We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.

Airbnb your place

Vacation rentals with a kayak in Islamorada

Find and book unique kayak rentals on Airbnb

Top-rated kayak rentals in Islamorada

Guests agree: these kayak rentals are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

Camper/RV in Key Largo

4.84 out of 5 average rating, 76 reviews

'The Hidden Port' w/ Kayaks in Paradise

Beautifully renovated camper in Key Largo with kayak's. Two bedroom and a sofa bed w/ 2 AC units. Fully equipped kitchen, new gas grill, and new patio furniture. Large, screened and tiled patio area. Bay sunsets that will leave you breathless, which can be experienced on land or water. 5 minutes to Pennekamp. Free WIFI. Guarded security gate with fishing docks around the whole property, swimming pool, kayaking, basketball, tennis courts and a park for the little ones. Kayak drop in on property.

Camper/RV in Key Largo

4.94 out of 5 average rating, 234 reviews

New Tinyhouse RV, Kayak, Beach, Fish, Marina, Pool

Newly replaced RV, lot# 19 at Key Largo Kampground and Marina Resort W/ 24 hour security. 1 Queen Bed in loft, Sofa bed, basement, Full Kitchen and Full Bathroom, Cable TV and Wi-Fi. In walking distance to Publix Supermarket, John Pennekamp State Park, deep sea Fishing, Diving and Snorkel Charter boats and first class Restaurants. Private nicely landscaped all-to-your-self lot approx. 26' x 56' and it's, conveniently near the pool, boat ramp w/ trailer parking, laundry area, toilet- bath house

Vacation home in Key Largo

4.95 out of 5 average rating, 100 reviews

Ocean Shores Villa 3 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 (boat slip, Kayaks, Bikes, Hammock and Pool). 32ft Dock Slip and Trailer Parking are included in the rental. Relaxing Balcony that looks down the Ocean Canal is the perfect place to have your morning coffee. Conveniently located near Sandbars, State parks and many attractions.

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

Home in Key Largo

4.89 out of 5 average rating, 104 reviews

NEW CASA PALMA VOTED BEST AIRBNB RENTAL! GOLF CART

NO HIDDEN FESS! CASA PALMA IS A LICENSED AND LEGAL VACATION RENTAL WITH HUNDREDS OF 5 STAR REVIEWS AND SUPER HOST STATUS ON ALL VACATION RENTAL SITES. VOTED #1 KEY LARGO VACATION RENTAL! LOCATED IN THE HEART OF KEY LARGO! IT'S THE PERFECT HOME BASE TO EXPLORE THE KEYS! 2 POOLS, BEACH, FREE GOLF CART, FAST WIFI, KAYAKS, TENNIS/PICKELBALL, MARINA WITH BOAT RAMP AND TRAILER PARKING! SLIP RENTAL AVAILABLE! SWIMMING LAGOON! 2 KING BEDS! PLAYGROUND! FREE PARKING! PACK AND PLAY AND BOOSTER SEAT!

Cottage in Islamorada

4.82 out of 5 average rating, 162 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.

Rental unit in Key Largo

4.92 out of 5 average rating, 251 reviews

Waterfront Studio 2| Couples Oasis | Kayaks | Pool

Enjoy gorgeous sunsets and excellent views of Manatee Bay from this beautifully upgraded studio apartment. The perfect spot for couples and small families, this modern studio comes with kayaks and paddle boards so you can get out on the water like a local. The ideal location offers easy access to the Bay, great restaurants, and local beaches. 10 Min Drive to the Gilbert’s Resort 15 Min Drive to John Pennekamp Coral Reef State Park Experience Key Largo With Us & Learn More Below!

Townhouse in Key Largo

4.92 out of 5 average rating, 88 reviews

Casa Laguna Remodeled Overlooking Lagoon 2 Kayaks

Casa Laguna is a coastal cottage that will ease you into your vacation before you put your bags down! This is a comfortable setting for families. If you enjoy a laid back home with style, this is for you! Family of 6-8, or a party of 2..... this is a great spot to call home for a while! Your view of the 4.5 acre salt water lagoon is perfect for relaxing on the patio. Grab your coffee or cocktail and walk around the gardens of the lagoon, which will take you around the community.

Home in Key Largo

4.96 out of 5 average rating, 142 reviews

Key Largo Waterfront Home with Tiki & Boat Dock

WATERFRONT Oceanside Keys delight In Key Largo Kampground- minimum stay 4 days. Your own private TIKI/ BOAT DOCK & swim ladder at the door; HOA boat launch. Bring or rent a boat up to 25' [ no jet skis] Snorkel in front of the house. Launch the PROVIDED tandem kayak from our beach down the street. 1 mile from the land base of Pennekamp State Park. Paddling, boating, fishing, snorkeling and diving are glorious in Pennekamp Park waters. No indoor smoking. No pets.

