Browse 6 vacation homes for large groups in Key West — entire homes sleeping 8 to 30+ guests.
Explore Group Homes in Key WestNo splitting across hotel rooms. No coordinating check-ins at separate properties. One home, one experience, your whole group together from arrival to check-out.
Square footage is the starting point, not the finish line. Our large group homes are selected for open-plan living areas, outdoor spaces, and amenities — private pools, game rooms, wraparound decks — that make a group trip actually work.
Every AvantStay property is professionally inspected and hotel-clean before you arrive. What you see in the listing is exactly what you get, backed by 24/7 support throughout your stay.
Key West draws large groups with its coastline, water activities, and outdoor dining culture. Groups find everything from family reunions to bachelorette weekends and destination weddings, all centered around the water and year-round sunshine. A single large home becomes your group's private beach resort. Groups prefer staying in one home in Key West over booking multiple hotel rooms because they stay connected, cook together, share common spaces, and often cut nightly costs in half. That single home becomes the heart of the trip rather than just a place to sleep.
We rented Casa de Rosalie for the month of January 2024 with a core group of four adults, a six month old and two dogs. We had friends and family visiting throughout the month. With the high ceilings and the backyard space the house never felt overcrowded. We walked or biked to everywhere we wanted to go. It is on a busy street (for Key West standards), so there is traffic noise. The kitchen was well equipped, the mattresses were a bit soft for my taste, and there were plenty of beach towels, chairs, and umbrellas. The backyard space was my favorite part of the house with a gas grill and a blackstone grill and several sunning and shade areas; morning coffee, after beach pool dip, and evening cocktails, and maybe another dip in the pool (opt for pool heating). So much fun!
We spent 2 weeks in this lovely, art filled home surrounded by lovely landscaping which created a nice privacy fence. Home was spotless & stocked with all the basics for cleaning and cooking (although I never really used the kitchen!) There is a dedicated parking space. The common pool is just steps away and was a friendly gathering spot in the afternoon. Home’s furniture is stylish & comfortable, beds are big & comfy & bathrooms were well appointed. Truman Little White House is around the corner. Downtown is a short walk, nice restaurants are close by and the Truman Annex Thursday Farmer’s Market & other special events are a 5 minute walk. We had our feet, a bicycle & a golf cart and could access anything in Key West. Also Key West Ubers are quick, not expensive & have very nice drivers. The management team, Avantstay, was wonderful, answered any question very quickly & even came to the house when we had a TV problem. Very nice group! We loved the little chicken family that visited every day & got used to the rooster! Very Key West. Picky negatives - patio furniture is not great but the space is wonderful. Uber drivers, grocery delivery folks had trouble finding the address. No fault of the owner of course & I reported it to Google Maps.
Fantastic home right within walking distance to almost anything you'd need to have a blast in the keys. Even more spacious than it looks in the listing and we had plenty of room for our larger group. The furnishings were nice, beds were large and comfortable, and the decorations match the vibe of the key perfectly. We spent a lot of time relaxing (and recovering) in the pool and the kitchen was adequate for the light meals we made. Our minivan fit easily in the drive but if you come during a peak time you might find parking/manoeuvring a larger SUV a challenge (or take advantage of the ride share/cab options that are available). Everything was very clean and the check-out requirements are very reasonable given the ($450 at our time) cleaning fee for the size and number of beds. I would strongly consider staying here again if I we come back to KW with a large group, we had an absolute blast! All communication was prompt and clear, and it might be the smoothest rental we have ever done
Explore more large group vacation rental destinations in Florida.
Destin's Emerald Coast is celebrated for its sugar-white sand, crystal-clear water, and year-round beach culture. The Gulf's calm waters are ideal for paddleboarding, snorkelling, and dolphin tours. The 30A corridor stretches with waterfront restaurants, beach shops, and an outdoor-first lifestyle. Large groups come for the beach, the water activities, and the ease of doing everything outdoors.
Emerald Coast draws large groups with its coastline, water activities, and outdoor dining culture. Groups find everything from family reunions to bachelorette weekends and destination weddings, all centered around the water and year-round sunshine. A single large home becomes your group's private beach resort.
Fort Lauderdale draws large groups with its coastline, water activities, and outdoor dining culture. Groups find everything from family reunions to bachelorette weekends and destination weddings, all centered around the water and year-round sunshine. A single large home becomes your group's private beach resort.
Marco Island draws large groups with its coastline, water activities, and outdoor dining culture. Groups find everything from family reunions to bachelorette weekends and destination weddings, all centered around the water and year-round sunshine. A single large home becomes your group's private beach resort.
Orlando attracts large families and multi-generational groups with its attractions and entertainment ecosystem. {activity} keeps every age group engaged, and a single large home gives the family privacy and flexibility throughout the day.
6 group homes are waiting in Key West. One property, everyone together, no compromise.
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