Last updated: 10/3/2022 With year-round beautiful warm weather and crystal clear water, it’s easy to see why the Florida Keys have been one of the most popular vacation destinations in the United States for decades. The Florida Keys stretch over 100 miles long and contain hundreds of islands. Each of the bigger islands has a unique identity, some more laid back, others more party oriented. Most of the islands that make up the Florida Keys are extremely narrow, so massive lots and properties are rare. This list contains the biggest Florida Keys Beach house rentals available at the time of writing. While some of these Keys vacation rentals seem extremely expensive at first, they are almost always a better value than booking multiple hotel rooms for a large group. Breaking the overall cost down on a per bedroom basis is a good way to compare prices. Now let’s get on to our list of the biggest Florida Keys beachfront rentals!
5. A Secluded 4BR Islamorada Estate on the Beach
This 4 bedroom beachfront Islamorada estate is the smallest on our list, but it still is rated to sleep 10. Islamorada is made up of several islands, and this rental is located on the island called Lower Matecumbe Key. This area is full of restaurants and attractions and is a great location for families. Right down the road at Robbie’s Marina and Restaurant you can do the famous hand feeding of giant Tarpon (https://www.robbies.com/tarpon.htm) or rent kayaks or jet skis.
The pool at this estate is one of the most beautiful on our list. The pool area is directly off the beach and also has a connected hot tub. The kitchen is equipped with high end commercial appliances, making it easy to have a relaxing dinner at the house. Jim, the owner of this property, takes a ton of pride in making sure every guest has a wonderful experience. This is evident by the fact that with over 50 verified reviews, they have not received anything other than 5.0/5.0 from every single guest. This is extremely rare, and tells you how amazing this Keys rental home really is. Find more pictures and check the availability of this house here: Islamorada 4BR Estate-VRBO Listing
4. Casa de Ivy, a 5BR Key Largo Beachfront House Rental
Casa de Ivy is a beautiful 5 bedroom Key Largo beachfront vacation rental home. This house has an infinity pool overlooking the white sand beach, a newly built dock, and sand volleyball court off the beach. Key Largo is the first island off of the Florida mainland, and is actually closer to Miami than Key West. This is nice if you are flying into Miami International Airport. Key Largo is also the largest island in the Keys.
This Florida Keys rental house is rated to sleep 12 people, with plenty of outdoor entertaining space for large groups. The views from the covered 2nd story patio are hard to beat, and most rooms in the home have views of the ocean. The calm water of Blackwater Sound is perfect for swimming, snorkeling or kayaking right off your own beach. You can even bring your own boat or rent one to utilize the large dock on the property. Casa de Ivy is extremely popular and it can be difficult to find openings, but if you are lucky enough to find an open time you won’t be disappointed. Find more pictures and check the availability of this house here: Casa de Ivy-VRBO Listing
3. A Luxury 5BR Marathon Beachfront House with a Dock and Private Beach
Although this beachfront Marathon rental house isn’t the biggest on our list, the location and outdoor amenities are our favorites. Off of the beautiful private beach there is a peninsula that extends out into the ocean. On this peninsula there is an awesome covered tiki hut with seating and a TV. There isn’t a better place to relax in the Keys. The saltwater pool lies between the house and the putting/chipping green off the beach. Yes, you can brush up on your golf game right off your own beach. The dock has space for 3 boats, including 1 space that can accommodate a 100 ft boat.
This 5 bedroom, 4 bath rental is rated to sleep 16, plenty of space for large families or multiple families. The Sub Zero commercial appliances complete the beautiful custom kitchen. The panoramic ocean views from both the 1st and 2nd floor will make it hard to leave. This property barely misses the perfect 5.0/5.0 average review score after over 40 verified reviews, coming in at 4.9/5.0. If fantastic outdoor amenities are big on your priority list, this Keys vacation rental is tough to beat. Find more pictures and check the availability of this house here: 5BR Marathon Beach House-VRBO Listing
2. Southern Diversion, A Sprawling 8BR Beachfront Florida Keys Rental Estate
Southern Diversion is a massive 8 bedroom, 6 bathroom beachfront estate in Marathon, Florida. This Keys vacation rental sleeps 20 comfortably, and is set up perfectly for hosting groups. The estate contains multiple buildings connected by covered walkways, making it seem more like a Carribean resort than a Florida Keys beach house. This is a perfect setup for multiple families, giving everyone ample space, but still keeping everyone close.
The 2 acre lot Southern Diversion sits on is massive by Florida Keys standards. There is 300 foot of beachfront on the property, complete with a deep water dock with power and water. You can catch a variety of fish right off the dock and clean them on the dock’s fish cleaning station. There are multiple kitchens on the property, but the main kitchen is equipped with a massive range, multiple sinks, and 2 dishwashers. This Keys estate is truly set up to cater to large groups. Find more pictures and check the availability of this house here: Southern Diversion-VRBO Listing
1. Villa Montelepre, The Largest Florida Keys House Rental Available
Villa Montelepre is the crown jewel of the Florida Keys. This 9 bedroom, 8.5 bath mansion is the biggest Florida Keys Beach house rental available. Included in the price of the rental is an amazing private chef and butler, including all cleanup and daily housekeeping. Chef Patty will make 2 seated meals a day for your entire group. This rental was built and designed in a beautiful Tuscany styling that could be straight out of a travel magazine.
If you value privacy and having a vacation that your group will never forget, Villa Montelepre is ideal. It is expensive, no question. But as we said at the beginning of this article, when you break the cost down on a per bedroom basis, the value is still there considering this mansion is more luxurious than even the most high end 5* resorts. This is a nearly all inclusive rental (bring your own alcohol) which are hard to find. This rental is the overall winner in the battle of the biggest Florida Keys beach houses. The reviews are unblemished (perfect 5.0/5.0) and if this Keys vacation rental fits in your budget, you are in for a trip you will never forget. Find more pictures and check the availability of this house here: Villa Montelepre-VRBO Listing
If you enjoy checking out large beach houses like the biggest Florida Keys beach houses in this post, here are a few of our other lists with mansions and large beach houses: