Places to Stay

Key West homes, cottages and condos across seven neighborhoods, from Bahama Village and Old Town out to Truman Annex and Sunset Key. A local agency since 2011, booking nightly stays and full-month stays in houses with porches instead of corridors.

Three accommodations on Atlantic Boulevard near Higgs Beach: a three-bedroom house sleeping eight with a wraparound ocean deck, and two adults-only garden suites. The house takes stays of 28 days or more, the suites from two nights.

Morning Star Sailing Charters offers personalized sailing experiences in the Florida Keys, including captained and bareboat charters, sunset cruises, and snorkeling tours.

Historic Azul Key West offers a serene, romantic oasis just steps from vibrant downtown.

Courtyard by Marriott Key Largo — comfortable Key Largo hotel with full-service marina, pool, fitness center and easy access to Florida Keys adventures.

Veterans Dive Center & Retreat — dive shop and veteran-friendly retreat in Summerland Key, Florida.

Oceanfront 3BR rental in gated community with panoramic views, boat slip, and top Islamorada location.

Doze in a hammock, swing on the porch, and wake up to complimentary breakfast — Key West Bed & Breakfast is a charming 10-room adult-only inn tucked into a Bahamian-built 1898 Victorian home on quiet William Street in the heart of Old Town, where the vibe is laid-back, the rooms are colorful, and the pace is gloriously slow.

Escape to Islander Resort: vibrant Florida Keys stays, beachside dining, and endless adventures!

Key Largo sanctuary awaits.

Island Bay Resort is an adults-only boutique escape with tropical cottages, a private beach, and free kayaks & SUPs.

Sugarloaf Key KOA Resort offers waterfront RV sites, deluxe cabins, and tent sites with resort-style amenities in the Florida Keys.

Mermaid’s Bay is a secluded boutique estate in Islamorada, offering three private waterfront homes with resort-style amenities, ideal for group getaways

Sunshine Key Tiny House Village is a vibrant collection of colorful tiny homes located on Ohio Key, offering a unique and charming way to experience the beauty of the Florida Keys.

Colocada Vacation Rentals specializes in upscale Key West accommodations, offering nightly, weekly, and monthly rentals with VIP-level guest services rooted in generations of local expertise.