Holiday rentals with a kayak in Key Colony Beach

4.94 out of 5 average rating, 50 reviews

Sea Glass Beach Bungalow in Key Colony Beach!

Key Colony Beach is truly the gem of the Keys! Located in the middle keys near Marathon, we are a convenient drive to nearly all activities in the Keys. Visit Key West for the day, take a fishing charter in Marathon, or snorkel/scuba at John Pennekamp Park in Key Largo. We love Key Colony Beach for it's small town feel, easy pedestrian paths all over the island for biking, running, and walking, and great restaurants. We provide Cabana Club Membership for easy beach and pool access with a tiki

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!

4.95 out of 5 average rating, 141 reviews

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.

4.95 out of 5 average rating, 117 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.

5 out of 5 average rating, 9 reviews

Cielo's Del Mar 2 - Pool / Dock / Beach Luxury in KCB

Cielo's Del Mar 2 is a luxurious new construction duplex home located within walking distance of Key Colony's best waterfront dining restaurants and beaches. This spacious home comes equipped with 40' of dockage, outdoor swimming pool, spacious balconies and full game room for enjoyment. The home was designed with vacation and relaxation in mind, it is the perfect place for family and friends to enjoy time together. Big families can rent both sides of the home for larger gatherings!

4.93 out of 5 average rating, 68 reviews

Waterfront Villa Bring Your Boat Cabana Club Beach

Beautiful, clean 2/2 villa with 40ft dock- bring your boat up to 50ft. Open concept with water views, great location in beautiful Key Colony Beach, walk to the beach, pool and tiki bar at the Cabana Club (membership included with the rental), close to Marathon and centrally located between Islamorada and Key West. Relax and grill on the back patio or use of our ocean kayaks on the beautiful canal. 10 minute ocean and gulf access, close to restaurants, shopping and nightlife.

4.82 out of 5 average rating, 28 reviews

Cozi home with dock

Beautiful two bedroom two bathroom home (half duplex) with 35ft of dock in Key Colony Beach, Fl. Enjoy ocean access within a 5 minute boat ride. Home master bedroom and two full beds in the second bedroom. Home has an open floor plan design with kitchen and living room. master bedroom and two full beds in the second bedroom. Home has an open floor plan design with kitchen and living room. Cabana club with pool access and beach included 7 night minimum!

4.89 out of 5 average rating, 121 reviews

Houseboat in Marathon

Houseboat Getaway In Marathon

Get ready to indulge in a relaxing and unforgettable experience at the first overwater houseboat getaway in Marathon, Florida! 🌴🌊 What awaits you is - fun filled days living and exploring out on the fabulous florida keys waters in your own private aqualodge, breathtaking sunsets, and a private sanctuary perched above the sea. 😍 Don't miss out on this one-of-a-kind experience! Book your stay now and create memories that will last a lifetime.

4.95 out of 5 average rating, 136 reviews

Paradise - Pool, Hot tub, Mini Golf, Dockage, Fish

House suits multiple families with kids, groups of couples, small and large families, or solos. Home is easy to get to, easy to get inside and the neighborhood is very peaceful. Plenty to do around the island or on the water. 5 large bedrooms and 3 large bathrooms with an open living room and a fully stocked kitchen. We look forward to hosting you. Very Short Walking distance to Sweet Savannah's Ice Cream and Sweets Parlor

4.96 out of 5 average rating, 23 reviews

Ocean's Edge Retreat

Ocean's Edge Retreat is a 3 bedroom / 3 bath home with open water views of the Atlantic Ocean. It includes Cabana Club access, a private new saltwater pool and spa, kayaks and a 40 ft dock for boats. Stunning views of the canal and ocean from the private upstairs master balcony. Kids playground across the street make this an ideal vacation for families. Come see what Ocean's Edge Retreat has to offer!

4.98 out of 5 average rating, 124 reviews

Paradise found!Key Colony Beach,Cabana Club.

