There are few vacation rentals in the world that can boast to have it all. And Sea Gypsy Vacation Rentals is in that lucky rare bunch. With over a 100 rentals to choose from, there’s something to fit everyone’s taste, budget, style and way of life…
Estero Island
You might not think that a little place like Estero Island, Florida could have so much going on – but you’d be wrong. With restaurants, day and night life both, the island is a hopping place, and quite a stunning little strip of land as well. Located in Southwest Florida, Estero Island is a hot spot of a destination for many the weary northern traveler, seeking a little bit of sun, sand and relaxation. But Estero Island is also not an average tourist destination because of it’s prohibitive costs. While on the island, I had a chance to speak with a local who rents out a three-bedroom condo, with a few of the trees in his backyard. Not even the ocean. He told me he pays over $3,000 monthly for his pretty little apartment, and while it might be a beautiful spot, it’s certainly not the average cost for rent.
Apartments, hotels and inns run high in this neck of the woods, but for good reason. Estero Island is a particularly beautiful piece of Florida and in an excellent location logistically. The Southwest Florida airport only 40 minutes north, Fort Myers only 20-30 minutes away (depending on where you need to go) and Naples only 20-40 minutes away (again, depending on your specific destination).
Beautiful white sand beaches, shopping and with only one or two grocery stores along the mere 7-mile or so island, it’s a quiet, yet dynamic spot.
Rentals for Everyone
Enter Sea Gypsy Inn. The little nook that is located at the northernmost part of the island, is owned and operated by Scott, a former AT&T cell tower builder, and his wife Jacki, who had previous experience in the medical device field. Just a few short years ago, while living on the east coast of Florida, he and his wife had a small vacation home on Fort Myers Beach.
“We started coming over for the weekend every now and then and progressively, those weekend stays started becoming more frequent, until we were spending more time in Fort Myers Beach than our home. We really fell in love with “island life” and finally in 2012, decided to sell our home and make the move full time. My wife went out house hunting one morning and she came home and said,
‘I think I just bought a hotel.’ And so began our life as innkeepers.”
According to Scott, the hotel was in rough shape,
“so we took a few months to fix things up, changed the name to Sea Gypsy Inn and we opned our doors in January of 2013. We have four different suites: an efficiency, 2 1-bedrooms and 1 2-bedroom.”
While things may have gotten off to a slow start, they have built a great following, he says as he goes on.
“This year we will end up close to 90% occupancy. We have survived a hurricane, red tide, and a global pandemic. Our motto is simple: clean rooms, happy guests. We want each guest to enjoy our island as much as we do. We fill them with local knowledge of where to go, what to do and where to eat. Lots of our guests have woud up becoming our friends over the years.”
The two are not originally from Florida, but rather from Wisconsin and Cleveland, respectively. Though they love the Midwest, the beach is now their home and as Scott puts it,
“Life is too short to be shoveling snow!”
The Name & Gift Shop
As every good story has, there is an origin for the Inn’s name. Jacki, being of Hungarian descent and loving the water, decided along with Scott, that The Sea Gypsy Inn was a good fit. And because there aren’t any other places like the inn on the island, the name gives it that special stand-out notability that other vacation spots just don’t have.
“We opened the gift shop the same time we opened the inn. Besides selling your average beach gear, we wanted to add products that support our local environment. We support “Captains for Clean Water” and “4 Ocean”.
The gift shop may just be the best thing to end your stay with either the inn or their vacation properties. I loved being able to grab some gear before heading off the island – and most especially love the lightweight hooded shirt I took home. And though that particular shirt doesn’t have their logo, I went home with several things that did, and there are plenty more on offer there for you to save as a nice keepsake to hold dear the memorable experience of the island’s best vacation rentals.
Because Sea Gypsy Inn became so popular over time, Scott and Jacki did not have enough rooms to fill the high demand they were receiving.
“We literally had people fighting over rooms a year in advance. We really couldn’t build more rooms or buy another hotel, so Sea Gypsy Vacation Rentals evolved in 2018. I had a friend who had an apartment on the beach and he was having trouble renting it out. One day we were talking about his problem, and I told him I could probably fill it with just my overflow. ‘Why don’t you let me rent it?’ I suggested. He agreed, and within 5 days I had booked the entire winter season for him with just a few phone calls. He told a friend, and then another – pretty soon I was managing 20 properties. Things have exploded over the last few years and we are now up to managing 100 properties!”
And that is how Sea Gypsy Vacation Rentals was born. With a wide variety of properties, they have a little bit of everything for everyone. Their prices range from low to high, and they have condos for people wanting to just hang out, houses for bigger families, canal and bay homes for boaters and of course, beach houses. And in my experience, even resorts! With properties stretching from one end to the other of the island, sometimes they will have guests stay at the inn, and then decide to stay at one of the properties the following time – or vice versa.
Which now brings me to my wonderful, and unforgettable experience with Sea Gyspy Vacation Rentals.
Love Stay Sea
The first property at which I had the pleasure to stay was Love Stay Sea. Located at the southern point of the island, Love Stay Sea was one of the most comfortable stays I had while on the island. A two-bedroom, two-bathroom condo with a spacious living room, fully stocked kitchen, and view of the bay – it was a highly unique experience.
