We found 2,330 holiday rentals — enter your dates for availability
Choose the right holiday home within easy reach of Southernmost Point. Holiday homes offer the best amenities for your stay with friends, family or just your pet, such as Wi-Fi and parking. Whatever you're looking for, you'll be sure to find a property to rent to meet everyone's needs, including a place that's non-smoking or offers accessibility.
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Frequently asked questions
What are the best holiday rentals near Southernmost Point?
The best holiday rentals near Southernmost Point are typically located within the charming Old Town Key West area. You will find a great selection of properties, from private holiday houses with classic island architecture to modern condos offering convenience. If you are willing to drive a bit further, renting in nearby areas can be an affordable option for finding larger properties. You will find many best holiday rentals near Southernmost Point.
Many top-rated rentals feature amenities so you can have a comfortable stay, such as private pools for cooling off, spacious decks or patios for outdoor dining, and laundry facilities for longer stays. These homes are ideal for families or groups looking to enjoy the Key West lifestyle.
What are the best pet-friendly holiday rentals near Southernmost Point?
There are hundreds of pet-friendly holiday rentals near Southernmost Point, with approximately 589 properties available. These rentals are predominantly found in Old Town Key West and offer a range of options from private homes to apartments. Many properties feature amenities such as fenced yards, private decks, and easy outdoor access, alongside essential comforts like fully equipped kitchens and Wi-Fi, ensuring a comfortable stay for both guests and their pets.
When searching for the best pet-friendly holiday rentals near Southernmost Point, it is important to verify each property's specific pet policy, including any size restrictions or additional fees. Southernmost Point itself is a welcoming outdoor area where pets are generally permitted.
What are the top holiday rentals with pools near Southernmost Point?
There are over 1300 holiday rentals near Southernmost Point that include access to swimming pools, with both private and shared options available. Properties in Old Town Key West offer stays with pools as part of a community complex or as private backyard features. Many of these rentals come fully equipped with amenities such as full kitchens, multiple bedrooms, Wi-Fi, and scenic decks, making them ideal for families or small groups looking to combine adventure with comfort.
To make the most of your stay, consider the type of pool that best fits your needs. Private pools offer seclusion and are great for families, while shared pools often come with access to additional perks like hot tubs or fitness rooms. Many pools are seasonal or heated, so checking availability based on your travel dates ensures you get the experience you seek.
What are the best family holiday rentals near Southernmost Point?
There are over 1000 family-friendly holiday homes in the Old Town Key West area near Southernmost Point, offering ample space and comfort for groups of all sizes. These rentals, predominantly private homes and condos, often boast multiple bedrooms and bathrooms, full kitchens, and generous living areas, all designed with families in mind. With such a wide selection, you can find stays with outdoor play areas, gardens, patios, and yards where kids can play, and many include highchairs, cribs, and even toys for children.
When choosing the best fit for your family, focus on properties where adults and kids each have space to unwind, and look for homes with practical amenities like well-equipped kitchens to save on dining out. Staying nearby means less travel time and more opportunity to enjoy the surroundings.
Are there any luxury holiday rentals near Southernmost Point?
Near Southernmost Point, guests can find several luxury holiday rentals that combine the scenic surroundings with modern comfort. These properties often feature amenities such as private heated pools, premium bedding, designer toiletries, and private chef services. Some homes also offer a private beach location or golf course access, providing upscale leisure options.
These stays are ideal for families or larger groups, offering conveniences like air conditioning and spacious living areas. Many of these exceptional properties are managed by highly rated Stayz hosts, ensuring a professional and premium experience.
Where should I stay when visiting Southernmost Point?
When visiting Southernmost Point, Old Town Key West is an excellent choice for a stay. This historic neighbourhood places guests within easy walking or cycling distance of Southernmost Point itself, as well as many other attractions like Mallory Square and Duval Street. Properties here often feature charming architecture and offer a classic Key West experience.
For those seeking a slightly quieter location while still maintaining convenient access, areas just beyond the immediate bustle of Duval Street in Old Town still provide superb holiday rentals. These properties are a short stroll or cycle ride from Southernmost Point, offering a relaxed environment with local eateries and unique shops nearby.
What is the cheapest month to stay near Southernmost Point?
The cheapest time to find holiday rentals near Southernmost Point is typically during the late Spring (May) and early Autumn (September). September is frequently the cheapest month, often providing the best deals on homes and properties, with rates potentially lower than the peak season. Guests can often find various savings and better availability during these months, as it is outside the main tourist rushes.
Are there any top beachfront holiday rentals near Southernmost Point
Beachfront holiday rentals near Southernmost Point are primarily found along the southern coastline of Key West, offering direct access to the sand and breathtaking ocean views. While Southernmost Point itself is a landmark, properties nearby, particularly around warmer waters, provide steps from the water and easy access to lively dining, nightlife, and shopping in Old Town Key West. For those seeking a quieter stay, properties slightly further east offer a more relaxed beachfront experience.
Many of these holiday rentals come equipped with essential beach amenities such as beach chairs and umbrellas, and some feature oceanfront pools for guests to enjoy. Accommodation types range from ocean-facing rooms and spacious suites to multi-bedroom units with private terraces or generous living spaces, suiting various guest needs.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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 Stayz customer service and Stayz™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare customer service is available 24/7 to support you every step of the way.
Stayz also offers support via live chat through our Help Centre, 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 Stayz?
Stayz's Trip Planner makes organising 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 favourites, and build the perfect itinerary together.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers 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, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive.
Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.