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Beachfront vacation rentals in Cudjoe Key

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Popular amenities for Cudjoe Key beachfront rentals

Pet-friendly beachfront home rentals

Superhost
An outdoor dining area is situated on a covered porch overlooking expansive water views. A large table is set with colorful dishware in blue and turquoise. Yellow kayaks are visible on the dock, complementing the serene backdrop of the water and sky.
Cottage in Cudjoe Key
4.87 out of 5 average rating, 67 reviews

Turtle Cove Views at Venture Out

CooganRating, 5 stars3 months ago
Enjoyed the stay - the cottage was cute and nicely decorated - met all of our needs. Great athletic facilities. Nice being on the water and watching the sun rise every morning.
Guest favorite
An outdoor area features a private pool with an adjoining spa, surrounded by lounge chairs. Lush palm trees provide shade, while a spiral staircase leads to the upper level of the house. The setting offers a relaxing space for guests to enjoy.
Home in Marathon
4.91 out of 5 average rating, 11 reviews

Endless Summer

LisaRating, 5 stars3 weeks ago
We very much enjoyed our stay, the house was as expected based on previous reviews & pictures. The location was perfect for us to access from Key Largo to Key West easily. The pool was nice & the kids had fun snorkeling off the back dock & looking for all kinds of wildlife both on land & in the water with their flashlights after dark. We found the sunsets at the house to be better than what we experienced in Key West. If you need beach chairs and/or beach umbrella, we recommend you rent those.
Guest favorite
The image captures a sandy beach scene with clear turquoise waters. Sunbathers and beachgoers are seen enjoying the sun on the shore, while lush palm trees line the beach. A beachfront villa is visible in the background, enhancing the coastal setting.
Home in Marathon
4.91 out of 5 average rating, 179 reviews

Beachfront Villa - Florida Keys

MorganRating, 5 stars4 weeks ago
We had a great stay at Loretta’s place. The location offered a good jumping off point to explore the keys. The beach nearby along with canal access and kayaks was a huge plus. The garden area was nice though the mosquitos were intense. The place accommodated our group of 7 ppl well and everything was clean and well furnished. Overall, the place worked great for our group and we’d stay again!
Guest favorite
The spacious canal-front home is showcased from an aerial view, highlighting its private pool and lush palm trees. A dock with boat access extends into the water, while comfortable outdoor seating is positioned nearby, creating a relaxed atmosphere for guests.
Home in Marathon
5 out of 5 average rating, 22 reviews

Spacious lux home, private pool/spa, 80' dock

HeatherRating, 5 stars1 month ago
The house was exactly how it was described online. Everything was well marked. Lots of stuff to do at the home. Very spacious and well maintained. There were only 7 of us, so lots of extra space. The pool is on the perfect side so your not blasted with the late afternoon sun. However, there is a huge umbrella in case it is needed. Kitchen is fully stocked so nothing was needed. There is a BBQ grill as well as a flat top which is nice for outside cooking. The only thing I would recommend is to bring your own pillow if your a particular pillow person (we love our feather pillows), house pillows were not feather ones. If you rent here and have a boat definitely go to the Sombrero Lighthouse to snorkel. Never saw so many fish in one place. The Conch Cafe and Coast to Coast pizza are both great food restaurants and walkable from the home. Publix is so close it was a daily visit. Truly enjoyed the week stay!!!!!
Superhost
A tiki bar with a thatched roof offers seating along a glass countertop. Two cocktails rest on the counter, with serene water views visible beyond. Boats are docked discreetly along the shoreline, surrounded by greenery and natural light.
Home in Key Colony Beach
4.74 out of 5 average rating, 141 reviews

NEW PET FRIENDLY Waterfront Single Home-Pool,Beach

MichaelRating, 5 stars4 weeks ago
Great place to stay for family vacation or guys fishing trip. Plenty of dock space to park the boat and easy access to the Atlantic. House is clean and all amenities worked as they should. Would definitely recommend to a family or friend. Mary was a great host who provided all information without even requesting it.
Superhost
An aerial view of the Venture Out community showcases a network of canals and residential homes, surrounded by lush palm trees. The expanse of blue water reflects the sky, while streets curve around the properties, providing access to the canalfront homes.
Home in Cudjoe Key
4.83 out of 5 average rating, 23 reviews

