| 
        
         
          490 found
         
       | 
    ||
![]()  | $25,000June 1-30th 2026  | Penn Cottage SouthamptonWebID# 4911161 2 BR 1 Single Family Rental  | 
![]()  | $15,000April 1-30th 2026 $60,000August 1st to Labor Day 2026 $10,000January 1-31st 2026 $100,000July 1st thru Labor Day 2026 $50,000July 1-31st 2026 $30,000June 1-30th 2026 $15,000March 1-31st 2026 $125,000Memorial Day to Labor Day 2026 $10,000November 1-30th 2026 $15,000October 1-31st 2026 $25,000September 1-30th 2026  | 4 Bedroom Southampton Beauty SouthamptonWebID# 4891909 4 BR 3½ Single Family Rental  | 
![]()  | $50,000August 1st to Labor Day 2026 $50,000August 1-31st 2026 $90,000July 1st thru Labor Day 2026 $45,000July 1-31st 2026 $175,000June 1-30th 2026 $110,000Memorial Day to Labor Day 2026  | 4 BR 4 Single Family Rental  | 
![]()  | $49,000August 1st to Labor Day 2026 $42,000August 1-31st 2026 $18,000November 1-30th 2026  | Bayfront Sag Harbor Traditional Sag HarborWebID# 4907489 3 BR 2 Single Family Rental  | 
![]()  | $30,000August 1-31st 2026 $30,000July 1-31st 2026 $30,500June 1-30th 2026  | Serene Waterfront Home in Southampton SouthamptonWebID# 4898016 4 BR 4 Single Family Rental  | 
![]()  | $20,000November 1-30th 2026 $25,000October 1-31st 2026  | Magnificent Water Mill Home with Pool & Gym!!! Water MillWebID# 4888134 6 BR 7½ Single Family Rental  | 
![]()  | $11,500November 1-30th 2026 $11,500October 1-31st 2026  | Sagaponack Tradional SagaponackWebID# 4888138 4 BR 3 Single Family Rental  | 
![]()  | $20,000August 1st to Labor Day 2026 $35,000July 1st thru Labor Day 2026 $18,000July 1-31st 2026 $45,000Memorial Day to Labor Day 2026  | Vacation in Style Minutes From the Village SouthamptonWebID# 4897983 2 BR 2½ Single Family Rental  | 
![]()  | $45,000August 1st to Labor Day 2026 $35,000July 1-31st 2026 $25,000June 1-30th 2026  | Wonderful Village Home SouthamptonWebID# 4898013 3 BR 2 Single Family Rental  | 
![]()  | $195,000August 1st to Labor Day 2026 $190,000August 1-31st 2026 $325,000July 1st thru Labor Day 2026 $185,000July 1-31st 2026 $90,000June 1-30th 2026  | Southampton Village 6 Br 8 Bath Near Ocean SouthamptonWebID# 4899190 6 BR 8 Single Family Rental  | 
![]()  | $20,000November 1-30th 2026  | Southampton Home With Bayview SouthamptonWebID# 4889573 5 BR 3 Single Family Rental  | 
![]()  | $43,000September 1-30th  | Five Bedroom Bayfront Traditional Westhampton BeachWebID# 4887990 6 BR 4 Single Family Rental  | 
![]()  | $33,000October 1-31st 2026  | Magnificent Oceanfront! Westhampton BeachWebID# 4887991 5 BR 5 Single Family Rental  | 
![]()  | $65,000August 1st to Labor Day 2026 $115,000July 1st thru Labor Day 2026 $55,000July 1-31st 2026 $35,000June 1-30th 2026  | 5 BR 3 Single Family Rental  | 
![]()  | $25,000August 1-31st 2026 $25,000July 1-31st 2026 $15,000June 1-30th 2026 $55,000Memorial Day to Labor Day 2026  | 4 BR 2½ Single Family Rental  | 
![]()  | $165,000July 1st thru Labor Day 2026 $50,000June 1-30th 2026 $35,000September 1-30th 2026  | 5 BR 4½ Single Family Rental  | 
![]()  | $125,000July 1-31st 2026 $125,000August 1st to Labor Day 2026 $70,000June 1-30th 2026 $325,000Memorial Day to Labor Day 2026  | 5 BR 5 Single Family Rental  | 
![]()  | $22,000May 1-31st 2026 $225,000Memorial Day to Labor Day 2026 $17,000January 1-31st 2026 $17,000March 1-31st 2026 $65,000June 1-30th 2026 $140,000June-July 2026 $100,000July 1-31st 2026 $200,000July 1st thru Labor Day 2026 $115,000August 1st to Labor Day 2026  | Southampton Village Close to the Ocean SouthamptonWebID# 4882074 4 BR 5 Single Family Rental  | 
