I’ve been to the Keys a handful of times. The first time was when I was dating my now husband and the second was a quick jaunt with the family over Labor Day weekend. This most recent time I was able to see the Keys from yet another perspective, with the well-thought-out planning of Ocean Sotheby’s International Realty.
DAY 1 – ISLAMORADA
Our day began with a warm welcome at the Islamorada Sotheby’s International Realty office followed by a delicious lunch catered by Sea Grapes Wine Bar & Bistro.
We had an opportunity to meet the many talented agents making up Ocean Sotheby’s International Realty’s Islamorada office.
After a tour of the adjacent Roberto Russell art gallery, we headed out to tour some of the available properties.
As we traveled from home to home Nikki, Maria, and the many agents we spoke with enlightened us with interesting facts about the history of Islamorada.
FIRST STOP
Located within Penn Key Club, the first home we toured has been completely remodeled and is ah-mazing. From the uber sleek kitchen to beautiful screened in patios that bring the outdoors in (did I mention the phenomenal bath tile?!), this 4 bedrooms 3 bath home is gorgeous.
SECOND STOP
A more traditional take on a Keys, this Terracotta tiled home backs right up to the bay. After enjoying the lime-ade from Bad Boy Burrito, we learned about the world-renowned fishing that is to be had in the Keys.
THIRD STOP
Southern Comfort, a beachfront home, housed not only a master bedroom with the most breathtaking views but a very cool pop up shop courtesy of Island Trendz. Keys fashion is all about going from the beach, bay, or pool to the bar with ease. The clothing, jewelry, and bags were on point with what I would imagine someone living in the Keys would wear.
LAST BUT DEFINITELY NOT LEAST
We arrived at our “home” for the next two evenings – aptly named the “Hidden Gem”. Located on Marathon Key, this 8 bedrooms, 10 full bathrooms, and 3 half bathrooms family compound was even more breathtaking in person than in the photos I pored over before the trip.
We stayed in the guest house – 2 stories, 4 bedrooms, 2 kitchens, 2 living areas, 4.5 baths – AMAZING.
I could totally see a family purchasing this home as their vacation home. There are enough rooms for the immediate – and extended – family, with an outdoor oasis that would make me want to be outdoors forever!
The beach entry pool offers a swim-up bar underwater stools, bridge, and waterfall. My husband would be at home cooking in the outdoor kitchen with a full-size fridge, amazing grill and smoker…I can only imagine the great times a family could have!
Did I mention the tennis court?
Be sure to watch out for my article all about Day 2!
Becca says
K, this is amazing!!!
Sounds and looks like the best trip!!
Can we talk about a GUEST HOUSE being 2 stories with 4 bedrooms and 2 kitchens? Sign me up!!
Dana says
LOLOLOL Becca! I know…the guest house is nicer than my real house!!!
Ann Snook-Moreau says
What gorgeous properties! Hidden Gem is amazing . . . I don’t know if I even know enough people to fill it though haha.
Dana says
LOLOLOL!
Frank says
Wow, beautiful home you got to stay in! I also love the artwork by Roberto “Pasta” Pantaleo! Thank you for sharing.
Dana says
Those are just two of the many gorgeous pieces by Pasta! Wait until Day 3 – we were lucky enough to spend some time with Pasta and talk about what inspired him to start painting!
Ann Snook-Moreau says
I’ve never visited the Florida Keys but I am dying to go. It looks like such a relaxing and unique place and I’d love to spend my trip in one of these beautiful homes!
Dana says
Ann, you have to go! You can rent some of the homes (or buy one 😉 )
Heather says
In my opinion the best part of any vacation is the food, and yours looked amazing!
Dana says
The food is a HUGE part of any vacation – I completely agree with you, Heather! The food was amazing…wait until you see Day 2 and Day 3!
Lili says
Wow! How luxurious! Dying to go to the Florida Keys now!
Dana says
Lili, you should go! It’s such a great vacation spot and an even better place to have a vacation home 😉
LaDonna Maxwell says
Breathtaking! I’ve been to Florida many times, but never the keys. Now I want to go!
Dana says
Make sure you take some time to visit the Keys when you’re back in Florida, LaDonna!
