Lexington and surrounding towns are a unique taste of Americana - from regal equestrian estates to downtown cottages with lots of character, our properties offer an authentic Bluegrass experience. The Holiday Life offers upscale vacation and seasonal home rentals along Southwest Florida's Paradise Coast and in Kentucky's Bluegrass Region.
From Marco Island and Naples to Lexington, each of our beautifully appointed private properties offers guests a unique and authentically local experience paired with the service and amenities you'd expect at a fine hotel. The Holiday Life family is dedicated to providing the ultimate vacation rental experience to all of our guests.
From Marco Island and Naples to Lexington, each of our beautifully appointed private properties offers guests a unique and authentically local experience paired with the service and amenities you'd expect at a fine hotel. The Holiday Life family is dedicated to providing the ultimate vacation rental experience to all of our guests.
Services
Casey Potter started The Holiday Life in 2013, after noticing a need for high quality, well-managed and easy to reserve rental properties in Naples, a favorite destination she visited often with family and friends. After a brainstorming session with her mom, Lisa, she quickly decided the Sunshine State was calling and left her career on Wall Street to begin managing a small handful of vacation homes.
Famous for legendary horse farms, historic Bourbon distilleries and scenic drives through the stunning landscapes, Kentucky's Bluegrass Region showcases the natural bounty of the state with charm and genuine Southern hospitality.
Lexington, Horse Capital of the World, is Kentucky's second-largest city and offers a vibrant mix of shopping, historic sites, craft breweries, charming neighborhoods, distilleries, bourbon bars, and inventive farm-to-table cuisine culture.Visit the childhood home of Mary Todd Lincoln, the thriving Distillery District, and elegant Keeneland Race Course.
Lexington, Horse Capital of the World, is Kentucky's second-largest city and offers a vibrant mix of shopping, historic sites, craft breweries, charming neighborhoods, distilleries, bourbon bars, and inventive farm-to-table cuisine culture.Visit the childhood home of Mary Todd Lincoln, the thriving Distillery District, and elegant Keeneland Race Course.
A natural and cultural gem tucked away in Southwest Florida, the Paradise Coast is where the Gulf of Mexico's turquoise water meets white sand, wild islands and downtowns filled with artful treasures, culinary delights and countless other discoveries. Explore Naples, Marco Island, Everglades City, Immokalee and Ave Maria and find your most idyllic Florida vacation.
We recommend that you browse all of the properties on our website and choose the property that best fits your needs in terms of location, availability and specific features. Our online calendars are up to date and we do our best to keep the amenities tabs populated with current information on each property.
Reviews (15)
Bryan Shiel
Jan 24, 2022
Report
Beware of the Fieldstone Beach House or any other properties run by The Holiday Life…We stayed 4 nights at The Holiday Life’s Fieldstone Beach House back in September for a family wedding. The accommodations were nice and proximity to wedding events was ideal. Overall, we enjoyed our stay. The negative experience started after we left the property.
There was an incident during our time there where someone in our group slipped getting out of the shower, resulting in a broken toilet. There was no floor rug in the room but since no one was hurt, we planned to accept the loss of the $500 security
There was an incident during our time there where someone in our group slipped getting out of the shower, resulting in a broken toilet. There was no floor rug in the room but since no one was hurt, we planned to accept the loss of the $500 security
Robin Davis
Dec 27, 2021
Report
Laurie Clark
Dec 18, 2021
Report
My husband and I have now rented 2 different homes during 2 holiday seasons in a row for our family through The Holiday Life. We have found their service to be exemplary. They are helpful and quick during the booking process. They have the BEST house options in Southwest Florida. During the rental stay, they are fast and responsive with any questions or issues that arise. We cannot compliment this service and rental provider enough - just wish they were in more resort towns nationwide!
Susan Huff
Oct 23, 2021
Report
Erik R.
