Vacation Rentals by Owner

Key West Vacation Rentals Show this location only Back to top

•   Sophisticated Southard Street Charmer 3BR/3BA – Sleeps 6 – Private Homes, Old Town #176314
  1
  $4800 to $10,000 per month

  View details
•   Amelia's Hideaway - Hidden Courtyard Villa with Private Pool 4BR/3.5BA – Sleeps 8-10 – Private Homes, Old Town #137983
  2
  $750-$850/nt - $4000-$5100/wk

  View details
•   Peaceful Gated Community -- Close to Everything! 3BR/3BA – Sleeps 6 – Coral Hammock #213322
  8
  $1100- $1800/wk

  View details
•   Gated Private Luxurious Getaway-Truman Annex (Private Pool) 4BR/4BA – Sleeps 8 – Truman Annex #99721
  0
  $5500- $7500/wk

  View details
•   Charming Home in Old Town Key West 3BR+/3BA – Sleeps 6-8 – Truman Annex #310066
  5
  $3500- $5500/wk

  View details
•   Paradise Found 2BR+/1.5BA – Sleeps 4-5 – Key West Golf Club #311501
  2
  $1015 - $1120 per week 7 night min stay

  View details
•   Fleming Street Townhouse in the Sky! 2BR+/2.5BA – Sleeps 4-6 – Private Homes, Old Town #289989
  5
  $3500- $5500/mo

  View details
•   Condo at Oceanside Marina, Stock Island, Key West 3BR/2BA – Sleeps 6-7 – Other Key West Properties #386233
  5
  1600.00- 2400wk

  View details
•   House by the Beautiful Sea- Stunning Key West Sunsets 3BR+/3BA – Sleeps 6-8 – Truman Annex #240137
  0
  $4800/wk

  View details
•   Tropical Hideaway for Laid Back Living 2BR+/1BA – Sleeps 4-6 – Truman Annex #263478
  6
  $1250- $1600

  View details
•   Captain's Quarters- 100 Yards from Key West Duval St. 1BR+/1BA – Sleeps 2-4 – Private Homes, DownTown #261747
  3
  $1050- $1400/wk

  View details
•   Waterfront Views from Dolphin Watch 4BR/3BA – Sleeps 8 – Truman Annex #297639
  1
  $4500- $6500/wk

  View details
•   Designer Dream 2BR/2BA with Heated Pool 2BR/2BA – Sleeps 2-4 – Private Homes, Old Town #190172
  0
  $4000- $7000/mo

  View details
•   Old Town Historic Eyebrow -One Block to Duval-Private Pool/Spa 4BR+/4BA – Sleeps 8 – Private Homes, Old Town #150378
  1
  3490/wk

  View details
•   Key West 3 Bedroom Condo- Direct Beach Front 3BR+/2BA – Sleeps 2-8 – 1800 Atlantic #205631
  0
  $2600- $3100/wk

  View details
•   Elegantly Furnished Key West Condo in the Truman Annex. 2BR+/1BA – Sleeps 3-6 – Truman Annex #347511
  0
  $165 per night 3 night min stay

  View details
•   Blue Lagoon 3BR/2BA – Sleeps 6 – Truman Annex #264827
  1
  $2500- $3500/wk

  View details
•   Stay in the Nicest Part of Key West 2BR+/1.5BA – Sleeps 4-6 – Truman Annex #279984
  5
  $1400- $2800/wk

  View details
•   'Amberjack' a Little Slice of Key West Heaven 2BR/1BA – Sleeps 4-6 – Truman Annex #3486581ha
  0
  $175 - $393 per night

  View details
•   Sea Breeze Cottage-Gulf View in Truman Annex 3BR/2BA – Sleeps 3-6 – Truman Annex #987489ha
  0
  $357 per night

  View details
•   Key West on the Water with a Spectacular Sunset View Sleeps 6 2BR+/2.5BA – Sleeps 4-6 – Truman Annex #362398
  3
  From $2,400 to $3,500 US

  View details
•   One of a Kind Luxury Home - Admirals Treasure 4BR/4BA – Sleeps 8 – Truman Annex #290548
  0
  $5900- $8900/wk

  View details
•   The Meeting Point - Key West - Elegant and Grand 11BR/0BA – Sleeps 24-26 – Private Homes, Old Town #457272
  0
  from $2100/night

  View details
•   Quaint Townhouse in the Heart of Old Town Key West 2BR/1.5BA – Sleeps 4-5 – Truman Annex #446454
  1
  $1505 - $2380 per week 7 night min stay

  View details
•   Monthly Rental: Historic Oasis Steps from Key West's Best Attractions 3BR/2BA – Sleeps 6 – Private Homes, Historic Seaport #449146
  0
  monthly rental 7,000.00-10,000.00

  View details
•   Oceanfront View Large Expansive Deck Great Sunsets 2wk-Monthly 2BR/2BA – Sleeps 4 – Truman Annex #337229
  0
  $6,500 - $8,000 mo. US

