Best Vacation Homes in Southport
10 Guests
6 Bedrooms
6 Bathrooms
Family Friendly
House
- Private Pool
- Fireplace/Heating
- Pool
US $1,735/Night
For 7 Nights US $12,142
1399.31 ft²
8 Guests
3 Bedrooms
2 Bathrooms
House
- Oceanfront
- Fireplace/Heating
- Ocean View
US $307/Night
For 7 Nights US $2,149
2 Guests
1 Bedroom
1 Bathroom
Ocean View
Apartment
- Spa
- Fireplace/Heating
- Ocean View
US $290/Night
For 7 Nights US $2,027
10 Guests
3 Bedrooms
2 Bathrooms
Pet Friendly
House
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
US $828/Night
For 7 Nights US $5,796
1194.79 ft²
5 Guests
2 Bedrooms
1 Bathroom
Apartment
- Fireplace/Heating
- View
- Pet Friendly
US $393/Night
For 7 Nights US $2,751
1000 ft²
3 Guests
1 Bedroom
1 Bathroom
Ocean View
Cottage
- Oceanfront
- Fireplace/Heating
- Ocean View
US $273/Night
For 7 Nights US $1,912
872 ft²
3 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $248/Night
For 7 Nights US $1,738
1206 ft²
5 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $401/Night
For 7 Nights US $2,809
Southport Luxury Rentals
12 Guests
5 Bedrooms
7 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $3,741/Night
For 7 Nights US $26,190
4250 ft²
14 Guests
6 Bedrooms
5 Bathrooms
Ocean View
House
- Private Pool
- Hot Tub
- Fireplace/Heating
US $2,664/Night
For 7 Nights US $18,649
8 Guests
5 Bedrooms
5 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Pool
US $2,454/Night
For 7 Nights US $17,181
6500 ft²
14 Guests
7 Bedrooms
7 Bathrooms
Ocean View
House
- Private Pool
- Hot Tub
- Fireplace/Heating
US $2,366/Night
For 7 Nights US $16,560
3800 ft²
12 Guests
5 Bedrooms
3 Bathrooms
Ocean View
Other
- Private Pool
- Hot Tub
- Fireplace/Heating
US $2,070/Night
For 7 Nights US $14,490
14 Guests
7 Bedrooms
6 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Pool
US $2,013/Night
For 7 Nights US $14,088
4200 ft²
14 Guests
6 Bedrooms
4 Bathrooms
Ocean View
House
- Private Pool
- Oceanfront
- Fireplace/Heating
US $1,806/Night
For 7 Nights US $12,639
3500 ft²
7 Guests
4 Bedrooms
3 Bathrooms
Ocean View
House
- Private Pool
- Oceanfront
- Fireplace/Heating
US $1,757/Night
For 7 Nights US $12,297
Southport Pet Friendly Vacation Rentals
7 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $518/Night
For 7 Nights US $3,623
871.88 ft²
3 Guests
1 Bedroom
1 Bathroom
Apartment
- Private Beach
- Fireplace/Heating
- Ocean View
US $390/Night
For 7 Nights US $2,730
1 Bedroom
1 Bathroom
Family Friendly
House
- Pet Friendly
- Kitchen
- Air Conditioner
US $167/Night
For 7 Nights US $1,169
6 Guests
4 Bedrooms
3 Bathrooms
Pet Friendly
House
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
US $1,179/Night
For 7 Nights US $8,251
1022.57 ft²
7 Guests
3 Bedrooms
2 Bathrooms
House
- Oceanfront
- Fireplace/Heating
- Ocean View
US $546/Night
For 7 Nights US $3,822
3285 ft²
10 Guests
3 Bedrooms
3 Bathrooms
Ocean View
House
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $714/Night
For 7 Nights US $4,999
1023 ft²
7 Guests
3 Bedrooms
2 Bathrooms
Ocean View
Cottage
- Oceanfront
- Fireplace/Heating
- Ocean View
US $745/Night
For 7 Nights US $5,216
1500 ft²
8 Guests
3 Bedrooms
2 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
US $480/Night
For 7 Nights US $3,359
Southport Large Vacation Homes
12 Guests
6 Bedrooms
7 Bathrooms
Ocean View
House
- Private Pool
- Oceanfront
- Hot Tub
US $1,568/Night
For 7 Nights US $10,977
10 Guests
5 Bedrooms
5 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
US $1,346/Night
For 7 Nights US $9,424
10 Guests
5 Bedrooms
7 Bathrooms
Group Friendly
House
- Fireplace/Heating
- Air Conditioner
- Internet
US $813/Night
For 7 Nights US $5,691
9 Guests
5 Bedrooms
3 Bathrooms
Ocean View
House
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $1,294/Night
For 7 Nights US $9,056
3600 ft²
11 Guests
6 Bedrooms
4 Bathrooms
Ocean View
House
- Hot Tub
- Fireplace/Heating
- Ocean View
US $1,571/Night
For 7 Nights US $11,000
10 Guests
5 Bedrooms
2 Bathrooms
Ocean View
House
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $1,495/Night
For 7 Nights US $10,465
10 Guests
4 Bedrooms
5 Bathrooms
Group Friendly
House
- Fireplace/Heating
- Air Conditioner
- Internet
US $1,416/Night
For 7 Nights US $9,910
3400 ft²
9 Guests
5 Bedrooms
2 Bathrooms
Ocean View
House
- Private Pool
- Oceanfront
- Fireplace/Heating
US $928/Night
For 7 Nights US $6,497
Why Choose Rent By Owner for your Southport Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Southport
When should you plan your Vacation Rentals stay?
