Southampton Rentals, Southampton Summer Vacation Rentals, Rent Southampton Homes & Properties
- Sales
- Rentals
 | 2 BR 2 bath | |
 | Bridgehampton South Winter Rental BridgehamptonWebID# 4893279 November 1-30th $5,000 May 1-31st $5,000 March 1-31st $5,000 January 1-31st $5,000 April 1-30th $5,000 3 BR 1 bath | $5,000April 1-30th $5,000January 1-31st $5,000March 1-31st $5,000May 1-31st $5,000November 1-30th |
 | Luxurious Modern Waterfront Rental 41 Shore Dr | $250,000Memorial Day to Labor Day 2026 $65,000June 1-30th 2026 $85,000July 1-31st 2026 $95,000August 1st to Labor Day 2026 $90,000August 1-31st 2026 |
 | Modern 5-Bedroom Hamptons Retreat Near Beaches., Bays & Vineyards 126 Malloy Dr | $15,000November 1-30th 2026 $15,000December 1-31st 2026 $30,000April through May 2026 $15,000April 1-30th 2026 $120,000May through Labor Day 2026 $20,000May 1-31st 2026 $100,000Memorial Day to Labor Day 2026 $80,000June-July 2026 $30,000June 1-30th 2026 $85,000July 1st thru Labor Day 2026 $40,000July 1-31st 2026 $45,000August 1st to Labor Day 2026 $40,000August 1-31st 2026 $130,000Extended season 2026 $35,000September 1-30th 2026 $35,000October 1-31st 2026 |
 | Hamptons Year Round or Summer Rental! 20 Old Canoe Place Rd | $22,000July 1-31st 2026 $27,000August 1-31st 2026 |
 | 6 BR 6 bath | $165,000Memorial Day to Labor Day 2026 |
 | Privacy With 3 Bedrooms and Heated Pool 393 Middle Line Hwy | $15,000June 1-30th 2026 |
 | In Southampton Village With 6 Bedrooms and Heated Pool SouthamptonWebID# 5058786 June 1-30th 2026 $20,000 September 1-30th 2026 $25,000 7 BR 4½ bath | $20,000June 1-30th 2026 $25,000September 1-30th 2026 |
 | Water Mill 5 Bed With Pool and Tennis Water MillWebID# 5058708 Memorial Day to Labor Day 2026 $185,000 5 BR 5½ bath | $185,000Memorial Day to Labor Day 2026 |
 | Close to Southampton Village SouthamptonWebID# 5058774 June 1-30th 2026 $20,000 July 1-31st 2026 $35,000 July 1st thru Labor Day 2026 $70,000 Memorial Day to Labor Day 2026 $90,000 August 1st to Labor Day 2026 $40,000 4 BR 3½ bath | $40,000August 1st to Labor Day 2026 $70,000July 1st thru Labor Day 2026 $35,000July 1-31st 2026 $20,000June 1-30th 2026 $90,000Memorial Day to Labor Day 2026 |
 | Casa Ilana SouthamptonWebID# 5054788 June 1-30th 2026 $62,000 July 1-31st 2026 $75,500 August 1st to Labor Day 2026 $88,000 4 BR 4 bath | $88,000August 1st to Labor Day 2026 $75,500July 1-31st 2026 $62,000June 1-30th 2026 |
 | 8 BR 4 bath | $30,000June 1-30th 2026 |
 | 7 BR 4½ bath | $30,000June 1-30th 2026 |
 | Southampton Townhouse! SouthamptonWebID# 5038954 July 1-31st 2026 $30,000 August 1st to Labor Day 2026 $30,000 3 BR 3 bath | $30,000August 1st to Labor Day 2026 $30,000July 1-31st 2026 |
 | Historic Georgian Main Street Home Sag HarborWebID# 5038958 July 1-31st 2026 $60,000 July 1st thru Labor Day 2026 $130,000 Memorial Day to Labor Day 2026 $150,000 August 1-31st 2026 $75,000 August 1st to Labor Day 2026 $75,000 4 BR 3½ bath | $75,000August 1st to Labor Day 2026 $75,000August 1-31st 2026 $130,000July 1st thru Labor Day 2026 $60,000July 1-31st 2026 $150,000Memorial Day to Labor Day 2026 |
 | Sag Harbor Village Three Bedroom and Cottage and Pool 99 Suffolk St | $27,500Short term 2026 |
 | 4 BR 2 bath | $75,000Year round 2026 |
 | Special 5 Bedroom Home in Water Mill Water MillWebID# 5023688 June 1-30th 2026 $10,000 July 1-31st 2026 $19,000 July 1st thru Labor Day 2026 $45,000 Memorial Day to Labor Day 2026 $55,000 August 1st to Labor Day 2026 $30,000 September 1-30th 2026 $10,000 May 1-31st 2026 $8,000 April 1-30th 2026 $8,000 5 BR 2 bath | $8,000April 1-30th 2026 $30,000August 1st to Labor Day 2026 $45,000July 1st thru Labor Day 2026 $19,000July 1-31st 2026 $10,000June 1-30th 2026 $8,000May 1-31st 2026 $55,000Memorial Day to Labor Day 2026 $10,000September 1-30th 2026 |
