Southampton Rentals, Southampton Summer Vacation Rentals, Rent Southampton Homes & Properties
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 | $10,000April 1-30th 2026 $40,000August 1st to Labor Day 2026 $35,000July 1-31st 2026 $30,000June 1-30th 2026 $10,000March 1-31st 2026 $20,000May 1-31st 2026 | Beautifully Renovated Home with a Fantastic Outside Space! SouthamptonWebID# 2546044 June 1-30th 2026 $30,000 July 1-31st 2026 $35,000 August 1st to Labor Day 2026 $40,000 May 1-31st 2026 $20,000 March 1-31st 2026 $10,000 April 1-30th 2026 $10,000 3 BR 3 bath |
 | $17,500September 1-30th 2026 $35,000August 1st to Labor Day 2026 $35,000August 1-31st 2026 $65,000July 1st thru Labor Day 2026 $30,000July 1-31st 2026 $50,000June-July 2026 $20,000June 1-30th 2026 $80,000Memorial Day to Labor Day 2026 | East Quogue South With a Brand New Pool! 9 Eisenhower Dr |
 | $10,000November 1-30th 2026 | Beach cottage with Shinnecock Bay views 14 Oceanview Rd |
 | $4,000April 1-30th 2026 $19,000August 1st to Labor Day 2026 $19,000August 1-31st 2026 $4,000January 1-31st 2026 $35,000July 1st thru Labor Day 2026 $16,000July 1-31st 2026 $4,000March 1-31st 2026 $40,000Memorial Day to Labor Day 2026 $4,000November 1-30th 2026 $4,000October 1-31st 2026 $4,000September 1-30th 2026 $4,000Winter 2026 | Beautifully refreshed cottage in Sag Harbor 47 Stoney Hill Rd |
 | $225,000August 1st to Labor Day 2026 $199,000August 1-31st 2026 $350,000July 1st thru Labor Day 2026 $199,000July 1-31st 2026 $225,000June-July 2026 $100,000June 1-30th 2026 $450,000Memorial Day to Labor Day 2026 | The LUXURY RESORT SouthamptonWebID# 2380760 June 1-30th 2026 $100,000 June-July 2026 $225,000 July 1-31st 2026 $199,000 July 1st thru Labor Day 2026 $350,000 Memorial Day to Labor Day 2026 $450,000 August 1-31st 2026 $199,000 August 1st to Labor Day 2026 $225,000 8 BR 11 bath |
 | $60,000August 1st to Labor Day 2026 $50,000August 1-31st 2026 $100,000July 1st thru Labor Day 2026 $50,000July 1-31st 2026 $45,000June 1-30th 2026 $120,000Memorial Day to Labor Day 2026 $165,000Year round 2026 | Newly Restored Southampton Summer Home 6 McGregor Dr |
 | $115,000April through Labor Day 2026 $19,000April through May 2026 $8,000April 1-30th 2026 $42,500August 1st to Labor Day 2026 $42,500August 1-31st 2026 $42,500July 1-31st 2026 $70,000June-July 2026 $82,000July 1st thru Labor Day 2026 $105,000May through Labor Day 2026 $90,000Memorial Day to Labor Day 2026 $8,000November 1-30th 2026 $12,000October 1-31st 2026 $15,000September 1-30th 2026 $175,000Year round 2026 $10,000May 1-31st 2026 $45,000June 1-30th 2026 | Southampton Summer Rental 4BR w Pool, Jeep Wrangler & Beach Pass 21 Kennedy Dr |
 | $40,000August 1-31st 2026 $35,000July 1-31st 2026 | Proven Sag Harbor Rental — Holiday Warmth, Summer Perfection 19 Tredwell Ln |
 | $40,000August 1st to Labor Day 2026 $40,000August 1-31st 2026 $75,000July 1st thru Labor Day 2026 $35,000July 1-31st 2026 $95,000Memorial Day to Labor Day 2026 $6,500April 1-30th 2026 $6,500January 1-31st 2026 $6,500March 1-31st 2026 $6,500November 1-30th 2026 | Waterfront in Sag Harbor Village! 11 Bluff Point Rd |
 | $40,000April through May 2026 $20,000April 1-30th 2026 $60,000August 1st to Labor Day 2026 $12,000January 1-31st 2026 $12,000March 1-31st 2026 $25,000May 1-31st 2026 $12,000November 1-30th 2026 $12,000October 1-31st 2026 $20,000September 1-30th 2026 $225,000Year round 2026 | Newly Renovated 6 Bedroom Southampton Home 106 Henry Rd |
