
Holiday rentals with a kayak in Monroe County
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Top-rated rentals with kayak in Monroe County
Guests agree: these rentals with kayak are highly rated for location, cleanliness and more.

Enjoy our Beautiful Home on a Fun Canal! Hot tub!
Beautiful & Modern 4/3 Canal House! completely renovated. Go Kayaking through the Canals.. Enjoy the views of the backyard and canal with jumping fish all day, House is in a centric and quiet neighborhood. Amazing backyard & terrace with a BBQ, 2 Kayaks provided for Guest. Home is near nice restaurants and close to main Highways.. ✔️15min from Miami International airport ✔️25min - Downtown Miami ✔️ 30min - Miami Beach ✔️10-15min - Dadeland Mall & Merrick Park Come Relax at our Paradise Home!

Island Sanctuary Islamorada
Stay aboard the eco-friendly two-story 63 ft River Queen with a 360 degree view with beautiful sunrises and sets, mored 1/8 mi offshore in a quite harbor close to shopping center, movie theater, hospital, bars & restaurants. A 10-foot dinghy with small outboard to come & go from shore "ONLY", nowhere else. I also offer Personal Training, deep tissue work & Life Coach sessions. I live on the vessel about a hundred yards from you so if there are any questions, etc. I will be there to assist you.

Oceanfront Lookout Point w/two Kayaks & Deck
Lookout Point is Wide open breathtaking Water View , Amazing Sunrises with a cup of Morning coffee, Refreshing breeze, Sound of water and Rustle of palm trees will start your day… Fishing right from the property, Kayaking. Taking sunbath on Chaise lounges or Reading books or just sitting under Tiki having a nice conversations and enjoying beautiful scenery of the view. You will see fishes jumping out of water, seagulls trying to catch up it , you might see manatee swimming by or dolphins.

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.

Oasis2 in Key Largo With a million dollar view
Million Dollar view at a fraction of the price! This property is on the water with amazing bay views. It includes one kayak for 2 people, paddle board, fishing rod, washer and dryer, kitchen with all cooking utensils. Note: The upstairs room is not comfortable for seniors or adults, the ceiling height is 4 feet (an adult has to walk on his knees). The property is located on a residential island, restaurants, bars, stores and grocery stores are within a 15 minute drive from the property.

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.

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.

The Lighthouse - Beach Houses Key West
If you’re reading this, you’re already one step closer to paradise. Thank you for considering us for your getaway. Our charming Lighthouse Bungalow is a 2-bedroom, 1-bath loft-style retreat located just steps from our private beach. The master bedroom loft, accessed by a spiral staircase, offers a stunning bird’s-eye view of the Atlantic Ocean. The nautical-inspired living area opens to an exterior deck overlooking the beach—an ideal spot for peaceful mornings and ocean breezes.

Amazing houseboat with 2nd floor observation deck
Escape to our one-of-a-kind houseboat “Wild One,” anchored minutes from Soencers boat yard Key West. Surrounded by turquoise waters, enjoy one complimentary round trip per day, with times arranged around our charters. Evening rides may be available on request, last ride 10 PM. Extra charge after 8 PM Special Promotion: End your day with a private Sunset Eco Trip (6–7 PM) as your nightly ride to the houseboat—watch the sky ignite before settling in for a peaceful night afloat.

0142 Skyline Serenity Apartment 1B/1B
Unique and beautiful condo with stunning views of Miami's financial and business district. Newly renovated pool, known as the longest pool in Florida This unit is close to the best restaurants and bars Miami has to offer, such as Capital Grille, Cipriani, Cantina La Veinte. Just steps away from Brickell City Center, the Shops of Mary Brickell Village and surrounded. PS. IDs will be requested by the Icon Brickell Building, like any hotel. Summer Sale on Monthly Stays: $8K

Kawama N2 Relaxing Lagoon View free bikes & kayaks
Relax and enjoy our family friendly 3 bedroom/3 bathroom Villa Lago in Key Largo! Salt water swimming lagoon, Pools, the Ocean, fishing pier, Marina, Tennis, Bikes, fire pit and playground. Enjoy resort like amenities in the comfort of a home. This beautifully decorated villa sleeps 8 and is conveniently located in a very central location in Key Largo. Close to some great restaurants, diving, fishing, boat tours, State Park. Kawama is fun for all ages.

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.
Popular amenities for kayak rentals in Monroe County
House rentals with a kayak

Discount Available! Pool 100' Dock, Fun Amenities!

NEW! CASA PALMA - Golf Cart, 2 King-Size Beds, Pool, Kayaks

Marathon Keys Escape • Pool • Hot Tub • Near Beach

Large Waterfront Home, w/Efficiency, Pool, Kayaks

Viamarhe House-Private beach, Kayak, yard games

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

Golf Coast Oasis near Sombrero Beach

The Mini Coconut
Cottage rentals with a kayak

Islamorada bungalow 2 beds & pool

Ocean Breeze @ VO - Kayaks, Bikes, 30 Min from KW

Oceanfront Getaway | Kayaks, BBQ & Stunning View!

FLOATING 1BD 1BA PRIVATE COTTAGE - MAKO

King MSTR, SS Quartz Kitchen, Bikes Kayaks, VIEWS!

Luxurious Oasis on: 2BR w/Private Pool, Tiki, Dock

OCEANIA... water front cottage retreat ~

THE PARADISE
Other holiday rentals with a kayak

Luxury Unit 1Bed W Residence ICON-Brickell

Waterfront Oasis w/Private Pool-Dockage-Beach

Chasing Sunrises | Family Style

Luxury Boating Paradise+Pool+Sailing Kayaks

Key Largo downstairs guest house

Sunrise Views in Key Largo | Boat Slip Access

Pet Friendly (Fee-Less) Half-Duplex Cottage

Waterfront Paradise Key Largo. Casa Luna
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- Everglades National Park
- Sombrero Beach
- John Pennekamp Coral Reef State Park
- Zoo Miami
- Coral Castle
- Calusa Beach & Loggerhead Beach
- History Of Diving Museum
- Sea Oats Beach
- Everglades Alligator Farm
- Conch Key
- Bahia Honda State Park
- Schnebly Redland's Winery & Brewery
- Monkey Jungle
- Long Beach
- Theater of the Sea
- Key Largo Kampground And Marina
- Florida Keys Aquarium Encounters
- Sunset Park
- Homestead-Miami Speedway
- Seven Mile Bridge
- Dolphin Research Center
- Calusa Campground
- Robbies Marina Of Islamorada
- Founder's Park
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