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Luxury Houses for Rent in Southold, NY

25 rentals

1100 Pine Ave - Photo 1 of 1

5d+ ago

Luxury house for rent in Southold

SINGLE_FAMILY - Ranch - Southold, NY

1100 Pine Ave, Southold, NY 11971

Luxury | Outdoor space | Hardwood floor

3 beds

2 baths

$28,000

House for rent

450 Sterling Woods Ln - Photo 1 of 1

5d+ ago

Luxury house for rent in Southold

SINGLE_FAMILY - Other - Southold, NY

450 Sterling Woods Ln, Southold, NY 11971

Luxury | Swimming pool | In-unit laundry

4 beds

3 baths

$100,000

House for rent

Top amenities
Dishwasher
In-Unit Laundry
365 Chablis Path - Photo 1 of 1

5d+ ago

Luxury house for rent in Southold

SINGLE_FAMILY - Contemporary - Southold, NY

365 Chablis Path, Southold, NY 11971

Luxury | Swimming pool | In-unit laundry

4 beds

3.5 baths

$30,000

House for rent

Top amenities
In-Unit Laundry
355 Windjammer Dr - Photo 1 of 1

5d+ ago

Luxury house for rent in Southold

SINGLE_FAMILY - Cape Cod - Southold, NY

355 Windjammer Dr, Southold, NY 11971

Luxury | Swimming pool | Outdoor space

3 beds

2 baths

$60,000

House for rent

1160 Goose Creek Ln - Photo 1 of 1

5d+ ago

Luxury house for rent in Southold

SINGLE_FAMILY - Colonial - Southold, NY

1160 Goose Creek Ln, Southold, NY 11971

Luxury | Swimming pool | Outdoor space

5 beds

3 baths

$50,000

House for rent

3825 S Harbor Rd - Photo 1 of 1

5d+ ago

Luxury house for rent in Southold

SINGLE_FAMILY - Ranch - Southold, NY

3825 S Harbor Rd, Southold, NY 11971

Luxury | In-unit laundry | Hardwood floor

2 beds

1 bath

$3,500

House for rent

Top amenities
Furnished
In-Unit Laundry

Nearby rental good for eco-living

$3,500

Greenport

Nearby rental good for social life

$30,000

Cutchogue

56765 Route 48 - Photo 1 of 1

5d+ ago

Luxury house for rent in Greenport

SINGLE_FAMILY - Ranch - Greenport, NY

56765 Route 48, Greenport, NY 11944

Luxury | Swimming pool | In-unit laundry

3 beds

2 baths

$100,000

House for rent

Top amenities
Dishwasher
Garage Parking
In-Unit Laundry
Swimming Pool
4 Summerfield Pl - Photo 1 of 1

5d+ ago

Luxury house for rent in Shelter Island Heights

5BR, 4BA Waterfront Victorian

4 Summerfield Pl, Shelter Island Heights, NY 11965

Luxury | Balcony | In-unit laundry

5 beds

4 baths

$9,000

House for rent

Available Jun 1

Top amenities
Dishwasher
In-Unit Laundry
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3375 Indian Neck Ln - Photo 1 of 1
New construction

5d+ ago

Luxury house for rent in Peconic

SINGLE_FAMILY - Other - Peconic, NY

3375 Indian Neck Ln, Peconic, NY 11958

Luxury | Garage parking | Hardwood floor

4 beds

4.5 baths

$80,000

House for rent

Top amenities
Garage Parking
24 S Midway Rd - Photo 1 of 1

5d+ ago

Luxury townhouse for rent in Shelter Island

24 S Midway Rd, Shelter Island, NY 11964

Luxury | Fitness center | Garage parking

4 beds

4 baths

$45,000

House for rent

Top amenities
Garage Parking
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Find sweet deals near Southold

These rentals are 10%-30% cheaper than the local average price for similar rentals.

$12,000

Peconic

$4,000

Southold

$7,000

East Marion

$20,000

Southold

1875 Bayview Ave - Photo 1 of 1

5d+ ago

Luxury house for rent in Southold

SINGLE_FAMILY - Cottage - Southold, NY

1875 Bayview Ave, Southold, NY 11971

Luxury | In-unit laundry | Garage parking

3 beds

2 baths

$4,000

House for rent

Top amenities
Carpet
Dishwasher
Fireplace
Garage Parking
Hardwood Floor
In-Unit Laundry
1100 Huntington Blvd - Photo 1 of 1

5d+ ago

Luxury house for rent in Peconic

SINGLE_FAMILY - Bungalow - Peconic, NY

1100 Huntington Blvd, Peconic, NY 11958

Luxury | Swimming pool | In-unit laundry

3 beds

3 baths

$12,000

House for rent

Top amenities
In-Unit Laundry
24 Worthy Way - Photo 1 of 1

5d+ ago

Luxury house for rent in Shelter Island

Shelter Island-Neat, Clean and close to beaches

24 Worthy Way, Shelter Island, NY 11964

Luxury | Balcony | In-unit laundry

3 beds

2 baths

$15,000

House for rent

Top amenities
Dishwasher
Fireplace
In-Unit Laundry
Microwave
6 Crab Creek Rd - Photo 1 of 1