Choosing the right time to visit here ensures you experience the region's unique charm at its best, whether you're seeking a lively summer escape or a peaceful off-season retreat in this scenic destination.
Peak Season Highlights
Late Spring to Early Summer (May to June)
During this time, the area experiences warm weather ideal for outdoor activities and sightseeing in Southport, Connecticut. The pleasant climate attracts visitors seeking a lively yet relaxed atmosphere.
Average Temperature Daytime: Mid-70s°F - Nighttime: High 50s°F to Low 60s°F
Summer (July to August)
The peak summer months bring the warmest weather, making it perfect for enjoying the region's scenic coastal views and outdoor recreational options. This season is popular among travelers looking for an energetic and vibrant experience.
Average Temperature Daytime: Upper 70s to Mid-80s°F - Nighttime: Mid to High 60s°F
Off-Season Highlights
Early Fall (September to October)
As the summer crowds diminish, you can enjoy cooler temperatures and fewer visitors while still experiencing the region’s natural beauty. It’s an ideal time for peaceful escapes and scenic walks in the area.
Average Temperature Daytime: Mid-60s°F to Upper 70s°F - Nighttime: High 40s°F to Mid-50s°F
Winter (December to February)
During the colder months, the region sees fewer visitors, offering a quiet retreat. While temperatures are lower, the serene landscape provides a charming setting for cozy getaways in the area.
Average Temperature Daytime: Low 40s°F - Nighttime: High 20s°F to Low 30s°F
Weekly Weather Forecast for Southport
How to Book Your Southport Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Southport
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy outdoor dining areas perfect for al fresco meals amid the scenic surroundings
- Relax in private outdoor patios or decks with comfortable seating options
- Make the most of lush, landscaped gardens that enhance the property's natural beauty
- Take advantage of well-maintained backyard spaces ideal for barbecues and gatherings
- Utilize outdoor fire pits for cozy evenings under the stars in this charming area
- Explore nearby walking trails or access to waterfront views right from your rental
- Benefit from ample parking spaces suited for exploring the region by car
Top Attractions Around Southport
What attractions are nearby?
Nearby, you can explore scenic beaches, charming local shops, and picturesque parks that offer a relaxing retreat in this inviting destination.
Family Activities
- Southport Beach: Spend a day relaxing and playing along the sandy shores, perfect for family picnics and water activities.
- Pequot Library: Explore engaging children’s programs and educational exhibits at this historic library in the area.
- Sherwood Island State Park: Discover outdoor adventures with hiking, swimming, and nature exploration suitable for all ages.
- Southport Farmers Market: Enjoy browsing local produce and handmade goods, offering a fun outing for families seeking authentic regional flavors.
Adult Activities
- Visit the Southport Beach: Enjoy a relaxing day soaking up the sun and strolling along the pristine shores of the area’s popular beach.
- Explore the Southport Historic District: Discover charming local architecture and quaint shops situated in this picturesque historic neighborhood.
- Play golf at the Wee Burn Country Club: Challenge yourself on well-manicured courses that offer both scenic views and a refined golfing experience within the region.
- Experience the outdoor trails at Elizabeth Park: Take a leisurely walk or bike ride through beautifully maintained gardens and scenic pathways near here.
Other Places to Stay in Southport, CT
Southport Beach
Southport Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Attractions: Take advantage of the region's charming outdoor spaces and cultural sites to enrich your stay here in Southport, Connecticut.
