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Luxury Houses for Rent in Southold, NY

25 rentals

1160 Goose Creek Ln - Photo 1 of 1

5d+ ago

Luxury house for rent in Southold

Single Family Residence, Colonial - Southold, NY

1160 Goose Creek Ln, Southold, NY 11971

Luxury | Swimming pool | Outdoor space

5 beds

3 baths

$40,000

House for rent

910 Glenn Rd - Photo 1 of 1
New construction

5d+ ago

Luxury house for rent in Southold

Single Family Residence, Farmhouse - Southold, NY

910 Glenn Rd, Southold, NY 11971

Luxury | Walk-in closets | Swimming pool

4 beds

3 baths

$25,000

House for rent

Top amenities
Fireplace
Garage Parking
Hardwood Floor
On-Site Laundry
Storage
Swimming Pool
1100 Pine Ave - Photo 1 of 1

5d+ ago

Luxury house for rent in Southold

Single Family Residence, Ranch - Southold, NY

1100 Pine Ave, Southold, NY 11971

Luxury | Outdoor space | Hardwood floor

3 beds

2 baths

$28,000

House for rent

480 N Bayview Rd - Photo 1 of 1

5d+ ago

Luxury house for rent in Southold

Single Family Residence - Southold, NY

480 N Bayview Rd, Southold, NY 11971

Luxury | On-site laundry | Outdoor space

3 beds

3 baths

$20,000

House for rent

Top amenities
On-Site Laundry
355 Windjammer Dr - Photo 1 of 1

5d+ ago

Luxury house for rent in Southold

Cape Cod, Single Family Residence - Southold, NY

355 Windjammer Dr, Southold, NY 11971

Luxury | Swimming pool | Outdoor space

3 beds

2 baths

$70,000

House for rent

250 Wesland Rd - Photo 1 of 1

5d+ ago

Luxury house for rent in Southold

Single Family Residence - Southold, NY

250 Wesland Rd, Southold, NY 11971

Luxury | In-unit laundry | Carpet

2 beds

2 baths

$10,500

House for rent

Top amenities
Ceiling Fan
Dishwasher
In-Unit Laundry

Nearby rental good for eco-living

$40,000

Sag Harbor

Nearby rental good for social life

$13,000

New Suffolk

Nearby rental good for wellness

365 Chablis Path - Photo 1 of 1

5d+ ago

Luxury house for rent in Southold

Single Family Residence, Contemporary - Southold, NY

365 Chablis Path, Southold, NY 11971

Luxury | Swimming pool | In-unit laundry

4 beds

3 baths

$26,000

House for rent

Top amenities
In-Unit Laundry
3825 S Harbor Rd - Photo 1 of 1

5d+ ago

Luxury house for rent in Southold

Single Family Residence, 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
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314 North St - Photo 1 of 1

5d+ ago

Luxury house for rent in Greenport

Single Family Residence, Cottage - Greenport, NY

314 North St, Greenport, NY 11944

Luxury | In-unit laundry

2 beds

1 bath

$3,000

House for rent

Top amenities
In-Unit Laundry
4630 Blue Horizon Blf - Photo 1 of 1

5d+ ago

Luxury house for rent in Peconic

Single Family Residence, Cottage - Peconic, NY

4630 Blue Horizon Blf, Peconic, NY 11958

Luxury | Garage parking

2 beds

1 bath

$10,000

House for rent

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

$13,000

New Suffolk

$3,500

Southold

$6,500

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1155 Tasker Ln - Photo 1 of 1

5d+ ago

Luxury house for rent in Greenport

Single Family Residence, Contemporary - Greenport, NY

1155 Tasker Ln, Greenport, NY 11944

Luxury | In-unit laundry | Storage

3 beds

2 baths

$4,800

House for rent

Top amenities
Dishwasher
Garage Parking
In-Unit Laundry
Listings within 10 miles
28 Windermere Dr - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

