Key West Compounds - A fenced and gated privately owned garden area joining multiple residential dwellings. They offer private retreat like settings with swimming pools, tropical gardens, sun decks, and covered porches, and are ideal for larger groups of family or friends. Compounds can sleep from 12 to 28 people.
Choose from our inventory of Key West vacation rentals. We offer something for everyone; from charming cottages, to beachfront condos, to luxury estates, to tropical pool-garden homes.
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Standard Rates: $18000 - $25000 per month
6BR 6.5BA - Sleeps 12
Luxurious Estate ~ 2 Houses plus Guest Cottage = Private Residential Resort
Gated and Grand
Premier Historic Seaport location! Steps from the boardwalk.
A whole vacation experience for the entire family. Rent this estate and live in luxury in the most requested Historic Seaport location in Key West. Three historic dwellings are seamlessly joined to become one private luxury Key West rental estate. A combination of unique design elements impart that elusive je ne sais quoi of island architectural history. Rent the best of Key West!
Standard Rates: $5500 - $11325 per week
6BR 5BA - Sleeps 14
2 heated swimming pools
3 Cottage Compound (2-cottage villa plus a cottage).
Less than 1/2 block off Duval Street
Get together for an 'Island Rendezvous' in Key West in this Award Winning Villa and Caribbean Style Cottage side-by-side steps from Duval St. and 3.5 Blocks from Mallory Square. Perfect solution for a gathering of family or friends for a week in paradise.
Standard Rates: $10350 - $19500 per week
11BR 11BA - Sleeps up to 24
2 heated swimming pools (1 with Spa Jets)
Steps from the 500 block of Duval Street
3-story historic Victorian home plus new 4 BR villa
"Let's stay together ... for a week or more." Start calling your family and make a plan. If you’re looking for luxury and plenty of room, The Meeting Point Key West is the grandest vacation rental licensed to rent weekly in Key West, both in stature and style. 7 BR 7 Full BA elegant Victorian Mansion plus 4 BR 4 Full BA luxury villa.
Standard Rates: $5700 - $11520 per week
9BR + Dens 6.5BA - Sleeps 22
Large swimming pool in tropical garden. Walk to Higgs Beach and stylish White St. gallery neighborhood. Boho beautiful main house plus renovated condo. Great value.
"Family's who play together, stay together." This is a spacious Key West rental for your family reunion vacation. Property includeds a main house and attached cottage suite decorated with a bohemian shabby chic flair, plus a renovated condo. Why not gather in a gated complex with a home, plus private attached cottage, and town home situated in a spacious garden, and large swimming pool.