Vacation rentals with a kayak in Windley Key

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Top-rated kayak rentals in Windley Key

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Guest favorite

Camper/RV in Key Largo

4.94 out of 5 average rating, 250 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

Top guest favorite

Home in Key Largo

4.97 out of 5 average rating, 156 reviews

Key Largo Waterfront Home with Tiki & Boat Dock

WATERFRONT Oceanside Keys delight In Key Largo Kampground- minimum stay 4 days. Your own private 29 footTIKI/ BOAT DOCK & swim ladder at the door; HOA boat launch & boat trailer parking. Bring or rent a boat up to 25' [ no jet skis] Snorkel in front of the house. Launch the PROVIDED tandem kayak from the 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.

Guest favorite

Vacation home in Key Largo

4.94 out of 5 average rating, 116 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.

Superhost

Home in Key Largo

4.91 out of 5 average rating, 100 reviews

New Oceanside Casa Azul! Voted #1! Golf Cart-Beach

No hidden fees! Casa Azul blends luxury and laid-back island vibes in the heart of Key Largo. With Superhost status and hundreds of 5-star reviews, a perfect escape. Voted the #1 Vacation Rental in Key Largo, it’s ideal for families, couples, and groups alike. Enjoy a free golf cart, fast Wi-Fi, 2 pools, private beach, saltwater lagoon, kayaks, tennis and pickleball courts with gear, marina access, boat ramp, trailer parking, and optional slip rentals. Salt Life meets luxury - this is the one.

Guest favorite

Home in Marathon

4.89 out of 5 average rating, 18 reviews

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

Inquire for monthly discounts. The happy house 339 at ghee mail. 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

Top guest favorite

Tiny home in Key Largo

4.96 out of 5 average rating, 133 reviews

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.

Top guest favorite

Houseboat in Tavernier

4.88 out of 5 average rating, 228 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 favorite

Home in Key Colony Beach

4.95 out of 5 average rating, 111 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.

Superhost

Apartment in Key Largo

4.92 out of 5 average rating, 264 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!

Top guest favorite

Boat in Islamorada

4.93 out of 5 average rating, 342 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 favorite

Townhouse in Key Largo

4.92 out of 5 average rating, 104 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.

Guest favorite

Condo in Key Largo

4.96 out of 5 average rating, 165 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 AND PICKLEBALL 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.

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What guests are saying

Huge Swim Spa~ Incredible Special Fall Pricing

5 out of 5 average rating, 5 reviews1 month ago

We really enjoyed our stay. The host, Sherry, gave timely information and quickly responded to messages. We were pleasantly surprised by the number of amenities that were available to us at the house. The Cabana Club was a real hit with my teenage daughters. It had reasonably priced drinks and lunch type meals. They enjoyed just laying by the pool or beach and sun tanning. We saw manatees one of the evenings right in the backyard of the home.

Home in Key Colony Beach

What guests are saying

Waterfront Escape -VACA-23-408

5 out of 5 average rating, 33 reviews1 week ago

We loved staying at this home in Marathon. My family of 5 (three young kids; 9, 6 & 1) plus 4 other adults all stayed here comfortably and thoroughly enjoyed ourselves. We all felt right at home! The home was spotless and kept very clean. The location was great and we LOVED the backyard with everything it offered. The kids especially loved the yard. There are numerous marinas right by the home, which made renting a boat very convenient. Highly recommend doing so! We loved having the extra amenities like the kayak and paddle boards as well! Whenever I needed to get in touch with the host Carmen, she was very communicative and responded right away. Would definitely stay here again and highly recommend! Thank you again!

Home in Marathon

What guests are saying

Oceanside Key Largo 3/3 kayaks included

4.88 out of 5 average rating, 82 reviews1 month ago

My husband and his friends stayed at Rich’s place in Key Largo to celebrate my husband's 40th birthday with some fishing in the Gulf and enjoying the sun (we miss it in Idaho this time of year!). Rich's place was the perfect base for enjoying the Keys--they went snorkeling at Pennekamp, drove to the Everglades, and drove to Key West to see Hemingway's House and Bahia Honda. They wanted to use the kayaks to explore the lagoon at Kawama, but they were so busy sightseeing, they didn't get the chance. Their favorite thing was heading down to the jetty to talk and visit each night. Thank you for providing a wonderful spot for my husband and his friends to celebrate!

Condo in Key Largo

What guests are saying

New Winnebago Trailer in the Heart of Key Largo.

4.97 out of 5 average rating, 39 reviews1 week ago

Rule's place is the perfect Key Largo spot! I especially loved the outdoor space - it was very relaxing. The RV was super clean, had everything needed and more, and is one of the nicest RVs I've ever seen! The bed was extremely comfortable and the AC kept the entire RV perfectly cool. The neighborhood feels very quiet and safe. Deanna and Rule were especially amazing, friendly, and had many recommendations. They truly are experts! I highly recommend staying here.

Camper/RV in Key Largo

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