Travel

Experiencing the Keys With the Best – Ocean Sotheby’s International Realty Day 1

Ocean Sotheby's International Realty Office

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.

aperol spritz

Salad, Tart and Dessert

We had an opportunity to meet the many talented agents making up Ocean Sotheby’s International Realty’s Islamorada office.

OSIR Team

After a tour of the adjacent Roberto Russell art gallery, we headed out to tour some of the available properties.

Amazing artwork by Roberto “Pasta” Pantaleo

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.

Penn Key Club Kitchen

Penn Key Club Living Room

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.

Southern Comfort Exterior

Southern Comfort Backyard

Southern Comfort SignOcean Dayz Bags

Ocean Dayz Jewelry

Ocean Dayz Fashion Pop Up

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.

Hidden Gem entryway

Gorgeous kitchen!

We stayed in the guest house – 2 stories, 4 bedrooms, 2 kitchens, 2 living areas, 4.5 baths – AMAZING.

Master bedroom in the guest house!

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?

Hidden Gem Tennis Court

Be sure to watch out for my article all about Day 2!

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53 Comments

  1. 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!!

    1. LOLOLOL Becca! I know…the guest house is nicer than my real house!!!

  2. 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.

  3. Wow, beautiful home you got to stay in! I also love the artwork by Roberto “Pasta” Pantaleo! Thank you for sharing.

    1. 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!

  4. 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!

    1. Ann, you have to go! You can rent some of the homes (or buy one 😉 )

  5. In my opinion the best part of any vacation is the food, and yours looked amazing!

    1. 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!

  6. Wow! How luxurious! Dying to go to the Florida Keys now!

    1. Lili, you should go! It’s such a great vacation spot and an even better place to have a vacation home 😉

    1. Make sure you take some time to visit the Keys when you’re back in Florida, LaDonna!

  7. Jessica Taylor says:

    Wow! Those properties are amazing! I’d love to visit one, even if just for a day!

    1. Jessica, you should definitely add the Keys to your bucket list!

  8. Are you planning on buying one of these houses? They are lovely.

    1. Now this would be the best place for a second honeymoon!!!

  9. This looks like such an awesome experience. Thank you for sharing these rad photos!!!

  10. 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

    1. Greg, I would love to join you! What’s an echo tour?!

  11. What a fun and great experience you had. The place is such a great spot!!

    1. There is so much to see and do, and it’s also very relaxing!

  12. Love the images you shared! Each space is gorgeous in their own way. I’m so glad that you had a great time.

  13. Everything looks so beautiful and relaxing. I have been on vacation in Florida but never to the Keys.

  14. 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

  15. 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.

  16. 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.

  17. 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!

    1. Your parents will need a vacation after dropping your sister off at college and the Keys is perfect!

  18. Princess Quinn says:

    Everything in this place looks extra ordinary. The interior looks amazing and intricate.

  19. 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!

  20. Sounds like an amazing trip! Loved seeing your pictures! It looked like a great event!

  21. We are headed to the Keys next month and I can’t wait. I love the vibe there!

  22. 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.

    1. I’m glad you enjoyed the post, Chai! I loved the tour and OSIR is the best!

  23. These are some really gorgeous properties and luxurious too. I hope they are equipped with all the necessary amenities.

    1. Sayanti, they have everything you could ever need AND more! I wanted to move in!

  24. 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!

    1. The Keys are famous for their scuba diving! I hope you get to go!

  25. 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!

  26. 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!

    1. Thank you, Megan! I’ve yet to go diving off the Keys but I heard it is amazing!

  27. Hello from key largo Dana, I love your pictures especially the southern comfort beach resort, IM dreaming over here: )

    1. Hi Danny! I love the Keys! Do you live there year round?

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