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Vacation rentals with a kayak in Sugarloaf Key

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Top-rated accommodations with a kayak in Sugarloaf Key

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

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Houseboat in Key West

4.81 out of 5 average rating, 285 reviews

Key West Houseboat Paradise

SuperHost for 5 years!! Over 280 reviews!! ~ Plush Queen Bed, 2 Full Size Sofas, Full Kitchen, Full Bath, Huge Living Rm, High Sped Internet & 3 Sun Decks. Modern and Rebuilt New from keel-up in 2022. 15 min from Duval St. The land side isn't fancy, there's a slightly industrial feel with a working auto garage & warehouse onsite. But the Water View is a mile-wide Channel and dozens of bright green islands where seabirds nest and two Sea Kayaks tied up waiting for you to untie and go exploring.

Guest favourite

Cottage in Cudjoe Key

4.92 out of 5 average rating, 101 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

Houseboat in Tavernier

4.88 out of 5 average rating, 217 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 Cudjoe Key

4.91 out of 5 average rating, 79 reviews

*Emerald Seas*-Florida Keys Ocean Front Paradise!

Welcome to our Florida Keys Ocean Paradise, Emerald Seas! Truly a special place to get away and relax. Enjoy the crystal-clear waters and amazing views. Bring or rent a boat, look for sea turtles, manatees, dolphins, lobster & tropical fish right from your patio or dock. Take in a glorious sunrise or moonlit night over the water. The amazing, 180 degree panoramic ocean views will take your breath away every moment you are there. Also see our other paradise, http://airbnb.com/h/keysshangrila

Cottage in Islamorada

4.82 out of 5 average rating, 164 reviews

FLOATING 1BD 1BA PRIVATE COTTAGE - MAKO

Tucked away in the vibrant Florida Keys, is our pristine paradise. We are located in the heart of Islamorada, where the weather is always gorgeous, the fishing never disappoints, and the sunsets are mesmerizing. If you are seeking a relaxing get away, look no further. Each unit is private, and the neighborhood is tucked off the beaten path. On site, you will have the luxury of renting your own private boat. Boat rentals are 20% off for guests! A 5% lodging tax will be charged on arrival.

Guest favourite

Home in Key Colony Beach

4.94 out of 5 average rating, 101 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

Boat in Islamorada

4.92 out of 5 average rating, 331 reviews

360 DEGREE WATERVIEW HOUSEBOAT

IMPORTANT Enjoy your own private retreat aboard a solar and wind powered houseboat moored 1/2 mile from land in the beautiful Islamorada Please do not arrive after dark and NO night riding. Need experience with hand pull outboard motors a 12 foot skiff with a 6hp outboard motor is provided reliable to go back and forth from shore NOT reliable for exploring No hot water on shower, heat water in Tpots or Solar bags. Please shave before arriving No suitcases, least amount of cloths.

Guest favourite

Home in Upper Sugarloaf Key

4.91 out of 5 average rating, 69 reviews

Lighthouse - Bungalows Sugarloaf Beach Key West

THE BEST TIME OF THE YEAR TO VISIT IS NOW!!!! TEMPERATURE IS AMAZING AND SEAWEED IS AT A MINIMUM. Our amazing Lighthouse is a 2 bed 1 bath Loft Bungalow sitting just a few feet from our private beach. The master bedroom loft is accessed by a spiral stair, and has a beautiful bird’s eye view of the Atlantic Ocean. Our cozy nautical inspired living room leads outside to an exterior deck facing the beach perfect for peaceful mornings relaxing and sipping your coffee or cocktails.

Home in Cudjoe Key

4.82 out of 5 average rating, 248 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!

Guest favourite

Home in Key Colony Beach

4.98 out of 5 average rating, 110 reviews

Super Nov. Savings! Key Colony Beach, Cabana Club

Second Wind is on the 9th Street canal, a beautiful corner lot with exceptional views and ocean breezes. Cabana Club! Dockage for a 20 ft boat. A two-minute walk to Sunset Park in the wonderful community of Key Colony Beach! Open floor plan with cathedral ceiling, large deck with seating for six overlooking the pristine turquoise canal. It is the perfect place for your Florida Keys getaway!

Guest favourite

Guest suite in Tavernier

4.97 out of 5 average rating, 269 reviews

POOL ! Key Largo! Tavernier! Welcome to Paradise!

POOL! A perfect tropical getaway! Life is good today! Bright, airy, 500 plus sq ft., canal front studio, close to the bay. From the dock you can KAYAK to mangrove tunnels, fish, or just relax. Cold drink in your hand, life is good today! You are going to have an awesome vacation!! ( NOTE: THE POOL MAY BE SHARED ON OCCASION, WITH OUR FAMILY. A SIGNED LIABILITY RELEASE IS REQUIRED AT CHECK IN )

Guest favourite

Home in Cudjoe Key

4.9 out of 5 average rating, 29 reviews

White Vacation Home. Free cancellation see details

Kayaks come with the rental. Small floating dock for your boat. We have 2 other vacation homes right next to this home if you are looking for a large family vacation. New large flat screen TV with over 300 free current movies, fast wifi, and TV. Outside shower by the pool. We provide bedding, towels, pots and pans. Private pool, heated in the winter months.

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Popular amenities for Sugarloaf Key kayak rentals

Free parking on premises

Air conditioning

House rentals with a kayak

Home in Marathon

5 out of 5 average rating, 8 reviews

Salty kisses beach house

Guest favourite

Home in Islamorada

5 out of 5 average rating, 16 reviews

Pristine pool front home w/ocean views Anglers 148

Guest favourite

Home in Marathon

4.98 out of 5 average rating, 59 reviews

Sombrero beach oasis,great location,many amenities

Guest favourite

Home in Marathon

5 out of 5 average rating, 24 reviews

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

Guest favourite

Home in Marathon

5 out of 5 average rating, 22 reviews

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

Guest favourite

Home in Marathon

4.98 out of 5 average rating, 42 reviews

Waterfront Private Home w/Pool-Family&Pet Friendly

Guest favourite

Home in Marathon

4.94 out of 5 average rating, 35 reviews

Tropical Dream Vacation - 3bdrm/2bath CANAL FRONT!

Guest favourite

Home in Marathon

4.88 out of 5 average rating, 17 reviews

Viamarhe House-Private beach, Kayak, yard games

Cottage rentals with a kayak

Cottage in Cudjoe Key

4.84 out of 5 average rating, 93 reviews

OCEANIA... water front cottage retreat ~

Guest favourite

Cottage in Islamorada

4.97 out of 5 average rating, 59 reviews

Islamorada bungalow 2 bed & pool

Cottage in Cudjoe Key

4.71 out of 5 average rating, 133 reviews

Calypso Cottage

Guest favourite

Cottage in Marathon

4.96 out of 5 average rating, 24 reviews

Catch n' Relax Canalfront Cottage in Marathon

Cottage in Islamorada

New place to stay

Cottage on Bayfront Estate – Pool, Beach, & Dock

Guest favourite

Cottage in Key Colony Beach

5 out of 5 average rating, 10 reviews

Luxurious Oasis: 2BR w/Pool, Tiki, Dock & Beach

Destinations to explore