, and coffee maker. With a dining room and living room, there is enough space for guests to relax and hang out. Also on the list for this house is laundry, television, parking, internet, and a grill.

There are a number of things to do nearby including fishing, boating, kayaking, and shopping. Not too far away you'll find Anne's Beach, Bud n' Mary's Dive Center, Long Key State Park, Fiesta Key, and Theater of the Sea. This is a great spot to enjoy your next trip to Islamorada.



4-Bedroom Private Oceanfront House in Islamorada

Islamorada, Florida
Need a oceanfront house in Islamorada? Add this one to your wish list, because it has plenty of great features. There's plenty of space here for the whole family or group to hang out. Places like this get booked up quickly. The extra space of this 4-bedroom house is an added bonus. With a large king bed, you'll sleep very comfortably. And with multiple rooms with queen beds, everyone will be able to sleep comfortably. Bunk beds are always great for kids, and one of the bedrooms here has them. And with the nice dining area and living room where you can spread out, this house will let you relax and unwind.

The full kitchen is well stocked and convenient, and features a dishwasher, refrigerator, stove, and oven. You'll also be very close to Theater of the Sea, Bud n' Mary's Dive Center, Founders Park, and Hurricane Monument. Places like this get booked up quickly.



Islamorada Fishing Paradise Vacation Home

Islamorada, Florida
A popular vacation rental in Islamorada is this roomy 4-bedroom, 3-bathroom house that has room for up to 10 people. With so much space, everyone can relax, hang out, plan the day's activities, and have a memorable vacation together. It's hard to find a place like this, so check it out before it's booked up. Have some wine on the balcony in the evenings. Enjoy the ocean view as you're right by the water. You'll also be very close to Anne's Beach, Bud n' Mary's Dive Center, Theater of the Sea, Long Key State Park, and Fiesta Key.

The dishwasher, refrigerator, and stove in the full kitchen will let you cook all of your meals if you like. There's also plenty of space in the dining area, porch, and living room, too. The house also includes laundry, television, parking, a garage, and internet. This location is also close to fishing, boating, kayaking, and shopping. This property is pet-friendly.



5-Bedroom Oceanfront Home in Lower Matecumbe

Islamorada, Florida
Visitors love this house and it makes a great place to stay for your vacation in Islamorada. The 5-bedroom, 4-bathroom vacation rental has room for 10 people. This is a family-friendly place with enough room for everyone, or it could be good for a group of friends. The fully equipped kitchen has everything you need such as a dishwasher, refrigerator, stove, and oven. There's also plenty of space in the living room, too.

Enjoy the ocean view as you're right by the water. Why not spend some time out on the balcony with a meal, your morning coffee, or to take in the evening weather? Included with this property is laundry, television, and parking. If you're looking for comfort and convenience, this is a great house. Fishing, boating, kayaking, and shopping are all nearby, too, making this location very convenient. You'll be close to plenty of things to do because within five miles you'll find Anne's Beach, Bud n' Mary's Dive Center, and Hurricane Monument.



Oceanfront with Private Beach

Islamorada, Florida
Here's a relaxing place for a small group of friends. The great views of the waterfront can be seen in almost every room. Use the kayaks to just roll out of bed and into the water. The inside of the house has a great kitchen, nice bedrooms, and a bright and happy vibe.



Key Largo, Florida Airbnb Vacation Rentals for Groups

Key Largo is the northernmost island of the Florida Keys and it's just a one-hour drive from Miami. If your group is interested in diving and snorkeling, then Key Largo is a great place to stay. It offers some of the best snorkeling and diving in the Florida Keys with much of the surrounding waters protected by marine parks. The most popular dive spots are found in John Pennekamp Coral Reef State Park, the Mosquito Bank or Sea Gardens, Molasses Reef, and the Grecian Rocks.

There's a friendly community vibe to Key Largo and there are plenty of water activities available. Your group will also enjoy the variety of local hangouts, shops, and dive shops. As the northernmost key, the water is blue, but not yet the striking blue that the Florida Keys are most known for. You'll find as you head further south the water takes on a more tropical quality.

You really need a car to get around as the town is not pedestrian friendly, but in general a car is essential for exploring the Florida Keys, wherever you stay.

There are a number of vacation rentals available in Key Largo. Prices are slightly more affordable than you'll find elsewhere in the Florida Keys. You can expect to pay anything from $150 a night for something small and simple to $300 a night for a house or bungalow.

Upscale Key Largo Villa

Key Largo, Florida
Visitors love this house and it makes a great place to stay for your vacation in Key Largo. The 3-bedroom, 3-bathroom vacation rental has room for 8 people. With space for the whole group, this is a great vacation rental for the entire family. You'll find a king sized bed in the master bedroom, too. One of the bedrooms also has a queen-sized bed. Enjoy cooking your meals in the kitchen, which has modern appliances including a dishwasher, refrigerator, stove, and oven. Everyone can spread out in the dining area and living room, too.