![]()  | $10,000November 1-30th 2026 $10,000October 1-31st 2026  | Southampton 5 Bedroom With Tennis! SouthamptonWebID# 4878284 5 BR 4 Single Family Rental  | 
![]()  | $96,000Year round 2026  | 3 BR 2 Single Family Rental  | 
![]()  | $275,000August 1st to Labor Day 2026  | 7 BR 9 Single Family Rental  | 
![]()  | $42,000June 1-30th $36,500September 1-30th  | Southampton Village Rental SouthamptonWebID# 4789578 6 BR 5.5 Single Family Rental  | 
![]()  | $80,000June-July 2026 $175,000May through Labor Day 2026 $185,000Memorial Day to Labor Day 2026  | 7 BR 7 Single Family Rental  | 
![]()  | $60,000August 1st to Labor Day 2026 $50,000August 1-31st 2026 $50,000July 1-31st 2026 $60,000June 1-30th 2026  | Private Oaisis in Southampton SouthamptonWebID# 4777414 4 BR 4 Single Family Rental  | 
![]()  | $35,000July 1-31st 2026 $25,000June 1-30th 2026 $39,500August 1st to Labor Day 2026  | Golfer's Hamptons Get-away! SouthamptonWebID# 4838005 4 BR 3 Single Family Rental  | 
![]()  | $35,000August 1st to Labor Day 2026 $65,000July 1st thru Labor Day 2026 $30,000July 1-31st 2026  | Private Gem in Southampton Near Peconic Bay SouthamptonWebID# 4776535 4 BR 3 Single Family Rental  | 
![]()  | $20,000August 1-31st 2026 $30,000July 1st thru Labor Day 2026 $20,000July 1-31st 2026 $20,000June 1-30th 2026 $40,000Memorial Day to Labor Day 2026  | Cozy SH Summer Retreat! SouthamptonWebID# 4765778 3 BR 2 Single Family Rental  | 
![]()  | $6,500April 1-30th 2026 $54,000August 1-31st 2026 $6,000January 1-31st 2026 $52,000July 1-31st 2026 $29,000June 1-30th 2026 $6,000March 1-31st 2026 $21,000May 1-31st 2026 $8,000November 1-30th 2026 $8,000October 1-31st 2026  | 5 BR 5½ Single Family Rental  | 
![]()  | $55,000August 1st to Labor Day 2026 $40,000July 1-31st 2026 $90,000Memorial Day to Labor Day 2026 $25,000September 1-30th 2026 $30,000June 1-30th 2026  | 3 BR 2 Single Family Rental  | 
![]()  | $70,000August 1st to Labor Day 2026 $50,000July 1-31st 2026 $40,000June 1-30th 2026  | Heart of Southampton Village! SouthamptonWebID# 4777415 3 BR 4 Single Family Rental  | 
![]()  | $75,000August 1-31st 2026 $70,000July 1-31st 2026 $40,000June 1-30th 2026  | 5 BR 6 6000 sq ft Single Family Rental  | 
![]()  | $7,500April 1-30th 2026 $72,000August 1st to Labor Day 2026 $70,000August 1-31st 2026 $7,500January 1-31st 2026 $70,000July 1-31st 2026 $35,000June 1-30th 2026 $7,500March 1-31st 2026 $7,500November 1-30th 2026 $7,500October 1-31st 2026 $20,000September 1-30th 2026  | Gorgeous Sag Harbor Home Sag HarborWebID# 5001020 4 BR 3 Single Family Rental  | 
![]()  | $5,000April 1-30th 2026 $20,000August 1st to Labor Day 2026 $5,000January 1-31st 2026 $40,000July 1st thru Labor Day 2026 $20,000July 1-31st 2026 $10,000June 1-30th 2026 $5,000March 1-31st 2026 $5,000May 1-31st 2026 $50,000Memorial Day to Labor Day 2026 $5,000November 1-30th 2026 $5,000October 1-31st 2026 $10,000September 1-30th 2026  | Southampton Village Rental 39 David Whites Ln | 
![]()  | $6,500April 1-30th 2026 $45,000August 1st to Labor Day 2026 $40,000August 1-31st 2026 $5,500January 1-31st 2026 $35,000July 1-31st 2026 $24,000June 1-30th 2026 $5,500March 1-31st 2026 $15,000May 1-31st 2026 $10,000November 1-30th 2026 $12,000October 1-31st 2026 $16,000September 1-30th 2026  | Southampton Village Ranch 45 James St | 
![]()  | $75,000July 1-31st 2026 $60,000June 1-30th 2026  | Southampton Village Retreat SouthamptonWebID# 4995217 3 BR 4.5 Single Family Rental  | 
![]()  | $80,000August 1st to Labor Day 2026 $120,000July 1st thru Labor Day 2026  | Southampton Waterfront Paradise! SouthamptonWebID# 4931644 6 BR 6.5 Single Family Rental  | 
| 490 found | ||