Vacation rentals in Coon Key

4.93 out of 5 average rating, 129 reviews

Cottage in Cudjoe Key

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.

Tiny home in Big Pine Key

4.81 out of 5 average rating, 196 reviews

Cheerful Tiny House in the Florida Keys

Enjoy your trip to the keys by staying at this wonderful tiny house, surrounded by nature and deers! This is a hidden gem in the keys for your relaxation, enjoyment. Cozy and roomy space for the whole family! The Tiny house is located in the small Breezy Pines RV Resort. It has everything you would need during your trip. Outdoor patio area with rattan sofa and armchairs, grill offer an additional comfort for incredible vacation! it has everything for your nice and comfy stay close to Key West!

Top guest favorite

A wooden dock extends over calm waters, flanked by posts leading to a serene view of the sky at sunset. Lush palm trees are visible in the background, enhancing the tranquil atmosphere of the canal.

Guest suite in Key Colony Beach

4.99 out of 5 average rating, 109 reviews

Turtle-By-The-Sea: the Best Deal in KCB!

A perfect get-away for couples or budget travelers, Turtle-by-the-Sea is the best priced vacation rental or hotel room in the middle-keys. Together with its prime location and amenities there simply isn’t a better deal to be had! Bursting with Keys charm, this cozy retreat is the perfect place to relax & escape. Owners Mallory & Steve infused their love of the Keys & its surrounding ocean into every aspect of their waterside home. Shoot us a message & start planning your dream Keyscation!

Condo in Key Colony Beach

A view from the balcony captures the serene beach setting with clear blue waters and palm trees swaying gently. A tiki hut is visible in the foreground, surrounded by well-maintained grass and pathways leading to the beach.

4.96 out of 5 average rating, 208 reviews

Oceanfront Sunrise Condo Private Beach Heated Pool

Impeccable condo directly on the ocean with water views from every window. Located in Key Colony Beach (middle Keys) with heated pool and private beach. Unit #20 is a studio condo with a classic Keys interior: newly renovated bathroom and crisp white kitchen stocked with everything needed to cook a complete meal (stove, oven, toaster, microwave, blender, fridge, etc). Enjoy the private back balcony and private beach with lounge chairs, patio tables, tiki's and BBQ grills for guest use.

4.8 out of 5 average rating, 271 reviews

A modern houseboat is anchored on calm waters during sunset. The structure features large windows and a spacious front deck with a grill station. The warm glow of the setting sun illuminates the exterior, reflecting off the water, creating a serene atmosphere.

Boat in Marathon

Paradise awaits on this cozy houseboat!

Our vision is for you to kick back, relax, and find your home away from home! Wether you want to celebrate with your loved one or retreat by yourself this floating home offers comfortable space for 2 adults. Located near the 7 mile bridge in Marathon Florida on the Atlantic Ocean nestled in a quiet, reserved mangrove area. This spot is fantastic because you have unparalleled access to out of this world sunset/sunrise views. Kayak through the mangrove and explore the surrounding areas.

Cottage in Little Torch Key

A long wooden dock extends into clear blue water, flanked by palm trees and lush greenery. Two turquoise chairs are positioned at the dock’s end, providing an ideal spot for relaxation and enjoying scenic water views under a bright sky dotted with clouds.

4.9 out of 5 average rating, 167 reviews

Waterfront Cozy Cottage with Boat Ramp & Dock!

Welcome to Paradise! Stay in the amazing Keys and beautiful waterfront home with 250 foot dock, ramp, and basin for your boat. It's a must-see rustic outdoor environment and fishery experience, very typical in the Keys! The property lot is almost an acre with a work section and still very spacious. Stunning panoramic water views, sunrise and sunset. Steps away from ocean water. Bring or rent fishing and snorkel gear nearby to fish right off the dock and enjoy the underwater scenery!

Top guest favorite

A wooden pier extends into calm waters, leading towards a beach with soft golden sand. In the background, a multi-story building is nestled among palm trees, set against a sky with scattered clouds and a single bird in flight.

