Vacation rentals with a kayak in Vaca Key

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.

Luxury Boating Paradise+Pool+Sailing Kayaks

Captains Quarters, Your 4BR Waterfront Oasis on a deep-water ocean canal. This meticulously remodeled home provides a unique unforgettable Florida Keys experience for your entire family. 🏊‍♂️ Luxury heated pool & spillover spa ⛵ Private 75ft dock with sailing kayaks for ocean adventures 🕹️ Epic game room with Golden Tee, Pack Man, foosball table, Ping Pong & Infinity Game Table 🍳 Outdoor patio with BBQ grill & waterfront dining 💻 High-speed Wi-Fi for streaming & remote work 🛏️ Comfortable

Fall discounts! Best Location in Marathon & KCB!

Luxury Meets Adventure at Seahorse Landing! 40’ of dockage, SUP, kayak & all the equipment you’ll need to explore the beautiful bays & wildlife frequented waterways. All that adventure is balanced by a newly renovated interior offering the perfect blend of comfort and style in a modern, spotless setting. Our family has created a home that is a perfect fit for adventurous couples or families seeking relaxation& exploration. Send us a message or book instantly & begin your luxurious adventure!

Boating Paradise Villa rental Lic# VACA-25-124

Stunning beautiful 3-bedroom, 2 bath home. House has a 50' of private dock and canal. The dock has room for a 22ft boat. House is minutes from the ocean. Great for fishing or lobster's enthusiast. Conveniently located in the center of Marathon, Florida. Home is fully furnished with all kitchen utensils and appliances. Includes 4 kayaks, 1 paddle board, 2 bicycles, boat dock, and spa. Also, each room has a smart tv with internet. The house also has a washer and dryer for your convenience.

Amazing Oceanfront Home

Mesmerizing views, directly on the Atlantic Ocean! Sleeps 10 with 4 bedrooms and 3 bathrooms. We have a 28 foot pool (heat, for an extra charge) with a view you will not forget. We have Paddle boards, Kayaks, bikes, snorkel gear, etc. We also have a game room with a ping pong table, big screen TV, card table, and a piano. We have a very nice Kid's Park (just down the street). I do Last Minute Deals, just contact me! We require a standard signed rental agreement in order to rent the house.

Tropical Keys Retreat | Pool | Hot Tub | Cinema

Welcome to Paradise Palms: ⭑ 1750 sqft liveable space on 10,500 sqft estate ⭑ Private home, deck, patio & backyard, overlooking a beautiful scenic landscape ⭑ Crystal pool, hot tub, movie theater, remote workspace, game room with arcade & more ⭑ Secure parking for up to six vehicles, boat trailer parking, RV and EV charging ⭑ 10 min to sombrero beach & just minutes to all island attractions ⭑ Fully stocked kitchen ⭑ Extremely safe neighborhood License #VACA-24-20 License #VACA-24-32

*NEW!*Life is a Marathon~VIEWS!~Pool~Dock~HotTub!

🏖️Welcome to Life is a Marathon!🌴☀️ This peaceful 4-BR sanctuary has everything you need for the perfect getaway. Enjoy open-water views, a dock just steps from the home, and a prime location minutes from the Ocean or the Gulf⛵. Relax by the pool, fire up the grill for a sunset BBQ, challenge friends to cornhole, and set off on a kayak adventure!🌅🐟 Life is a Marathon is the retreat you and your family have been looking for. Don't wait until it's booked, secure your stay 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.

Private Pool! Luxury Paradise Pointe, Pet Friendly

Beautiful Key Colony Beach waterfront duplex with a private pool! Featuring a newly updated, 3/2, spacious 1440 sf home, deep water private boat slip & lift, Tiki Hut w/TV, kayaks, pet friendly, ice machine, bait freezer, large kitchen, Cabana Club, restaurant, and beach access. Family friendly location w/Golf, a playground, and dog park. Sit under the tiki hut, enjoy the outdoor TV after a day on the water, & grill your catch. Relax on the upper deck sunbathe and enjoy the vistas!

Waterfront Keys Home | Pool, Hot Tub & 35’ Dock

Escape to our luxurious waterfront retreat in the heart of the Florida Keys—perfect for an unforgettable family vacation or a coastal getaway with friends! Boaters will love the 35-foot private dock and convenient access to both the Atlantic Ocean and the Gulf of Mexico. Traveling with a larger group? Ask about combining your stay with our nearby Unit C, allowing everyone to vacation together. Your Florida Keys getaway awaits! Vacation Rental License: VACA-22-349

Direct Oceanfront Private Paradise - Pool/Spa/Dock

A peaceful oasis with every detail and convenience in place for the perfect Keys getaway. The huge private saltwater pool / spa and sun deck affords sweeping views of the Atlantic Ocean while the large outdoor living area offers open ocean breezes or shaded poolside dining. This property was specifically chosen, and the house thoughtfully designed, to maximize family fun while enjoying the laidback waterfront lifestyle of the Florida Keys.

Golf Coast Oasis near Sombrero Beach,

Escape to a stunning modern home in the Keys with a heated pool, private putting green (Mini Golf) , and dock for your boat. Relax on the plush sectional sofa or explore the outdoors with complementary bicycles and kayaks. Conveniently located 7 minutes to sombrero beach. Close by dining, and shopping, this single-story home with three bedrooms has everything you need for a fun-filled vacation. You'll love our Golf Coast Oasis!