Southport holiday homes

We found 318 holiday rentals — enter your dates for availability
Scroll through and select from holiday rentals in Southport to find one that's perfect for your trip. Whether you're staying in a holiday rental with a group or just with your pet, you'll have the amenities that you expect and more, such as Wi-Fi and cable TV. What you'll find is a property to rent for everyone's needs, including options that are accessible or non-smoking.

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Why visit Southport

  • Picturesque beaches: Southport boasts stunning coastal scenery, perfect for relaxing and enjoying the outdoors.
  • Cultural heritage: Explore local museums and historic sites that showcase the town's rich history and artistic spirit.
  • Charming village atmosphere: Stroll through the quaint streets of Southport, filled with unique shops and delightful eateries.
  • Outdoor activities: Engage in various leisure activities, from walking trails to water sports, catering to all ages.
  • Family-friendly experiences: Southport offers numerous attractions that create lasting memories for visitors of all ages.

Top attractions near Southport

Southport, Connecticut offers a blend of outdoor adventures, urban parks, and cultural hotspots. Enjoy scenic beaches, explore local museums, and embrace the city’s vibrant cultural scene. Ideal for family outings and city escapades, Southport provides a perfect setting for a diverse and engaging holiday experience. Discover the charm of this coastal town and create lasting memories with its rich attractions and leisurely outdoor activities.

  • The Glass House: Experience a unique museum showcasing local culture, set a short drive from Southport, where art and history merge beautifully.
  • Walnut Beach: Enjoy the coastal charm at Walnut Beach, offering pristine sands and refreshing sea breezes, a wonderful spot for a seaside stroll near Southport.
  • Milford Green: Discover the vibrant urban park with city, family, and outdoor vibes, perfect for a leisurely day out near Southport.

Things to do recommended for couples

Experience Southport's charm with a romantic harbour walk, scenic seaside dining, and a sunset sail. Enjoy local delights and intimate moments in this picturesque coastal town.

Things to do recommended for families

Families visiting Southport, Connecticut can enjoy a fun-filled day exploring local parks and engaging in interactive exhibits at nearby museums, perfect for kids and parents alike.

Things to do recommended for groups

In Southport, your group can enjoy the adrenaline of ziplining and rope challenges at The Adventure Park at Discovery Museum, located 10km away, embracing an outdoor adventure and local charm in true Kiwi style.

*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 in Southport

If you're travelling with a group, family, pets, or seeking extended stays, it's important to use the right filters to match your priorities. Here are some helpful booking tips from Vrbo for you.

  • Traveling to Southport with a group: Consider how many bedrooms you'll require, along with features like a complete kitchen or an outdoor area for a group gathering. Luckily, you can use filters on Vrbo to search for all these options and more.
  • Traveling to Southport with young kids: Travelling with young children can present its challenges. It’s important to prioritise their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Southport: For many, a family holiday wouldn’t be the same without their furry companion. If this resonates with you, take a look at Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Southport: If you're in search of holiday rentals that offer special deals 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 include options like a parking space, a well-equipped kitchen, or even a private pool in your search.

Where to stay near Southport

Discover Southport, Connecticut’s charming blend of outdoor adventures, cultural experiences and family-friendly vibes. Wander the vibrant Southport centre, explore the quaint neighbourhood, and savour the sunny, business-friendly atmosphere. Local landmarks and scenic settings reflect a unique blend of heritage and modernity, making Southport a must-visit destination for a memorable holiday in the USA.