Condo in Key West

4.97 out of 5 average rating, 100 reviews

Hidden Beach unit 1 The Perfect Place to stay

This place is extraordinary. There is nothing like it in Key West. Just 3 blocks from Duval Street, this property sits on Key West’s only natural beach. Hidden Beach is right on the Atlantic Ocean nestled between Key West’s best restaurant (Louie’s Backyard) and the beautiful, luxurious Reach Resort.Here, you can enjoy spectacular views and sunsets from one of the islands only private beaches or you can stroll through Old Town, an amazing architectural and botanical treasure.

4.91 out of 5 average rating, 321 reviews

Three colorful Adirondack chairs, yellow, turquoise, and green, are positioned on a sandy beach facing a calm blue ocean. A rocky shore and sparse greenery surround the seating area, while fluffy white clouds drift in a bright sky, enhancing the serene water view.

Villa in Marathon

New Aqua Lodge 2Beds 1 Bath with Full Kitchens

This hip spot is the new thing in lodging. Aqua Lodge is all the modern amenities while being on the water. Full kitchens, flat screen tv's, wi-fi , pool, bikes, sunset beach. We have it all right at your finger tips. You can sleep up to 5 people comfortably. We have great air conditioning and big showers. The deck is furnished with a dining table for those romantic outdoor dinners in the moonlight. We also have a sunset beach area for the best sunsets in the Florida keys!

A spacious balcony is shown with a sectional seating area facing the water, complemented by a white table. A chaise lounge is positioned nearby, offering ample space to relax. The view includes palm trees and distant boats under a clear blue sky.

4.97 out of 5 average rating, 159 reviews

Cudjoe Key Home with a View

We are so excited to share our little piece of paradise with you! Our unit is located a short walk away from all the amenities the Venture Out community has to offer such as a pool, hot tub, lagoon, bocce ball, tennis courts, playground and boat marina. On the property we have a 2-person hybrid kayak for your enjoyment. We also provide table games (we love a game night) as well as the equipment to play bocce ball and darts which can be played in the recreation center.

A serene view of a waterfront canal is captured from a covered porch. The calm water reflects the sky, with boats docked along the edges. Palm trees gently sway in the breeze, enhancing the coastal setting. Nearby structures suggest a vibrant community atmosphere.

4.83 out of 5 average rating, 264 reviews

OCEAN PARADISE AT VENTURE OUT + 4 BIKES/ 2 KAYAKS!

*PERFECT LOCATION! * 35' Seawall *AWWSOME 2 bedroom 2 full bath waterfront stilted house in Cudjoe Key. Located in the lower Florida Keys at MM# 23 only 25minutes to Key West. Located in the gated community of Venture Out Resort. *Sleeps 6 *55" TV *A/C & heat *Fully equipped kitchen *Brand New Amenities including grill, 4 Bikes & 2 two-person Kayaks *PLUS: Pool, HotTub, Marina, Boat Ramp, Store, Playground, Game Room, Tennis, Library, etc. Too much to list!

A view from the balcony captures neighboring houses and a landscaped area, with palm trees visible below. The calm waters of the Atlantic ocean stretch in the background under a clear, blue sky. The white railing frames the scenic vista.

4.93 out of 5 average rating, 178 reviews

106 Newly Renovated House with Oceanview and Pool

"This three-story home overlooks the Atlantic ocean in a gated community of only 10 other homes. Just south enough to enjoy the bluest water in the keys and only 20 minutes away from Key West! This pristine home sleeps 6 comfortably and makes a great destination to exploring all the wonders the FL Keys. Come enjoy the pool, fishing, boating, diving or just relax with the ocean breeze. This location has all the best of the Keys."

A light-filled living area features comfortable seating arranged around a central coffee table. Large sliding glass doors offer unobstructed views of the turquoise waters outside. Decorative elements include wall art and potted plants, enhancing the space's tranquil ambiance.

4.9 out of 5 average rating, 107 reviews

*Emerald Seas*-Florida Keys Ocean Front Paradise!

Welcome to our Florida Keys Ocean Paradise, Emerald Seas! Truly a special place to get away and relax. Enjoy the crystal-clear waters and amazing views. Bring or rent a boat, look for sea turtles, manatees, dolphins, lobster & tropical fish right from your patio or dock. Take in a glorious sunrise or moonlit night over the water. The amazing, 180 degree panoramic ocean views will take your breath away every moment you are there.