Condo in Key Largo

4.97 out of 5 average rating, 156 reviews

KEYS BEACH RETREAT WITH CAPTIVATING WATERVIEW!

LICENSED 3/3 VACATION HOME ON THE OCEAN SIDE WITH LOTS OF OUTDOOR LIVING/DINING SPACE. TWO POOLS, FREE GOLF CART, FAST FREE WIFI, TWO ADULT KAYAKS, TWO KIDS KAYAKS, TWO BICYCLES, TWO TENNIS COURTS. MARINA FOR YOUR BOAT WITH FREE BOAT RAMP AND FREE PARKING WITH QUICK ACCESS TO THE ATLANTIC OCEAN. SLIP RENTAL AVAILABLE FROM THE DOCK MASTER. PIRATE SHIP PLAYGROUND! FREE PARKING! SANDY BEACH! SALTWATER SWIMMING LAGOON! PACK AND PLAY AVAILABLE AND A BOOSTER SEAT.

Camper/RV in Key Largo

5 out of 5 average rating, 66 reviews

My Little Paradise

Your slice of paradise, Shasta Phoenix 36 feet long, One bedroom and one bath. This is a waterfront property located at Manatee Cove. Kayak and flotation devices included for you to use during your stay. Use our kayak at your own risk. By far the best place for Kayaking, Fishing and relaxing by the pool area or grill your catch of the day on the outdoor BBQ. Free internet is available and included with your rental. NO BOATS OR JET SKIS ALLOWED ON THIS PROPERTY.

Home in Marathon

4.86 out of 5 average rating, 14 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

Vacation rentals for every style

Get the amount of space that is right for you

Villas

Luxurious estates for the ultimate escape

Apartments

Convenient locations with everyday essentials

Houses

A space thats all yours, with room for everyone

Popular amenities for Islamorada kayak rentals

Free parking on premises

Air conditioning

House rentals with a kayak

Home in Marathon

4.73 out of 5 average rating, 15 reviews

Sunset Views, Pool and Dock

Home in Marathon

4.77 out of 5 average rating, 26 reviews

Stunning Waterfront Retreat with Dockage & Pool

Home in Key Largo

4.93 out of 5 average rating, 69 reviews

Large Waterfront Home, w/Efficiency, Pool, Kayaks

Home in Tavernier

5 out of 5 average rating, 4 reviews

Waterfront Islamorada Pool Home private Dock

Home in Key Colony Beach

4.94 out of 5 average rating, 98 reviews

Waterfront Home 37.5-ft dock, Cabana Club Included

Home in Key Largo

4.81 out of 5 average rating, 54 reviews

Deckhouse

Home in Marathon

4.85 out of 5 average rating, 13 reviews

Golf Coast Oasis

Home in Marathon

5 out of 5 average rating, 23 reviews

Amazing Bayfront Newer House with Dock and Pool!

Cottage rentals with a kayak

Cottage in Key Largo

4.93 out of 5 average rating, 76 reviews

Waterfront Retreat w/Kayaks, Private Dock & BBQ

Cottage in Islamorada

4.96 out of 5 average rating, 56 reviews

Islamorada bungalow 2 bed & pool

Cottage in Key Largo

4.97 out of 5 average rating, 75 reviews

Oceanfront Paradise w/ Relaxing View! Kayaks & BBQ

Cottage in Key Largo

5 out of 5 average rating, 3 reviews

1 Bedroom Home in Key Largo

Cottage in Marathon

4.96 out of 5 average rating, 24 reviews

Catch n' Relax Canalfront Cottage in Marathon

Private room in Key Largo

4.57 out of 5 average rating, 661 reviews

Cottage Sunroom Waterfront Retreat 2 ppl

Cottage in Key Colony Beach

5 out of 5 average rating, 10 reviews

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

Cottage in Key Largo

5 out of 5 average rating, 6 reviews

200ft of Waterfront/Private Swim Spa/Tiki

Quick stats about vacation rentals with a kayak in Islamorada

Total rentals
100 properties
Nightly prices starting at
$50 before taxes and fees
Total number of reviews
1.4K reviews
Family-friendly rentals
90 properties are a good fit for families
Pet-friendly rentals
40 properties allow pets
Rentals with a pool
70 properties have a pool

Destinations to explore