Complete Guide to Key West vacation rentals offering luxury poolside amenities

For those eyeing the island lifestyle at a relaxed pace, consider an extended-stay vacation home with a private pool and special amenities in tropical Key West! Historic Key West Vacation Rentals offers many deluxe homes with especially luxurious poolside amenities for the ultimate tropical retreat.

Imagine lounging in your own private oasis with friends or family, cooking fresh seafood on an outdoor grill and enjoying a variety of living spaces for both relaxation and fun — all just steps from the charm and excitement of Old Town Key West. After all, Key West rarely dips below 70 degrees even in the middle of winter.

Historic Key West Vacation Rentals offers luxury properties that blend historic charm with modern amenities. The island way means embracing an indoor-outdoor lifestyle. And many of our monthly rentals include fabulous outdoor spaces.

 Here’s why our extended-stay rentals with enhanced poolside amenities are the ideal way to experience Key West:

• A personal oasis: In Key West’s warm, tropical climate, having a private pool isn’t just a luxury — it’s a refreshing sanctuary. Many of our extended-stay rentals feature gorgeously landscaped pool areas, giving you an extra secluded space to unwind. The convenience of having a dedicated pool house with changing rooms means you can effortlessly move from a busy day of exploring the island to a cozy, refreshing swim back at your rental.
• Water features add to the ambiance: Fountains or cascading waterfalls are more than just decorative — they create an atmosphere of serenity that elevates your experience. These additions not only enhance the natural beauty of your private pool area but also provide a soothing soundtrack as you relax or dine alfresco. Let the gentle sounds of water transform your outdoor space into a tranquil oasis, perfect for reading, meditating, or simply savoring the island ambiance.
• Outdoor grills and dining areas: With access to an outdoor grill and dining space, you can bring the flavors of Key West home. Fire up the grill for freshly caught seafood or local produce from the farmers market, and cook under the stars. An extended stay allows you to take full advantage of these features, making every meal an opportunity to gather with loved ones, enjoy the island’s flavors and dine in your own private paradise.
• Lounge areas: From cozy cabanas to lavishly appointed outdoor seating with plenty of loungers, our vacation homes come with spacious areas for gathering, escaping or entertaining. These areas offer the perfect setting for spending time with friends and family, reading a good book, or enjoying cocktails at sunset. With your own extended stay rental, there’s no rush or need to leave the comfort of your home away from home — everything you need for relaxation is right at your fingertips.

Check out this sampling of some of our favorite properties that offer special poolside experiences.

• Tropical Dream: You’ll be living the dream the minute you check into this fabulous 4BR, 4.5BA monthly rental with room for eight people. Relax with a drink in the intimate sitting pool, which spills into a larger pool with a lovely waterfall feature. Enjoy alfresco meals on the surrounding deck complete with outdoor dining area. In the serenity of this quiet oasis, you’ll never know you’re just five blocks from the bustling action on Duval Street and at the Marina.

• Blue Haven: Spread out and live both indoors and out for a month in this 4BR, 3BA home. Featuring a Jandy pool system (with controls for jets, chilling and heating), you can’t help but plunge into relaxation mode. Blue Haven’s outdoor space offers tropical landscaping with an outdoor shower, beautiful decking, loungers and outdoor seating, a dining table, fire pit and sunshades. You’ll be within easy walking and biking distance of Old Town’s most memorable attractions, then return for a dip in your own luxury pool.

• Sanctuary on South: This fabulous two-story retreat in the Casa Marina District offers plenty of room to spread out. You can’t help but love the large pool out back, rimmed by decking and featuring a fabulous pergola with comfortable seating and plenty of loungers. The gas grill makes cooking alfresco a snap. Inside, upscale furnishings and airy interior spaces highlight this 4BR, 2.5BA showplace, which includes a gourmet kitchen featuring high-end appliances. You’ll want to stay a month or more living like a local in Key West! 

 Search the best Key West vacation rentals, including luxury homes with private pools, and book directly with us at www.historickeywestvacationrentals.com.