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Other great vacation rentals in Coon Key

A serene waterfront view is presented, featuring a palm tree standing tall beside a calm body of water. Two benches are positioned for seating, with a picnic table nearby on a pebbled area. The sky is clear with soft clouds, reflecting a sense of tranquility.

4.9 out of 5 average rating, 52 reviews

Keys Island Villa - Venture Out Home 354

ClaudiaRating, 5 stars1 month ago

Fantastic stay w great views. House made us feel right at home. place was in gated community. it felt safe and well maintained. Fun to walk around in the evenings.

5 out of 5 average rating, 19 reviews

Houseboat in Marathon

Adventurers escape breathtaking off-grid houseboat

YulieskaRating, 5 stars3 weeks ago

A great experience, beautiful place. Joe is fantastic. Always attentive and willing to help.

A bright living space features large windows with light-filtering shutters, offering a view of the outside. A spacious day bed is positioned near the windows, complemented by a rustic dining table and chairs. The adjacent kitchen includes modern appliances, enhancing the open layout.

Home in Summerland Key

4.82 out of 5 average rating, 57 reviews

Kelly’s Kabin - Private FL Keys Cottage

LadyRating, 5 stars3 weeks ago

The cabin was cozy and super cute. It was impeccably clean. I only stayed one night but wish I stayed longer. She had all the necessary amenities. I didn’t get to use the patio since I mostly stayed out on the boat but wish I had more time to do so. Kristin had board games, shampoo, conditioner, body wash, blow dryer, washer, dryer and everything you would want in an AirBNB. There are plenty of restaurants nearby and the supermarket wasn’t too far. I felt safe in the neighborhood. I hope to come back and stay here again!

5 out of 5 average rating, 21 reviews

An outdoor space showcases a wooden deck surrounded by lush greenery. A gazebo is positioned at one end, providing shaded seating. A picnic table and lounge chairs offer various seating options, while a grill is visible nearby, inviting outdoor gatherings.

Apartment in Key West

Honeymoon Palm Suite near Higgs Beach

KrystalRating, 5 stars1 week ago

If you are looking for a place to stay that's away from the partying and busy spots this is a great location. Easy walk to the Salute! on the beach, nice garden club to visit, too. Bikes were very convenient, but the heat pushed us to use Lyft often. Private Patio was a wonderful area to wind down, or sit while you want the 30 seconds for your Lyft to pop around the corner. Nice place!

5 out of 5 average rating, 11 reviews

A private hot jacuzzi is nestled under a sheltered area, surrounded by green foliage. Soft seating is positioned nearby, and natural light filters through the striped curtains. A staircase in the background leads to an upper level, while a wooden fence offers privacy.

Apartment in Key West

Heron Hideaway

AllisonRating, 5 stars4 days ago

Great place to stay while in Key West far enough from Duval to be quiet yet close enough to walk to wherever you want to go. Very responsive host. The accommodations were just as pictured and described. I would recommend this place.

A bright living space features a round dining table surrounded by bamboo chairs, complemented by floral decor. In the background, a comfortable seating area with a green sofa and plush ottomans is visible, alongside large windows allowing natural light to illuminate the room.

4.93 out of 5 average rating, 60 reviews

Betty's Place

EmilyRating, 5 stars2 weeks ago

Honestly I was super impressed with how quick Jacqueline responded and how smooth the check in went. Betty’s Place was such a beautiful home and very clean and spacious. We had an amazing time and can’t wait to plan another keys trip at Betty’s place!

A spacious living area is visible, featuring a large dining table with mixed seating arrangements. Vibrant blue curtains frame the glass doors, which offer a view of the ocean and outdoor seating. A decorative seahorse wall piece adds a coastal touch.

4.8 out of 5 average rating, 92 reviews

Palm Breezes! Room for Everyone on the Ocean.

GerritRating, 5 stars1 month ago

10 out of 10 stay. Beautiful, serene property where we often felt we had the mangrove and key to ourselves. Several days were spent on a recurring rotation of kayaking, pool, hot tub, repeat. Perfect distance from Key West for adventuring there, but plenty on Cudjoe Key and Big Pine if you don't want to venture to the hustle and bustle. Sincerely hope to return!!