Holiday rentals with a kayak in Sugarloaf Key

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Top-rated Accommodation with a Kayak in Sugarloaf Key

Guests agree: these holiday homes with a kayak are highly rated for location, cleanliness and more.

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Guest favourite

Home in Marathon

4.87 out of 5 average rating, 31 reviews

Waterfront&Dock/ kayaks,Hot tub/3mims to the beach

Waterfront Vacation Home! Direct access to the ocean ! Relax at Beauty and The Sea beach house. The house has 3 bedroom ,and 3 bathroom full kitchen, and spacious living room with a sofa bed queen. Enjoying the sun and Florida keys view from your balcony. Smart TV on every room including living room. High speed Internet , and local canals. The house is fully furnished, washer & dryer, all kitchen utensils, towels and more. Bringing your own boat/jetski, and have it docked from your backyard

Guest favourite

Home in Marathon

4.96 out of 5 average rating, 70 reviews

Oceanside, Smart Home with SUP/kayaks - 60 FT Dock

This pet-friendly, waterfront home upgraded in 2021 (see notes) has two rooms with ample bedding - 1 king-size bed, one queen (pull-out sofa bed), and one full. The home has a cute kitchen that is well-equipped. A nice open area allows you to walk and enjoy the canal. Enjoy the ocean view or simply sunbathe in serenity. There is house parking in front for boats and trailers and covered parking for one car. It only takes minutes to access the ocean. We just completed construction of a 60FT dock.

Guest favourite

Cottage in Cudjoe Key

4.92 out of 5 average rating, 106 reviews

King Master, 2BR, 2BA, 35' Seawall, SUP, Kayaks

Updated, waterfront, 2BR, 2BA with King Master and a 35' seawall.Bring your boat!Fully stocked kitchen w stainless appliances. So much to do here for up to 6 at this family friendly, quiet resort-Venture Out, a gated,secure community. Fishing, lobstering, oversized pool, children's pool, hot tub, pickleball, tennis and basketball courts.Rec center. Bike, kayak, and SUPs.Between Key West(20Mi)and Marathon, this property and area is not to be missed! Free WIFI; Both bedrooms and LR have Roku TVs.

Guest favourite

Cottage in Marathon

4.96 out of 5 average rating, 27 reviews

Catch n' Relax Canalfront Cottage in Marathon

Enjoy our cottage right on a deep canal with 50' dock. Step right into your boat to fish the Atlantic Ocean & Gulf or just relax & enjoy the view! Enjoy an outdoor kitchen space for fish fry & Happy Hour drinks. Tan on our loungers or enjoy dinner under the stars. Kayaks/Bikes for you too. A Perfect location Minutes from Airport, 7Mile Bridge, Sombrero Beach & other Attractions. Close to shops & restaurants. Easily launch your boat from a free public marina nearby. Rental License #VACA-22-85

Guest favourite

Houseboat in Tavernier

4.88 out of 5 average rating, 222 reviews

Clean Fully Remodled Houseboat Luxery on the water

Very spacious, Comfortable and "super clean" Houseboat. Rent daily “Baycation” is a 44'x15' triple level upper deck Houseboat completely remodeled. This is an adventure, unlike any hotel room! Live on the water, in an amazing marina, with so much to do you need to come back! Sleep like you never have before, all my guests tell me that! Bonus Lay on the upper deck and see the amazing star ambiance...... This is for everyone......Couples, families & just friends, Its perfect

Guest favourite

Home in Marathon

5 out of 5 average rating, 22 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.

Guest favourite

Home in Key Colony Beach

4.94 out of 5 average rating, 106 reviews

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.

Guest favourite

Home in Marathon

4.9 out of 5 average rating, 71 reviews

Dream Vacation KCB Marathon with private pool !

Dream Vacation Duplex in Key Colony Beach. Private pool Brand New state of the art house with all commodities and amenities, 3 bicycles 2 kayaks near to restaurants, fast WIFI, washer ,dryer, blue tooth speakers, night mood lights. A modern lift for boat up to 18000 lb Main canal Use of electric golf car Gem and jet sky and boat can be arrange Electric Gem-4 car offered for a minimum extra charge Options of private boat or jet sky (ask) Heated pool on demand (extra cost)

Guest favourite

Boat in Key West

4.99 out of 5 average rating, 76 reviews

Living the Dream, Key West Style

Reconnect with nature at this unforgettable escape. Experience and enjoy what life is like living on a large 60 ft world cruising sailboat on the sailing vessel Serenity. Staying on Serenity is what Key West is known for and living a carefree lifestyle. Experience and enjoy the Artistic and Tropical landscaped private marina with spectacle views of the harbor. This is a all-inclusive price. No cleaning fee and includes 2 Paddle boards ,4 Kayaks and a large floating mat.

Superhost

Home in Marathon

4.88 out of 5 average rating, 16 reviews

Boaters delight! 1 min to open water, Dock & Beach

Inquire for monthly discounts. Quaint and charming home nestled in the Florida Keys. Secluded single family property with open water access. Private Dock, Beach, kayak launch area with kayaks and bikes available to use. Very private tranquil location. See manatees/fish swimming by. Enjoy endless sunsets from the front porch. Fantastic views from every room in the house. Beds: 1 King bed, 2 twins, 2 trundle Marathon Vacation Rental License#. VACA-22-375

Superhost

Home in Cudjoe Key

4.83 out of 5 average rating, 258 reviews

OCEAN PARADISE AT VENTURE OUT + 4 BIKES/ 2 KAYAKS!

*PERFECT LOCATION! * 35' Seawall *AWWSOME 2 bedroom 2 full bath waterfront stilted house in Cudjoe Key. Located in the lower Florida Keys at MM# 23 only 25minutes to Key West. Located in the gated community of Venture Out Resort. *Sleeps 6 *55" TV *A/C & heat *Fully equipped kitchen *Brand New Amenities including grill, 4 Bikes & 2 two-person Kayaks *PLUS: Pool, HotTub, Marina, Boat Ramp, Store, Playground, Game Room, Tennis, Library, etc. Too much to list!