The nearby beach offers a stunning view
Purchased roughly 6 months ago by the owners, a realtor couple in their 40s from nearby Estero, Florida, it is currently the only rental property they own. With 800 square feet of space, the condo is located at the Estero Island Yacht and Racquet club. Built in 1978, but just recently renovated, there is nothing like the covered lanai to sit out and enjoy the view. Whether it’s the boats drifting by slowly in the peaceful quiet of the water, or the dolphins jumping up out of nowhere – the scene is something else.
The beach is only about a 6 or 7 minute walk from the condo, and are free to enjoy the beach chairs and toys that are provided inside the condo at your convenience.
And if there is one thing that is most certainly the best part of the stay, it’s the panoramic view from the master bedroom. With the view wrapping from window to the sliding glass door, you can wake up to the most spectacular sight after a restful night sleep on a deliciously comfortable king size bed.
Ocean Breeze
The second unit at which I had the privilege to stay was Ocean Breeze. There is a reason for its name. The studio apartment is located on the 8th floor of the complex located on the property of the Estero Island Beach and Tennis club – just across the street from the Yacht and Racquet Club. With the most awesome view you could possibly conceive of, this unit faces the ocean head on with the most incredible vantage point possible.
The unit is owned by a couple in their 60s from Michigan. They bought the unit about a year ago and have recently just purchased another one in the same complex that we will be managing. Built in the 1980s, the unit has been recently updated, and has a few very cute touches, including a sign with “beach rules” which will give you a smile and giggle upon reading them. While there may not be any “private beaches” here, you might as well call it that, considering there are few strangers to be seen on the white sand behind the complex.
I took the opportunity to sit out there in one of the many beach chairs provided by the owners, and was the only person for roughly an hour in the morning. That may have changed later, but the solitude for that short time was enjoyable and certainly a nice added bonus for being in such a tasteful area.
Southern Comfort
As if the views I’d had up to this point weren’t spectacular enough, the third stay I had at Southern Comfort was by far and away the most incredible. Located at the Lover’s Key Resort – yes, an actual resort – this property is something one dreams about in their cold, little one-bedroom apartment in Northwest Indiana during the winter. Oh, that’s just me? Well, even if it is, I think I speak for all of us when I say, this place was a fantasy come to life. A wrap around view spanning from the far corner of the dining room and living room area, all the way to the bedroom, this place was highly romantic and highly desirable. Which is why next time I stay there, I will go with someone other than my mother.
And though I say that, the stay was perfect for family as well. Indeed, the apartment is spacious enough for more than 2 people, and even has an extra pull-out sofa if kids or non-marital tag-alongs are accompanying your stay.
Ironically, the unit is owned by a couple from Indiana, and they have been the owners for a year now. Though it’s their first investment property, so far, so good. The condo was built back in the 90s, but was just recently updated. The unit is owned by a couple in their 50s from Indiana. They bought the unit a year ago and it’s their first investment property. The condo was built back in the 90s, but the unit was just updated. In fact, the bathroom is one of best I experienced while renting with Sea Gypsy. A large enough jacuzzi style tub to hold two people, the jets are a perfect touch when you want to relax in something a little more decadent than your usual garden tub. The shower is big enough to hold 4 people (not that that sounds realistic), and has a bench, you know, in case you get tired.
With 700 square feet to roam around in, the kitchen is large and fully stocked, and even includes beautiful granite counter tops. A King size bed, plenty of pool gear, and a lovely dining and living room area. There is even a terrace with chairs and a table in case you want to enjoy your morning coffee staring out at the view that lay before you: the ocean and the resort pool. But perhaps the most memorable part of your stay (aside from the swimming pool area) is the view of the pool from your floor-to-ceiling window.
Ocean Jewels
My final stay on the island through Sea Gyspy Vacation Rentals was at one of their three Ocean Jewels units. I chose the largest, since my mother was with me on my trip, and this unit has two-bedrooms. Though it doesn’t have a view of the beach, per se, the beach is only a three-minute walk (if that) from the unit. And best of all, it’s in the Times Square area, a.k.a. the downtown of the island. Literally steps from shopping, restaurants, and quick grub (and of course the ocean), you’re in the most desirable part of the island when staying at Ocean Jewels.
Owned by a private investor on the island, he is in his 60s and owns several units, which are naturally managed by Sea Gypsy. This 900 square foot unit has a king in one room, a full in the second and a sleeper sofa in the living room, and was just built in 2017.
The newly constructed apartment is quite chic and more comfortable and cozy than I’d originally anticipated when I saw the pictures online. Though it’s something I would expect to see more in a fast-paced city rather than a beach town, the comfort, quality and amenities are all there. Most especially the bed. Oh, that bed. How I loved that king bed in the master bedroom. I wanted to take that bed. I insist on knowing what kind of bed and mattress they were. They were divine, as was the rest of the unit – simply divine.
Overall, Sea Gypsy Vacation Rentals is spectacular and offers guests a variety that they can’t get elsewhere. From chic and elegant, to comfortable and affordable, there’s something for everyone, at every size, budget and location. Estero Island is certainly diverse, but Sea Gypsy Vacation Rentals absolutely capitalize on that, and showcase everything that the island has to offer. There’s absolutely no question that the next time I’m in the area, I’ll be staying with them again. There’s nothing better in my opinion, and I wouldn’t even want to try to find something else.
So when you’re in the greater Fort Myers area next, you know now where you need to stay. Just make sure that when you do book your stay with Sea Gypsy Vacation Rentals, you let them know Lisa sent you!
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