Cutthroat Harbor Estates vacation rentals

We found 308 vacation rentals — enter your dates for availability

Discover a selection of 71 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 dominate the rental market, with about 68 available throughout the area. These homes are typically spacious, featuring multiple bedrooms, fully equipped kitchens, and outdoor spaces such as decks or patios, superb for enjoying the warm Florida weather. Additionally, there are several apartments and cottages that provide alternative accommodations, often located in scenic spots near the waterfront. These properties generally offer the comforts of home, allowing travelers to relax after a day of exploring the beautiful surroundings.
Are there any beach house rentals in Cutthroat Harbor Estates?
In Cutthroat Harbor Estates, Florida, there are about 107 beach house rentals available. These vacation homes are primarily located in a tranquil neighborhood that offers direct access to the beautiful waterways and nearby beaches. Travelers can expect amenities such as private pools, outdoor patios for dining and relaxation, fully equipped kitchens, and spacious living areas. Many properties also feature boat docks or proximity to local marinas, making it easy for guests to enjoy fishing, boating, or simply taking in the stunning coastal views.
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 rental amenities include fully equipped kitchens, which allow guests to prepare their own meals, and blenders for making smoothies or cocktails. Many properties also feature outdoor spaces such as patios or decks, providing a great spot for relaxation and enjoying the warm Florida weather. Additionally, travelers can expect coffee and tea makers in most rentals, ensuring they can start their day with a fresh brew.
Are there any family house rentals in Cutthroat Harbor Estates?
In Cutthroat Harbor Estates, there are numerous family-friendly house rentals available—around 37 to choose from. This area, known for its beautiful waterfront views, offers a variety of spacious homes ideal for families. Many properties feature inviting living areas, fully equipped kitchens for family meals, and outdoor decks or patios great for relaxing after a day of exploration. Some homes even come with amenities like private pools and game rooms, ensuring that everyone has a great time during their stay.

Travelers will appreciate the proximity to local attractions, including the nearby Florida Keys, where activities like snorkeling, fishing, and boating are easily accessible.
Can I rent a vacation home with a pool or hot tub in Cutthroat Harbor Estates?
In Cutthroat Harbor Estates, there are plenty of vacation homes available for rent with desirable amenities such as pools and hot tubs, with around 26 options offering pools and 10 featuring hot tubs. This serene neighborhood, located in the Florida Keys, provides a great backdrop for relaxation and outdoor enjoyment. Many properties are designed with spacious layouts, allowing for family gatherings or group retreats.

Travelers can expect amenities such as private pools, hot tubs, outdoor patios, and fully equipped kitchens, ideal for both leisurely days by the water and comfortable evenings. Additionally, some rentals may include features like barbecue grills and easy access to local waterways, enhancing the tropical experience.
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.
Are there pet-friendly vacation rentals in Cutthroat Harbor Estates?
Yes, you can book pet-friendly vacation rentals in Cutthroat Harbor Estates, where there are around 40 options available for travelers. This area offers a variety of accommodations, including charming homes and cozy cottages, many of which feature amenities such as private pools, outdoor spaces, and fully equipped kitchens, making them ideal for families or groups traveling with pets.

The serene surroundings provide easy access to nearby parks and natural areas, great for outdoor adventures with your furry friends. Cutthroat Harbor Estates is known for its peaceful atmosphere and proximity to the beautiful waters of the Florida Keys, offering opportunities for fishing, boating, and enjoying the scenic views.
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 time to visit Cutthroat Harbor Estates, ideal for travelers seeking a blend of relaxation and adventure in this beautiful Florida destination. During the peak season from July to September, visitors can enjoy warm temperatures averaging in the mid to high 80s Fahrenheit, superb for outdoor activities like kayaking, fishing, and exploring the stunning coastal scenery.

In September, the summer crowds begin to thin, allowing for a more tranquil experience while still enjoying pleasant weather. This month is particularly favorable for those looking to take leisurely strolls along the beach or engage in water sports, all while soaking in the picturesque sunsets that the area is known for.

If you're considering a more budget-friendly option, November is a great time to visit. While temperatures might dip slightly to the low 70s, the quieter atmosphere allows for a more intimate experience of the local culture and natural beauty without the hustle and bustle of peak season.

Ultimately, whether you're drawn to the vibrant summer energy or the peaceful charm of the shoulder months, Cutthroat Harbor Estates offers an array of options for every type of traveler.
Are there any remote work vacation rentals in Cutthroat Harbor Estates?
In Cutthroat Harbor Estates, Florida, there are numerous vacation rentals ideal for remote work, with around 50 options available. This picturesque area offers a tranquil environment, superb for focusing on work while enjoying the serene surroundings. Many of these rentals come equipped with essential remote work amenities such as high-speed Wi-Fi, designated desks, comfortable chairs, and even computer monitors in some properties, suiting those who need a dedicated workspace.

The neighborhood itself is known for its close proximity to the beautiful Florida Keys, allowing for quick escapes to stunning beaches and outdoor activities during breaks. Travelers can expect amenities like fully equipped kitchens, private patios, and sometimes pools or outdoor lounges, making it easy to unwind after a productive day. 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.
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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