Plantation Key Holiday Rentals

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Holiday Rentals in Plantation Key

A 57-foot trawler in Islamorada
8.4 out of 10, Very good, 19 reviews
"Dated, but very clean. Niced friendly marina. Joe"
A 57-foot trawler in Islamorada
Capt Craig's 1 Bedroom /1 Bath Apartment in Islamorada, Florida Keys
9.6 out of 10, Exceptional, 8 reviews
"Although we only stayed one night, this place was clean and had everything we needed. It was centrally located and was perfect for us!"
The price is NZ$486
includes taxes & fees
17 Jun - 18 Jun
Capt Craig's 1 Bedroom /1 Bath Apartment in Islamorada, Florida Keys
Best Location for Your best vacation! June Special!
10.0 out of 10, Exceptional, 23 reviews
"My husband and I rented this property for the month of February 2024. It was conveniently located near Founder’s Park, Theater of the Sea, several restaurants, grocery stores, businesses and in a very safe and quiet neighborhood. Our daughter and her family visited for several days during our stay and the back of the property was great for entertaining. Although these owners reside on the premises they vacated the property during most of our stay so as to allow us our privacy as we enjoyed our...
Best Location for Your best vacation! June Special!
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Oceanfront Estate with Private 350 foot Pier, Heated Pool, Pet Friendly
9.4 out of 10, Exceptional, 79 reviews
"We had a fantastic vacation! It was like our own little resort! The house and pool were perfect. The view and the dock were amazing. We saw turtles, manatee, lobster, fish, birds and stingray! The host was very easy to communicate with and made sure we had everything we needed. We couldn’t have asked for a better place to stay!"
Oceanfront Estate with Private 350 foot Pier, Heated Pool, Pet Friendly
Breezy Palms Resort
2.5 star property
8.4 out of 10, Very good, 331 reviews
"For those who enjoy boating jet skiing is amazing!!!"
The price is NZ$300
includes taxes & fees
26 Jun - 27 Jun
Breezy Palms Resort
Mangrove Marina and Resort Aqualodge Houseboats
3.0 star property
9.4 out of 10, Exceptional, 316 reviews
"Wonderful weekend trip! Will definitely return. Staff was super helpful with advice about things to do while visiting. "
Mangrove Marina and Resort Aqualodge Houseboats
Amazing Ocean view at Ocean Pointe w/Heated Pool
9.6 out of 10, Exceptional, 9 reviews
"The condo was nicely decorated. The kitchen was well stocked with everything for cooking. The beds were comfortable and plenty of bath and beach towels. Bring your own necessities, tp, paper towels, shampoo, soap everything else was there! The pool and beach are fantastic! We enjoyed our stay and would definitely stay again!"
Amazing Ocean view at Ocean Pointe w/Heated Pool
VOTED BEST KEY LARGO VACATION RENTAL
10.0 out of 10, Exceptional, 63 reviews
"Norman is the best!!made us feel at home explained how to access all the amenities that came with the property The property was clean I always check for myself also we were a short drive from many other activities!!!"
VOTED BEST KEY LARGO VACATION RENTAL
Island Bay Resort
2.5 star property
9.8 out of 10, Exceptional, 75 reviews
"Quiet and tidy boutique property. Great little beach on property, across A1A is a convenience/gas store. Walking distance is a retail center with WinnDixie. Rooms are essentially individual cottage with kitchenette, walk in shower, TV and little front porch. Dock space for a boat, all water amenities and protected lagoon for floating. Tavernier is very quiet and an easy drive south to Islamorada and all the shoppping and dining. Friendly staff and good place to stay for extended time as well "
Island Bay Resort
Anchorage Resort & Yacht Club
3.0 star property
8.6 out of 10, Excellent, 262 reviews
"Very nice and quaint property with a very relaxing charm! We definitely recommend ❤️"
The price is NZ$411
includes taxes & fees
23 Jun - 24 Jun
Anchorage Resort & Yacht Club
Key Largo-Islamorada area-1 BR, 1 Bath -Privately Owned Condo -Fab Reviews!
10.0 out of 10, Exceptional, 139 reviews
"Very nice area, safe and secure. easy check in and out process. pool is nice and has a nice little beach close to condo. All the beaches near to area are not worth paying recommend sombrero beach and miami/ fort lauderdale beaches"
Key Largo-Islamorada area-1 BR, 1 Bath -Privately Owned Condo -Fab Reviews!
Two Panoramic Ocean Views from the Living room and Master Bedroom in this Condo