5d+ ago

Luxury house for rent in Shelter Island

Shelter Island-Silver Beach Community

6 Crab Creek Rd, Shelter Island, NY 11964

Luxury | Balcony | In-unit laundry

3 beds

2 baths

$10,000

House for rent

Available Jun 1

Top amenities
Carpet
Furnished
In-Unit Laundry
1050 Pine Ave - Photo 1 of 1

5d+ ago

Luxury house for rent in Southold

SINGLE_FAMILY - Cottage - Southold, NY

1050 Pine Ave, Southold, NY 11971

Luxury | Outdoor space

3 beds

2 baths

$10,000

House for rent

695 Rogers Rd - Photo 1 of 1

5d+ ago

Luxury house for rent in Southold

SINGLE_FAMILY - Other - Southold, NY

695 Rogers Rd, Southold, NY 11971

Luxury | In-unit laundry | Outdoor space

5 beds

2 baths

$12,000

House for rent

Top amenities
Dishwasher
In-Unit Laundry
4 Glynn Dr - Photo 1 of 1

5d+ ago

Luxury house for rent in Shelter Island

SINGLE_FAMILY - Modern - Shelter Island, NY

4 Glynn Dr, Shelter Island, NY 11964

Luxury | Swimming pool | Outdoor space

4 beds

3 baths

$30,000

House for rent

744 Main St #2 - Photo 1 of 1

5d+ ago

Luxury house for rent in Greenport

Residential Rental, Traditional - Greenport, NY

744 Main St #2, Greenport, NY 11944

Luxury | In-unit laundry | Outdoor space

2 beds

2 baths

$3,400

House for rent

Top amenities
In-Unit Laundry
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237 6th St - Photo 1 of 1

5d+ ago

Luxury house for rent in Greenport

SINGLE_FAMILY - Other - Greenport, NY

237 6th St, Greenport, NY 11944

Luxury | In-unit laundry | Garage parking

2 beds

2.5 baths

$16,000

House for rent

Top amenities
Dishwasher
In-Unit Laundry
205 Pine Ave - Photo 1 of 1

5d+ ago

Luxury house for rent in Southold

SINGLE_FAMILY - Other - Southold, NY

205 Pine Ave, Southold, NY 11971

Luxury | Balcony | Walk-in closets

3 beds

3 baths

$9,500

House for rent

Top amenities
Ceiling Fan
Dishwasher
Garage Parking
Hardwood Floor
In-Unit Laundry
On-Site Laundry
8515 Soundview Ave - Photo 1 of 1

5d+ ago

Luxury house for rent in Southold

SINGLE_FAMILY - Cottage - Southold, NY

8515 Soundview Ave, Southold, NY 11971

Luxury | Outdoor space

2 beds

1 bath

$4,000

House for rent

8415 Soundview Ave - Photo 1 of 1

5d+ ago

Luxury house for rent in Southold

SINGLE_FAMILY - Bungalow - Southold, NY

8415 Soundview Ave, Southold, NY 11971

Luxury | In-unit laundry | Outdoor space

2 beds

1 bath

$5,000

House for rent

Top amenities
In-Unit Laundry
Listings within 10 miles
250 Oak Rd - Photo 1 of 1

5d+ ago

Luxury house for rent in New Suffolk

SINGLE_FAMILY - Ranch - New Suffolk, NY

250 Oak Rd, New Suffolk, NY 11956

Luxury | Outdoor space | High ceilings

2 beds

2 baths

$14,500

House for rent

2465 Fairway Dr - Photo 1 of 1

5d+ ago

Luxury house for rent in Cutchogue

2465 Fairway Dr, Cutchogue, NY 11935

Luxury | Balcony | Walk-in closets

5 beds

3.5 baths

$30,000

House for rent

Top amenities
Air Conditioning
Dishwasher
Fireplace
In-Unit Laundry
Microwave
165 Marine Pl - Photo 1 of 1

5d+ ago

Luxury house for rent in Greenport

SINGLE_FAMILY - Modern - Greenport, NY

165 Marine Pl, Greenport, NY 11944

Luxury | Swimming pool | In-unit laundry

4 beds

4.5 baths

$20,000

House for rent

Top amenities
Hardwood Floor
In-Unit Laundry
Showing 1 - 25 of 25 results
Home > House Rentals in Southold > Southold Luxury Houses For Rent
Updated: May 5, 2026

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Discover houses for rent in Southold, NY

🌇Available luxury house rentals25 houses
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