Southampton Rentals, Southampton Summer Vacation Rentals, Rent Southampton Homes & Properties
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 | 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 |
 | 6 BR 6 bath | $165,000Memorial Day to Labor Day 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 |
 | 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 |
 | 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 |
 | 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 |
 | 7 BR 4½ bath | $30,000June 1-30th 2026 |
 | 8 BR 4 bath | $30,000June 1-30th 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 |
 | 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 |
 | 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 |
 | 4 BR 3½ bath | $75,000August 1st 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 |
 | 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 |
 | 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 |
 | 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 |
 | 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 |
 | Southampton Home With Bayview SouthamptonWebID# 4889573 June 1-30th 2026 $23,400 November 1-30th 2026 $20,000 5 BR 3 bath | $20,000November 1-30th 2026 $23,400June 1-30th 2026 |
 | Spacious Modern With 4 Bedrooms - All New With Pool SouthamptonWebID# 4889576 June 1-30th 2026 $30,000 June-July 2026 $85,000 July 1-31st 2026 $65,000 July 1st thru Labor Day 2026 $120,000 Memorial Day to Labor Day 2026 $150,000 August 1st to Labor Day 2026 $70,000 September 1-30th 2026 $30,000 October 1-31st 2026 $30,000 4 BR 4 bath | $70,000August 1st to Labor Day 2026 $120,000July 1st thru Labor Day 2026 $65,000July 1-31st 2026 $30,000June 1-30th 2026 $150,000Memorial Day to Labor Day 2026 $30,000October 1-31st 2026 $30,000September 1-30th 2026 $85,000June-July 2026 |
 | Southampton Village Close to the Ocean SouthamptonWebID# 4882074 June 1-30th 2026 $65,000 June-July 2026 $140,000 July 1-31st 2026 $100,000 July 1st thru Labor Day 2026 $200,000 Memorial Day to Labor Day 2026 $225,000 August 1st to Labor Day 2026 $115,000 Year round 2026 $369,500 November 1-30th 2026 $17,000 March 1-31st 2026 $17,000 January 1-31st 2026 $17,000 May 1-31st 2026 $22,000 4 BR 5 bath | $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 $17,000November 1-30th 2026 $369,500Year round 2026 |
 | Spacious Estate in Water Mill - Seven Bedrooms and Tennis SouthamptonWebID# 4865060 June-July 2026 $80,000 Memorial Day to Labor Day 2026 $185,000 May through Labor Day 2026 $175,000 7 BR 7 bath | $80,000June-July 2026 $175,000May through Labor Day 2026 $185,000Memorial Day to Labor Day 2026 |
 | Golfer's Hamptons Get-away! SouthamptonWebID# 4838005 June 1-30th 2026 $30,000 July 1-31st 2026 $35,000 July 1st thru Labor Day 2026 $70,000 Memorial Day to Labor Day 2026 $95,000 August 1st to Labor Day 2026 $39,500 4 BR 3 bath | $35,000July 1-31st 2026 $30,000June 1-30th 2026 $95,000Memorial Day to Labor Day 2026 $70,000July 1st thru Labor Day 2026 $39,500August 1st to Labor Day 2026 |
 | Private Gem in Southampton Near Peconic Bay SouthamptonWebID# 4776535 July 1-31st 2026 $30,000 July 1st thru Labor Day 2026 $65,000 August 1st to Labor Day 2026 $35,000 4 BR 3 bath | $35,000August 1st to Labor Day 2026 $65,000July 1st thru Labor Day 2026 $30,000July 1-31st 2026 |
 | Southampton Retreat Minutes from Village & Ocean Beaches 565 Montauk Hwy | $65,000August 1st to Labor Day 2026 $120,000July 1st thru Labor Day 2026 $60,000July 1-31st 2026 |
 | Southampton Village Rental 39 David Whites Ln | $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 |
 | Experience serenity in this Sag Harbor 3-bed, 2-bath home! 30 Oak Ln | $35,000August 1-31st 2026 $35,000July 1-31st 2026 $12,000June 1-30th 2026 $90,000Memorial Day to Labor Day 2026 $13,000September 1-30th 2026 $130,000Year round 2026 |
 | 4 Bedroom Bridgehampton South 79 Hildreth Ln | $55,000July 1-31st 2026 $85,000June-July 2026 |
 | 4 Bedroom Village Rental 140 Pelletreau St | $55,000August 1st to Labor Day 2026 $90,000July 1st thru Labor Day 2026 $45,000July 1-31st 2026 |
 | Water Mill Tranquility 474 Water Mill Towd Rd | $55,000August 1st to Labor Day 2026 $88,000July 1st thru Labor Day 2026 $45,000July 1-31st 2026 $30,000June 1-30th 2026 $98,000Memorial Day to Labor Day 2026 |
 | The Secret Garden 379 Ferry Rd | $10,000October 1-31st 2026 $15,000September 1-30th 2026 $30,000August 1st to Labor Day 2026 $45,000July 1st thru Labor Day 2026 $25,000July 1-31st 2026 $20,000June 1-30th 2026 $53,000Memorial Day to Labor Day 2026 |
 | Charming Waterfront Southampton Rental 65 Waters Edge Rd | $9,000April 1-30th 2026 $30,500June 1-30th 2026 $9,000November 1-30th 2026 $9,000October 1-31st 2026 $18,000September 1-30th 2026 $18,500May 1-31st 2026 $9,000March 1-31st 2026 $32,000July 1-31st 2026 $5,000January 1-31st 2026 $39,000August 1-31st 2026 $96,000Memorial Day to Labor Day 2026 |
 | Newly Renovated Summer Rental close to village with new pool! 20 Robinson Rd | $5,000November 1-30th 2026 $78,000Year round 2026 $20,000August 1st to Labor Day 2026 $20,000August 1-31st 2026 $38,000July 1st thru Labor Day 2026 $20,000July 1-31st 2026 $30,000June-July 2026 $15,000June 1-30th 2026 $49,000Memorial Day to Labor Day 2026 |
 | Westhampton Oceanfront Rental 329 Dune Rd | $165,000August 1st to Labor Day 2026 $290,000July 1st thru Labor Day 2026 $155,000July 1-31st 2026 $60,000June 1-30th 2026 |
 | Close to US Open! In Sag Harbor. Noyac Rd. Sag Harbor | $16,000June 1-30th 2026 |
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