9.8 out of 10, Exceptional, 181 reviews
"Very nice view. Convenient. Low water pressure. Not sure if was an overall property issue or just unit. But not a reason for not recommending. Try Chef Michael’s restaurant. Best seafood meal we have had in US and comparable to our favorite place in Sardinia Italy!"
Two Panoramic Ocean Views from the Living room and Master Bedroom in this Condo
Oceanfront Property with Elevator, Lagoon and 2 Heated Pools
9.6 out of 10, Exceptional, 119 reviews
"My mom, my daughter, and I all stayed here and had a wonderful vacation. Such a beautiful place to stay inside and out. We enjoyed swimming in the pool and also just a short walk to the ocean. Lots of activities nearby. Only had one question about getting food delivered since it is in a gated community and the owner answered my question right away. If I ever go to Key Largo again I will stay here 🙂"
Oceanfront Property with Elevator, Lagoon and 2 Heated Pools
Beautiful Modern House in Key Largo
10.0 out of 10, Exceptional, 26 reviews
"Great access to multiple islands. No water access or dock in community. Very clean and comfy beds."
The price is NZ$819
includes taxes & fees
8 Jul - 9 Jul
Beautiful Modern House in Key Largo
Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool
9.8 out of 10, Exceptional, 27 reviews
"2-story condo in a gated community with 2 pools. There is a private oceanfront area for watching the sunset. Condo has a wonderful screened-in porch."
Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool
Ocean front 1/1,AMAZING OCEAN/MARINA VIEWS,Tavernier/Key Largo Fl. Florida Keys
10.0 out of 10, Exceptional, 236 reviews
"The place was fantastic. Balcony is very small, but not much can be done about that."
Ocean front 1/1,AMAZING OCEAN/MARINA VIEWS,Tavernier/Key Largo Fl. Florida Keys
Lady Blue Yacht in FL KEYS
7.0 out of 10, Good, 4 reviews
"We loved the experience until we couldn't access the WiFi for the television. There were a couple of wet places in the forward bedroom and bed, dirty underwear and shorts were left in the washer. We loved it though!"
The price is NZ$593
includes taxes & fees
28 Jun - 29 Jun
Lady Blue Yacht in FL KEYS
Beautiful Escape In Paradise
7.0 out of 10, Good, 2 reviews
"It took us little longer to find out how things worked. Only thing is the toilet had no water the last day"
Beautiful Escape In Paradise
New Tiny Home- Paddle Boards, Kayaks, Pool, Marina
9.6 out of 10, Exceptional, 33 reviews
"It was a beautiful home. They were very responsive. House was clean and it was great for a family with young kids. Location was close to everything we needed."
The price is NZ$765
includes taxes & fees
17 Jun - 18 Jun
New Tiny Home- Paddle Boards, Kayaks, Pool, Marina
Key Largo, Calusa, 2 bedroom 1.5 bath with screened in patio
9.2 out of 10, Wonderful, 59 reviews
"Dated RV that fulfilled our needs as an older couple. The host was wonderful! The grounds were very nice and the location made it easy for us to visit all the Keys. We had never lived in an RV before and the pull outs were nice. It had a few issues due to age, but we improvised and went with the flow. Enjoy your island time."
Key Largo, Calusa, 2 bedroom 1.5 bath with screened in patio
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See all available properties in Plantation Key
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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

Creekside Inn Islamorada
2.5 star property
8.0 out of 10, Very good, 1,000 reviews
"Excellent stay, friendly staff. Perfect boat dockside access!"
Creekside Inn Islamorada
Treasure Harbor
2.0 star property
9.4 out of 10, Exceptional, 29 reviews
"Clean, adorable house boat. Would definitely stay again."
The price is NZ$659
includes taxes & fees
14 Jul - 15 Jul
Treasure Harbor
Ragged Edge Resort & Marina
2.5 star property
9.4 out of 10, Exceptional, 128 reviews
"Just one word. Excellent!!"
The price is NZ$433
includes taxes & fees
16 Jun - 17 Jun
Ragged Edge Resort & Marina
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Plantation Key holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Plantation Key. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Plantation Key. Seeing all the best attractions is bound to make you fall in love with Plantation Key. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Plantation Key short-term rentals, that won’t be hard to do.

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