28 Windermere Dr, Sag Harbor, NY 11963

Luxury | Swimming pool | Fireplace

4 beds

3 baths

$45,000

House for rent

30 Sunset Rd - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

30 Sunset Rd, Sag Harbor, NY 11963

Luxury | Roof deck | Swimming pool

3 beds

2 baths

$45,000

House for rent

Top amenities
On-Site Laundry
Swimming Pool
68 W Water St ##Unit - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

68 W Water St ##Unit, Sag Harbor, NY 11963

Luxury | Swimming pool | Outdoor space

3 beds

2 baths

$40,000

House for rent

Top amenities
Furnished
Swimming Pool
28 Dartmouth Rd - Photo 1 of 1

2d ago

Our team has verified this company

Verified

28 Dartmouth Rd, Sag Harbor, NY 11963

Luxury | Balcony | Swimming pool

5 beds

6 baths

$100,000

House for rent

Top amenities
Fitness Center
Swimming Pool
23 Marjorie Ln - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

23 Marjorie Ln, Sag Harbor, NY 11963

Luxury | Outdoor space | Garage parking

2 beds

2 baths

$30,000

House for rent

156 Main St - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

156 Main St, Sag Harbor, NY 11963

Luxury | Swimming pool | Outdoor space

5 beds

6 baths

$25,000

House for rent

Top amenities
Swimming Pool
1155 Old Harbor Rd - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

1155 Old Harbor Rd, New Suffolk, NY 11956

Luxury | Fireplace

4 beds

3 baths

$13,000

House for rent

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640 Orchard St - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

640 Orchard St, New Suffolk, NY 11956

Luxury | Outdoor space | Air conditioning

3 beds

2 baths

$13,000

House for rent

1 Dogwood St - Photo 1 of 1

4d ago

Luxury house for rent in Sag Harbor

1 Dogwood St, Sag Harbor, NY 11963

Luxury | In-unit laundry | Outdoor space

5 beds

2 baths

$8,500

House for rent

Top amenities
In-Unit Laundry
3045 Rocky Point Rd - Photo 1 of 1

5d+ ago

Luxury house for rent in East Marion

Single Family Residence, Ranch - East Marion, NY

3045 Rocky Point Rd, East Marion, NY 11939

Luxury | Swimming pool | In-unit laundry

3 beds

2 baths

$45,000

House for rent

Top amenities
Dishwasher
Fireplace
Garage Parking
High Ceilings
In-Unit Laundry
Swimming Pool
270 North St - Photo 1 of 1

5d+ ago

Luxury house for rent in Cutchogue

270 North St, Cutchogue, NY 11935

Luxury | Walk-in closets | In-unit laundry

2 beds

2 baths

$5,000

House for rent

Top amenities
Dishwasher
In-Unit Laundry
2435 Cedar Ln - Photo 1 of 1

5d+ ago

Luxury house for rent in East Marion

Single Family Residence, Cottage - East Marion, NY

2435 Cedar Ln, East Marion, NY 11939

Luxury | In-unit laundry | Outdoor space

4 beds

3 baths

$7,000

House for rent

Top amenities
Air Conditioning
Fireplace
High Ceilings
In-Unit Laundry
Storage
35 Bayberry Ln - Photo 1 of 1

5d+ ago

Luxury house for rent in Sag Harbor

A-frame, Single Family Residence - Sag Harbor, NY

35 Bayberry Ln, Sag Harbor, NY 11963

Luxury | In-unit laundry | Outdoor space

3 beds

1 bath

$4,500

House for rent

Top amenities
In-Unit Laundry
970 Village Ln - Photo 1 of 1

5d+ ago

Luxury house for rent in Mattituck

Single Family Residence, Exp Cape - Mattituck, NY

970 Village Ln, Mattituck, NY 11952

Luxury | Walk-in closets | In-unit laundry

4 beds

2 baths

$4,800

House for rent

Top amenities
Dishwasher
Garage Parking
Hardwood Floor
In-Unit Laundry
Showing 1 - 25 of 25 results
Home > House Rentals in Southold > Southold Luxury Houses For Rent
Updated: October 5, 2025

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Discover houses for rent in Southold, NY

🌇Available luxury house rentals25 houses
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