Plantation Key Vacation Rentals from CA $114: Short-Term Rentals for 2025

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Vacation Rentals in Plantation Key

"From the very moment i reached out to the host he was extremely friendly and very accommodating. The property was absolutely perfect for what we needed and we loved having the dock and water access. The property is very clean and well maintained. There are plenty of trash cans and more than enough space for large families. I stay in a vrbo property every year and i will be back this was our favorite !by far our favorite. "

"The property is central location in Islamorada, best location....The outdoor area is perfect,pool heated very enjoyable.. great neighborhood..Friendly Host JoAnn is amazing, and prompt response, a delightful person, and a wonderful host!"

" the location of the house is wonderful. The layout of property is spectacular and the views are outstanding however, it’s time for the owner to spend a little bit of the 10,000 a week on some routine maintenance. For example, the pool heater does not operate by thermostat only full on or full off. the hot tub has no jets and you are unable to make it hotter than the pool( this is a know issue by the owner),no operating lighting in the pool and there should be handrails near the steps of the...

"Expedia let me down. I ordered a room with two beds, and when we arrived, they gave me a room with a king bed. We are two hetero men on a fishing trip, and we were not really wanting to share a bed. BP blamed it on Expedia and said they couldn't give me a different room and said they didn't have another room with two beds to give us anyway. They did give us a roll-away bed, but the couch was more comfortable! We toughed it out in the King bad, but that was a bad start to the stay! "

CA $245 total

includes taxes & fees

May 13 - May 14

2 outdoor pools, open 8:00 AM to 6:00 PM, sun loungers

"The property was amazing & our Villa was exceptional! We had a wonderful time! The staff & service they provided was exceptional! They took care of our every need & were very prompt. The Villa was super clean & looked like it was brand new. Having stayed at many high end properties in Islamorada, this was the best! "

CA $1,008 total

includes taxes & fees

May 4 - May 5

"Love this place! Very friendly and secluded. Not your typical resort-look elsewhere if that’s what you want. But if you want a friendly private sailing camp where you hang out with other fun people and like to sail and kayak, this is absolutely it! The use of the sailboat alone more than pays for the room."

Private beach, sun loungers, beach umbrellas, beach towels

"This place was absolute paradise. From the moment you enter the gate to the second you leave, it is an absolute dream. It’s a tropical paradise but even better because it’s so small and so intimate. The beach is quiet and never too busy. The cottages are absolutely adorable and meticulously clean. The bay is AMAZING. We had coffee on our porch every morning with the friendly little lizards. We kayaked and saw green iguanas in the mangroves. We fed the snappers off of the dock. Our last day at...

"This property is amazing. Close to everything and has everything you need."

"Word can not explain the place everything was the best and would stay again and again "

CA $393 total

includes taxes & fees

May 1 - May 2

"We had such a nice time at the Windley Cottage. The owners effectively communicated information about the home and check in before the stay, making arrival very easy. The home was very clean and had everything that we needed. The Anglers Reef area was nice and quiet. We enjoyed walks to the docks, kayaking, and swimming in the pool. We absolutely loved Islamorada and hope to visit again!"

"This home was the perfect place and location for our Key Largo visit. The owner and property manager were both excellent at communicating check-in and property details. We were 3 adults and the tiny home size was perfect for us. We had access to a community pool which looked wonderful. Only one minor issue was the shower water pressure was low but there was a very clean community bath house with private showers we used which worked out even better as we were all able to take a shower at the...

CA $500 total

includes taxes & fees

May 14 - May 15

"This property was very clean and comfortable, and the property manager was super responsive when we had questions. I would definitely recommend this rental to family and friends!"

"great time"

CA $298 total

includes taxes & fees

May 1 - May 2

"2 Grandparents,2 Parents, and 2 Kids had a great spring break full of adventures with this as our home base. It was very nice! Clean and handy. Beach area was small and surrounded by mangrove forest. The pool was great. The balcony was not kid safe for a 4 year old, so maybe BYO kid exclusion device/gate, if applicable. It could have used another comfortable chair. Just had a small couch. "

"Thank you for the great place and hospitality "

CA $607 total

includes taxes & fees

May 17 - May 18

"Really nice place, no surprises. Location was excellent and pictures and description very accurate. Unfortunately, the weather was not in our favor but can't control that! Would definitely stay here again."

CA $490 total

includes taxes & fees

May 6 - May 7

"Absolutely wish we had more time there. Wonderful place to stay!"

On the beach, sun loungers, beach towels

"The place was perfect for us and was exactly like the pictures! We had everything we needed for our stay. The pool and pool bar were very nice. We loved the location close to great restaurants and boating activities as well as a drive to Key West. When we come back we will definitely stay here again. "

"We were looking for a ni e quiet get and thats what we got. It was nice and clean condo. The manager and stsff were grrat as well. Our only disappointment was that there was no sandy beach. There was a coral sand walk way and a nice coral sand beachy area at the land locked lagoon within the community. That disappointment was more due to our lack of knowledge of the area. Sandy beaches arent really around in the keys. Other than that everything was fantastic. "

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Other types of properties in Plantation Key you may be interested in

"This was an amazing stay. I loved the low key vibe, the canal and views. Well stay again 100%"

CA $260 total

includes taxes & fees

May 11 - May 12

25-inch flat-screen TV with digital channels, TV

"Nice property on a cove. We were only here one night but the place was clean and had everything needed for a longer stay. Enjoyed the gentle rocking at bedtime. "

CA $443 total

includes taxes & fees

May 28 - May 29

3 restaurants, breakfast, lunch, dinner served; American cuisine

"We had the most amazing time. The food was great. Family friendly atmosphere and friendly staff Great vacation vibes with music and bar right by the poolside . Beach and water sports right on the property was a plus! Definitely coming back again very soon!"

CA $521 total

includes taxes & fees

May 4 - May 5

Find out more about Plantation Key

Everything you need to know about Plantation Key vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Plantation Key vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Plantation Key vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Plantation Key vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Plantation Key. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Plantation Key vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Plantation Key vacation rentals we have selected for you start as low as CA $114 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Plantation Key rentals

At Expedia, we put the best Plantation Key vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Plantation Key rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Plantation Key vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Plantation Key. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Recent reviews of Plantation Key properties

5/5 Excellent

"Absolutely breath taking experience. The only thing I would recommend is for the property to have coffe and water available around the clock and for the pool to stay open past sun down."

A verified traveller from Pinellas Park stayed at Amara Cay Resort

Posted 3 hours ago