Vacation rentals with a kayak in Vaca Key

A sandy beachfront is framed by palm trees, with the glistening Atlantic ocean in the background. A volleyball net is set up on the sand, along with multiple seating areas for relaxation, inviting guests to enjoy the tranquil environment and scenic views.

4.91 out of 5 average rating, 34 reviews

Viamarhe House-Private beach, Kayak, yard games

If you are looking to enjoy the natural beauty and the captivating views of the Florida Keys, our charming Oceanfront house is the place for you. Enjoy the breathtaking views of the sunrise and the starry night show over the beautiful Atlantic ocean. You and your family can enjoy the exclusivity this property will give you, Viamarhe is its own little resort, 5 kayak and fishing rods, volleyball, chess and bowling ground, Domino, Billiards, Ping-Pong, and Football. the propane BBQ grill, fire pit

A private pool is bordered by lush palm trees and a thatched Tiki Hut. Lounge chairs are arranged around the pool area, and colorful outdoor decor adds a cheerful touch. Clear blue skies and sunshine illuminate the space, creating an inviting outdoor retreat.

4.95 out of 5 average rating, 20 reviews

Private Pool! Luxury Paradise Pointe, Pet Friendly

Beautiful Key Colony Beach waterfront duplex with a private pool! Featuring a newly updated, 3/2, spacious 1440 sf home, deep water private boat slip & lift, Tiki Hut w/TV, kayaks, pet friendly, ice machine, bait freezer, large kitchen, Cabana Club, restaurant, and beach access. Family friendly location w/Golf, a playground, and dog park. Sit under the tiki hut, watch the game on the outdoor TV after a day on the water, & grill your catch. Relax on the upper deck sunbathe and enjoy the vistas!

A two-story home is showcased, featuring a spacious backyard with a swimming pool surrounded by lounge chairs and umbrellas. The exterior is illuminated under a twilight sky, while a stone walkway leads to the inviting entrance. Lush greenery adds a vibrant touch to the setting.

5 out of 5 average rating, 32 reviews

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

Experience the relaxing setting of this 4BR 4.5Bath home, ideally situated in the picturesque waterfront neighborhood of Marathon, FL. Discover the area's scenic beauty and a diverse selection of water activities, attractions, and landmarks. After a day of exploring, return to our home for a rejuvenating stay. ✔ 4 Comfy BRs ✔ Open Design Living ✔ Full Kitchen ✔ Balcony ✔ Backyard (Pool, Games, BBQ, Lounges, Dining) ✔ 73-Foot Dock ✔ Smart TVs ✔ High-Speed Wi-Fi ✔ Free Parking See more below!

5 out of 5 average rating, 10 reviews

Ocean Views Galore- Bring Boat- Built New 2024

Immerse into the finest Marathon Key has to offer.. Escape to the long ocean views, endless ocean sounds and breeze in this Brand New Built in 2024 Stunning Water Front Home. With Amities galore. Heated/ Chilled Pool/Spa/ Kayaks, Paddle Boards, Bicycles, Boat Dock, Games, Perfect Location, Walk or Bike to all. Fisherman's paradise. Instant Ocean or Gulf Access. One of 3 homes on this one-acre private ocean gulf lot that has the look and feel of a private island with 400 feet of bulk head

4.95 out of 5 average rating, 139 reviews

The front of a blue kayak is viewed from a waterway, reflecting the soft colors of the sky. Green foliage can be seen along the shoreline, while distant villa rooftops provide a serene backdrop against the calm water.

Villa in Duck Key

Beach House - Kayaks & 2/2.5 Villa

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.

A modern two-story home features a clean white exterior with navy blue accents. A set of black stairs leads to a covered balcony adorned with potted plants. Large windows allow natural light to enter, while a gravel driveway provides ample space in front.

5 out of 5 average rating, 37 reviews

Waterfront Escape -VACA-23-408

Come stay at this brand new home construction on a deep and wide canal leading to the ocean with pool and exotic decor. 75 foot dock with water and electric. Top of the line appliances with a fully stocked kitchen. Spa style showers with high end decor. Luxury at its best. Heated pool with sundeck and lots of seating around the edges. (Pool heater is an additional $100 per stay). Ground level cooking and dining for those beautiful days after boating or while laying around in the pool.

A scenic pool area is visible, featuring a hot tub adjacent to the water's edge. Palm trees sway gently in the breeze, providing a tropical atmosphere. The blue sky reflects on the tranquil water, enhancing the serene setting.