  • Fairfield: Located a mere mile from Southport, Fairfield is a vibrant city that offers a delightful mix of city life and outdoor adventures. Visitors flock to Fairfield for its rich cultural experiences, including educational institutions and recreational areas. The city is home to scenic beaches, perfect for family outings, and a modern university that adds to its youthful energy. Golf enthusiasts will also appreciate the local golf courses, making Fairfield a well-rounded destination for both relaxation and activity.
  • Stamford: Situated 23km away from Southport, Stamford is a bustling city known for its family-friendly atmosphere and vibrant urban scene. With an array of shopping areas and theatres, visitors can indulge in a leisurely day of retail therapy or catch a captivating performance. Stamford's tourist precinct and modern squares are perfect for exploring local culture and dining experiences, providing a taste of the city’s diverse offerings. The combination of outdoor spaces and city charm makes Stamford an attractive stop on your journey.
  • Norwalk: Just 11km from Southport, Norwalk is another fantastic city that caters to families seeking both fun and culture. With its charming beaches and shopping areas, Norwalk offers plenty of options for leisurely days out. The presence of educational institutions adds to its appeal, while the local golf courses invite visitors to enjoy a round in a picturesque setting. Norwalk’s family beaches are particularly inviting, making it an ideal destination for those looking to relax and explore.

Best time to go to Southport

If you're planning a trip to Southport, it's a good idea to check both the weather and property rates. The warmest month is July.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January31.6°F (-0.2°C)Light RainMostly SunnySlightly Low
February32.9°F (0.5°C)Light RainMostly SunnyAverage
March39.2°F (4.0°C)Light RainMostly SunnyAverage
April49.3°F (9.6°C)Light RainMostly SunnyAverage
May59.2°F (15.1°C)Light RainMostly SunnyAverage
June68.2°F (20.1°C)Light RainMostly SunnySlightly High
July75.4°F (24.1°C)Light RainMostly SunnySlightly High
August74.1°F (23.4°C)Light RainMostly SunnyAverage
September67.6°F (19.8°C)Light RainMostly SunnySlightly High
October57.6°F (14.2°C)Light RainMostly SunnySlightly Low
November46.2°F (7.9°C)Light RainMostly SunnyAverage
December38.3°F (3.5°C)Light RainMostly SunnySlightly Low

Booking with Vrbo is simple

Are you keen to save on your next adventure? Being flexible with your travel dates can help, as prices often vary. Additionally, opting for a longer stay typically results in significant savings. To discover the perfect Vrbo property that fits your budget, utilise our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning made easy

Vrbo’s new Trip Board offers a convenient way for you to plan your journeys, allowing you to start fresh, pick up right where you left off, or easily view and organise your travel plans. You can find properties that you’ve previously saved or booked under Potential, Upcoming, or Current Trips. To explore Trip Boards, simply visit: https://www.bookabach.co.nz/trips.

**Based on Vrbo properties bookings.

The lively city of Southport awaits you

The area's temples and opera are just some of the reasons to come on holiday to Southport. Renowned for its hockey games, beaches and restaurants, this city welcomes all visitors. If you're looking for accommodation options with space to entertain friends and family, HomeAway has plenty of options to choose from. Many rental homes offer full kitchens and laundry facilities, perfect for big groups.

Activities and attractions in Southport

Do you want to discover top things to see and do in the area? Venture out of your holiday home and experience everything that makes Southport a fun spot to go on holiday. These are some of the top attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Country Club of Fairfield (0.8 mi / 1.3 km)
  • Norwalk Maritime Aquarium (7.4 mi / 11.9 km)
  • Beardsley Zoo (7.4 mi / 11.9 km)
  • Chelsea Piers (13.4 mi / 21.5 km)
  • Hand & Stone Massage and Facial Spa (14.5 mi / 23.4 km)
  • Del Vino Vineyards (15.6 mi / 25.2 km)

Exploring the natural features in Southport

Whether you're an active traveller or just want to spend some time taking in the scenery, Southport is a great place to get out in nature. These are some of the area's noteworthy features, all within 30 miles (48.2 km) of the city centre:

  • Fairfield Beach (1.8 mi / 2.8 km)
  • Penfield Beach (2.2 mi / 3.6 km)
  • Jennings Beach (2.4 mi / 3.9 km)
  • Compo Beach (4.3 mi / 6.9 km)
  • Seaside Beach (4.5 mi / 7.2 km)
  • Seaside Park (4.8 mi / 7.7 km)

How to get to and around Southport

Fly into Bridgeport, CT (BDR-Igor I. Sikorsky Memorial), the closest airport, located 8.1 mi (13 km) from the city centre. If you can't find a flight that works for your travel itinerary, you might consider flying into Danbury, CT (DXR-Danbury Municipal), which is 19.4 mi (31.2 km) away.