There's something special about a vacation rental with an ocean view. With a nice balcony, you can relax and enjoy the weather. Included with this property is laundry, television, parking, and internet. This one is a good find for anyone headed to Key Largo. Fishing, boating, and kayaking are all nearby, too, making this location very convenient. Located less than five miles away you'll find Jimmy Johnson's Big Chill, Dolphins Plus Bayside, Key Largo Undersea Park, Caribbean Club Bar, and Dolphins Plus.



Waterfront Town Home in Key Largo

Key Largo, Florida
For the price and everything that's included, this rental is a great option. This 3-bedroom, 3-bathroom waterfront house can fit up to 6 people. This is a great option for a family as there's room for everyone. Enjoy the beautiful ocean view. The balcony offers a chance to spend time outdoors. Take in the nice weather while you stay here.

Enjoy cooking your meals in the kitchen, which has modern appliances including a dishwasher, refrigerator, and stove. There's even more space to hang out in the dining area and living room. The house also includes laundry, television, and parking.

Not too far away you'll find Jimmy Johnson's Big Chill, John Pennekamp Coral Reef State Park, Dolphins Plus Bayside, Key Largo Undersea Park, and Caribbean Club Bar. Also nearby is fishing, boating, and kayaking. Add this one to your wish list!



Kawama Townhouse

Key Largo, Florida
This house is a popular option in Key Largo, as it has 3 bedrooms and 3 bathrooms. There's plenty of space here for the whole family or group to hang out. You can either go out to eat or just stay in and cook all of your meals in the kitchen. It's equipped with everything you need with a dishwasher, refrigerator, stove, and oven. The dining area, which offers even more space to relax, will make you feel right at home.

You can take in the fresh air from the balcony and enjoy some time to unwind. Laundry, television, parking, internet, a grill, and a coffee maker are also on the list of amenities. There are a number of things to do nearby including fishing, golf, boating, and kayaking. Jimmy Johnson's Big Chill, Caribbean Club Bar, and Dolphins Plus are all less than a mile away. Check out the photos!



Waterfront House with Dock

Anglers Park, Key Largo, Florida
If you're looking for a waterfront vacation rental in Key Largo, this 3-bedroom, 2-bathroom house is a great option. If you're looking for comfort and convenience, this is a great house. There's plenty of space here for the whole family or group to hang out. The property is in a great spot near the beach. You can take in the fresh air from the balcony and enjoy some time to unwind. You can either go out to eat or just stay in and cook all of your meals in the kitchen. It's equipped with everything you need with a dishwasher, refrigerator, stove, oven, and microwave. There's also plenty of space in the dining area and living room, too. Everyone will enjoy this house's game room.

Laundry, television, parking, internet, and a grill are also on the list of amenities. John Pennekamp Coral Reef State Park, Jimmy Johnson's Big Chill, Key Largo Undersea Park, Dolphins Plus Bayside, Dolphin Cove, and Florida Keys Visitor Center are also very close by. This location is also close to fishing, boating, and kayaking.



Villa Marina

Rock Harbor, Key Largo, Florida
This waterfront villa is a great place to base yourself during your time in Key Largo. You'll be close to plenty of things to do because within a few miles you'll find Jimmy Johnson's Big Chill, Caribbean Club Bar, and Harry Harris Park. Fishing, boating, kayaking, and tennis are all nearby, too, making this location very convenient.

This villa has a terrific ocean view as you're right by the water. Relax on the balcony and enjoy the views. Featuring 3 bedrooms and 3 bathrooms, there's plenty of room for up to 7 people here, so add it to your bucket list. This is a family-friendly place with enough room for everyone. Or, it could be good for a group of friends. You'll be able to cook all of your meals in the fully-equipped kitchen with a dishwasher, refrigerator, stove, and oven. Enjoy meals or relaxing in this property's living room.

The game room is an added bonus which both kids and adults will love. Also on the list for this villa is laundry, television, parking, a garage, internet, and a grill. This place will quickly feel like a home away from home.



Casa Azul

Key Largo, Florida
This is a 2-bedroom, 2-bathroom oceanfront house that is spacious and beautiful. It can accommodate up to 7 guests. This is a family-friendly place with enough room for everyone. Or, it could be good for a group of friends. And with several bedrooms that have king sized beds, everyone will be able to sleep comfortably. The bunk beds in the other bedroom are perfect for kids. You'll be able to spread out through the dining area, porch, and living room here, too. The kitchen in this house is very nice, and with a refrigerator, stove, oven, and microwave you'll be able to cook for everyone. You'll be able to spread out through the dining area, porch, and living room here, too.

There's even a private swimming pool where guests can hang out. There's a beautiful ocean view, too. Have some wine on the balcony in the evenings. You'll also find Caribbean Club Bar and Dolphins Plus less than a mile away. Fishing, horseback riding, golf, surfing, and boating are all nearby, too, making this location very convenient. Places like this get booked up quickly.



Happy Travels!

If you're interested in more accommodation options in Key West, you should also see Dive Resorts in the Florida Keys, The Best Florida Keys Vacation Rentals and Airbnbs for Families, and The Best VRBO's & Airbnb's in the Florida Keys for a Romantic Couple's Getaway.
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The Best Airbnb's in the Florida Keys for a Group Getaway (May 2021) | Budget Your Trip

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