Best Vacation Homes in Southold
New
House
10.0(1 Review)
3 Bedrooms
3 Baths
6 Guests
Private Pool
Fireplace/Heating
Pool
Ocean View
US $1,773/Night
7 Nights - US $12,412
House
10.0(1 Review)
4 Bedrooms
2 Baths
8 Guests
1646.88 ft²
Oceanfront- Fireplace/Heating
- Ocean View
Balcony/Terrace
US $391/Night
7 Nights - US $2,737
Hotel
9.4(257 Reviews)
1 Bath
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
View
US $201/Night
7 Nights - US $1,407
New
House
4 Bedrooms
5 Baths
8 Guests
Hot Tub- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $779/Night
7 Nights - US $5,453
House
10.0(1 Review)
3 Bedrooms
2 Baths
6 Guests
11000.72 ft²
Parking
Child Friendly
US $389/Night
7 Nights - US $2,723
New
House
3 Bedrooms
3 Baths
6 Guests
- Fireplace/Heating
Kitchen
Air Conditioner
Internet
US $773/Night
7 Nights - US $5,410
Cottage
10.0(82 Reviews)
3 Bedrooms
1 Bath
6 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $520/Night
7 Nights - US $3,639
Cottage
10.0(35 Reviews)
2 Bedrooms
1 Bath
4 Guests
1400 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $474/Night
7 Nights - US $3,319
Southold Luxury Rentals
House
10.0(12 Reviews)
6 Bedrooms
4 Baths
14 Guests
- Private Pool
- Oceanfront
- Hot Tub
Spa
US $3,903/Night
7 Nights - US $27,324
House
10.0(3 Reviews)
3 Bedrooms
4 Baths
6 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $3,265/Night
7 Nights - US $22,853
House
10.0(16 Reviews)
4 Bedrooms
4 Baths
11 Guests
4300 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $2,801/Night
7 Nights - US $19,604
House
10.0(11 Reviews)
5 Bedrooms
3 Baths
10 Guests
3500 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $2,600/Night
7 Nights - US $18,203
House
10.0(1 Review)
5 Bedrooms
6 Baths
12 Guests
4500 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $2,318/Night
7 Nights - US $16,224
House
10.0(5 Reviews)
4 Bedrooms
2 Baths
10 Guests
- Hot Tub
- Fireplace/Heating
- Air Conditioner
- Internet
US $2,130/Night
7 Nights - US $14,907
House
10.0(3 Reviews)
4 Bedrooms
6 Baths
10 Guests
- Private Pool
- Pool
- Kitchen
- Air Conditioner
US $2,077/Night
7 Nights - US $14,537
House
9.8(7 Reviews)
4 Bedrooms
3 Baths
12 Guests
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $1,885/Night
7 Nights - US $13,194
Southold Pet Friendly Vacation Rentals
House
10.0(5 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $352/Night
7 Nights - US $2,467
House
1 Bedroom
2 Baths
6 Guests
1797.57 ft²
- Fireplace/Heating
- View
Pet Friendly- Parking
US $801/Night
7 Nights - US $5,607
House
10.0(39 Reviews)
4 Bedrooms
2 Baths
8 Guests
2100 ft²
- Spa
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $874/Night
7 Nights - US $6,115
House
10.0(4 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $434/Night
7 Nights - US $3,039
House
1 Bedroom
2 Baths
6 Guests
1097.92 ft²
- Fireplace/Heating
- Pool
- View
- Pet Friendly
US $304/Night
7 Nights - US $2,128
Cottage
10.0(2 Reviews)
2 Bedrooms
1 Bath
5 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $595/Night
7 Nights - US $4,166
House
10.0(1 Review)
1 Bedroom
2 Baths
4 Guests
2400 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $292/Night
7 Nights - US $2,042
Apartment
9.6(37 Reviews)
2 Bedrooms
1 Bath
4 Guests
850 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $434/Night
7 Nights - US $3,039
Southold Large Vacation Homes
House
10.0(42 Reviews)
4 Bedrooms
4 Baths
10 Guests
3400 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $1,100/Night
7 Nights - US $7,701
House
4 Bedrooms
3 Baths
10 Guests
2615.63 ft²
- Balcony/Terrace
- Pet Friendly
- Kitchen
- Parking
US $438/Night
7 Nights - US $3,066
House
10.0(29 Reviews)
6 Bedrooms
3 Baths
10 Guests
3200 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $1,332/Night
7 Nights - US $9,325
House
10.0(19 Reviews)
4 Bedrooms
2 Baths
10 Guests
3200 ft²
- Hot Tub
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $708/Night
7 Nights - US $4,958
Apartment
10.0(13 Reviews)
5 Bedrooms
4 Baths
12 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- View
US $885/Night
7 Nights - US $6,198
House
10.0(11 Reviews)
4 Bedrooms
3 Baths
10 Guests
2500 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $546/Night
7 Nights - US $3,819
House
10.0(10 Reviews)
8 Bedrooms
7 Baths
12 Guests
6000 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
US $1,488/Night
7 Nights - US $10,413
House
10.0(9 Reviews)
5 Bedrooms
3 Baths
8 Guests
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $843/Night
7 Nights - US $5,903
Why Choose Rent By Owner for your Southold 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 Southold
When should you plan your Vacation Rentals stay?
