Vacation rentals in Deer Key

Renovated Anglers Reef 2BR + Sleeper + Ocean Views

Welcome to Anglers Reef, a bright coastal cottage in Islamorada, FL, with access to resort-style amenities. Enjoy a private boat slip, tropical pool, sandy beach, and walkable marina. Inside, relax in open living spaces, a fully equipped kitchen, and serene bedrooms. Unwind on breezy porches or explore nearby snorkeling, fishing, dining, and Keys adventures. Ideal for families, couples, and boaters seeking laid-back luxury. Thoughtfully designed for comfort, privacy, and effortless island life.

*New Luxury Beachfront* Kokomo Views-Private Beach

Welcome to Kokomo Views, a brand new condo steps from your own private beach with expansive ocean views due to unit’s close proximity to the water,an impeccable designer decorated 2 bedroom, 2 bath unit with fully equipped gourmet kitchen and upscale patio furniture over looking the crystal waters of the Florida Keys.This unit is equipped with washer and dryer, and custom designed closets. This luxurious costal retreat offers a private beach, pool access, tiki huts, and BBQ grills! Come join us!

Beach House, Private Pool, Dock, Gulf View Sunsets

You don’t come to the islands to stay in a town—you come to slow down. Welcome to our tropical keys beach home, tucked away from the traffic and noise of US Hwy #1. Sway with the palms on the wraparound deck, soak in wide-open panoramic bay views, and catch fiery sunsets right off your dock. Fire up the BBQ, brew a Keurig, float in the private pool, or cast a line from the 300’ private pier/dock. Easy going island living with ocean / gulf breezes, comfy beds, quality linens, Wi-Fi, and cable TV.

Water Views | Private Pool Oasis + Gazebo + Kayaks

Modern 4BR/4.5BA waterfront getaway in Marathon’s Coco Plum, set on a wide open canal with gorgeous water views—perfect for boaters, families, and friend groups. Spend your days in the huge private pool, relax under the gazebo, and come home to a newer, beautifully kept 2012 house designed for easy Keys living. 🏊 Huge private pool + gazebo (with poolside bathroom) 🛶 Kayaks included + big open-canal view ⚓ Pier-style dockage for your boat or rental boat 🌅 Wraparound covered porch for sunrise/

Key Colony Beach Waterfront 321

This unique home has a style all its own. Beautiful Island in Marathon: Key Colony Beach. Upgraded Home on a large canal, each side has a 3/2, each with its large garage, sharing an 80 ft dock where you can dock your boat & trailer. If you need the additional 3/2 home, please inquire (Totaling 2 homes, 6 rooms, 4 baths). Plenty of parking and one trailer per home. Canal opens to Ocean & Bay via Vaca Cut. Member of the amazing Gluntz Resort: Private Beach, Pool, bar & Restaurant (Havana Jack).

World-Class Oceanfront Pool/Hottub Sunset Escape

Escape to Oceans Cay Villas—luxury oceanfront in the Florida Keys. Why you’ll love the Islander: ✨ Heated swimming pool + Relaxing HOT TUB! ✨ Fire pit with perfect sunset views ✨ Fishing, snorkeling, and swimming in your backyard ✨ Free kayaks, paddle boards, and bicycles ✨ Walk or ride to Seven Mile Bridge ✨ Walking distance to restaurants and attractions ✨NO SEAGRASS SMELLS! ✨ Ping pong table ✨ Private dock for your boat ✨ Stylish, modern villa design ✨ Breathtaking SUNRISE and SUNSET views

*NEW!*Paradise Palms~Dock~Pool~Kayaks Grill~View!

🌴 Welcome to Paradise Palms!🌊☀️ This stunning 4-BR retreat has it all. Boating right from your private dock, easy open-water access, waterfront views, unwinding in your private heated pool🔥 Fire up the grill for a sunset BBQ, challenge friends to cornhole or game room fun, and set off on a kayak adventure right from your backyard! Paradise Palms is the dream getaway your family & entire group won’t want to leave! 🌅🏝️✨ Don't wait 'til it's booked! Secure your stay at Paradise Palms today!

Captain’s Quarters Ahoy Mateys! Florida, Keys

This is located at the Florida Keys in Key Colony, Marathon. It is a spacious two bedroom, two bathroom duplex surrounded by water. It is a renovated beauty and close to the best restaurants and the tranquility of this city. It is the perfect getaway where you can recharge your exhausted batteries. Captain’s Quarters is a clean and spacious base camp location for the many adventures that await you in this amazing location. Water views and the accessibility to the best fishing in the world.

Coco Plum Paradise - Marathon 5 BR 4 BA Waterfront

Entire Waterfront Home. 5 Bedroom, 4 Full Baths, Heated Pool with attached Soaking Tub, Tiki Hut with bar and seating, Ample Parking, Big Fenced Yard, First and Second Floor Covered Balconies, 110' waterfront with 80' Dock, 5 Minute Walk to Beach, 10 Minutes to ValHala Sand Bar, on a 200' Wide Canal. Licensed to sleep up to 12 guests; 5 King Beds, 1 Pullout Sofa Bed. Outdoor 4 lounge chairs, 12 adirondack chairs. Fully stocked kitchen. Beautiful location. License No. VACA-22-157

Waterfront Home 37.5-ft dock, Cabana Club Included

Bright, Open Floor Plan with new floors & kitchen. East facing for sunny mornings and shady afternoons on the great screened porch. Two roomy bedrooms and 2 full baths. Plenty of parking on the paved driveway. Perfectly located with the boater and angler in mind on a 37. 5 ft concrete dock, on deep & wide canal. Here on Key Colony Beach you can walk or bike the entire city to the marina, Sunset Park, 3 restaurants, play golf, tennis, pickle ball, bocce ball, horseshoes & basketball.

P98 - 75ft dock with shore power, 4 bed, 4 bath ho

75-foot dock with shore power 30 and 50amp This fabulous 4 bedroom, 4.5 bathroom home was designed and built for comfort and style with extra attention given to each and every detail. This property is warm and inviting and located in the desirable neighborhood of Sombrero Beach. This home is perfectly positioned on the property to maximize full use of the grounds, providing ample parking in the front, while creating an abundant outdoor living space in the back.

Boat Dock+King Bed & Cabana Club

2 Bedroom 2 Bath Master with King Bed and Private Bathroom Central Air Conditioning Waterfront Dock with Private Boat Slip on the 7th Street Canal Cabana Club Tiki Bar with Beach Hot Tub and Junior Olympic Pool Patio with Propane Grill Patio Furniture and Sun Lounges Fully Equipped Kitchen and Coffee Bar World Class Sport Fishing Coral Reef Diving and Snorkeling Water Sports Kayaking and Sandbars Crane Point Hammock and Nature Center