Key West Vacation Rental Specials

August & September Monthly Stays in Key West

Trade your routine for island living this August and September.

Whether you're escaping for a month, working remotely from paradise, or simply craving a change of scenery, Historic Key West Vacation Rentals offers the perfect opportunity to experience Key West like a local. Our featured monthly rentals require a 28-night minimum stay and place you in the heart of one of America's most unique island communities.

Casablanca

Your Private Retreat in Old Town Key West

Wake up each morning just steps from the charm, culture, dining, and waterfront beauty of Historic Old Town. Casablanca is a welcoming one-bedroom, one-bath duplex designed for guests who want more than a vacation—they want to experience the rhythm of island life.

Spend your days exploring local cafés, biking palm-lined streets, watching sunsets at Mallory Square, and returning home to your own private Key West retreat.

Available for August and September 2026 monthly stays.

https://www.historickeywestvacationrentals.com/vacation-rentals/casablanca

Casablanca Too

Freshly Redesigned for Relaxed Island Living

Discover the freedom of slowing down at Casablanca Too. This beautifully updated one-bedroom, one-bath duplex combines comfort, style, and an unbeatable location near Key West's most beloved attractions.

Perfect for remote workers, snowbirds planning ahead, or anyone seeking a month immersed in tropical surroundings, Casablanca Too offers everything you need to settle in and truly enjoy island life.

Available for August and September 2026 monthly stays.

https://www.historickeywestvacationrentals.com/vacation-rentals/casablanca-too

Casablanca Grande

Bring Family, Friends, or Simply Enjoy More Space

Why choose one space when you can have both?

Casablanca Grande combines Casablanca and Casablanca Too into one spacious property, creating the perfect setting for extended family stays, visiting friends, creative retreats, or longer getaways with room to spread out.

Enjoy the privacy of two unique living spaces while sharing the experience of a month in beautiful Key West. Walk to local restaurants, discover hidden neighborhood gems, and experience the island as locals do.

Available for August and September 2026 monthly stays.

https://www.historickeywestvacationrentals.com/vacation-rentals/casablanca-grande

Experience Key West Beyond the Weekend

The best part of Key West isn't checking attractions off a list—it's becoming part of the island's daily rhythm. Morning walks under swaying palms. Fresh seafood dinners. Sunset celebrations. Friendly neighborhood cafés. The simple joy of living where others vacation.

Reserve your August or September monthly stay today.

For reservations and availability, call 305-296-1010 or email [email protected].