Embrace valuable family time in Key West with a poolside extended vacation rental

Dreaming of taking your family on an extended vacation in the beautiful, sun-soaked paradise of Key West? Consider a family-friendly rental that offers extra space and a private pool. At Historic Key West Vacation Rentals, we know that a comfortable, well-equipped space is top of mind for a memorable family vacation — so much the better when you add in a private pool.

Whether you’re planning a family getaway to relax, explore, or both, Historic Key West Vacation Rentals has you covered. We offer many of our fabulous homes as monthly rentals, affording the option of working from your home away from home, while still enjoying plenty of down time to relax with your family in your own private backyard oasis.

The perks of a pool

 When you’re staying for an extended period, having a private pool isn’t just a luxury — it’s an incredible convenience. Imagine starting your mornings with a refreshing swim or jumping in for spontaneous pool games with the kids in the afternoons. A pool keeps everyone entertained without needing to leave the comfort of your rental, and offers your family endless fun. Relax poolside while your kids dive in and create memories that last a lifetime.

Key West offers myriad attractions for the whole family. And after a day exploring charming Old Town or soaking up the sun on the beach, coming home to your private pool adds another layer of relaxation. Our extended-stay rentals provide all the comforts of home, so you can enjoy the spaciousness of your own kitchen, comfy bedrooms and inviting living spaces — all just steps away from your personal poolside retreat.

A month-long family-friendly rental with a pool also gives you the flexibility to explore Key West at your own pace. Take the time to dive into the rich history and vibrant culture of Old Town, explore the island’s beaches and nature spots, or spend an afternoon swimming in turquoise waters. After a full day, you and your family can simply come home, grill up the catch of the day, sip a cocktail, lounge around the pool and take an evening swim.

Some prime picks for families

Following is a taste of what Historic Key West Vacation Rentals has to offer families desiring to visit for a month or more. And all feature fabulous private pools!

• La Casita en Cima: This charming 2BR, 2BA home is a winner of the Historic Florida Keys Foundation’s Preservation Award. That means you’ll have all the perks of modern amenities via a full renovation, while appreciating the traditional architectural features Key West is famous for — especially in the fenced private outdoor garden featuring a pool, covered lanai, loungers, grill and plenty of outdoor seating. With room for six, you and your family will enjoy plenty of space to sprawl for the entire month.

• Three Arches in Paradise: Spend a month or more in this 3BR, 3.5BA renovated historic home, just a stone’s throw from the beach and all the action on Duval Street. There’s room for everyone here, including a tropical oasis in the back, with a private pool offering built-in benches and a water feature, loungers and outdoor showers. Rather than hunting for a restaurant every night, you’ll appreciate the option of cooking on the gas grill, sipping cocktails around the pool and swimming with the kids.

• The Pink House: Go ahead and stay a month! This lovely 2BR, 3BA home for up to five people offers plenty of space for you and your family. Two large ensuite rooms with balconies and plenty of seating areas (including a desk for homework or working remotely) make for a perfect fit. French doors give way to the back deck, a private oasis surrounded by lush landscaping. Here, too, is a saline cocktail pool and smaller sitting pool for younger children. An outdoor shower, loungers, gas grill and dining setup round out the amenities that will make your extended family vacation something to remember. 

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