Choosing the optimal time to visit here can enhance your experience, as the region offers seasonal charm and various activities that suit different preferences throughout the year.
Peak Season Highlights
Summer (June to August)
During the peak summer months, you can enjoy warm weather and longer daylight hours, making it ideal for outdoor activities and waterfront relaxation.
Average Temperature Daytime: 75°F to 85°F - Nighttime: 60°F to 70°F
Fall (September to October)
Early fall offers pleasant temperatures and vibrant foliage, providing a picturesque setting for exploring local scenery and enjoying seasonal events.
Average Temperature Daytime: 65°F to 75°F - Nighttime: 50°F to 60°F
Off-Season Highlights
Winter (November to February)
This quieter season features cooler temperatures and fewer visitors, offering a peaceful environment to unwind and experience the region’s winter charm.
Average Temperature Daytime: 40°F to 50°F - Nighttime: 30°F to 40°F
Spring (March to May)
Late spring welcomes milder weather and blooming landscapes, making it an ideal time for those seeking tranquility away from the bustling tourist season.
Average Temperature Daytime: 55°F to 65°F - Nighttime: 40°F to 50°F
Weekly Weather Forecast for Southold
How to Book Your Southold 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 Southold
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 a private outdoor patio or deck perfect for relaxing and dining al fresco amid the region’s scenic views.
- Take advantage of a fully equipped barbecue grill to host outdoor cookouts during your stay in this destination.
- Make the most of spacious gardens or lawns ideal for outdoor games and family activities in this area.
- Relax by an outdoor swimming pool that offers refreshing respite during warm summer days here.
- Benefit from access to a fire pit, perfect for cozy evenings under the stars with friends or loved ones.
- Utilize outdoor seating areas designed for enjoying the natural beauty that surrounds you in this region.
- Appreciate the convenience of ample parking space, often included in vacation rentals here, for easy vehicle access.
Top Attractions Around Southold
What attractions are nearby?
During your stay here, you can enjoy a variety of outdoor activities and exploring local wineries, all just a short drive from your Southold vacation rentals in this charming region of New York.
Family Activities
- Visit Southold's North Fork Trolley Museum: Discover the region’s rich transportation history through engaging exhibits that appeal to the whole family.
- Explore local farms and orchards: Enjoy seasonal fruit picking and learn about sustainable farming practices in this charming part of the area.
- Spend a day at Silver Sands State Park: Relax on sandy beaches, build sandcastles, or take nature walks along scenic trails by the water.
- Discover historic sites around Southold: Tour historic landmarks and gain insight into the area's cultural heritage during your family vacation here.
Adult Activities
- Wine Tasting Tours: Explore renowned vineyards nearby, where you can sample locally produced wines and learn about the region’s wine-making heritage.
- Beach Relaxation and Activities: Spend your days enjoying the sandy shores, swimming, or simply unwinding while taking in the scenic views along the region's beaches.
- Historic Lighthouse Visits: Discover the local maritime history by touring the historic lighthouses that dot the area and offer stunning vistas of the coastline.
Other Places to Stay in Southold, NY
The Old Field Vineyards
Croteaux Vineyards
Mattebella Vineyards
Osprey's Dominion
Sannino's Bella Vita Vineyard
Sparkling Pointe
Horton Lane Beach
Horton Point Park
Southold Travel Tips
How Can You Make the Most of Your Stay?
- Plan Ahead for Local Events: Research any festivals or seasonal happenings in the region to enhance your experience without missing out on popular activities.
- Select the Perfect Accommodation: Opt for a well-reviewed vacation rental that offers convenient access to the area's charming beaches and local attractions.
- Explore Dining Options: Take advantage of the area’s renowned seafood spots and dine like a local during your stay in this coastal destination.