 | Serene Bridgehampton Summer BridgehamptonWebID# 5008160 July 1-31st 2026 $70,000 July 1st thru Labor Day 2026 $145,000 August 1st to Labor Day 2026 $80,000 5 BR 5½ bath | $80,000August 1st to Labor Day 2026 $145,000July 1st thru Labor Day 2026 $70,000July 1-31st 2026 |
 | Gorgeous Sag Harbor Home Sag HarborWebID# 5001021 June 1-30th 2026 $24,000 July 1-31st 2026 $78,000 July 1st thru Labor Day 2026 $135,000 Memorial Day to Labor Day 2026 $178,000 August 1-31st 2026 $78,000 August 1st to Labor Day 2026 $78,000 Year round 2026 $250,000 May 1-31st 2026 $18,000 March 1-31st 2026 $6,400 January 1-31st 2026 $6,400 April 1-30th 2026 $6,400 September 1-30th 2026 $20,000 October 1-31st 2026 $7,500 November 1-30th 2026 $7,500 4 BR 3 bath | $7,500November 1-30th 2026 $7,500October 1-31st 2026 $20,000September 1-30th 2026 $6,400April 1-30th 2026 $6,400January 1-31st 2026 $6,400March 1-31st 2026 $24,000June 1-30th 2026 $78,000August 1st to Labor Day 2026 $78,000August 1-31st 2026 $78,000July 1-31st 2026 $18,000May 1-31st 2026 $135,000July 1st thru Labor Day 2026 $178,000Memorial Day to Labor Day 2026 $250,000Year round 2026 |
 | Open Living in Home With Pool, Beach and Pickleball Court SouthamptonWebID# 4987224 Memorial Day to Labor Day 2026 $40,000 3 BR 2 bath | $40,000Memorial Day to Labor Day 2026 |
 | Ultra Luxury 6 Bedroom Southampton Village with Pool & Tennis SouthamptonWebID# 4992632 July 1-31st 2026 $200,000 August 1st to Labor Day 2026 $250,000 6 BR 6 bath | $250,000August 1st to Labor Day 2026 $200,000July 1-31st 2026 |
 | 4 BR 3½ bath | $75,000August 1st to Labor Day 2026 |
 | Brand New Construction Bridgehampton 4 Bedroom With Pool! 9 Chester St | $30,000Extended season 2026 $20,000September 1-30th $55,000July 1-31st $75,000August 1st to Labor Day |
 | Bayfront Sag Harbor Traditional Sag HarborWebID# 4907489 June 1-30th 2026 $32,000 August 1-31st 2026 $42,000 August 1st to Labor Day 2026 $49,000 3 BR 2 bath | $32,000June 1-30th 2026 $49,000August 1st to Labor Day 2026 $42,000August 1-31st 2026 |
 | Southampton Village 6 Br 8 Bath Near Ocean SouthamptonWebID# 4899190 June 1-30th 2026 $90,000 July 1-31st 2026 $185,000 July 1st thru Labor Day 2026 $325,000 August 1-31st 2026 $190,000 August 1st to Labor Day 2026 $195,000 6 BR 8 bath | $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 |
 | SAG HARBOR WATERFRONT COMMUNITY WITH PRIVATE BEACH ACCESS 4 Waterview Rd | $25,000August 1-31st 2026 $25,000Short term 2026 $60,000Memorial Day to Labor Day 2026 $28,000August 1st to Labor Day 2026 $25,000July 1-31st 2026 $30,000June 1-30th 2026 |
 | Wonderful Village Home SouthamptonWebID# 4898013 June 1-30th 2026 $25,000 July 1-31st 2026 $35,000 August 1st to Labor Day 2026 $45,000 3 BR 2 bath | $45,000August 1st to Labor Day 2026 $35,000July 1-31st 2026 $25,000June 1-30th 2026 |
 | Vacation in Style Minutes From the Village SouthamptonWebID# 4897983 July 1-31st 2026 $18,000 July 1st thru Labor Day 2026 $35,000 Memorial Day to Labor Day 2026 $45,000 August 1st to Labor Day 2026 $20,000 2 BR 2½ bath | $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 |
 | Designer Decorated Classic Hamptons Home With 4 bedrooms & Pool SouthamptonWebID# 4896603 June 1-30th 2026 $30,000 June-July 2026 $85,000 July 1-31st 2026 $55,000 July 1st thru Labor Day 2026 $120,000 Memorial Day to Labor Day 2026 $130,000 August 1-31st 2026 $65,000 August 1st to Labor Day 2026 $65,000 September 1-30th 2026 $18,500 October 1-31st 2026 $14,000 November 1-30th 2026 $9,500 4 BR 3½ bath | $65,000August 1st to Labor Day 2026 $65,000August 1-31st 2026 $120,000July 1st thru Labor Day 2026 $55,000July 1-31st 2026 $85,000June-July 2026 $30,000June 1-30th 2026 $130,000Memorial Day to Labor Day 2026 $9,500November 1-30th 2026 $14,000October 1-31st 2026 $18,500September 1-30th 2026 |
