
Vacation rentals with a kayak in Florida Keys
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Top-rated kayak rentals in Florida Keys
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King MSTR, SS Quartz Kitchen, Bikes Kayaks, VIEWS!
Updated waterfront 2BR/2BA with King Master, 2nd Queen and pullout couch. 35' seawall—bring your boat! Enjoy a fully stocked quartz kitchen with stainless appliances. Located in Venture Out, a quiet, family‑friendly gated resort with fishing, lobstering, pools, hot tub, pickleball, tennis, basketball, rec center, bikes, kayaks, and SUPs. Between Key West (20 mi) and Marathon. Free WiFi; Roku TVs in both bedrooms and living room. Kayaks, SUPs and storage area with extra fridge and bait freezer.

Tiny Home on Waterfront | Bay Views | Deck | Pool
Down by the waters of Manatee Bay, you’ll find this idyllic tiny home for 6. With a full kitchen, three comfy beds,and access to a community pool, this is a prime location to enjoy the best of Key Largo. Sit on the deck and dip your toes in the water or explore the bay using the available kayaks and paddle boards. 10 Min Drive to the Gilbert’s Resort 15 Min Drive to John Pennekamp Coral Reef State Park 22 Min Drive to African Queen Canal Cruise Experience Key Largo With Us & Learn More Below!

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.

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.

Waterfront View Cottage
Come and stay at the only location on the island with the one of a kind exceptional view of the Everglades. Step right out to the waters edge of the Goodland Bay, where you will be able watch the dolphins right from your porch and private patio. The cottage has great sliding glass doors that hold the magnificent view of the water, right from the living room. A freshly remodeled fully furnished, up to date, 1 bedroom cottage. Boat Parking, Dockage, kayaks, and bikes available.

Ocean Shores Villa 2 with pool and boat slip
This centrally located boater's paradise is the perfect place to relax. Walk to restaurants, cook in kitchen or grill downstairs. With only 4 units in the building the guests have half an acre of waterfront entertainment (boatslip,kayaks,bikes,fire pit,hammock and heated pool). 32ft dock slip and trailer parking are included in the rental. Conveniently located near Sandbars, State Parks and many attractions.

Key Largo! Tavernier! Welcome to Paradise!
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 )

Oceanfront Getaway | Kayaks, BBQ & Stunning View!
Imagine yourself "Paradise Living" at this completely remodeled modern Oceanfront Tiki Stay! Enjoy the beautiful Florida Keys in the relaxing community of Manatee Bay! This oceanfront tiny home feels just like your home away from home. Located right at the entrance of Monroe County, this hidden gem is just off Mile Marker 112 in Key Largo, FL. Booking relaxation is just a click away!

Delightful Waterfront Tiny Home
Reconnect with nature in this waterfront Tiny Home located in Key Largo, Florida. NO PETS and NO KIDS less than 3 years old allowed This is a small gated community consisting of 23 Tiny Homes in a very wide canal. NO BOATS AND NO JET SKIS This tiny home has two bedrooms with two queen beds, one in Master Bedroom and the other in the loft upstairs.
Popular amenities for Florida Keys kayak rentals
House rentals with a kayak

Marathon Keys Escape • Pool • Hot Tub • Near Beach

Luxury Boating Paradise+Pool+Sailing Kayaks

Golf Coast Oasis near Sombrero Beach,

Pet Friendly (Fee-Less) Half-Duplex Cottage

Serenity Oasis~Pool!~Putt-Putt!~Kayaks~Bikes~Spa

World-Class Oceanfront Pool/Hottub Sunset Escape

Canalfront Home Ocean accessible

Spanish Queen @Venture Out
Cottage rentals with a kayak

Islamorada bungalow 2 bed & pool

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

Keys Cottage with Sleeping Loft Sleeps 6

FLOATING 1BD 1BA PRIVATE COTTAGE - MAKO

Keys Waterfront Oasis • Tiki • Private Pool • Dock

Beautiful 3 bedroom cottage with private rooftop

OCEANIA... water front cottage retreat ~

THE PARADISE
Other vacation rentals with a kayak

Waterfront with Boat Lift/Kayaks and Hot Tub

Waterfront Private Home w/Pool-Family&Pet Friendly

Chasing Sunrises | Family Style

NEW - Luxury Seascape w/Pool+Free Dockage+Gameroom

Saltwater Social ~ Game Room ~ Pool ~ Dock ~ Views

The Mini Coconut

Ocean Shores Villa 1 with Pool and Boat Slip

Keezy Dream House+Beach, Pool & Kayaks at Anglers
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- Bayfront Park
- Bayside Marketplace
- Brickell City Centre
- Kaseya Center
- Everglades National Park
- University of Miami
- Calle Ocho Plaza
- Sombrero Beach
- LoanDepot Park
- Florida International University
- John Pennekamp Coral Reef State Park
- Dolphin Mall
- Zoo Miami
- Key Biscayne Beach
- Biscayne National Park
- Crandon Beach
- Biltmore Golf Course Miami
- Phillip and Patricia Frost Museum of Science
- Coral Castle
- Fairchild Tropical Botanic Garden
- CG Cosmetic Surgery
- Miami Seaquarium
- Sea Oats Beach
- Schnebly Redland's Winery & Brewery
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