Oct 07, 2021
Report
By far the most professional VRBO type property management group I have ever dealt with as a renter/tennant
Casey & staff go above and beyond to make the whole stay enjoyable from the time of booking to check-out
I can only assume that all the 1 star reviews in a one week span are in attempt to spam by either the competition or some jealous people that were up to no good when asked to leave
Casey & staff go above and beyond to make the whole stay enjoyable from the time of booking to check-out
I can only assume that all the 1 star reviews in a one week span are in attempt to spam by either the competition or some jealous people that were up to no good when asked to leave
Michele D'Ambrosio
Oct 02, 2021
Report
The Holiday Life goes above and beyond to provide exceptional service to create a seamless vacation for the guests. They proactively reach out to ensure guests are happy and comfortable and go above and beyond in the service they provide. You are ensured to be well cared for as a vacationer or owner of a home they service. As an owner, I have been able to trust my home in the hands of The Holiday Life. In reading countless happy reviews on my home, I feel so rewarded that The Holiday Life’s management is the key in creating beautiful vacation memories. You can trust Holiday Life with your home
Matt Stephen
Sep 28, 2021
Report
I accepted a 13 month job in Naples and needed a place to rent. The wife wanted something vacation style we are from Ohio and beach Florida lifestyle has appealing. Cant say enough about the team and the property we got. Hit every one of our needs spacious kitchen, great backyard for entertainment. Communication flawless, if we needed to get a hold of them they were there in no time.
Sylvia Garfinkle
Sep 25, 2021
Report
I cannot say enough good things about my experience with The Holiday Life. The team is so kind and professional. They think of every detail and when I mistakenly locked myself out, the owner came to my rescue in ten minutes! I also really love the hospitality app they use. The answer to every question was at my fingertips which is so convenient. I highly recommend The Holiday Life.
John O.
Sep 22, 2021
Report
I have been doing business with The Holiday Life for 4 years. I have always found Casey and her staff to be professional, courteous and efficient... The Holiday Life's attention to detail and communication have always been excellent. I am a real estate professional and would highly recommend The Holiday Life's services.
Stu R.
Sep 22, 2021
Report
My experience with Holiday Life was incredible. Our accommodation was in a great location, the house was spotless on our entry. We had a few problems during our stay and presto, you call, and the problem was taken care of. I am not one to post online, but when I read the post by Jordan U, and Karley S I wanted everyone to know that they do NOT speak the truth of this wonderful and accommodating business.
Jen Graham
Sep 15, 2021
Report
My family and I had a wonderful experience with the team of The Holiday Life before, during and after our stay at their gorgeous Naples property, Neapolitan Sky! Your every need will be met- just think it and it will be taken care of! Everything was prepared in advance of our stay and the home was so meticulously cared for, clean & comfortable.The whole team is extremely professional and prompt. Once home, I realized I had left my Bose headphones behind. They were returned so quickly to me and with such ease! I highly recommend a stay at any of their fabulous properties.
Carley E.
Sep 12, 2021
Report
I cannot say enough great things about The Holiday Life! My experience from start to finish was beyond wonderful! The level of professionalism from every team member, especially the owner Casey & reservationist Kelly, was so refreshing. They have been SO helpful- quick to respond with any questions I had, great local recommendations and an overall 5 star experience. I highly recommend working with The Holiday Life for your next Naples vacation! 🌟🌟🌟🌟🌟
Elyse G.
Sep 10, 2021
Report
I absolutely love working with the Holiday Life. My family and I aren't familiar with Naples so when it came to finding a good rental property, we were pretty clueless! Casey and Kelly happily answered all of our questions and found us a BEAUTIFUL home.
Seamless process every step of the way. Can't wait to go back!
Seamless process every step of the way. Can't wait to go back!
Karley S.
Sep 09, 2021
Report
Jordan U.
Aug 06, 2021
Report
Worst Experience ever. Kicked from 27k "GolfShore Grand" rental with no proof of "breach of contract" we were asked to leave by a hired security guard on day 2of7 then ignored by holiday life and VRBO. when finally getting ahold of vrbo we are told the The holiday life (Casey potter) has kicked us out due to 1 misspelled letter in 1 out of 11 peoples names as we'll as a past provocative instagram of one of our guests. due to miss Casey potters anxiety of the "owners finding out about said instagram post" we were wrongfully discriminated against and booted from