- Respect the Natural Environment: Practice eco-friendly habits to preserve the area's scenic beauty and ensure a sustainable visit for future travelers.
Transportation Options
- Southold Local Bus Service: This regional bus service offers convenient transportation around the area, making it easy to explore your surroundings without a car.
- Rental Car Services: Numerous rental options are available here, providing flexibility and ease for visitors wanting to fully experience this destination at their own pace.
- Taxis and Ride-Sharing: Reliable taxi firms and ride-sharing services operate in the region, offering quick transit for short trips or airport transfers.
- Bike Rentals: Cycling is a popular way to discover the scenic views of this area, with bike rentals readily accessible to get you around in an eco-friendly manner.
Local Customs Options
- Seafood Traditions: Here, enjoying fresh local seafood is a cherished custom that reflects the region’s coastal heritage and is a must-try during your stay.
- Community Events: Participating in seasonal festivals and local gatherings is an integral part of experiencing the area’s welcoming atmosphere.
- Historical Preservation: Respect for historical sites and local landmarks demonstrates the community’s pride in preserving its rich past.
- Farmers’ Markets: Visiting weekly farmers’ markets offers a glimpse into the region's agricultural roots and supports local artisans and farmers.
Southold Vacation Rental Frequently Asked Questions
1. What are the top vacation rentals in Southold?
There are a lot of options in Southold. If you plan on staying in the Southold area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Southold:
- Southold Waterfront with Boat Dock, Boat Ramp, Hot Tub & Beaches
- Private Coastal Two Bedroom Cottage on the Water
- Newly Renovated Gem on the Cedar Beach Peninsula!
- Family and dog-friendly getaway near amazing wineries, beaches and restaurants!
- Perfect Waterfront Family Vacation Home next to the best vineyards in NY!
- Great Location! Walk to Town & Train!
- Charming Cottage
- Beachfront - endless sunsets, sandy beach, cozy sunroom & open concept kitchen
- 6BR, Saltwater Pool - open! DISCOUNTS avail for Mother’s Dat, MDW and August!
- Renovated American Farmhouse in the heart of Southold with heated saltwater pool
2. How many vacation rentals have private pools in Southold?
There are 44 vacation rentals with private pools near Southold. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Southold are best for families?
If you are looking for a family-friendly vacation home in Southold, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Southold:
4. How many Rentbyowner vacation rentals are available in Southold?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 241 in the Southold 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 Southold.
5. What is the cancellation policy for accommodations in Southold, NY?
Cancellation policies vary depending on the property listing. You should review the specific cancellation terms listed for each vacation rental before booking, and contact the property owner if you have any questions.
6. Are there any additional fees I should be aware of when booking a vacation home in Southold?
Additional fees such as cleaning, service charges, or security deposits are often specified in the listing details. It's recommended to read the full description and reach out to the owner for clarification on any extra costs.
7. How do I ensure the vacation rental I choose in Southold is suitable for my needs?
Each listing provides detailed descriptions, amenities, and photos. Be sure to review these carefully and contact the property owner directly if you need more information or specific accommodations.
8. What is the check-in and check-out process for rentals in Southold?
Check-in and check-out procedures are outlined in each listing. To ensure a smooth experience, communicate with the owner beforehand if you have special requirements or need guidance on arrival and departure times.
9. Is there a secure way to pay for my vacation rental in Southold?
Payments are processed securely through the booking platform. For your safety, avoid transferring money outside the official payment system and verify all payment instructions with the property owner if needed.
Southold Top Rated Vacation Rentals
House
10.0(29 Reviews)
4 Bedrooms
2 Baths
8 Guests
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
US $1,177/Night
7 Nights - US $8,237
House
10.0(8 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
US $895/Night
7 Nights - US $6,262
House
10.0(6 Reviews)
3 Bedrooms
1 Bath
6 Guests
1100 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
US $488/Night
7 Nights - US $3,417
House
10.0(4 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
US $796/Night
7 Nights - US $5,572
House
10.0(2 Reviews)
4 Bedrooms
4 Baths
8 Guests
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $832/Night
7 Nights - US $5,822
House
10.0(1 Review)
5 Bedrooms
3 Baths
12 Guests
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $1,328/Night
7 Nights - US $9,299
Bed & Breakfast
10.0(1 Review)
1 Bedroom
1 Bath
2 Guests
1241 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $460/Night
7 Nights - US $3,223
Bed & Breakfast
10.0(1 Review)
1 Bedroom
1 Bath
2 Guests
1193 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $420/Night
7 Nights - US $2,939