- Plan Dining Experiences: Discover the area's renowned eateries and local markets to enjoy authentic regional flavors during your visit.
- Utilize Waterway Access: Make the most of the nearby waterfront by engaging in boating, fishing, or relaxing by the shore, all easily accessible from your vacation rental.
- Book Well in Advance: Secure your preferred vacation rentals early to ensure a seamless experience and optimal options in this sought-after destination.
Transportation Options
- Southport Train Station: Conveniently located nearby, offering frequent Amtrak and Metro-North services to major cities and facilitating easy travel in the region.
- Public Bus Services: Local bus routes provide affordable transportation options within the area and connect you to neighboring towns and attractions.
- Car Rentals: Several rental agencies operate within a short drive, giving you the flexibility to explore the scenic region at your own pace.
- Taxi and Rideshare Services: Reliable taxi companies and rideshare options like Uber and Lyft are readily available for quick trips around town or to nearby destinations.
Local Customs Options
- Gathering for Local Festivals: Participating in community festivals reflects the region's rich traditions and offers an authentic glimpse into local customs.
- Respecting Maritime Heritage: Honoring maritime practices is important here, as they shape many aspects of daily life and community identity in the area.
- Supporting Seasonal Agriculture: Engaging with seasonal farmers' markets and locally grown produce demonstrates appreciation for the area's agricultural roots.
- Preserving Historic Etiquette: Observing historic social norms and respectful manners helps you connect with the tradition and charm of this destination.
Southport Vacation Rental Frequently Asked Questions
1. What are the top vacation rentals in Southport?
There are a lot of options in Southport. If you plan on staying in the Southport area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Southport:
- Westport "Gold Coast" across from Southport beach
- Studio Flat Above Historic Cider Mill
- Charming Fairfield Beach Cottage
- Cozy Cottage with Fire Pit, near Beach, 1 mile to NYC train
- Beautiful Fairfield Beach Area home, 5 minute walk to beach, town & train
- Fairfield Old Post Road-heated pool & Guest Cottage-walk to NYC train and Beach!
- 2BR Flat above Historic Cider Mill
- 4 BR Classic Country House in CT
- Stareway to Heaven Su
- Fairfield Beach Modern Colonial
2. How many vacation rentals have private pools in Southport?
There are 11 vacation rentals with private pools near Southport. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Southport are best for families?
If you are looking for a family-friendly vacation home in Southport, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Southport:
4. How many Rentbyowner vacation rentals are available in Southport?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 151 in the Southport area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Southport.
5. What is the cancellation policy for my vacation rental booking in this area?
The cancellation policy varies by property, so it's important to review the specific listing details. You can find this information on the listing page or contact the property owner directly for clarification.
6. How do I confirm my reservation and what are the payment options?
Reservations are confirmed once you complete the booking process and submit your payment through the platform. Payment methods typically include credit cards, but details will be provided during checkout or in the booking confirmation email.
7. Are there any additional fees or charges I should be aware of when booking here?
Additional fees, such as cleaning or service charges, are specified in each property’s listing. Make sure to review these details before finalizing your reservation to understand the total cost involved.
8. What amenities are usually included in vacation rentals in this region?
Amenities vary by property, but common inclusions often feature Wi-Fi, parking, fully equipped kitchens, and outdoor spaces. Check the specific listing to see what amenities are offered at your chosen rental.
9. Is it possible to modify or extend my stay after booking in this destination?
Modifications or extensions depend on the property's availability and owner approval. Contact the host directly through the platform to inquire about changing your reservation dates or length of stay.
Southport Top Rated Vacation Rentals
3800 ft²
8 Guests
4 Bedrooms
4 Bathrooms
Ocean View
House
- Private Pool
- Oceanfront
- Fireplace/Heating
US $1,190/Night
For 7 Nights US $8,329
US $282/Night
For 7 Nights US $1,971
8 Guests
4 Bedrooms
3 Bathrooms
Ocean View
House
- Private Pool
- Oceanfront
- Hot Tub
US $1,642/Night
For 7 Nights US $11,495
US $340/Night
For 7 Nights US $2,379
US $292/Night
For 7 Nights US $2,047
330.75 ft²
2 Bathrooms
Free Cancellation
Hotel
- Oceanfront
- Fireplace/Heating
- Pool
US $125/Night
For 7 Nights US $876
US $431/Night
For 7 Nights US $3,015
1005 ft²
4 Guests
2 Bedrooms
1 Bathroom
Ocean View
Apartment
- Private Pool
- Oceanfront
- Hot Tub
US $707/Night
For 7 Nights US $4,951
