Vacation rentals with a kayak in Vaca Key

A two-story house is surrounded by lush greenery and palm trees. A spacious backyard features a heated pool and a wooden dock. Loungers are arranged near the pool, providing a relaxing outdoor space. The exterior showcases large windows and a balcony with seating.

4.97 out of 5 average rating, 72 reviews

Sombrero beach vacation oasis, great location

Your family will be close to everything when you stay at this centrally-located home. Close to Sombrero beach you can walk ride a bike, kayak or take a short drive there. Many attractions near by. Publix and winn dixie and many restaurants near by. Key West just one hour away for any day trip. House has an ice maker, refrigerator and freezer downstairs to keep bait or fish .Private pool and Dock, back yard oasis There is a paddle board and 4 bikes and 2 kayaks for your use. Amazing location!

A two-story home is showcased, featuring a spacious backyard with a swimming pool surrounded by lounge chairs and umbrellas. The exterior is illuminated under a twilight sky, while a stone walkway leads to the inviting entrance. Lush greenery adds a vibrant touch to the setting.

5 out of 5 average rating, 39 reviews

Mermaid's Paradise ~ Pool ~ Dock ~ Games ~ Views!

Experience the relaxing setting of this 4BR 4.5Bath home, ideally situated in the picturesque waterfront neighborhood of Marathon, FL. Discover the area's scenic beauty and a diverse selection of water activities, attractions, and landmarks. After a day of exploring, return to our home for a rejuvenating stay. ✔ 4 Comfy BRs ✔ Open Design Living ✔ Full Kitchen ✔ Balcony ✔ Backyard (Pool, Games, BBQ, Lounges, Dining) ✔ 73-Foot Dock ✔ Smart TVs ✔ High-Speed Wi-Fi ✔ Free Parking See more below!

A tray displays two coconut cups filled with a refreshing beverage, each adorned with a pink paper umbrella. Slices of watermelon are arranged on a plate beside the drinks. The vibrant blue water of the heated pool glistens in the sunlight, surrounded by tropical greenery.

5 out of 5 average rating, 59 reviews

Waterfront, Pool w/ Spa, Dock & 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 canal adventures 🕹️ Epic game room with a pool table & Infinity Game Table 🍳 Outdoor patio with BBQ grill & waterfront dining 💻 High-speed Wi-Fi for streaming & remote work 🛏️ Comfortable beds for a perfect night's rest

A modern kitchen features granite countertops and a large island with seating. Natural light floods the space through multiple windows. Light-colored cabinetry contrasts with vibrant blue tile accents, creating a welcoming atmosphere. The kitchen opens to a living area, showcasing comfortable seating and views of the outside.

4.95 out of 5 average rating, 22 reviews

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

4.95 out of 5 average rating, 153 reviews

A spacious outdoor porch features a round dining table surrounded by four chairs. A kayak is positioned nearby, and lush greenery and water views are visible in the background, enhancing the inviting outdoor space.

Villa in Duck Key

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.

An inviting outdoor space features comfortable seating and a hot tub, surrounded by lush greenery. A large screen is set up for movie nights, and ambient lighting enhances the evening atmosphere as the sun sets.

5 out of 5 average rating, 51 reviews

Movie Theater | HotTub | Pool | Boat/RV/EV Parking

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

A modern two-story home features a clean white exterior with navy blue accents. A set of black stairs leads to a covered balcony adorned with potted plants. Large windows allow natural light to enter, while a gravel driveway provides ample space in front.

5 out of 5 average rating, 42 reviews

Waterfront Escape -VACA-23-408

Come stay at this brand new home construction on a deep and wide canal leading to the ocean with pool and exotic decor. 75 foot dock with water and electric. Top of the line appliances with a fully stocked kitchen. Spa style showers with high end decor. Luxury at its best. Heated pool with sundeck and lots of seating around the edges. (Pool heater is an additional $100 per stay). Ground level cooking and dining for those beautiful days after boating or while laying around in the pool.

Superhost

A scenic pool area is visible, featuring a hot tub adjacent to the water's edge. Palm trees sway gently in the breeze, providing a tropical atmosphere. The blue sky reflects on the tranquil water, enhancing the serene setting.

4.73 out of 5 average rating, 30 reviews

Sunset Views, Pool and Dock

Beautiful two bedroom two bath single family home with pool and spa with dock right on the water! Enjoy the beautiful sunset and bay views from our dock, deck or pool! Bring your boat and bathing suits and enjoy this wonderful home in the Heart of the Florida Keys! Pool heat is an additional fee Kayaks and golf carts rental available upon request Saturday to Saturday during busy months except September and October. And you can always ask 7 night minimum no exceptions VACA-22-34

4.95 out of 5 average rating, 125 reviews

A paved outdoor patio features two lounge chairs and a small round table, surrounded by tropical plants and palms. The tranquil canal is visible in the background, offering a serene waterfront view.

Home in Key Colony Beach

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.

An aerial view displays a spacious, upscale home surrounded by lush greenery and water. The teal roof contrasts against the natural landscape, while the clear waters of Florida Bay extend into the horizon, showcasing shades of blue and green.

5 out of 5 average rating, 35 reviews

Ocean Dream

Ocean Dream.... a bright beautiful upscale home with fantastic ocean views over Florida Bay. Watch sunsets and sunrises from either balcony and the new observation platform extending 60 feet into the water. Experience nature at its finest from your 140 foot ocean frontage estate or go further afield on the included kayaks and SUPs. Beautiful gardens, outdoor living area, new pool and spa*, ping pong and bocce, all included in your week of paradise. License VACA 23-380

4.87 out of 5 average rating, 54 reviews

A waterfront view captures a serene canal lined with tropical greenery and residential boats. The white boat is positioned on the dock, with steps leading to an inviting home painted in a soft yellow. Clear blue skies enhance the tranquil atmosphere.

Apartment in Marathon

Little Venice in Marathon (in the Beautiful Keys)

Little Venice in Marathon is a beautiful 2 bed / 2 bath fully remodeled waterfront home that offers the best Florida Keys Living. There are plenty of fun and adventurous activities to do just steps from your door. Including but not limited to boating, kayaking, biking, sport fishing and many more fun activities. Our home is equipped with everything you may possibly need to spend an enjoyable, relaxing vacation. Also this dream home has a 50 feet boat dock.