Cutthroat Harbor Estates vacation rentals

We found 301 vacation rentals — enter your dates for availability

Discover a selection of 67 homes and other vacation rentals in Cutthroat Harbor Estates that are perfect for your trip. Whether you’re staying in a vacation home with family or friends, you'll have the best amenities for spending time at your home away from home, which might include WiFi and a fireplace. Whatever you're looking for, you're sure to find a rental to meet everyone's needs, including accessible or non-smoking choices.

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Find out more about Cutthroat Harbor Estates

Why visit Cutthroat Harbor Estates

  • Beautiful Beaches: Enjoy stunning sandy shores perfect for relaxation and family fun.
  • Outdoor Adventures: Explore lush vegetation and unique ecosystems through hiking and nature excursions.
  • Family-Friendly Activities: Engage in various activities catering to all ages, ensuring memorable family experiences.
  • Local Charm: Visit nearby Wildwood for a taste of local culture and charm.
  • Variety of Accommodations: Choose from spacious homes, cozy cottages, and comfortable condos for a perfect stay.

Popular types of accommodation around Cutthroat Harbor Estates

Vrbo offers a variety of vacation rental options in Cutthroat Harbor Estates, perfect for your getaway. Whether you're looking for a spacious single-family home, a cozy cottage, or a comfortable condo, you’ll find the ideal spot for your family. Enjoy outdoor areas for relaxation and recreation, ensuring a memorable stay. Choose the accommodation that best suits your needs and start making unforgettable memories today.

  • Houses: The top choice among travelers, offering spacious and comfortable accommodations perfect for families or groups.
  • Condos: A popular selection that combines convenience and amenities, ideal for those seeking a home away from home.
  • Cottages: These quaint and cozy retreats provide a charming atmosphere for a relaxing getaway.
  • Apartments: A practical option for visitors, offering flexibility and essential comforts during your stay.
  • Villas: Luxurious and spacious, perfect for those looking for an upscale experience in paradise.**

Top attractions near Cutthroat Harbor Estates

Cutthroat Harbor Estates in Cudjoe Key, Florida, offers an ideal setting for outdoor and family vacations, featuring stunning beaches and marine parks. Visitors can explore the beautiful islands and engage with the area's endangered ecosystems. Whether you're seeking relaxation on the beach or adventure in nature, this destination caters to all, making it a perfect spot for memorable family experiences in the Florida Keys.

  • Florida Keys Beaches: Experience the quintessential beach vibes with crystal-clear waters and soft sandy shores. Perfect for sunbathing, swimming, and enjoying water sports, this beach is a tropical paradise just six miles from Cutthroat Harbor Estates.
  • Upper Sugarloaf Key: Immerse yourself in the local culture of this charming neighborhood. Located three miles away, it offers a unique blend of city vibes with a laid-back atmosphere, featuring local eateries and shops.
  • Upper Sugarloaf Sound: Explore this picturesque island, just five miles away, where outdoor enthusiasts can enjoy serene beaches and stunning natural beauty, perfect for kayaking and wildlife watching.

Things to do recommended for couples

Discover romance in Cutthroat Harbor Estates with sunset kayaking tours or a cozy beach picnic under the stars. Explore the nearby tropical trails hand-in-hand, or indulge in a couples' massage at a local spa for the perfect getaway.

Things to do recommended for families

Families will love exploring the beautiful waters of the Florida Keys, with activities like snorkeling at the nearby reefs or kayaking around the mangroves. You can also enjoy a day of fishing or take a scenic bike ride along the picturesque coastline.

Things to do recommended for groups

Groups visiting Cutthroat Harbor Estates can enjoy shopping at the Big Pine Key Flea Market, tee off at the Key West Golf Club, and experience culture at the Tennessee Williams Fine Art Center, all while soaking up the vibrant local atmosphere and scenic views of the Florida Keys.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation around Cutthroat Harbor Estates

When traveling with a group, family, pets, or planning for extended stays, it's important to prioritize your preferences while searching. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Cutthroat Harbor Estates with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to Cutthroat Harbor Estates with young kids: Traveling with young kids can be a bit daunting. It's important to prioritize their comfort and safety, along with having suitable amenities like a private pool. Additionally, think about how close you'll be to family-friendly activities.
  • Taking your pets with you to Cutthroat Harbor Estates: For many, a family vacation feels incomplete without their furry companion. If that resonates with you, explore Vrbo listings that welcome pets. Most pet-friendly properties come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Cutthroat Harbor Estates: If you're in search of vacation rentals that offer discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to consider including amenities like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Cutthroat Harbor Estates

Cutthroat Harbor Estates offers a perfect blend of outdoor adventures and family-friendly fun in the heart of Florida's Lower Keys. Explore the lush woody vegetation and unique wet prairie landscapes, or take excursions to nearby Wildwood for a taste of local charm. With a relaxed atmosphere and friendly locals, this tropical paradise is ideal for budget-conscious travelers seeking memorable experiences amidst nature's beauty.