  View details
•   On the Ocean 2BR+/2BA – Sleeps 2-5 – La Brisa #322566
  4
  From $1400/wk - $4000/mo

  View details
•   Seaside 33 2BR/3BA – Sleeps 4 – Other Key West Properties #3174186ha
  2
  $150 - $196 per night

  View details
•   Turtle Cay Spa 2BR/2.5BA – Sleeps 6 – Other Key West Properties #3175770ha
  1
  $133 - $178 per night

  View details
•   The Loft at Echo Gardens 1BR/1BA – Sleeps 4 – Other Key West Properties #3499642ha
  6
  $100 - $124 per night

  View details
•   The Pearl in Paradise 2BR/2BA – Sleeps 4 – Other Key West Properties #3174190ha
  2
  $117 - $178 per night

  View details
•   Eaton Manor 2BR/2BA – Sleeps 6 – Other Key West Properties #3174191ha
  10
  $108 - $250 per night

  View details
•   Shipyard 253 2BR/1BA – Sleeps 6 – Truman Annex #3174183ha
  39
  $117 - $300 per night

  View details
•   Garden Villa 1BR/1BA – Sleeps 4 – Other Key West Properties #3174181ha
  1
  $100 - $124 per night

  View details
•   205e La Brisa 2BR/2BA – Sleeps 4 – Other Key West Properties #3174194ha
  12
  $133 - $300 per night

  View details
•   Pelican Landing Andros Retreat 2BR/2BA – Sleeps 8 – Other Key West Properties #3174198ha
  18
  $167 - $350 per night

  View details
•   Pelican Landing Aruba Retreat 2BR/2BA – Sleeps 8 – Other Key West Properties #3174199ha
  35
  $167 - $350 per night

  View details
•   Pelican Landing Eleuthera Retreat 2BR/2BA – Sleeps 8 – Other Key West Properties #3174202ha
  23
  $167 - $350 per night

  View details
•   Pelican Landing Florida Retreat 2BR/2BA – Sleeps 8 – Other Key West Properties #3174205ha
  20
  $167 - $350 per night

  View details
•   Pelican Landing St.John Retreat 3BR/3BA – Sleeps 10 – Other Key West Properties #3174206ha
  25
  $200 - $450 per night

  View details
•   Pelican Landing St. Kitts Retreat 3BR/4BA – Sleeps 10 – Other Key West Properties #3174204ha
  19
  $200 - $450 per night

  View details
•   Pelican Landing Antigua Retreat 2BR/2BA – Sleeps 8 – Other Key West Properties #3174207ha
  23
  $167 - $350 per night

  View details
•   Pelican Landing Bonaire Room 1BR/1BA – Sleeps 4 – Other Key West Properties #3174216ha
  5
  $100 - $200 per night

  View details
•   Pelican Landing Antigua Suite 1BR/1BA – Sleeps 4 – Other Key West Properties #3174210ha
  6
  $133 - $300 per night

  View details
•   Pelican Landing Eleuthera Suite 1BR/1BA – Sleeps 4 – Other Key West Properties #3174221ha
  5
  $133 - $300 per night

  View details
•   Pelican Landing Antigua Room 1BR/1BA – Sleeps 4 – Other Key West Properties #3174211ha
  3
  $100 - $200 per night

  View details
•   Pelican Landing Flamingo Room 1BR/1BA – Sleeps 4 – Other Key West Properties #3174225ha
  5
  $100 - $200 per night

  View details
•   Pelican Landing Bermuda Suite 1BR/1BA – Sleeps 4 – Other Key West Properties #3174226ha
  3
  $133 - $300 per night

  View details
•   Pelican Landing Florida Room 1BR/1BA – Sleeps 4 – Other Key West Properties #3174229ha
  4
  $100 - $200 per night

  View details
•   Southard Square 2BR/2BA – Sleeps 6 – Other Key West Properties #3174233ha
  1
  $117 - $160 per night

  View details
•   Sunrise Suites 2BR/2BA – Sleeps 6 – Other Key West Properties #3488360ha
  23
  $117 - $299 per night

  View details
•   Sunrise Suites 2BR/2BA – Sleeps 6 – Other Key West Properties #3488372ha
  26
  $117 - $299 per night

  View details
•   Sunrise Suites 2BR/2BA – Sleeps 6 – Other Key West Properties #3488397ha
  22
  $117 - $299 per night

  View details
•   Sunrise Suites 2BR/2BA – Sleeps 6 – Other Key West Properties #3488387ha
  33
  $117 - $299 per night

  View details
•   Sunrise Suites 2BR/2BA – Sleeps 6 – Other Key West Properties #3488389ha
  16
  $117 - $299 per night

  View details
•   Sunrise Suites 2BR/2BA – Sleeps 6 – Other Key West Properties #3488390ha
  28
  $117 - $299 per night

