Holiday houses in Plantation Key

Island Sanctuary Islamorada

Stay aboard the eco-friendly two-story 63 ft River Queen with a 360 degree view with beautiful sunrises and sets, mored 1/8 mi offshore in a quite harbor close to shopping center, movie theater, hospital, bars & restaurants. A 10-foot dinghy with small outboard to come & go from shore "ONLY", nowhere else. I also offer Personal Training, deep tissue work & Life Coach sessions. I live on the vessel about a hundred yards from you so if there are any questions, etc. I will be there to assist you.

Sunrise Escape - Ocean Front Villa - Sleeps 10

Wake up to the sunrise over the ocean and unwind with sunset views from your private jetty. This marina-front, ocean-view townhouse in Kawama Yacht Club puts you steps from kayaking, snorkeling, and the best of the Keys. Spacious, stylish, and designed for unforgettable family and friend getaways. Breathtaking sunrises from one of two private terraces, coffee in hand, overlooking the marina and the Atlantic Ocean. Located in an exclusive, quiet section of Kawama Yacht Club, this beautifully po

OceanView 2/2.5 w Beach Pool & Marina Islamorada

Everything you need for your Islamorada vacation is here including 2 gorgeous private beaches, kayaks, paddle boards, heated resort style pool, porch seating with ocean view, and 2 balconies. Located in the middle row of Anglers Reef, this home accommodates up to 6. Boat slip can be reserved for additional fee, if available. REELaxation is our only vacation rental and with an extensive background in customer service, extraordinary guest service and helping to make lifetime memories are our goal.

Baycation Houseboat • Florida Keys Waterfront Stay

Escape to the laid-back luxury of the Florida Keys aboard your own floating oasis. This fully equipped houseboat offers the perfect blend of comfort, adventure and true waterfront living. Wake up to breathtaking sunrises, sip your morning coffee as the marine life glide by, and fall asleep to the gentle sway of the water. Whether you’re celebrating something special or simply craving a one-of-a-kind getaway, this houseboat is the ideal home base for both keys adventures and peaceful retreats 💫

Cottage By The Sea

Cottage By The Sea...! If you love turtles.This is the spot for you.I have a 150 pound giant sulcata tortoise in the front yard.And then I have four other little turtles that live in an enclosement , also in the front yard and a giant snapping turtle in my koi pond Our 2 bedroom Guest House is located on the Oceanside of Key Largo in a quaint and quiet neighborhood, with a huge yard surrounded by exotic flowers and trees. It is walking distance to a famous local's Tiki Bar and Restaurant

Perfect escape to the ocean

Enjoy the sounds of nature when you stay in this unique place. What awaits you is fun filled days living and exploring out on the fabulous florida keys waters in your own private floating paradise that is completely solar powered and all the amenities run 24/7! This fabulous floating home was build in 2025 and very nice, update and comfortable, it is 100% solar powered and eco friendly All the amenities run off batteries and solar power so you'll be able to enjoy cold ac, fridge, tv , 24/7

Flakey's

Flakeys, short for Florida Keys is everything you would expect to find on the small Caribbean island. Its paradise! Located in the heart of Islamorada there is no need for a car. You can walk or bike to the best restaurants, bars, beaches and shops this island has to offer. On Morada Way in the middle of the Art and Culture district. Everything at Flakeys is brand NEW! All new appliances, furniture and decor. Shabby Island Chic! Affordable, super clean and you can't beat the location.

360 DEGREE WATERVIEW HOUSEBOAT

IMPORTANT Enjoy your own private retreat aboard a solar and wind powered houseboat moored 1/2 mile from land in the beautiful Islamorada Please do not arrive after dark and NO night riding. Need experience with hand pull outboard motors a 12 foot skiff with a 6hp outboard motor is provided reliable to go back and forth from shore NOT reliable for exploring No hot water on shower, heat water in Tpots or Solar bags. Please shave before arriving No suitcases, least amount of cloths.

Islamorada Waterfront House on Canal w Boat dock

BEST Location in the Florida Keys! 🌴 Waterfront 3/3 home on a Bayside canal in the Village of Islamorada. 60ft of canal frontage to park boat. Unique two-story layout perfect for two families or one big family. Private living space downstairs AND upstairs. Wifi, Roku TVs, quartz kitchen, BBQ, garage, trailer parking, bikes included. Pets welcome. Free access to Founders Park pickleball, beach & dog park. Book and explore paradise! 📸 Insta as keyshouses Monroe Tax ID #137670

Ocean Pointe Condo | Beach, Pool, Hot Tub & Tennis

Stylish, fully remodeled end-unit condo in Ocean Pointe — steps to the beach! ☞ Resort access (pool + hot tub) ☞ Private beach access w/ sun loungers ☞ Fully equipped + stocked kitchen ☞ Smart TVs + bluetooth sound system ☞ Workspace + 350 Mbps wifi ☞ Tennis/pickleball courts ☞ BBQ grill + picnic tables ☞ Parking lot (2 cars max) 5 mins → DT Tavernier (cafes, dining, shopping) 15 mins → John Pennekamp Coral Reef State Park

5-Star Sandy Beach Sunsets & Pool in Best Location

Come immerse your body, mind, and soul in soothing waters that surround our Florida Keys paradise. Amazing sandy beaches, sunset fishing pier, new heated pool, and modernized clubhouse. Best community for fun activities! We offer as is bikes, kayaks, and many more amenities. Semi-private backyard. Sleep in 2.5 separate bedrooms and 2-bed loft. Nice bedding & towels. 2 desk/office areas w/ fastest fiber optic.

Fishing Getaway | Dock, Pool & Sunrise

Wake up to breathtaking oceanfront sunrises in the Sportfishing Capital of the World. This luxury 3BR, 3BA townhome in Islamorada features a private dock, waterfront resort-style pool, and a quiet gated community just minutes from the Keys’ best fishing, marinas, restaurants, and attractions. Pet-friendly and fully equipped, it’s the perfect escape for anglers, families, couples, and extended stays.