Second Wind is on the 9th Street canal, a beautiful corner lot with exceptional views and ocean breezes. Cabana Club! Dockage for a 20 ft boat. A two-minute walk to Sunset Park in the wonderful community of Key Colony Beach! Open floor plan with cathedral ceiling, large deck with seating for six overlooking the pristine turquoise canal. It is the perfect place for your Florida Keys getaway!

Superhost

4.74 out of 5 average rating, 23 reviews

Private Beach, Deep Water Dockage, Cabana Club

Reel Catch UPDATED CANAL FRONT, CABANA CLUB 2/2, with DOCK ** CABANA CLUB ACCESS - Includes private beach, swimming pool, whirlpool & tiki bar with food & drinks! Cast a line and kick back while you enjoy a beautiful Key Colony Beach sunrise from this freshly remodeled 2/2 canal front half-duplex. Boasting 37.5’ of deep water dockage and a 100' wide canal, this home is every fisherman’s dream.

Holiday rentals for every style

Get the amount of space that is right for you

Apartments

Convenient locations with everyday essentials

Houses

A space that's all yours, with room for everyone

Hotels

Stylish accommodation and amenities

Popular amenities for Key Colony Beach kayak rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with a Kayak

Superhost

4.89 out of 5 average rating, 18 reviews

Salty kisses beach house

AnaRating, 5 stars1 month ago

Had a wonderful time at Salty Kisses. The area was beautiful and we were able to relax with the stunning views of the backyard. The house had everything we needed in the kitchen, bedrooms, bathrooms, and even outside for entertainment. Lazaro was very attentive making sure everything was good. Neighborhood was quiet. We spent a lot of time in the pool, grilling, and out on the water which was easily accessible with the dock at the front of the house. The whole family was in love with the decorations of the house which were truly beautiful and making us feel right at home. Thank you Laz and Leslie!

4.91 out of 5 average rating, 34 reviews

Oasis Canal-Front Home: Pool, Dock, BBQ, and more!

CheungRating, 5 stars5 days ago

Beautiful clean inviting home! Comfortable and felt right at home. Our family had a great vacation here! Location was perfect for our stay as our family loves to Scuba dive, snorkel, fish, explore museums and nature and just relaxing and eating out.

4.98 out of 5 average rating, 47 reviews

Flamingo Palms-Spring discounts-NOW available

LaurenceRating, 5 stars2 months ago

Excellent host and great home and location. Fishing from the dock, grill on the patio. Lovely decor throughout the property. Made for an excellent choice for my wife’s milestone birthday celebration and Ramon and Ana made that extra special with a birthday banner. Would visit again travel plans permitting

Superhost

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!

4.96 out of 5 average rating, 52 reviews

Waterfront Private Home w/Pool-Family&Pet Friendly

LoganRating, 5 stars3 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.

5 out of 5 average rating, 76 reviews

New Private 4/3 Single Family - Kayaks & Bicycles+

SusanRating, 5 stars2 months ago

Our gals trip was wonderful. The pool, ping pong table, corn hole, kayaks, nice bikes, and paddle boards were great amenities to have. The home is located just a couple blocks from Sombrero Beach. All of the outdoor patio furniture was great quality. Nice appliances all around. The beds were very comfortable.

4.88 out of 5 average rating, 24 reviews

Golf Coast Oasis

AmandaRating, 5 stars1 month ago

This was the most perfect Airbnb for our vacation. First of all, Marathon is the perfect location if you are looking to explore multiple parts of the Keys. 1 hour to Key Largo, 1 hour to Key West. We could not have asked for a better location. The home looks just like the photos and was perfect for our family of 4 + our pup. The beds were comfortable, the living space had plenty of room for our crew, but the real show stopper was the pool. If we weren't out and about exploring the Keys, we were definitely in/by the pool! A few added bonuses: (1) K-cups for our use for that first morning. This kept us from having to worry about an emergency grocery store trip the evening of our arrival (2) pool floats available for our use (3) bikes & kayaks for everyone (4) EVERYTHING. We couldn't have asked for better - we will definitely be back!