  • Summerland Key: Summerland Key is a picturesque island city known for its stunning natural beauty and outdoor activities. Located conveniently near Cutthroat Harbor Estates, this charming destination is perfect for families seeking a beach getaway. Visitors can enjoy a variety of recreational areas, shopping centers, and family-friendly beaches. With its tranquil atmosphere and access to the sparkling waters, Summerland Key offers a perfect blend of relaxation and adventure, making it an ideal spot for water sports, sunbathing, and exploring the local flora and fauna.
  • Cudjoe Key: Cudjoe Key, a quaint village situated on an island, provides a serene escape for travelers. Just a short distance from Cutthroat Harbor Estates, this village offers an abundance of outdoor activities, including beach outings and island explorations. Visitors can indulge in shopping at local stores and enjoy the vibrant community atmosphere. Cudjoe Key's beautiful beaches and stunning views of the surrounding archipelago make it a haven for nature lovers and families alike, ensuring a memorable experience filled with fun and relaxation.
  • Cudjoe Gardens: Located 2 miles from Cutthroat Harbor Estates, Cudjoe Gardens is a delightful neighborhood that captures the essence of island life. Known for its inviting outdoor spaces and family-friendly environment, this area features various recreational opportunities and shopping venues. Visitors can explore the nearby beaches and enjoy the picturesque scenery of the island. Cudjoe Gardens is perfect for those looking to unwind and immerse themselves in the local culture, making it a wonderful addition to your vacation itinerary.

Booking with Vrbo is a breeze

Are you hoping to cut costs on your upcoming adventure? Keeping your travel dates flexible can really pay off, as prices can vary significantly. Additionally, opting for a longer stay often leads to substantial savings. To discover the perfect Vrbo property that fits your budget, feel free to use our filters to refine your search by price, location, and type of vacation rental.

Unlock savings with One Key

When you reserve a qualifying Vrbo for your group getaway, you'll receive OneKeyCash on the full booking amount. It truly benefits you to take on the role of organizer. By joining our One Key rewards program, you can unlock exclusive savings for members and accumulate OneKeyCash on eligible stays. Sign up today and begin reaping the rewards.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board offers a user-friendly area to plan new trips, resume your previous arrangements, or manage your travel plans. Here, you can easily access your saved or booked properties, which are organized into categories like Potential, Upcoming, or Current Trips. To start making the most of Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of vacation rental in Cutthroat Harbor Estates?
In Cutthroat Harbor Estates, vacation houses are the most popular rental option, with about 59 available throughout the area. These spacious homes typically feature multiple bedrooms, fully equipped kitchens, and outdoor spaces like patios or decks for enjoying the warm Florida weather. Additionally, there are several cottages and apartments, which provide cozy alternatives for smaller groups or couples. Campsites are also available for those seeking a more rustic experience close to nature.
Are there any beach house rentals in Cutthroat Harbor Estates?
In Cutthroat Harbor Estates, there are about 84 beach house vacation rentals available. These properties are typically spacious and well-equipped, featuring amenities such as multiple bedrooms, fully stocked kitchens, and private outdoor areas for relaxation. Many of the rentals also provide easy access to the waterfront, making them ideal for those looking to enjoy water activities.
How much does it cost to rent a vacation home in Cutthroat Harbor Estates?
Prices for vacation rentals in Cutthroat Harbor Estates vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Cutthroat Harbor Estates to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Cutthroat Harbor Estates vacation house rentals?
You can find great discounts on house rentals in Cutthroat Harbor Estates on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
What are popular rental amenities in Cutthroat Harbor Estates?
In Cutthroat Harbor Estates, popular vacation rental amenities include fully equipped kitchens, allowing guests to prepare their own meals with ease. Many rentals also feature balconies or decks, providing outdoor spaces to enjoy the pleasant Florida weather. Additionally, travelers can expect patios for relaxing outside, coffee and tea makers for a quick morning brew, and onsite parking for convenience.
Can I find family house rentals in Cutthroat Harbor Estates?
In Cutthroat Harbor Estates, there are around 30 family-friendly house rentals available. This charming community offers spacious homes that are great for families, featuring amenities such as full kitchens, ample living areas, and outdoor spaces suitable for children to play. Many properties also boast private pools and easy access to nearby waterways, making it a great spot for water activities and family bonding.

