Southampton Rentals, Southampton Summer Vacation Rentals, Rent Southampton Homes & Properties
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388 found
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 | $85,000July 1-31st 2026 $95,000August 1st to Labor Day 2026 $85,000August 1-31st 2026 $30,000Short term | Luxurious Sagaponack Home, Newly Renovated. Spacious and Modern! 18 E Woods Path |
 | $25,000October 1-31st $50,000September 1-30th $20,000December 1-31st $20,000November 1-30th $150,000August 1-31st $100,000July 1-31st $40,000June 1-30th | Southampton Resort Style Living- 4 Level Modern with Pool, Beach +Bay Access 8 Middle Pond Ln |
 | $55,000September 1-30th $150,000August 1st to Labor Day | FURNISHED 5 BR 7.5 4500 sq ft Single Family Single Family |
 | $100,000July 1-31st $150,000August 1-31st $150,000August 1st to Labor Day $50,000Extended season $50,000September 1-30th $25,000October 1-31st $25,000November 1-30th $25,000December 1-31st | EXQUISITE MASTERPIECE IN SOUTHAMPTON - A PRIVATE RESORT RETREAT 8 Terrace Ave |
 | $60,000September 1-30th $60,000October 1-31st $60,000November 1-30th $60,000December 1-31st $550,000Year round $200,000August 1st to Labor Day $175,000July 1-31st $370,000July 1st thru Labor Day | Southampton Village 39 Adams Ln |
 | Magnificent Southampton Resort Style 5 Bedrooms 5.5 Bath Pool Lounge 102 McGregor Dr | |
 | $25,000February 1-28th $25,000March 1-31st $25,000December 1-31st $35,000April 1-30th $35,000November 1-30th $50,000September 1-30th $40,000May 1-31st $40,000October 1-31st $25,000January 1-31st $75,000Winter | 6 BR 6.5 6000 sq ft Single Family Single Family |
 | $85,000July 1st thru Labor Day $125,000Memorial Day to Labor Day $18,000Short term | 6 BR 6 4776 sq ft Single Family Single Family |
| $140,000Memorial Day to Labor Day $100,000July 1st thru Labor Day $160,000April through Labor Day | 4 BR 3.5 4000 sq ft Single Family Single Family |
 | $55,000July 1st thru Labor Day $32,000August 1st to Labor Day | FURNISHED 3 BR 3 House Single Family |
 | $130,000July 1-31st $250,000July 1st thru Labor Day $170,000June-July $140,000August 1st to Labor Day $425,000Year round $40,000September 1-30th $20,000October 1-31st $20,000November 1-30th $20,000December 1-31st $50,000June 1-30th | 7 BR 6.5 5647 sq ft Single Family Single Family |
 | $30,000July 1st thru Labor Day $15,000August 1st to Labor Day | Southampton Village Gem 11 Henry St |
 | $25,000July 1-31st | Private Hamptons Getaway SouthamptonWebID# 1086810 3 BR 2 1700 sq ft Single Family Single Family |
 | $23,000Short term $19,999Standard monthly rent 2026 | Sag Harbor Modern Oasis 170 Northside Dr |
 | Hamptons Retreat for U.S. Golf Open Water MillWebID# 4889588 4 BR 4.5 Single Family Rental | |
 | $160,000Memorial Day to Labor Day $23,000November 1-30th $23,000October 1-31st $23,000September 1-30th $19,999Year round | Sag Harbor Compound Sag HarborWebID# 4857915 5 BR 3.5 Single Family Rental |
 | $50,000September 1-30th $20,000October 1-31st $15,000November 1-30th $20,000April 1-30th $150,000August 1st to Labor Day $15,000January 1-31st $225,000July 1st thru Labor Day $100,000July 1-31st $75,000June 1-30th $15,000March 1-31st $25,000May 1-31st $150,000August 1-31st | Southampton Resort Style Living- 4 Level Modern with Pool +Beach 8 Middle Pond Ln |
 | $18,000September 1-30th $18,000October 1-31st | 3 BR 2 Single Family Rental |