 | $30,000April 1-30th 2026 $25,000January 1-31st 2026 $375,000July 1st thru Labor Day 2026 $150,000June 1-30th 2026 $25,000March 1-31st 2026 $40,000May 1-31st 2026 $425,000Memorial Day to Labor Day 2026 $25,000November 1-30th 2026 | Exquisite Newly Renovated Southampton Village Home 81 Leos Ln |
 | $30,000January 1-31st 2026 $30,000March 1-31st 2026 $30,000November 1-30th 2026 $175,000August 1st to Labor Day 2026 | Beautiful Southampton Village Retreat Pool + Tennis 298 Narrow Ln |
 | $125,000August 1st to Labor Day 2026 $100,000July 1-31st 2026 $50,000June 1-30th 2026 $250,000Memorial Day to Labor Day 2026 $50,000September 1-30th 2026 | Gorgeously Renovated Southampton Village Home! 241 Hill St |
 | $20,000July 1st thru Labor Day 2026 $25,000Memorial Day to Labor Day 2026 $5,000September 1-30th 2026 | Village Apartment 89 Jobs Ln Apt 4 |
 | $20,000August 1st to Labor Day 2026 $37,000July 1st thru Labor Day 2026 $20,000July 1-31st 2026 | Seconds to the Bay! 35 Lynn Ave |
 | $185,000August 1st to Labor Day 2026 $350,000July 1st thru Labor Day 2026 $175,000July 1-31st 2026 $235,000June-July 2026 $70,000June 1-30th 2026 $400,000Memorial Day to Labor Day 2026 $40,000April 1-30th 2026 $25,000January 1-31st 2026 $25,000March 1-31st 2026 $50,000May 1-31st 2026 $25,000November 1-30th 2026 $25,000October 1-31st 2026 $45,000September 1-30th 2026 | Amazing Southampton Summer Retreat! 126 Somerset Ave |
 | $10,000November 1-30th 2026 $10,000October 1-31st 2026 $25,000September 1-30th 2026 $75,000July 1-31st 2026 $100,000June-July 2026 $35,000June 1-30th 2026 | Perfection on Shinnecock Bay 46 Atterbury Rd |
 | $9,800October 1-31st 2026 $11,900September 1-30th 2026 $59,000Memorial Day to Labor Day 2026 $22,000July 1-31st 2026 $50,000July 1st thru Labor Day 2026 $29,000August 1st to Labor Day 2026 $25,000June 1-30th 2026 | Nice and Easy Summer Rental in Shinnecock Hills SouthamptonWebID# 1086530 June 1-30th 2026 $25,000 July 1-31st 2026 $22,000 July 1st thru Labor Day 2026 $50,000 Memorial Day to Labor Day 2026 $59,000 August 1st to Labor Day 2026 $29,000 September 1-30th 2026 $11,900 October 1-31st 2026 $9,800 4 BR 3½ bath |
 | $55,000August 1st to Labor Day 2026 $95,000July 1st thru Labor Day 2026 $50,000August 1-31st 2026 $115,000Memorial Day to Labor Day 2026 $25,000June 1-30th 2026 $45,000July 1-31st 2026 | Sag Harbor Waterfront Home 27 Clearview Dr |
 | $10,000September 1-30th 2026 $15,000August 1st to Labor Day 2026 $30,000July 1st thru Labor Day 2026 $15,000July 1-31st 2026 $10,000June 1-30th 2026 $40,000Memorial Day to Labor Day 2026 | Canal Front - 4 Bedroom - Hampton Bays Southampton |
 | $18,000August 1-31st $18,000August 1st to Labor Day | Beautiful Home in The Bucolic Hamlet of Remsenburg 20 Basket Neck Ln |
 | $4,500December 1-31st $4,500January 1-31st 2026 $4,500February 1-28th 2026 $4,500March 1-31st 2026 $4,500April 1-30th 2026 $16,000May 1-31st 2026 $35,000June 1-30th 2026 $30,000Short term 2026 $60,000July 1-31st 2026 $70,000August 1-31st 2026 $150,000Memorial Day to Labor Day 2026 | Water Mill -Big Blue Open Skies-Yearly Rental 896 Deerfield Rd, Water Mill |
 | $40,000October 1-31st $40,000November 1-30th $50,000December 1-31st $30,000January 1-31st 2026 $25,000February 1-28th 2026 $40,000March 1-31st 2026 $55,000April 1-30th 2026 $80,000May 1-31st 2026 $200,000June 1-30th 2026 $110,000July 1-31st 2026 $130,000August 1-31st 2026 $80,000September 1-30th 2026 | Southampton Retreat 30 Rosko Ln, Southampton |
 | $150,000June 1-30th 2026 $500,000July 1st thru Labor Day 2026 $250,000July 1-31st 2026 $275,000August 1st to Labor Day 2026 $145,000September 1-30th 2026 $50,000Short term 2026 $695,000Year round 2026 | Sagaponack Elegance with Pool and Tennis June 1-30th 2026 $150,000 July 1-31st 2026 $250,000 July 1st thru Labor Day 2026 $500,000 August 1st to Labor Day 2026 $275,000 Short term 2026 $50,000 Year round 2026 $695,000 September 1-30th 2026 $145,000 FURNISHED 8 BR 6½ bath |
