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Boutique by design. Personal by nature.
Handpicked vacation homes in the Florida Keys and Palm Beach.
A small, carefully chosen collection, each home with its own setting, personality and amenities. Book direct with Meredith, who knows every one of them personally and answers her own phone.
Text or call Meredith at (407) 733-2128
Start here
What does your perfect vacation look like?
Every vacation looks a little different. Whether you are dreaming of days on the water, afternoons by the pool or the beach, time with the whole family, being close to everything you came to see, or some combination of all of it, start with what matters most to you.
Homes with private pools and docks
Twelve homes in our portfolio have private pools, and all of our homes have pool access. Most pools can be heated, and some chilled, for a modest fee.
See the pool and dock homesHomes for large families and groups
From ten to twenty people, enjoy everything together. Built for family reunions, three generations, and groups of friends who travel together every year.
See the group homesKey West homes
From a condo for two to a three bedroom townhome, all have pool access and all the amazing activities Key West has to offer.
See the Key West homesPalm Beach
Our tiny condo for two, nestled in a hundred year old historic building on the fabulous island of Palm Beach. Walking distance to everything, including the beach.
See the Palm Beach condoHow it works
Your vacation is just a few clicks away.
- 01 Find your perfect stay
Browse our homes, check your dates and see live availability. No inquiry form, and no waiting to hear back.
- 02 Book direct and save
Choose your dates and book securely online in just a few minutes, without the hefty booking fees charged by the big platforms.
Would you rather talk to a person? Text or call Meredith at (407) 733-2128 and she will help you find the right property and walk you through the booking. She can also take payment by check if you prefer.
- 03 Arrive and start enjoying
Unpack, settle in and make yourself at home. Then do whatever you came to do. Get out on the water, head to the beach, relax by the pool, explore the area, or simply do absolutely nothing.
Settle right in
We have already taken care of the little things and the big things.
Every Pineapple Properties home is well prepared and thoughtfully stocked with the everyday essentials that make vacation easier from the moment you arrive. Fresh bed linens, bath and pool towels, paper towels, toilet paper, hand and dish soap, dishwasher and laundry detergent, and basic cleaning supplies are all provided.
And that is just the beginning. Depending on the property you choose, you may also find extras like:
- Beach cruiser bikes
- Kayaks and stand-up paddleboards
- Beach chairs, umbrellas, coolers and pool toys
- Bait freezers and fish cleaning stations
- Ice makers
- Pack-n-plays, high chairs, baby gates and kids’ dishes
- Cornhole, ping pong, giant Jenga and board games
- Complimentary coffee
Each home has its own amenities, so check the individual property listing to see everything that is included with your stay. At properties where pool heating or chilling is available, it can be added for a modest additional fee. Just ask when you book and we will make sure it is ready for your arrival.
From the moment we arrived to the moment we left, we had permanent smiles on our faces! The home is lovely and well appointed, with so many amenities.
Mary C. · August 2026
Meet Meredith
Boutique by design. Personal by nature.
Pineapple Properties is a local boutique vacation rental company with a thoughtfully curated collection of homes throughout the Florida Keys, along with a special retreat in Palm Beach. I believe the best vacation rental experience comes from knowing the homes, knowing the destinations, and being there when my guests need me.
That is why I stay personally involved with every property I manage. When you have a question before your trip, need something during your stay, or simply want a recommendation for dinner, you are not calling a call center. You are reaching me.
I am a fifth-generation Floridian, and my love affair with the Keys started more than forty years ago on my first trip here, when I was eighteen and went sport fishing with the legendary Captain Skip Bradeen out of Islamorada. I was hooked. My husband Barry and I vacationed in the Keys for years while raising our family in Winter Park, and once our children were grown we made the Keys our home.
So whether you are planning a laid-back stay in the Florida Keys or an escape to Palm Beach, you are booking with someone who knows her properties personally and genuinely wants you to have a wonderful stay. And when you want to know where to eat, what to do, or how to make the most of your time here, I am always happy to share my favorites.
Meredith Tracy
Owner & Property Manager
In their words
Our guests say it best.
★★★★★
“I’ve been coming to the keys for over 30 years for lobster season. This is the best house and the best service I’ve ever had.”
Philip G. · Lobster season
★★★★★
“This house had EVERYTHING and then some! Every time I thought, I wish I had packed ___, I would look around and realize the house already had it. Super clean, beautifully kept, and incredibly well stocked.”
Ryan L. · August 2026
★★★★★
“This condo is in a perfect location on the island, is true to its photos, and comes with everything you could possibly need for a long weekend away. Meredith is an excellent host!”
Lauren · Palm Beach, February 2026
Where you will find us
Find your favorite place.
From the laid-back islands of the Florida Keys to the timeless charm of Palm Beach, each of our destinations offers its own way to experience the Florida lifestyle. Where will you make yourself at home?
- Marathon The heart of the Florida Keys. Easygoing, family friendly and surrounded by water, Marathon puts you close to Sombrero Beach, boating, fishing, waterfront restaurants and everything there is to love about the Middle Keys. See these homes
- Key Colony Beach A little island with a lot to love. Quiet, walkable and wonderfully relaxed, Key Colony Beach has a true neighborhood feel, with beautiful sunsets, nearby dining and easy access to everything the Middle Keys have to offer. See these homes
- Duck Key Island living with a resort feel. Duck Key combines laid-back island living with beautiful surroundings. Enjoy access to The Cabana Club’s beach, pool and tiki bar. See these homes
- Key West Colorful, historic and unmistakably Key West. Come for the restaurants, nightlife, history, architecture and one-of-a-kind island personality, and discover why people fall in love with Key West and keep coming back. See these homes
- Palm Beach Palm Beach style, Pineapple hospitality. Our Palm Beach retreat brings the Pineapple Properties experience to Florida’s Atlantic coast, with beautiful beaches, exceptional dining and shopping, and the unmistakable style of Palm Beach just outside your door. See this home
Before you book
Questions we get a lot.
- Where are your vacation homes?
Most of our homes are in the Florida Keys, in Marathon, Key Colony Beach and Duck Key, with several in Key West. We also have one condo in Palm Beach on Florida’s Atlantic coast.
- Do the homes have pools?
Every one of our homes has pool access, and twelve have a private pool of their own. At homes where pool heating or chilling is available it can be added for a modest fee. Just ask when you book.
- Can I bring my boat?
Several of our Keys homes have a private dock or an assigned slip, and the listing for each one tells you the length it will take. Not every home has dockage, so check the property page or ask Meredith before you book.
- Are pets allowed?
Most of our homes are not pet friendly, though a small number are. The house rules on each listing say for certain, or text Meredith and she will tell you what is open for your dates.
- Is there a minimum age to rent?
Yes. The guest signing the reservation needs to meet the minimum age for that home and stay in the house for the whole booking. The age is listed in the house rules on each property page.
- What is the cancellation policy?
Cancellation terms are shown on each property page before you book, and you will see them again at checkout. If you are booking well ahead, travel insurance is worth a look.
Not sure which home is right for you? Ask Meredith.
Tell her what you are looking for, who is coming, and what matters most to you. Meredith knows her properties personally and will help you find the home that fits your vacation best, with an honest recommendation every time.
(407) 733-2128