 | $20,000September 1-30th | 4 BR 4.5 Single Family Rental |
 | $6,000September 1-30th $6,000October 1-31st $6,000November 1-30th | Oasis on the North Fork Bay Southampton |
 | $75,000June-July $30,000June 1-30th $125,000Memorial Day to Labor Day $50,000July 1-31st $100,000July 1st thru Labor Day $55,000August 1st to Labor Day $20,000September 1-30th $12,000October 1-31st $12,000November 1-30th | 4 Bedroom Upper Condo 404 High Pond Ln |
 | $15,000August 1st to Labor Day $15,000July 1-31st $30,000July 1st thru Labor Day $7,000September 1-30th $3,000January 1-31st $3,000March 1-31st $3,000April 1-30th $3,000October 1-31st $3,000November 1-30th | 3 BR 2 1440 sq ft Single Family Rental |
 | $160,000August 1st to Labor Day $300,000July 1st thru Labor Day $150,000July 1-31st $75,000June 1-30th $200,000June-July $50,000May 1-31st $350,000Memorial Day to Labor Day $45,000Winter $475,000Year round $15,000October 1-31st $15,000November 1-30th $30,000September 1-30th | 7 BR 7.5 5200 sq ft Single Family Rental |
 | $11,800September 1-30th | 3 BR 1 768 sq ft Single Family Rental |
 | $20,000September 1-30th $15,000October 1-31st $12,000November 1-30th | 4 BR 4 2700 sq ft Single Family Rental |
 | $45,000Memorial Day to Labor Day $10,000June 1-30th $18,000July 1-31st $20,000August 1-31st $10,000November 1-30th $20,000August 1st to Labor Day $15,000May 1-31st $15,000September 1-30th $12,000October 1-31st | Boat Lover’s Heaven! 8 Hyler Dr |
 | $50,000September 1-30th $40,000October 1-31st $95,000June 1-30th $40,000May 1-31st | Luxury Southampton Village Rental – Elegant Shingle-Style Estate 111 Post Ln |
 | $30,000September 1-30th $100,000August 1st to Labor Day $80,000June 1-30th $80,000August 1-31st | Hamptons Hideaway: Your Dream Escape in Water Mill! 59 Mill Creek Close |
 | $145,000July 1-31st $20,000January 1-31st $20,000March 1-31st $375,000Memorial Day to Labor Day $65,000June 1-30th $35,000May 1-31st $30,000April 1-30th $165,000August 1st to Labor Day | 6 BR 7.5 4900 sq ft Single Family Rental |
 | $85,000Memorial Day to Labor Day $30,000June 1-30th $40,000August 1-31st $40,000August 1st to Labor Day $75,000July 1st thru Labor Day $35,000July 1-31st $20,000May 1-31st $65,000June-July $15,000April 1-30th $15,000November 1-30th $18,000October 1-31st $20,000September 1-30th $12,000Winter $12,000January 1-31st $12,000March 1-31st | 4 BR 3.5 2800 sq ft Single Family Rental |
 | $10,000September 1-30th | Charming, Well-Built Post-Modern Just Minutes from a Private Bay 10 Foxboro Rd |
 | $60,000Memorial Day to Labor Day $10,000March 1-31st $8,000January 1-31st $40,000August 1-31st $35,000July 1-31st $30,000June 1-30th $13,000May 1-31st $12,000April 1-30th $15,000September 1-30th $12,000October 1-31st $10,000November 1-30th | 4 BR 2 1934 sq ft Single Family Rental |
 | $275,000August 1-31st $275,000August 1st to Labor Day | 6 BR 4.5 4976 sq ft Single Family Rental |
 | $50,000September 1-30th $25,000October 1-31st $25,000November 1-30th | 6 BR 7.5 6700 sq ft Single Family Rental |
 | $395,000Memorial Day to Labor Day $180,000July 1-31st $350,000July 1st thru Labor Day $190,000August 1st to Labor Day $495,000Year round | Summer on Gin Lane 477 Little Plains Rd |
 | $10,000September 1-30th | East Quoge Stunner 3 Clara Dr |
| 388 found | ||
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