If you're travelling by train, you can make your way to Southport Station.

Frequently asked questions

What is the best area to stay in Southport when booking a holiday rental?
When considering a holiday rental in Southport, Connecticut, the charming neighbourhood of Southport Beach stands out as an excellent choice. This picturesque area boasts a beautiful sandy beach, great for sunbathing and leisurely strolls along the shoreline. Visitors can enjoy stunning views of Long Island Sound and take advantage of the nearby Southport Harbour, which is a lovely spot for boating and sailing enthusiasts.Another appealing area is the historic district, where you'll find quaint streets lined with lovely historic-style homes and vibrant local shops. This area is home to the iconic Southport Congregational Church, which adds to the neighbourhood's charm. In addition, the picturesque landscapes of the Southport Golf Club provide a serene backdrop for those who appreciate a bit of greenery.In terms of holiday rentals, Southport offers a diverse selection of properties ranging from cosy cottages to elegant waterfront homes, suiting a variety of preferences.
Where are the best areas for renting a beach house in Southport?
For renting a beach house in Southport, travellers should consider the picturesque areas along the Long Island Sound. The neighbourhoods of Southport and nearby Fairfield offer charming coastal homes with easy access to sandy beaches and scenic waterfront views. Many properties in this vicinity come equipped with amenities such as private decks, outdoor grilling areas, and spacious gardens, making them ideal for families or groups eager to enjoy outdoor living by the sea.The Southport Beach area is particularly popular, where rentals often feature easy access to the beach and stunning sunsets over the water. Properties here frequently include modern kitchens, comfortable living spaces, and some even provide bicycles for exploring the nearby coastal paths.In addition, the nearby Fairfield town offers additional options, with its vibrant downtown area and local shops and restaurants adding convenience for visitors. Rentals in this area tend to be well-appointed, with many featuring amenities like air conditioning, Wi-Fi, and laundry facilities, ensuring a comfortable stay.
What is the most popular type of holiday rental accomodation in Southport?
In Southport, holiday houses are the most popular type of holiday rental, with around 12 available throughout the area. These homes are typically situated in charming neighbourhoods, offering a spacious environment ideal for families or groups. Most holiday houses come with fully equipped kitchens, comfortable living areas, and outdoor spaces for relaxation. In addition to these, there are several cottages that provide a cozier, more intimate setting, often featuring rustic decor and gardens.
Are there any family house rentals in Southport?
In Southport, Connecticut, there are several family-friendly house rentals available, making it an excellent choice for groups seeking a coastal retreat. The area is known for its charming neighbourhoods and proximity to picturesque beaches. Properties often feature spacious living rooms, fully equipped kitchens for family meals, and outdoor areas where children can play or relax.Visitors can explore nearby attractions such as the scenic Southport Beach, great for sunny days, and the beautiful Southport Historic District, where local shops and eateries can be found. Additionally, many rentals come with amenities like Wi-Fi and air conditioning, ensuring a comfortable stay for families.
Are there pet-friendly house rentals in Southport?
In Southport, there are several pet-friendly house rentals available, great for travellers looking to enjoy a charming coastal community. Many of these properties come equipped with amenities such as spacious backyards, fully equipped kitchens, and comfortable living areas, making them ideal for families or groups travelling with pets.The neighbourhood itself offers a picturesque setting with easy access to local parks and the stunning waterfront. Nearby, the beautiful Southport Beach provides a lovely spot for walks with your furry companions. Additionally, the area features pet-friendly cafes and shops that welcome four-legged visitors, enhancing the overall experience for pet owners.
Are there any remote work holiday rentals in Southport?
In Southport, Connecticut, there are several holiday rentals suitable for remote work, with around 12 options available. This charming coastal town offers a serene atmosphere, making it an ideal setting for those looking to balance work and leisure. Many of these properties feature essential amenities such as high-speed Wi-Fi, comfortable workspaces, and inviting living areas that allow for productivity during your stay.Travellers can expect to find a mix of charming cottages and more spacious homes, often equipped with full kitchens for convenient meal preparation and outdoor spaces for relaxation after a long day of work. Southport's picturesque surroundings, including its lovely beaches and quaint shops, provide plenty of opportunities for breaks and exploration. To help narrow your search, insert your dates and apply the "WiFi" filter on Bookabach.