 | $95,000August 1st to Labor Day 2026 $80,000July 1-31st 2026 | Traditional Style Southampton Home! SouthamptonWebID# 4969828 July 1-31st 2026 $80,000 August 1st to Labor Day 2026 $95,000 5 BR 7 bath |
| $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 June 1-30th 2026 $35,000 July 1-31st 2026 $70,000 August 1-31st 2026 $70,000 August 1st to Labor Day 2026 $72,000 September 1-30th 2026 $20,000 October 1-31st 2026 $7,500 November 1-30th 2026 $7,500 March 1-31st 2026 $7,500 January 1-31st 2026 $7,500 April 1-30th 2026 $7,500 4 BR 3 bath |
 | $80,000August 1st to Labor Day 2026 $120,000July 1st thru Labor Day 2026 | Southampton Waterfront Paradise! SouthamptonWebID# 4931644 July 1st thru Labor Day 2026 $120,000 August 1st to Labor Day 2026 $80,000 6 BR 6½ bath |
 | $125,000July 1-31st 2026 $125,000August 1st to Labor Day 2026 $70,000June 1-30th 2026 $325,000Memorial Day to Labor Day 2026 | One of a Kind in Heart of Horse&Wine Country with Pool and Tennis Water MillWebID# 4882075 June 1-30th 2026 $70,000 July 1-31st 2026 $125,000 Memorial Day to Labor Day 2026 $325,000 August 1st to Labor Day 2026 $125,000 5 BR 5 bath |
 | $69,500August 1st to Labor Day 2026 | Bridgehampton Perfect Hamptons Getaway and More BridgehamptonWebID# 4887994 August 1st to Labor Day 2026 $69,500 4 BR 3 bath |
 | $145,000July 1st thru Labor Day 2026 $200,000Memorial Day to Labor Day 2026 $50,000June 1-30th 2026 $75,000July 1-31st 2026 $80,000August 1-31st 2026 $75,000August 1-31st 2026 | Refined Restoration in Southampton Village - 6 Bed With Pool 305 North Main St |
 | $75,000July 1-31st 2026 $60,000June 1-30th 2026 | Southampton Village Retreat SouthamptonWebID# 4995217 June 1-30th 2026 $60,000 July 1-31st 2026 $75,000 3 BR 4½ bath |
 | $275,000August 1st to Labor Day | Stunning Estate:Luxury Living Just Minutes from the Ocean! 108 Fairfield Pond Ln |
 | $75,000July 1st thru Labor Day $96,000Year round $15,000September 1-30th | Southampton Summer or Year Round Rental Close to Village & Beach 16 Kings Ln |
 | $65,000August 1st to Labor Day | 5 BR 4 bath |
 | $85,000August 1-31st $25,000September 1-30th $85,000July 1-31st $190,000July 1st thru Labor Day $290,000Year round | Southampton New Construction with Pool House 264 S Magee St |
 | $210,000April through Labor Day $30,000April through May $15,000April 1-30th $215,000May through Labor Day $17,500May 1-31st $205,000Memorial Day to Labor Day $215,000Extended season $115,000June-July $115,000June 1-30th $175,000July 1-31st $110,000August 1st to Labor Day $100,000August 1-31st $20,000September 1-30th $15,000October 1-31st $13,500November 1-30th $13,500December 1-31st $220,000Year round $12,500January 1-31st $12,500February 1-28th $13,500March 1-31st $15,000April 1-30th $115,000June 1-30th $175,000July 1-31st | True Mediterranean Vill in the Hamptons - 5BD/6BA w/ pool June 1-30th $115,000 June-July $115,000 July 1-31st $175,000 Memorial Day to Labor Day $205,000 August 1-31st $100,000 August 1st to Labor Day $110,000 Extended season $215,000 Year round $220,000 December 1-31st $13,500 November 1-30th $13,500 October 1-31st $15,000 September 1-30th $20,000 May 1-31st $17,500 May through Labor Day $215,000 April 1-30th $15,000 April through May $30,000 April through Labor Day $210,000 March 1-31st $13,500 February 1-28th $12,500 January 1-31st $12,500 FURNISHED 5 BR 6 bath |
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