Cutthroat Harbor Estates vacation rentals

We found 307 vacation rentals — enter your dates for availability
Discover a selection of 66 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.
  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, yards and more
  • More for less

    More space, more privacy, more amenities — more value
  • A place for everyone

    We stand for diversity, inclusion and families everywhere.
    Learn more

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.

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 accommodation in Cutthroat Harbor Estates?
Condos are the most popular style of vacation rental in Cutthroat Harbor Estates, according to our data. Even if you've got a different idea in mind, Vrbo has vacation homes in a variety of shapes and sizes. Look through our options to find your perfect Cutthroat Harbor Estates pad.
How much does it cost to rent a vacation rental in Cutthroat Harbor Estates?
The average price for a vacation home in Cutthroat Harbor Estates is determined by a number of factors, including property type, length of stay and season. Whether you're thinking about a sprawling villa with a pool or a quaint cottage perfect for just you and the kids, just enter your dates of travel to discover stays with exceptional value.
How much does it cost to rent a beach house in Cutthroat Harbor Estates?
Prices for beach houses in Cutthroat Harbor Estates may differ depending on the size and style of the property and time of year you're traveling. All you need to do is enter your travel dates into Vrbo and the number of guests to see your rental options and prices. From there you can use our filter tool to refine your search results by ratings, nearby activities, amenities and more.
Are there pet-friendly vacation rentals in Cutthroat Harbor Estates?
Good news! Yes. You can pick from 50 vacation rentals that cater to pets in Cutthroat Harbor Estates. Many of our pet-friendly vacation rentals even come with an outdoor area for your fur baby to play in, complimentary treats, special dog beds and proximity to parks. Apply the "Pets allowed" filter to find your place on Vrbo.
Can I rent a house with a pool in Cutthroat Harbor Estates?
Tick the "pool" box in our handy filter tool and you'll find 21 houses with private pools in Cutthroat Harbor Estates on Vrbo. Morning dip, sunset soak or midnight swim? How you spend your leisure time is up to you when your vacation home has a swimming pool.
What are popular rental amenities in Cutthroat Harbor Estates?
An ocean view, a nearby river and a swimming pool top the list of most popular rental amenities in Cutthroat Harbor Estates. Whether you're taking a trip on your own, with your sweetheart or a group of friends, Vrbo will help you find a vacation rental that fits your style with all the features you're looking for.
Are there large group vacation rentals in Cutthroat Harbor Estates?
With seven properties that can sleep 10 people or more in Cutthroat Harbor Estates, you don't have to leave anyone off your invite list. From extended family vacations to events like weddings and birthday parties, Vrbo can help you find a large group rental to suit the occasion.
Are there vacation rentals in Cutthroat Harbor Estates that welcome kids?
Bring the whole group together for a fun-filled adventure in Cutthroat Harbor Estates at one of our 49 family-friendly vacation homes. Many of these stays feature amenities that are just perfect for trips with children, like laundry facilities, bunk beds and private pools. Simply check the "Properties good for families" filter and pick your favorite.
Can I find two-bedroom vacation rentals in Cutthroat Harbor Estates?
Cutthroat Harbor Estates has 15 two-bedroom properties to select from. Go for a vacation home with all the space and comfort you want at a price you'll love on Vrbo.
Are there vacation rentals with WiFi in Cutthroat Harbor Estates?
Whether you'd like to keep up with world events, look over emails or surf your social networks, there are 20 vacation homes with WiFi in Cutthroat Harbor Estates. Check the "WiFi" box when searching on Vrbo and stay connected on your getaway.
How can I find vacation rentals with air conditioning in Cutthroat Harbor Estates?
You'll find 50 Vrbo vacation homes with air conditioning in Cutthroat Harbor Estates giving you that cool, cool breeze and extra comfort level. Simply enter your chosen travel dates and then use our handy filters to help you find stays with air conditioning.
How old do you have to be to rent a vacation rental in Cutthroat Harbor Estates?
You'll have to check with the Cutthroat Harbor Estates vacation rental you're considering on Vrbo as age restrictions differ. However, it's typically 16, 18 or 21.
How long can I rent a vacation rental in Cutthroat Harbor Estates for?
The length of time you can book a vacation rental in Cutthroat Harbor Estates is down to the property. Simply enter your desired dates to look at a list of options offering extended stays. With loads of amenities like full kitchens and air conditioning, as well as some offering weekly or monthly discounts, you're sure to find somewhere just right to call your home away from home in Cutthroat Harbor Estates.
Does Vrbo offer discounts for vacation homes in Cutthroat Harbor Estates?
On Vrbo, we've got plenty of fabulous deals and discounts for Cutthroat Harbor Estates. Take a look at our newly listed homes, as well as our weekly and monthly discounts on vacation rentals. Whether you're off on a mini vacay or an extended escape, Vrbo has options for all styles and budgets.

More Vacation Ideas