Waterfront 2BR w/ Dock, Kayaks & Pool Access

AlyxRating, 5 stars1 week ago
Loved the house and location, neighborhood was very cute and quiet, easy to get in, we had no issues at all! Everything was perfect EXCEPT for the security that works the park1 they are rude and not tolerant to the kids in the park- which isn't a reflection of Bluescape- just of the park. We would still come back.
Superhost
The outdoor area features a sandy patio surrounded by palm trees, with several blue Adirondack chairs facing a shaded seating area under a white gazebo. The spacious home stands in the background, showcasing multiple balconies and a light-colored exterior.
Home in Marathon
4.89 out of 5 average rating, 64 reviews

Gorgeous Ocean View Home!

ChristinaRating, 5 stars1 month ago
We had an amazing time with our family and a beautiful Easter dinner with our friends. The location is perfect to travel all of the keys as it's just over an hour to Key West and Key Largo. The sun rose over the top floor guest bedroom with such a beautiful view of the water every day. Morning coffee with the view was awesome. Evenings spent wrapped on the couch watching movies with really nice big TV and unwinding. Sitting down by the water in evenings before sunset hanging with family watching niece play in sand was great too. Highly recommend.
Superhost
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
4.86 out of 5 average rating, 51 reviews

Little Venice in Marathon (in the Beautiful Keys)

AlisonRating, 5 stars3 weeks ago
We (two couples) enjoyed a great week here. Being on the canal was nice, outside sitting spots were great. The house had plenty of cooking supplies needed. Was a tad bit smaller than I expexted, but worked out just fine. Remember to bring your shampoo, body wash etc as it's not provided. Comfortable and bright, was quiet even with boats going by. Would definitely stay here again!

Beachfront home rentals with a pool

Superhost
A light green house raised on stilts is depicted. Sturdy steps lead to the entrance on the right. A large, screened lanai offers views of the surroundings. The area is made accessible with ample parking on concrete and crushed stone surfaces.
Home in Cudjoe Key
4.85 out of 5 average rating, 52 reviews

Keys getaway

JamiRating, 5 stars1 month ago
We were there to celebrate my husband's 50th birthday. The master bed, pillows and linens were very comfortable. The screened in porch with plenty of comfortable seating was our favorite amenity of the property. We hope to rent there again when we are back in the area. Very comfortable and very clean. 😁
Top guest favorite
Home in Marathon
5 out of 5 average rating, 28 reviews

Luxe Super Snapper-Heated Pool, Tiki, Dock, Lanai

KashRating, 5 stars4 weeks ago
This property was everything and more. Clean, all amenities provided as advertised and the perfect location in Marathon. Randy was very responsive and went out of his way to provide us with top notch service. We had a wonderful time and will definitely be returning again.
Top guest favorite
A serene swimming pool, featuring a vibrant logo of the Fishing Village at its center, is set against a backdrop of clear blue skies and palm trees. Lounge chairs line the edges of the pool area, offering a tranquil space for relaxation.
Home in Marathon
4.97 out of 5 average rating, 38 reviews

Grouper Getaway @ Ocean Isles Fishing Village

GaryRating, 5 stars1 month ago
Great property, exactly like the photos and descriptions. Ben was extremely proactive and responsive. I would highly recommend this property.
Guest favorite
A spacious beachfront home is depicted, featuring a large outdoor area with neatly arranged tropical plants. A well-maintained pool is visible in the backyard, alongside a staircase leading to wraparound balconies that provide ample views of the surroundings.
Home in Marathon
4.89 out of 5 average rating, 66 reviews

