newhometest
Marathon · Key Colony Beach · Key West
Pull up to the dock. Everything else is already here.
Canal-front rental homes in the Florida Keys with a private pool out back, your own dock, and the bikes, kayaks, paddleboards and beach chairs already waiting for you. Booked direct with Meredith, who answers her own phone.
Text or call Meredith at (407) 733-2128
Start here
What kind of week are you planning?
Every one of our homes is on the water. Where they differ is what is waiting in the backyard, so start with the part your group cares about most.
Homes with a private pool
Twelve of our homes have a pool of their own. No shared resort deck, no hunting for a chair, and most can be heated or chilled on request before you arrive.
See the pool homesHomes with your own dock
Tie up out back and be fishing before coffee. Docks run from 30 to 100 feet, several are minutes from open water, and most have a fish cleaning station and bait freezer.
See the boater homesHomes for the whole crew
Ten to eighteen people, everyone in a real bed and usually with their own bathroom. Built for family reunions, three generations, and friends who travel together every year.
See the group homesHow it works
No inquiry forms. No waiting to hear back.
- 01 Pick the house
Browse by what your group actually cares about, or go straight to your dates. What you see is live availability, not a request waiting to be considered.
- 02 Book it right there
Choose your dates and book direct in a couple of minutes, with no platform service fee stacked on top. Every stay is booked with payment protection, so your money is covered from the moment you pay.
Would rather talk to a person? Text Meredith and she will walk through it with you.
- 03 Show up and start your week
The bikes, the boards, the beach chairs and the coffee are already there. Park the car, unlock the door, get in the pool.
Packed light on purpose
The stuff you would have had to rent is already in the garage.
Guests say this more than anything else in their reviews. You walk in, and it is all there.
- Kitchen stocked down to the spices, with coffee included
- Beach cruiser bikes for the whole group
- Kayaks and stand-up paddleboards
- Beach chairs, umbrellas, coolers and pool toys
- Bait freezer and fish cleaning station
- Pack-n-play, high chair, baby gates and kids’ dishes
- All linens, bath towels and beach towels
- Paper goods, soap and laundry detergent to start you off
- Cornhole, ping pong, giant Jenga and board games
Pool heat or chill can be added to most homes for a small fee. Just ask when you book, and it will be ready the day you get there.
We have rented other houses in the area with other agencies and have been disappointed. We will be a loyal client of both Blue Turtle and Pineapple Properties.
Cheri H. · February 2025
Who you are actually booking with
A small group of homes, on purpose.
I know the feeling of booking something you are not quite sure of and hoping for the best. That is the whole reason this company stays small.
Pineapple Properties is a local boutique company, and it stays that way on purpose. A short list of homes means every one of them gets real hands-on attention, and it means guests and owners can text me any time and hear back right away.
I am a fifth-generation Floridian. My first trip to the Keys was more than thirty years ago, when I was eighteen and went sport fishing with the legendary Captain Skip Bradeen out of Islamorada. That was it, I was hooked. My husband Barry and I vacationed down here for years while we raised our family in Winter Park, and once the kids were grown we moved to the Keys for good.
So when you ask me where to eat, where the fish are biting, or which beach is worth the drive, you are getting an actual answer from someone who lives here.
Meredith Tracy
Owner & Property Manager
In their words
The same families keep booking the same weeks.
★★★★★
“We ran out of dishwasher detergent and it was brought out right away. The water filter in the fridge needed to be replaced and this was done within a couple of hours of letting them know.”
Kendra M. · Thanksgiving week
★★★★★
“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 is by far the best house we’ve stayed at in The Keys. The pool chillers were the best after a day on the boat. Best stocked house ever!”
Morgan M. · Summer with the family
Where you will find us
Five places, all of them on the water.
- Marathon The heart of the middle Keys. Canal-front homes, Sombrero Beach and quick runs to the reef. See these homes
- Key Colony Beach Quiet streets you can walk at sunset, with the canal and your dock right behind the house. See these homes
- Duck Key Townhomes inside Hawks Cay, with Cabana Club beach, pool and tiki bar included. See these homes
- Key West Old Town and the Key West Golf Club, for couples who want to walk everywhere. See these homes
- Palm Beach Our one spot off the islands, a short walk from the beach with a heated pool. See this home
Before you book
The questions Meredith gets most.
- Can the pool be heated?
At most of our homes, yes, and several can be chilled in the summer too. It runs about $125 a week plus tax. Ask when you book and it will be ready the day you walk in.
- Can I bring my boat?
Most homes have a private dock or an assigned slip, anywhere from 30 to 100 feet, and several are minutes from open water. Each listing states the size it will take. Key Colony Beach has no on-site trailer parking, the city lot runs about $150 a week.
- What do I need to bring?
Clothes and groceries. Bikes, kayaks, paddleboards, beach chairs, umbrellas, coolers, linens, bath and beach towels, coffee and the kitchen basics are already in the house.
- Is there a minimum age to rent?
Yes. At most homes the guest signing the booking needs to be at least 30, and they need to be staying in the house for the whole reservation.
- Are pets allowed?
Most of our homes are not pet friendly, though a small number are. Check the individual listing, or just text Meredith and she will tell you what is open for your dates.
- What if I have to cancel?
Cancel more than 30 days before you arrive and you are refunded in full. Inside 30 days the booking is non refundable, so it is worth looking at travel insurance for a trip booked well ahead.
Not sure which house fits your group?
That is the easiest problem to solve. One text and she will point you at the right backyard, and she will tell you straight if she has nothing that fits your week.
(407) 733-2128