Vacation rentals with a kayak in Cudjoe Key

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Top-rated kayak rentals in Cudjoe Key

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

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Guest favorite

Home in Key Colony Beach

5 out of 5 average rating, 5 reviews

Huge Swim Spa~ Incredible Special Fall Pricing

3 Bedroom~ 2 Bath Duplex With Outdoor Solar Shower, on a Deep Water Canal in Key Colony Beach. Near The Vaca Cut Makes For Easy Access To The Gulf Of Mexico or Atlantic Ocean. Boat Dockage for up to a 34' Boat. Golf Course, Pickle Ball~Tennis Courts, and Great Playground. We have a Large Swim Spa in The Private Garden, Arcade Game Room~Ice Maker, Paddle Board, 2 Kayaks, 4 Fishing Rods & Bait, Margarita Machine, Outdoor Shower. Cabana Club Membership With Free Beach/ Ocean Access & Huge Pool.

Guest favorite

Home in Marathon

4.96 out of 5 average rating, 73 reviews

Oceanside, Smart Home with SUP/kayaks - 60 FT Dock

This pet-friendly, waterfront home upgraded in 2021 (see notes) has two rooms with ample bedding - 1 king-size bed, one queen (pull-out sofa bed), and one full. The home has a cute kitchen that is well-equipped. A nice open area allows you to walk and enjoy the canal. Enjoy the ocean view or simply sunbathe in serenity. There is house parking in front for boats and trailers and covered parking for one car. It only takes minutes to access the ocean. We just completed construction of a 60FT dock.

Guest favorite

Home in Cudjoe Key

4.83 out of 5 average rating, 30 reviews

Yellow Home Free Pontoon Rental! See details

If you book your stay for the days shown below March 30th - April 15th, 2025 April 23rd - May 3rd, 2025 May 17th - May 31st, 2025 June 6th - June 13th, 2025 Receive a free 2 day boat rental for a week reservation, 1 day for a 3 days or more reservation. Please reach out before booking for boat availability. Beautiful 3 bedroom 2 bath home nestled off of US 1. Kayaks included with the rental. Private heated pool and deck with a view of the Atlantic Ocean. Boat dockage available with parking.

Guest favorite

Cottage in Cudjoe Key

4.93 out of 5 average rating, 121 reviews

King Master, 2BR, 2BA, 35' Seawall, SUP, Kayaks

Updated, waterfront, 2BR, 2BA with King Master and a 35' seawall.Bring your boat!Fully stocked kitchen w stainless appliances. So much to do here for up to 6 at this family-friendly, quiet resort-Venture Out, a gated,secure community. Fishing, lobstering, oversized pool, children's pool, hot tub, pickleball, tennis and basketball courts.Rec center. Bike, kayak, and SUPs.Between Key West(20Mi)and Marathon, this property and area is not to be missed! Free WIFI; Both bedrooms and LR have Roku TVs.

Top guest favorite

Cottage in Marathon

4.97 out of 5 average rating, 32 reviews

Catch n' Relax Canalfront Cottage in Marathon

Enjoy our cottage right on a deep canal with 50' dock. Step right into your boat to fish the Atlantic Ocean & Gulf or just relax & enjoy the view! Enjoy an outdoor kitchen space for fish fry & Happy Hour drinks. Tan on our loungers or enjoy dinner under the stars. Kayaks/Bikes for you too. A Perfect location Minutes from Airport, 7Mile Bridge, Sombrero Beach & other Attractions. Close to shops & restaurants. Easily launch your boat from a free public marina nearby. Rental License #VACA-22-85

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

Guest favorite

Home in Marathon

5 out of 5 average rating, 33 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.

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.

Top guest favorite

Boat in Islamorada

4.93 out of 5 average rating, 343 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

Home in Marathon

4.9 out of 5 average rating, 72 reviews

Dream Vacation KCB Marathon with private pool !

Dream Vacation Duplex in Key Colony Beach. Private pool Brand New state of the art house with all commodities and amenities, 3 bicycles 2 kayaks near to restaurants, fast WIFI, washer ,dryer, blue tooth speakers, night mood lights. A modern lift for boat up to 18000 lb Main canal Use of electric golf car Gem and jet sky and boat can be arrange Electric Gem-4 car offered for a minimum extra charge Options of private boat or jet sky (ask) Heated pool on demand (extra cost)

Guest favorite

Boat in Key West

4.99 out of 5 average rating, 101 reviews

Living the Dream, Key West Style

Reconnect with nature at this unforgettable escape. Experience and enjoy what life is like living on a large 60 ft world cruising sailboat on the sailing vessel Serenity. Staying on Serenity is what Key West is known for and living a carefree lifestyle. Experience and enjoy the Artistic and Tropical landscaped private marina with spectacle views of the harbor. This is a all-inclusive price. No cleaning fee and includes 2 Paddle boards ,4 Kayaks and a large floating mat.