What are popular rental amenities in Southport?
In Southport, popular holiday rental amenities include fully equipped kitchens, which allow guests to prepare their own meals, and air conditioning for comfort during warmer months. Many properties are also pet-friendly, making it easier for travellers to bring their furry companions along. Additional amenities often found in these rentals include blenders for making smoothies or cocktails, and coffee and tea makers to enjoy a warm beverage upon waking.
When is the best time to visit Southport for a holiday rental?
The best time to visit Southport for a holiday rental is during the peak season from July to September. This vibrant period is great for those seeking a quintessential New England summer experience, with warm temperatures averaging between 20 to 30 degrees Celsius. Visitors can indulge in outdoor activities such as sailing, beach days, and strolling along the scenic coastline, all while enjoying the charming atmosphere of this picturesque seaside town.July stands out as the most popular month, attracting families and leisure travellers eager to soak up the sun and engage in local festivals and events. The lively streets come alive with music, art, and delicious offerings from nearby restaurants, making it an excellent time for socialising and exploring.For those looking for a more budget-friendly option, consider visiting in December. While the weather is cooler, averaging around 0 to 5 degrees Celsius, Southport's winter charm is undeniable. This quieter month allows for a peaceful retreat, great for enjoying cozy local cafes and festive holiday decorations without the summer crowds.
What are the top attractions in Southport?
In Southport, visitors can enjoy a blend of natural beauty and historic charm. The picturesque Southport Beach offers sandy shores and scenic views of Long Island Sound, making it a lovely spot for relaxation and seaside strolls. The nearby Pequot Library is a great cultural institution, renowned for its distinctive architecture and extensive collection of books and art, often hosting community events and exhibitions.For a taste of local history, the Southport Historic District features charming 19th-century buildings and the iconic Southport Railway Station, which adds to the area's quaint atmosphere. Additionally, the nearby Connecticut Audubon Society offers opportunities for birdwatching and enjoying nature trails, appealing to outdoor enthusiasts.
Are all fees included in the Southport holiday homes prices shown on Bookabach?
Bookabach 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.
Are there any Southport holiday homes with parking?
Bookabach offers a wide selection of holiday homes in Southport with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details 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 any discounts for Southport holiday homes?
You can find great discounts on holiday homes in Southport on Bookabach, 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.
Can I change or cancel my Southport holiday home booking on Bookabach?
To find Southport holiday rentals with free cancellation, just use Bookabach'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". Whether you're adjusting your plans or looking for flexible payment options, Bookabach makes it easy to book with confidence.
Can I find long-stay holiday homes in Southport?
A long-stay holiday home in Southport is the best way to experience local living. Plus, you can make the most of long-stay discounts. 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.
Can I plan a group trip on Bookabach?
Bookabach'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.
How early should I book a Southport holiday home?
Book your Southport holiday home 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 Bookabach booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Southport?
Prices for holiday homes in Southport 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 travelling solo, as a couple, with family, or in a group. Bookabach offers something for every taste and budget, from affordable homes in Southport to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach 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.
What is Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, 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.
Why should I join Bookabach as a host?
Joining Bookabach 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, Bookabach 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 Bookabach handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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