4.76 out of 5 average rating, 25 reviews

Sunset Views, Pool and Dock

Beautiful two bedroom two bath single family home with pool and spa with dock right on the water! Enjoy the beautiful sunset and bay views from our dock, deck or pool! Bring your boat and bathing suits and enjoy this wonderful home in the Heart of the Florida Keys! Pool heat is an additional fee Kayaks and golf carts rental available upon request Saturday to Saturday during busy months except September and October. And you can always ask 7 night minimum no exceptions VACA-22-34

A paved outdoor patio features two lounge chairs and a small round table, surrounded by tropical plants and palms. The tranquil canal is visible in the background, offering a serene waterfront view.

4.95 out of 5 average rating, 115 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.

4.93 out of 5 average rating, 349 reviews

The image features a distant houseboat silhouetted against a vibrant sunset, reflecting shades of orange and purple on the water's surface. The view is taken from a skiff, with gentle ripples seen in the foreground, creating a serene atmosphere.

Boat in Islamorada

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.

A tray displays two coconut cups filled with a refreshing beverage, each adorned with a pink paper umbrella. Slices of watermelon are arranged on a plate beside the drinks. The vibrant blue water of the heated pool glistens in the sunlight, surrounded by tropical greenery.

5 out of 5 average rating, 51 reviews

Luxury Boating Paradise+Pool+Sailing Kayaks

“Our boys loved the game room and the Infinity game table. The location is perfect!” - Marie Set your compass for Captain's Quarters, your tropical paradise nestled in Marathon. Minutes from the shores of Sombrero Beach, this 4BR/3BA home casts off into luxury with a heated pool/spa, 2 elite sailing kayaks, a full kitchen with BBQ, and private deep-water dock access. Embark on nearby ocean adventures with top-notch fishing and snorkeling waiting to be discovered!

4.86 out of 5 average rating, 50 reviews

A waterfront view captures a serene canal lined with tropical greenery and residential boats. The white boat is positioned on the dock, with steps leading to an inviting home painted in a soft yellow. Clear blue skies enhance the tranquil atmosphere.

Apartment in Marathon

Little Venice in Marathon (in the Beautiful Keys)

Little Venice in Marathon is a beautiful 2 bed / 2 bath fully remodeled waterfront home that offers the best Florida Keys Living. There are plenty of fun and adventurous activities to do just steps from your door. Including but not limited to boating, kayaking, biking, sport fishing and many more fun activities. Our home is equipped with everything you may possibly need to spend an enjoyable, relaxing vacation. Also this dream home has a 50 feet boat dock.

A comfortable brown leather sofa is adorned with striped decorative cushions and a prominent 'love home' pillow. A wooden coffee table holds various brochures and a remote. In the background, fishing rods are visible, and a neutral-colored wall adds to the relaxed atmosphere.

4.89 out of 5 average rating, 27 reviews

Pet Friendly Half-Duplex Cottage w/40' Slip Option

We have a lovely oceanside cottage in Marathon Key, Florida, close to everything with many amenities. The cottage has a large yard and plenty of room to park boats, RVs, and wave runners. This modernized cottage is for you if you all need a great place to stay. This quaint and cozy home offers good value and features new furniture and brand-new state-of-the-art stainless steel appliances. There is one bedroom and a pull-out queen-size sofa bed.

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Villas

Luxurious estates for the ultimate escape

Apartments

Convenient locations with everyday essentials

Popular amenities for Vaca Key kayak rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a kayak

A two-story house is surrounded by lush greenery and palm trees. A spacious backyard features a heated pool and a wooden dock. Loungers are arranged near the pool, providing a relaxing outdoor space. The exterior showcases large windows and a balcony with seating.

4.97 out of 5 average rating, 68 reviews

Sombrero beach oasis,great location,many amenities

KendallRating, 5 stars2 weeks ago

Incredible for a family vacation. 🏝️The property feels very private, clean, well decorated, and many amenities. We tried out the paddle boards and spent a lot of time in the pool. When going to the beach, Aileen already had chairs and towels to bring! This property really is a gem. Thank you Aileen!

5 out of 5 average rating, 40 reviews

Yellowtail Getaway with Boat Dock and Pool 2

HopeRating, 5 stars2 months ago

We absolutely loved the place , it was spacious , clean and had all the extras you would need. So convenient with the boat dick and loved having the pool. Would definitely return.

A spacious pool area is framed by tropical landscaping, showcasing a large, clear swimming pool. Sun loungers are arranged around the pool, providing places to relax. A tiki hut offers shaded seating options, enhancing the outdoor living experience with serene water views.

4.81 out of 5 average rating, 37 reviews

Luxury Waterfront Retreat with Dockage & Pool

KathrynRating, 5 stars1 month ago

We had a wonderful family vacation at Naomi’s place. The place was perfect for our family of 4. There was so much to do to keep our active family busy. The house was well stocked with everything you may need for meals. Host was very responsive and helpful throughout our stay. We rented a boat and the dock was perfect for storing. We are looking forward to staying here again on our next visit to the keys!