Visitors to this area can enjoy close proximity to beautiful natural surroundings, including the Florida Keys' stunning landscapes and vibrant marine life. Opportunities for fishing, boating, and exploring local parks can enhance your family's experience.
Can I rent a vacation home with a pool or hot tub in Cutthroat Harbor Estates?
In Cutthroat Harbor Estates, there are several vacation homes available for rent that feature both pools and hot tubs, with approximately 26 options that include pools and around 11 that come with hot tubs. This tranquil neighborhood in Florida offers a relaxed atmosphere, ideal for families or groups looking to unwind.

Travelers can expect amenities such as private swimming pools, spacious outdoor areas for lounging, and hot tubs superb for soaking after a day of exploration. Many properties are equipped with fully stocked kitchens and comfortable living spaces, making them great for extended stays.
Are there any Cutthroat Harbor Estates vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Cutthroat Harbor Estates with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Can I find long-stay vacation rentals in Cutthroat Harbor Estates?
A long-stay vacation rental in Cutthroat Harbor Estates is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
When is the best time to visit Cutthroat Harbor Estates for a vacation rental?
September is the most popular month to visit Cutthroat Harbor Estates, as it marks the tail end of the peak season that runs from July to September. During this period, visitors flock to the area for its warm weather and abundant outdoor activities, making it an ideal time to enjoy the beautiful beaches and vibrant local culture.

The summer months bring delightful temperatures, typically ranging from the mid-70s to low 90s Fahrenheit, great for sunbathing, boating, and water sports. You'll find plenty of opportunities for fishing, kayaking, and exploring the unique wildlife that thrives in this coastal paradise. Additionally, the proximity to local attractions ensures you can easily enjoy both relaxation and adventure.

If you're looking for a more budget-friendly experience, consider planning your visit in November. This month offers a quieter atmosphere with pleasant weather, allowing for leisurely strolls along the shore and peaceful exploration of the area's natural beauty. While you may miss the bustling summer crowds, the tranquility of Cutthroat Harbor Estates in the fall provides a great opportunity to unwind and appreciate the stunning scenery.

Ultimately, the best time to book a vacation rental in Cutthroat Harbor Estates depends on your preferences for lively summer festivities or the serene charm of the off-peak months.
Are there any remote work vacation rentals in Cutthroat Harbor Estates?
In Cutthroat Harbor Estates, there are numerous options for remote work vacation rentals, with around 49 available in the area. This beautiful community in Florida offers a serene environment ideal for working remotely while enjoying a coastal lifestyle. Many of the rentals come equipped with essential amenities such as high-speed Wi-Fi and dedicated workspaces, suiting the needs of digital nomads or those needing to balance work and leisure.

Travelers can expect comfortable accommodations featuring open living spaces, fully equipped kitchens, and outdoor areas that allow for relaxation during breaks. The area is close to various points of interest, including waterfront parks and boating access, providing opportunities for outdoor activities after work hours. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a Cutthroat Harbor Estates vacation rental?
Book your Cutthroat Harbor Estates vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Cutthroat Harbor Estates, Florida, United States of America?
Cutthroat Harbor Estates is a serene neighborhood located in the Florida Keys, offering a unique tropical experience. One of the main attractions is the proximity to the beautiful waters of Florida Bay, ideal for boating, fishing, and kayaking. The nearby island of Key Largo provides opportunities for snorkeling and diving, particularly at John Pennekamp Coral Reef State Park, renowned for its underwater beauty.

For those interested in local wildlife, the Everglades National Park is not far and offers a chance to explore unique ecosystems and spot diverse wildlife. Additionally, the charming town of Marathon is just a short drive away, featuring attractions like the Dolphin Research Center and the Seven Mile Bridge, which offers breathtaking views and photo opportunities.
Can I change or cancel my Cutthroat Harbor Estates home rental booking on Vrbo?
To find Cutthroat Harbor Estates vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Cutthroat Harbor Estates vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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