Key West Monthly Summer Cottages

Our Key West guests recommend these monthly summertime cottages and Caribbean vacation rentals for your end-of-summer getaways. Historic Vacation Rentals has the premier collection of luxury boutique cottages, condos, townhomes, and conch-style houses. We're always happy to help you choose the best long term or Key West monthly rental for your needs. We're so confident we will make your stay we happily share what our guests have been saying.  After all, our guests say it best and they speak from experience. 

"We have stayed in Key West for many years now. This was the best rental property so far. The location is perfect for beach days at Ft. Zach and walking both ends of Duval at night. The property itself was very clean and had all the amenities we needed and was run well by the property managers. The Hot tub is huge. The neighbors were nice & friendly. We stayed a month and parked right in front of the house every night. We would definitely stay here again. This is the second time we have rented from Historic Key West vacation rentals. We have already booked with them for next year." Guests at Bahama Getaway - Monthly Rental 4 Bedrooms 3 Bath Sleeps 8

"The pool and surroundings are ideal for relaxation. And dining. The Bedrooms and Baths are spacious & comfy. The kitchen worked well for cooking 10-12 times. So close for us walkers to our favorite spots. And the free bus stops right outside. Clean, well-maintained home. Historic KW staff & crews were so helpful & considerate." = Guests at Cayo Limón - Monthly Rental 2 Bedrooms 2.5 Bath Sleeps 6

"I loved this Cottage!! The location was ideal, the neighborhood Key West at her most charming, the service and whole experience were first-class. I highly recommend staying at this home and with HKWVR. Cindy in Guest Services and Steve in Operations went above and beyond in taking great care of me. I would return again any time!!" - Guests at  Copa Cabana - Monthly Rental 2 Bedrooms 1.5 Bath Sleeps 4

"After 2 failed attempts to book a 1 bedroom condo, Historic Key West Vacation Rentals went above and beyond to make our trip amazing! The property was flawless! Beautiful, amazing location, fantastic customer service! She even helped up book bikes and snorkeling! “My Happy Place” will always hold so many memories for us!" - Guests at My Happy Place - Monthly Rental 2 Bedrooms 2 Bath Sleeps 4

"We had a wonderful 3-month stay in this lovely cottage, which is located in a very convenient and quiet part of town. The management company, Historic Key West Vacation Rentals LLC, is a very professional and customer-focused group." - Guests at Petunia Cottage - Monthly Rental 2 Bedrooms 1 Bath Sleeps 4

 "Amazing 28-day minimum property in an amazing patio villa home scenario. Once that property gate goes shut, so does all the noise and bustle of Key West! The majority of units are permanent residents and it is no-nonsense managed and kept spotless. The pool is amazing and the unit is well appointed and easy to feel comfortable in. Outside lanai is lovely in the mornings and evenings. This is NOT a party house but it IS a relaxing place to come home to when you’re done with that part of KW! Winner winner ⭐️ ⭐️⭐️⭐️" - Guests at Starfish - Monthly Rental 2 Bedrooms 2 Bath Sleeps 4

 " This year was the second time we had stayed with Steamplant. The uni"The unit we had this year was nearly perfect for us. We loved our balconies and the view; we were especially thrilled with the plunge pool, and our sunset visits up there with a great view of the sunset... We love our bedroom, which is spacious and cool. The staff at Steamplant cannot be better. We felt like we could call and ask for any assistance and we would have a prompt and efficient response. Although we stayed home quite a lot because of COVID worries, we know from our previous trip that the location is darn near perfect. We can walk easily to multiple restaurants, and the Duval Shuttle stops right across the street. We love this condo and have booked again for next year. We did really hate to leave. - Guests at Steamplant 207 - Monthly Rental 3 Bedrooms 3.5 Bath Sleeps 8

Our Historic Key West Vacation Rentals team is proud to share these comments. Our guests recommend these Key West monthly vacation cottages for your end-of-summer getaways. Reserve your monthly stay today! It's summer and our Key West island life is ideal!