Jessica Taylor says
Wow! Those properties are amazing! I’d love to visit one, even if just for a day!
Dana says
Jessica, you should definitely add the Keys to your bucket list!
Nancie says
Are you planning on buying one of these houses? They are lovely.
Dana says
Nancie, I would love to!
Brittany Vantrease says
Maybe I can convince my husband to go on a second honeymoon… it all looks so beautiful!
Dana says
Now this would be the best place for a second honeymoon!!!
Brittany says
This looks like such an awesome experience. Thank you for sharing these rad photos!!!
Dana says
My pleasure, Brittany!
Greg Poland says
It was great to meet you & share some of our rich fishing history while you were in town. Next trip I hope you can join me out on the water either to catch a fish for an echo tour into the everglades. Bring the family for a trip to the world famous sandbar or alligator lighthouse. http://www.Gregpoland.com
Dana says
Greg, I would love to join you! What’s an echo tour?!
Preet says
What a fun and great experience you had. The place is such a great spot!!
Mom Life Optimizes says
I would love to visit the Keys! I’ve never been down there but Ink ow there is so much to see.
Dana says
There is so much to see and do, and it’s also very relaxing!
kourtnie says
Love the images you shared! Each space is gorgeous in their own way. I’m so glad that you had a great time.
Larrisha Hester says
Everything looks so beautiful and relaxing. I have been on vacation in Florida but never to the Keys.
Lisa Rios says
I love that beach view, and that guitar is so cool. I would love to go. Take me with you next time haha
Dana says
I’d love to, Lisa! 🙂
Ruth I. says
These properties are top notch. I think that just by looking at how the exteriors are well detailed and the interiors are arranged. The trips must be worth it.
Emma Riley says
Those properties are amazingly beautiful maybe if I see in this in person the first word that will come out into my mouth is the word “WOW”. Definitely a nice trip and it’s all worth it.
aisasami says
Ooooh, the Keyd! I have to share this with my parents, they are taking my sister to college next week in Northern Florida. Maybe your luxurious pictures could help persuade them to take a little trip to the Keys to relax and enjoy!
Dana says
Your parents will need a vacation after dropping your sister off at college and the Keys is perfect!
Princess Quinn says
Everything in this place looks extra ordinary. The interior looks amazing and intricate.
Becca Holloman says
This looks like it would be such an amazing time and trip. I love to see the inside of that place, so beautiful!
Dana says
Becca, it was awesome!
Claudia Krusch says
Sounds like an amazing trip! Loved seeing your pictures! It looked like a great event!
Dana says
Thanks Claudia!!
Heather says
We are headed to the Keys next month and I can’t wait. I love the vibe there!
Chai says
hmm.. Images show a great vacation you have. Thank you for sharing this experience with Ocean Sotheby’s International Realty’s. It is so inviting, specially the idea of relaxing tour.
Dana says
I’m glad you enjoyed the post, Chai! I loved the tour and OSIR is the best!
Sayanti says
These are some really gorgeous properties and luxurious too. I hope they are equipped with all the necessary amenities.
Dana says
Sayanti, they have everything you could ever need AND more! I wanted to move in!
LiveLoveAndAdventure says
I have never been to the Florida Keys before but it’s on my list of places to visit for Scuba Diving adventures. The diving there is supposed to be amazing!
Dana says
The Keys are famous for their scuba diving! I hope you get to go!
Charli Bruce says
What an amazing place to stay, that guest house is amazing!
Jocelyn @ Hip Mama's Place says
I have been to the Keys and Islamorada a couple times in the early 2000’s and I’ve enjoyed each visit. Those properties from Sotheby’s definitely look amazing!
Megan Jones says
Your photographs are magical. They really brought these properties to life. I’ve visited the Keys many times on dive trips but had no idea there were so wonderful places tucked away. I guess I need to spend less time on the Dive Boats and explore!
Dana says
Thank you, Megan! I’ve yet to go diving off the Keys but I heard it is amazing!
Danny says
Hello from key largo Dana, I love your pictures especially the southern comfort beach resort, IM dreaming over here: )
Dana says
Hi Danny! I love the Keys! Do you live there year round?