Beautiful Beachfront Villa w/ Pool/Tiki/Dock

RobinRating, 5 stars2 weeks ago
This home is even more than the pictures show! It is an extraordinary home for people who love the sun, shade, beach, and the beautiful home just makes it a luxurious vacation. I could not find one aspect I didn’t love.❤️
Superhost
A serene outdoor space includes a private pool surrounded by a spacious deck. Palm trees frame the scene, casting shadows on the white tiles. A furnished sitting area can be seen nearby, offering a relaxing spot to enjoy the warm weather.
Home in Key Largo
5 out of 5 average rating, 4 reviews

Newely Renovated 3/2-private pool/dock/cabana club

OliviaRating, 5 stars2 weeks ago
Absolutely amazing place to stay! Dennis is amazing and had several great recommendations for us to eat and do! The dock out back was beautiful and we were even able to see manatees! The pool was a GREAT addition and my family wouldn’t have wanted to explore the Keys any other way! The neighbors are also friendly and great to talk to! Overall beautiful place! My family and I would stay again!
Guest favorite
A private pool is surrounded by a lush tropical garden, featuring tall palm trees and vibrant foliage. The clear water of the pool reflects the sunlight, while stone pathways and colorful blooming plants enhance the natural ambiance.
Home in Marathon
4.95 out of 5 average rating, 60 reviews

Beach House, Private Pool & Dock, Gulf Sunset view

DanielRating, 5 stars3 weeks ago
Our 7 day stay was the most relaxing vacation we’ve had in years. The location was somewhat remote but only a short drive into Marathon. We hope to come back soon!!!
Top guest favorite
Home in Islamorada
5 out of 5 average rating, 16 reviews

Keezy Dream House+Beach, Pool & Kayaks at Anglers

Robert JamesRating, 5 stars2 weeks ago
A Perfect Keys Getaway! We absolutely loved our stay at Anglers Way in Islamorada! The property was spotless, charming, and perfectly located—just steps from the water. The unit had everything we needed for a relaxing stay, from a well-equipped kitchen to cozy, comfortable beds. The outdoor area was a true highlight: peaceful, beautifully maintained. Largo was incredibly friendly and responsive, making everything from check-in to check-out smooth and easy. We can’t wait to come back—highly recommend for anyone looking for a quiet slice of paradise in the Keys!
Superhost
Condo in Key Colony Beach
4.88 out of 5 average rating, 105 reviews

Beachside Unit 27 - The Beach is Calling You!

MaryRating, 5 stars6 days ago
Cindy’s beachside condo was absolutely perfect! The location couldn’t be better—just 10 steps from the beach. The condo was impeccably clean, peaceful, and quiet, making it ideal for a relaxing getaway. It was the perfect place to celebrate our ten-year anniversary. We couldn’t have asked for more and will definitely be back!

Private beachfront home rentals

Top guest favorite
The exterior of a charming waterfront home is depicted, showcasing a canal with clear turquoise water. Lush palm trees frame the property, and well-maintained landscaping adds to the serene environment. The two-story building features a spacious porch and multiple balconies, enhancing outdoor living.
Home in Marathon
4.95 out of 5 average rating, 66 reviews

Coral Lagoon #23- Private Villa Home

ReneeRating, 5 stars3 days ago
Wonderful Stay! Place was super clean and nicely decorated with minimal decor. (Sometimes places are over decorated and busy) Beach Towels were provided. Kitchen was organized & clean. Pool was nice! We brought our small dogs and the grounds were very pet friendly. Jessica’s recommended list of restaurants was spot on! Had a great time eating at several of the places. Would visit again and recommend to others.
Superhost
A spacious concrete dock extends into clear blue waters, featuring thatched-roof palapas for shade. Palm trees sway gently, while colorful buoys line the water. The sky is mostly sunny with a few clouds, enhancing the serene waterfront setting.
Campsite in Cudjoe Key
5 out of 5 average rating, 13 reviews

Little Palm By The Sea- RV Site, Cudjoe Key Fl.