A wooden dock extends alongside a calm, turquoise canal, with boats docked nearby. The modern home is positioned adjacent to the water, featuring a covered patio with seating. Clear skies and sunshine create a serene waterfront atmosphere.

4.85 out of 5 average rating, 26 reviews

Pelican Inn

JamesRating, 5 stars2 weeks ago

Karen’s place was amazing. Sitting on the deck and fishing was fun to do during the day and in the evenings when we wanted to relax. We were visited by manatees and saw some very cool fish in the canal. The location was perfect right in the middle of the keys with an hour to get to key west and key largo each direction. Local restaurants were bike riding distance. The house was clean and very nicely taken care of. Most of the local neighbors were nice or the people who owned the surrounding homes as vacation homes. Except for the guy who owns the house directly in front of Karen’s closest to the street, yellow house I believe, he had some rude things to say regarding us fishing but it’s not Karen’s fault the neighbor was a rude person, all the others were lovely. We enjoyed our stay so much and would love to return one day.

A private outdoor space features a heated pool surrounded by lounge chairs on a grassy area. Tropical palm trees provide shade, and the house displays large windows that allow natural light. An inviting patio area is visible, enhancing outdoor relaxation.

4.96 out of 5 average rating, 52 reviews

Waterfront Private Home w/Pool-Family&Pet Friendly

LoganRating, 5 stars2 weeks ago

The location and access to the beach and canal was amazing! We had such a fun time with the kayaks while being able to see all the wildlife and sail boats. The house was exactly what we needed. Jose was very helpful and flexible throughout our stay.

A light-filled living area features a comfortable seating arrangement with leather sofas and a large area rug. A television is housed within a white entertainment unit, flanked by decorative glass vases. Expansive sliding glass doors open to the outside, providing an airy ambiance.

4.94 out of 5 average rating, 49 reviews

Sea Glass Beach Bungalow in Key Colony Beach!

SallyRating, 5 stars6 days ago

Our family enjoyed our stay here. Very peaceful setting and we were able to ride the bikes provided by hosts to the beach nearby. The backyard of home offered outdoor relaxation and privacy. The grill worked great too. The home was very clean and comfortable. It is decorated so cute. All kitchen utensils were provided so made cooking meals easy. We did eat out often at nearby keys and the drive was not too far from where we stayed. Lindsey was a great host. She is very responsive and friendly. She checked in to make sure our stay was going well and gave us good info for our stay. We really enjoyed staying here and if we make it back to Key Colony will plan to stay here again. I strongly recommend staying here.

A serene waterfront property is shown, featuring a private heated pool surrounded by lush palms. A boat dock is visible alongside the tranquil canal, with kayaks available for exploration. The exterior of the house showcases a balcony overlooking the water, creating a peaceful retreat.

5 out of 5 average rating, 3 reviews

*NEW!*Paradise Palms~Dock~Pool~Kayaks Grill~View!

NuciaRating, 5 stars1 month ago

We had a wonderful family vacation getaway at Katie and Cody’s place. The house was very clean, and the location is great as well with accessibility to food, Publix, and great beaches. Our favorite aspect of the house was the small pool. Our teenagers played in it endlessly, and when they were gone we enjoyed relaxing on the pool floats. Communication with Katie was top notch. She always responded quickly and had great follow through with any issues we had. they definitely go above and beyond to provide resources of fun activities and resteraunts in the area. We would definitely stay here again!

A shaded outdoor seating area features white cushioned chairs surrounding a dark wooden table. Brightly colored kayaks are visible on the water's edge, alongside a boat dock. Lush greenery encircles the space, complementing the serene canal views.

4.93 out of 5 average rating, 68 reviews

Waterfront Villa Bring Your Boat Cabana Club Beach

LeeRating, 5 stars3 weeks ago

This place was perfectly located in the middle keys. Easy to get to key west and to Islamorada for our chosen activities. cabana club was very welcoming.

Show all

Cottage rentals with a kayak

4.96 out of 5 average rating, 84 reviews

A comfortable living area is highlighted by a light-colored sofa with textured cushions, accompanied by a woven coffee table. Natural light enters through multiple windows, revealing touches of coastal decor and a glimpse of a bedroom in the adjacent space.

Cottage in Islamorada

Islamorada bungalow 2 bed & pool

LynnRating, 5 stars3 weeks ago

Such a warm, quaint place. Clean, right next to the pool and close to nearby restaurants, activities and much more. Loved it.