 | 5 BR 3 bath | $23,400June 1-30th 2026 |
 | Bright Contemporary Sag HarborWebID# 4891916 June 1-30th 2026 $25,000 July 1-31st 2026 $45,000 August 1-31st 2026 $50,000 Year round 2026 $160,000 September 1-30th 2026 $10,000 October 1-31st 2026 $5,000 November 1-30th 2026 $5,000 May 1-31st 2026 $10,000 March 1-31st 2026 $5,000 January 1-31st 2026 $5,000 April 1-30th 2026 $7,000 4 BR 3½ bath | $7,000April 1-30th 2026 $50,000August 1-31st 2026 $5,000January 1-31st 2026 $45,000July 1-31st 2026 $25,000June 1-30th 2026 $5,000March 1-31st 2026 $10,000May 1-31st 2026 $5,000November 1-30th 2026 $5,000October 1-31st 2026 $10,000September 1-30th 2026 $160,000Year round 2026 |
 | Summer Charm SouthamptonWebID# 4893280 June 1-30th 2026 $30,000 June-July 2026 $65,000 July 1-31st 2026 $50,000 July 1st thru Labor Day 2026 $85,000 Memorial Day to Labor Day 2026 $99,900 August 1-31st 2026 $55,000 August 1st to Labor Day 2026 $58,000 Winter 2026 $36,000 Year round 2026 $169,000 September 1-30th 2026 $25,000 October 1-31st 2026 $20,000 November 1-30th 2026 $15,000 May 1-31st 2026 $18,500 May through Labor Day 2026 $119,900 March 1-31st 2026 $12,500 January 1-31st 2026 $12,500 April 1-30th 2026 $20,000 April through May 2026 $30,000 April through Labor Day 2026 $139,900 5 BR 4 bath | $139,900April through Labor Day 2026 $30,000April through May 2026 $20,000April 1-30th 2026 $58,000August 1st to Labor Day 2026 $55,000August 1-31st 2026 $12,500January 1-31st 2026 $85,000July 1st thru Labor Day 2026 $50,000July 1-31st 2026 $65,000June-July 2026 $30,000June 1-30th 2026 $12,500March 1-31st 2026 $119,900May through Labor Day 2026 $18,500May 1-31st 2026 $99,900Memorial Day to Labor Day 2026 $15,000November 1-30th 2026 $20,000October 1-31st 2026 $25,000September 1-30th 2026 $36,000Winter 2026 $169,000Year round 2026 |
 | 4 Bedroom Southampton Beauty SouthamptonWebID# 4891909 June 1-30th 2026 $30,000 July 1-31st 2026 $50,000 July 1st thru Labor Day 2026 $100,000 Memorial Day to Labor Day 2026 $125,000 August 1st to Labor Day 2026 $60,000 September 1-30th 2026 $25,000 October 1-31st 2026 $15,000 November 1-30th 2026 $10,000 March 1-31st 2026 $15,000 January 1-31st 2026 $10,000 April 1-30th 2026 $15,000 4 BR 3½ bath | $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 |
 | Spectacular Ocean Front in Westhampton Dunes Westhampton BeachWebID# 4889044 June 1-30th 2026 $100,000 July 1-31st 2026 $200,000 August 1-31st 2026 $210,000 September 1-30th 2026 $80,000 October 1-31st 2026 $40,000 November 1-30th 2026 $40,000 May 1-31st 2026 $50,000 March 1-31st 2026 $30,000 January 1-31st 2026 $22,000 April 1-30th 2026 $35,000 6 BR 5½ bath | $35,000April 1-30th 2026 $210,000August 1-31st 2026 $22,000January 1-31st 2026 $200,000July 1-31st 2026 $100,000June 1-30th 2026 $30,000March 1-31st 2026 $50,000May 1-31st 2026 $40,000November 1-30th 2026 $40,000October 1-31st 2026 $80,000September 1-30th 2026 |
 | Sagaponack Tradional SagaponackWebID# 4888138 June 1-30th 2026 $50,000 June-July 2026 $100,000 July 1-31st 2026 $50,000 July 1st thru Labor Day 2026 $100,000 Memorial Day to Labor Day 2026 $150,000 August 1-31st 2026 $50,000 May 1-31st 2026 $30,000 March 1-31st 2026 $12,500 January 1-31st 2026 $12,500 4 BR 3 bath | $50,000August 1-31st 2026 $12,500January 1-31st 2026 $100,000July 1st thru Labor Day 2026 $50,000July 1-31st 2026 $100,000June-July 2026 $50,000June 1-30th 2026 $12,500March 1-31st 2026 $30,000May 1-31st 2026 $150,000Memorial Day to Labor Day 2026 |
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