Vacation rentals in Cudjoe Bay

A serene view overlooks the water at sunrise, with soft pastels reflecting on the surface. A white patio table and chairs are positioned under the covered porch, inviting relaxation. The horizon features gentle clouds and distant islands, creating a peaceful atmosphere.

4.91 out of 5 average rating, 34 reviews

Rise And Shine On The Water

Spectacular sunrise view! Room to park one vehicle, but we do have a free overflow lot if needed. Community amenities include tennis, pickle ball, bocce ball, heated pool, hot tub, designated swim area, pool table, ping pong, & darts. We provide bedding, towels, pots & pans. TV in living room & one bedroom. We will also have boat bumpers installed all along the concrete dock that will accommodate a 40' boat. We offer 100% money back if your rental is in the projection cone of a named hurricane.

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, 195 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!

Two white Adirondack chairs are positioned beside a small table on a paved area near the water. Each chair is complemented by a yellow pillow, creating a comfortable seating space for relaxation. A few personal items, including a bag and a cooler, are visible on the table.

4.93 out of 5 average rating, 54 reviews

Private Ocean Oasis by Key West, Florida

Beautiful stilted two bedroom/two bathroom vacation home awaits your arrival. Break taking views of the Atlantic Ocean are picture worthy. This home hosts a 36' seawall on a wide canal. Dock equipped with fishing cleaning station, cleats, swim ladder, outdoor shower and bait freezer. King-, queen-, full- and twin-size mattresses provide comfortable sleeping accommodations for all guests. Extensive indoor and outdoor furniture allow for all to relax, recharge and enjoy their time in paradise!!

4.75 out of 5 average rating, 8 reviews

The exterior of the home is illuminated by green lights, showcasing a raised structure surrounded by palm trees. Large glass doors are visible, along with a spacious deck that offers views of the water. A tranquil canal reflects the soft glow of the lights.

Home in Summerland Key

Sailfish Dream on Cudjoe Key-28 day minimum

Sailfish Dream is your keys getaway to indulge in the keys lifestyle. Located at MM 23. For boating enjoy deep channels, quick access to all waterways, Looe Key 20 min by boat. Explore islands bordering channel to Gulf. This 2nd floor home has lots of natural light, vaulted ceiling, plenty of parking, 75 ft of seawall, wrap around balcony, swim in canal, sleeps 6 people. This 2 bed/2 bath home is family friendly for wonderful memories to be made. We are working with a 28 day minimum.

4.8 out of 5 average rating, 270 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.

Top guest favorite

Lush tropical foliage frames a serene view of sandy beach and calm waters. In the distance, colorful kayaks rest on the shore, while vibrant greenery provides a natural backdrop against the bright blue sky.

4.89 out of 5 average rating, 18 reviews

Oceanside home 109, dock,kayaks,bikes,pool,fishing

This luxurious home overlooking the Atlantic Ocean is part of Sunrise Beach Resort, an exclusive gated community built in 2007 with only 10 other homes. This is #109 and I also rent adjacent homes 111 and 107 in case you need more than one. We are 80 feet from the water's edge facing Southwest. Lounge in your private hammock or enjoy the gorgeous tropical landscaping and cool breezes on the balconies or poolside, where you can sun, fish or boat from the docks. Key West is 17 miles away.

4.9 out of 5 average rating, 30 reviews

Waterfront FL Keys Cottage @ Venture Out

Welcome to the BEAUTIFUL Florida Keys! The Keys Cottage 116 is a cute 2 bed, 1 bath home ON THE WATER in the desirable and SAFE Venture Out community on Cudjoe Key just 20 minutes from Key West. Starting at $195/night with weekly & monthly discounts & NO fees for EXTRA GUESTS! The amenities are INCREDIBLE! Large pool, hot tub, kiddie pool, PICKLEBALL, tennis, Bball, marina, 24 hr security, store, launch ramp, etc. We can do NIGHTLY rentals & WE ALLOW PETS for much less than a hotel.

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!

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."

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Other great vacation rentals in Cudjoe Bay

A wooden dock extends over calm waters, lined with colorful adirondack chairs in yellow and blue. Lush greenery borders the dock, and a clear blue sky completes the serene waterfront scene.

5 out of 5 average rating, 16 reviews

Keysie Does It at Cudjoe Key

MeganRating, 5 stars3 months ago

We absolutely loved our stay! Our checkin was smooth and flexible. The home was squeaky clean, linens and beds were unbelievably soft and comfortable, and there were more supplies/ amenities in the home than listed. We felt right at home and would love to come back! Absolutely 5 star place!

An expansive sea wall features a bright blue surface and is equipped with cleats and a ladder. Two ropes extend from the wall's edge, providing stability. The calm water reflects the surrounding structures and palm trees in the background, creating a serene waterfront view.

4.98 out of 5 average rating, 47 reviews

Waterfront 35’ Dock,80’ pool,20 min Key West

KimberlyRating, 5 stars1 week ago

We had a great stay! House was neat and tidy and in a great location.

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 stars2 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!

4.72 out of 5 average rating, 248 reviews

A dining area is visible, featuring a dark wooden table surrounded by four chairs. Through a window adorned with blinds, a view of lush palm trees and a bright blue sky extends beyond, framing the serene landscape outside.

Apartment in Marathon

Knight's Key Suites Deluxe Double Room w/ Kitchen

SeanRating, 5 stars5 days ago

Very pleasant stay at this suite. Great view of the bridge from the front. The immediate area is quite quiet, even with the Sunset Grille just a few hundred yards away. Would definitely stay there again in the future!

4.81 out of 5 average rating, 321 reviews

Houseboat in Key West

Key West Houseboat Paradise

AbbyRating, 5 stars4 weeks ago

WOW. I feel like it's hard to describe such an incredible stay at a wonderful place. Brad was beyond welcoming, and made us feel right at home. Upon entering the location, it was very clean and exactly how described. The beautiful back deck was incredible and all the wildlife around. The neighborhood was very low-key, all around were very nice and good at conversation. Any questions or accommodations we needed Brad was right there and easy to get ahold of. We already have our next trip planned with Brad and hope to continue to see him and support him for the rest of our times to Key West. This has hands down been the best vacation we have ever had and can not recommend Brad's place enough!!!