Vacation rentals with a kayak in Vaca Key

Sunset Key Escape/Pool, Dock, Kayaks & Gulf Access

Welcome to Sunset Key Escape Your Private Waterfront Retreat in Marathon Bask in the beauty of the Florida Keys at Sunset Key Escape, a stylish and serene 3 bedrooms, 3 bathroom waterfront getaway designed for comfort, adventure, and unforgettable views. Whether you are unwinding poolside, launching a kayak at sunrise, enjoying dinner by the water under the stars, or challenging friends and family to a ping pong match, this home offers a true Keys escape surrounded by nature and coastal charm.

Salt&Seaglass. Key Colony. Screen Porch. Pool Club

This Key Colony Beach home is a welcoming, modern canal-front duplex home provides a relaxing and comfortable atmosphere for your vacation in the Florida Keys! The home features 2 large bedrooms and 2 bathrooms, a modern kitchen with large island and granite counter tops, a master bedroom with private bathroom and modern, plank flooring tile throughout the home. Enjoy the relaxing 9 X 20 ft porch & comfortable furniture. Outside: Lounge chairs & other seating, a kayak, a 37 foot dock

Beach House - Kayak 2/2.5 Villa - OS Slip/Ramp/Pkg

Welcome to Beach House Getaway, a charming villa tucked away on the serene island of Duck Key and perfectly situated in the heart of the Florida Keys. Nestled between Key Largo and Key West, Duck Key serves as a peaceful yet convenient base for your island getaway. Its central location means you’re just a short drive from some of the most iconic destinations in the Keys, including the natural wonders of Bahia Honda State Park, the famous waters around Islamorada, and the lively Key West.

Tiki Time! Private Pool~Tiki Hut~Kayaks~Grill!

Tiki Time ~ your private paradise in beautiful Marathon, heart of the Florida Keys! This is the perfect place for a family vacation or relaxing getaway. Gorgeous 3BR home with your own private salt water pool, Tiki Hut, space to park a 30' boat/trailer, and ocean views from the balcony~Kayaks, grill, beach toys await you for your beautiful day in the Florida Keys! Less than 5 min to Sombrero Beach, Dining & Local Bars! Experience the Florida Keys like a local and book Tiki Time today!

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.

Viamarhe Cabin-Private beach, Kayak, yard games

If you are looking to enjoy the natural beauty, and romantic stay in a rear cabin with complete bath and kitchen independent of the main house but with a patio that shares the amenities of games and entertainment of a mini resort our Oceanfront small apartment is the place for you. You and your couple can enjoy the exclusivity this property will give you, like the 5 kayak and fishing rods, volleyball, chess, bowling, carbon and propane BBQ grill, and a fire pit.

The Roseate House at Grassy Key Lic. #VACA-25-222

Lic. #VACA-25-222: Make The Roseate House at Grassy Key your next get away. Relax, fish, swim and explore at your own personal resort. The home is perfect for couples, family or girls retreat. Families return year after year to create their memories. Honeymooners appreciate the privacy as well as the attention to detail. Come live among the treetops in this vintage conch Key West style cottage situated half way between Key Largo and Key West.

Pet Friendly (Fee-Less) Half-Duplex Cottage

We have a lovely oceanside cottage in Marathon Key, Florida, close to everything with many amenities. The cottage has a large yard and plenty of room to park boats, RVs, and wave runners. This modernized cottage is for you if you all need a great place to stay. This quaint and cozy home offers good value and features new furniture and brand-new state-of-the-art stainless steel appliances. There is one bedroom and a pull-out queen-size sofa bed.

Houseboat Getaway In Marathon

Get ready to indulge in a relaxing and unforgettable experience at the first overwater houseboat getaway in Marathon, Florida! 🌴🌊 What awaits you is - fun filled days living and exploring out on the fabulous florida keys waters in your own private aqualodge, breathtaking sunsets, and a private sanctuary perched above the sea. 😍 Don't miss out on this one-of-a-kind experience! Book your stay now and create memories that will last a lifetime.

Florida Keys Resort-Style Home w/ Pool & Dock 5/3

Perfect for families, couples, groups, or solo travelers, this spacious home offers 5 bedrooms, 3 bathrooms, an open living room, and a fully stocked kitchen. Easy to reach and simple to access, it’s set in a peaceful neighborhood close to island fun and water adventures. Just a short walk to Sweet Savannah’s Ice Cream & Sweets Parlor, this retreat is ideal for relaxing or exploring. We look forward to hosting you!

Private Beach, Deep Water Dockage, Cabana Club

Reel Catch UPDATED CANAL FRONT, CABANA CLUB 2/2, with DOCK ** CABANA CLUB ACCESS - Includes private beach, swimming pool, whirlpool & tiki bar with food & drinks! Cast a line and kick back while you enjoy a beautiful Key Colony Beach sunrise from this freshly remodeled 2/2 canal front half-duplex. Boasting 37.5’ of deep water dockage and a 100' wide canal, this home is every fisherman’s dream.

Discount Available! Pool 100' Dock, Fun Amenities!

This newly renovated tastefully decorated 3 bedroom, 3 bath home (pull-out couch) has a peek-a-boo view of the ocean and is seconds to open water in your boat! It has an open floor plan and is ground level with plenty of natural light and a fully fenced yard! Available for guest use are 2 bikes, 3 kayaks, and a paddleboard! It has a large pool with plenty of room for everyone to swim and play.