GregRating, 5 stars2 months ago
We really liked Venture Out and Cudjoe Key. It was a short drive to everything you need for a great stay. We will be back.
Top guest favorite
An aerial view captures the duplex home situated near a canal with multiple boats docked along the water. The vibrant homes are seen in a tangle of greens and blues, with sandy pathways and lush landscaping complementing the serene coastal environment.
Home in Marathon
5 out of 5 average rating, 18 reviews

Waterfront with Boat Lift/Kayaks and Hot Tub

JohnRating, 5 stars2 weeks ago
The place was amazing!! plenty of room for our family of 5. All of the fishing equipment was awesome!! From the rods and tackle, to the deep freezer with bait, the extras made the whole trip more enjoyable. Loved the house. It was perfect!!! Will definately be back in the future!! 10 out of 10 would recommend!!
Guest favorite
A spacious outdoor area features a well-maintained dock alongside calm waters. Luce lounge chairs are arranged for comfort, with palm trees offering shade. The exterior of the duplex is visible, showcasing large windows and a patio area adjacent to the dock, enhancing the waterfront experience.
Home in Marathon
4.94 out of 5 average rating, 35 reviews

Florida Keys Oceanside Utopia

CaroleRating, 5 stars1 month ago
Shane and Kelly were fabulous! My husband and I enjoyed a week away and loved exploring Marathon. Fishing from the back deck was so much fun. We caught some mangrove snapper that we made for dinner which was exquisite! I also caught a Jack Cravalle and my hubby caught a shark. Definitely fun times! Explored beaches, hiked and went to Key West for a day. Weather did not disappoint. Highly recommend this great vacation home!
Superhost
A serene view of a tranquil waterway is presented from the deck of the floating house. Two black chairs are positioned on the wooden deck, facing the peaceful water. Lush green trees frame the scene, with sunlight reflecting off the calm surface.
Houseboat in Key West
4.71 out of 5 average rating, 173 reviews

A slice of paradise in the Florida Keys

CarmenRating, 5 stars3 months ago
Wonderful night! Only a few bugs around dusk that left by nightfall. Lots of planes took off from 5-7 PM, but again they stopped by nighttime and not sure that it happens every day. The boat itself was perfect, exactly as described!
Top guest favorite
A private pool is situated beside a spacious deck, surrounded by tropical plants and palm trees. Comfortable lounge chairs are placed near the pool, and stairs lead to the upper level of the stilted structure. The area offers direct access to the canal.
Home in Marathon
5 out of 5 average rating, 14 reviews

P36 - Charming and immaculate 2 Bedroom, 2 bathroo

BradleyRating, 5 stars3 weeks ago
Great place! Very spacious, nice dock and out door and area to enjoy with the pool! It was nice having a large deep freezer for ice and fish!
Superhost
A covered balcony featuring several green rocking chairs provides a relaxing space overlooking the Atlantic Ocean. The view includes palm trees swaying in the breeze, with vibrant blue and green water stretching into the horizon.
Condo in Key West
4.85 out of 5 average rating, 55 reviews

Ocean front 1BR/1BA Suite w/ kitchen & living rm

NoraRating, 5 stars1 month ago
We had an amazing few days to disconnect. The resort exceeded my expectations - the property is on a private beach with beach chairs, umbrellas, primitive shower to rinse off, a decent size pool, and tall coconut palm trees. So dreamy! The property is very clean, staff is friendly. The apartment is well stocked with kitchen essentials like plates, cups, silverware, pots, etc. We are definitely coming back!
Guest favorite
Home in Marathon
4.91 out of 5 average rating, 34 reviews

Viamarhe House-Private beach, Kayak, yard games

AmandaRating, 5 stars2 weeks ago
Loved our week-long stay at Marjorie’s! As pictured and described. Checked out the other reviews for useful tips.

Quick stats about beachfront rentals in Cudjoe Key

  • Total rentals

    10 properties

  • Nightly prices starting at

    ﺩ.ﺇ845 before taxes and fees

  • Total number of reviews

    530 reviews

  • Family-friendly rentals

    10 properties are a good fit for families

  • Rentals with a pool

    10 properties have a pool

  • Wifi availability

    10 properties include access to wifi

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Monroe County
  5. Cudjoe Key
  6. Beachfront rentals