Superhost

Home in Marathon

4.88 out of 5 average rating, 34 reviews

Waterfront&Dock/ kayaks,Hot tub/3mims to the beach

Waterfront Vacation Home just 1 minute from Publix & Winn-Dixie, and 3 minutes from Sombrero Beach! Beauty and The Sea beach house offers direct ocean access, 2 bedrooms, 2 bathrooms, a full kitchen, and spacious living room with queen sofa bed. Enjoy ocean views from your balcony, smart TVs in every room, high-speed internet, and local canals. Fully furnished with washer/dryer, kitchenware, towels, and more. Bring your boat or jetski—dock it right in your backyard!

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What guests are saying

100' Dockage, Pool, Kayaks, Paddle Board, Bikes!

5 out of 5 average rating, 38 reviews3 months ago

We have enjoyed our time! The pool was excellent and the back yard very private, which was wonderful! Close walk to the beach and near walking paths. Had to drive to restaurants, but plenty of options w/in 10 min. Living space great, beds comfy. Floaties and kayaks in the garage, we used both. Caught some fish off the back canal, we even ate some! Would stay here again!

Home in Marathon

What guests are saying

Sunset Views, Pool and Dock

4.73 out of 5 average rating, 22 reviews2 months ago

We really liked the location. It was peaceful and private and a great neighborhood to walk around and to walk our dog. Yet, a short drive into Marathon for restaurants or any other needs. The house isn’t new but it was exactly as represented and it was perfect for us. Frank was very responsive. There were a couple of issues that he addressed immediately. It wasn’t his fault that because of the location, receiving repair parts can take some time. But Frank took care of our situations.

Home in Marathon

What guests are saying

The Pink Dolphin House.

4.95 out of 5 average rating, 21 reviews2 weeks ago

Beautiful ocean views and great local recommendations from the host! Some aspects of the interior were a bit dated, but with multiple areas to enjoy the outdoors (offering full shade to full sun and everything in between), we didn't do much inside except sleep. Kids spent hours per day in the pool and adults most enjoyed lounging on the jetty with 345 degrees of ocean views. Board games (and a ps3) were available for the occasional down time. The location allows for a feeling of privacy on the ocean while offering many hidden gems for dining and activities nearby.

Guesthouse in Marathon

What guests are saying

Key West Houseboat Paradise

4.81 out of 5 average rating, 313 reviews3 weeks ago

Brad’s houseboat was exactly as shown and described. He was easy to work with and helpful in getting checked in. Once I arrived, I spent some time enjoying the sun and view from the rooftop and got a bonus in watching the Blue Angels practice for an air show. The best part by far was waking up and sitting on the back deck watching the sun come up over the mangroves. The warm salt air mixed with a light breeze was so relaxing. There are plenty of places to eat within walking distance and it’s the keys so there’s plenty to go see and do. The neighbors were also kind and very friendly. I definitely hope to stay again if I travel back to the keys anytime soon and highly recommend it to anyone looking for a great and affordable place to stay!

Houseboat in Key West

What guests are saying

Amazing Bayfront New House with Dock and Pool!

5 out of 5 average rating, 34 reviews1 month ago

We had a great stay. The highlights were the view of the bay and the heated pool. The beds were comfortable and the open space was great to gather as a family. Unfortunately we didn’t catch too many fish but had a great time trying. The paddle boards were perfect for our teenage kids. Would definitely love to return.

Home in Marathon

What guests are saying

NEW!Serenity Oasis~Kayaks~Bikes!~Hot Tub~Spa!

5 out of 5 average rating, 17 reviews5 days ago

Really excellent house! We visited with our 3 kids and everyone had their own comfortable spaces! Location was perfect -- about 10m from everything in Marathon, 30m to Islamorada, and 1.5h to Key West. Katie and Cody were very responsive to questions and offered a ton of great suggestions for our visit.

Home in Marathon

What guests are saying

Private Pool! Luxury Paradise Pointe, Pet Friendly

4.93 out of 5 average rating, 15 reviews5 months ago

This place was wonderful for our family. Located on the water with boat lift. We caught tons of fish and saw manatees off the dock. The pool and cabana were great during the gorgeous days and to catch sports at night. I loved the morning sunrise in the top deck. Kitchen well equipped and beds comfy. The paddle boards and kayaks provided were an added bonus. I only wish we had brought bikes. The community was perfect for biking. The cabana Club was great. My kids loved the playground across the street. We played pickleball, bocce ball, and shuffleboard everyday. Centrallt located nears tons of great restaurants. I recommend Castaways and Sparky’s. Also for boat rental Vacation Boat Rental. The owner is very responsive with any issues we may have had. The property manager Tony is wonderful to work with if needed also. I cannot say enough great things about this location. 5 star all the way.

Home in Key Colony Beach

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