  View details
•   Luxury Truman Annex Condo - Walk to Beach/Duval St. 2BR/1BA – Sleeps 4-5 – Truman Annex #200351
  32
  $1300- $1925/wk, discounted monthly rates

  View details
•   Gated Private Luxurious Getaway-Truman Annex (Private Pool) 3BR/3.5BA – Sleeps 7 – Truman Annex #99722
  2
  $4500- $6500/wk

  View details
•   Spacious Ocean Front Resort - 3 Bedroom Condo 3BR+/3BA – Sleeps 6-8 – 1800 Atlantic #256294
  25
  $325-$500/nt - $2,275-$3,150/wk

  View details
•   Casa Marina Elegance 3BR/3.5BA – Sleeps 6 – Casa Marina #401222
  1
  $29200 per month 28 night min stay

  View details
•   Enjoy Ocean Views and Breezes.(Handicap Accessible) 2BR/2BA – Sleeps 4 – 1800 Atlantic #256053
  0
  From $200/nt - $380/nt

  View details
•   Island Oasis Garden Home - Hidden in the Heart of Old Town 2BR/2BA – Sleeps 4 – Windward Park #184037
  0
  $300-$400/nt - $1500-$2100/wk

  View details
•   Cute, Clean, Cozy and Close to All 1BR/1BA – Sleeps 2-3 – Private Homes, Old Town #250411
  30
  $135-$225/nt - $895- $1500/wk

  View details
•   Amanda's Dream Suites-Good Value with Giant Pool in Key West 4BR+/3BA – Sleeps 8-10 – Private Homes, Mid Town #183990
  0
  $3275/wk - $4550/wk or $550/nt - $750/nt

  View details
•   Oceanside Marina - Luxury 3 BR Condo 3BR/2BA – Sleeps 6 – Oceanside Marina (formerly Kings Pointe) #138365
  1
  $225- $275//nt

  View details
•   Tropical Dreaming - 2 Bedroom Home - Private Pool 2BR/2.5BA – Sleeps 4-6 – Private Homes, Old Town #251642
  0
  $340-$470/nt - $2100-$3000/wk

  View details
•   Quiet Lane Retreat in the Heart of Old Town 2BR+/1.5BA – Sleeps 6 – Private Homes, Old Town #425235
  0
  $2500- $6000/mo.

  View details
•   The Kingfisher - Historic Old Town Luxury Home (Monthly Only) 3BR/2.5BA – Sleeps 6 – Private Homes, Old Town #430740
  0
  $6000- $10000/mo

  View details
•   Enjoy Your Own Sunset Escape & Private Pool! 3BR/3BA – Sleeps 6 – Key West Golf Club #429182
  0
  $4,500- $6,500/month

  View details
•   4 Palms Two Bedroom 1800 Atlantic Condo 2BR+/2BA – Sleeps 6 – 1800 Atlantic #93287
  0
  From $1250/wk

  View details
•   Oceanfront Views of Key West's Atlantic Shore 2BR/2BA – Sleeps 6 – 1800 Atlantic #23443
  0
  From $1200/wk

  View details
•   Egret Cottage: 1 Bedroom Cottage Old Town Key West 1BR+/1BA – Sleeps 4 – Private Homes, Old Town #92567
  0
  $1050- $1550/wk

  View details
•   Summer Rates from $3000/Month - Louisa Bella 2BR+/1BA – Sleeps 4-6 – Private Homes, Old Town #101530
  0
  $3000- $6500/mo

  View details
•   Sailor House, Luxurious Two Bedroom 1/2 Block from Duval St. 2BR+/1.5BA – Sleeps 4-6 – Private Homes, Old Town #321456
  1
  $265- $399/nt plus 12.5% tax

  View details
•   Southern Wind Two Bedroom Home in Old Town Key West 2BR/2BA – Sleeps 4 – Windward Park #93459
  2
  From $1300/wk

  View details
•   A Zen Ocean Garden - 2 BR/2 BA - Ocean View - 1800 Atlantic 2BR+/2BA – Sleeps 6 – 1800 Atlantic #92460
  0
  $300-$390/nt - $1800-$2425/wk

  View details
•   Duval Street Hideaway - Two Bedroom Townhome W/Private Jacuzzi 2BR+/2.5BA – Sleeps 6 – Duval Square #93296
  0
  $240- $315/nt

  View details
•   Spa on Duval Two Bedroom W/Private Jacuzzi Just Steps to Duval 2BR+/2.5BA – Sleeps 6 – Duval Square #93476
  0
  $240-$315/nt - $1400-$1900/wk

  View details
•   Beautiful Key West Condo on the Ocean 2BR+/2BA – Sleeps 4-6 – 1800 Atlantic #249337
  3
  $225- $425/nt

  View details
•   Key West 2 Bedroom 2 Bath Condo Rental 2BR+/2BA – Sleeps 6 – La Brisa #362097
  0
  3,250- 4,200/mo long term

  View details
•   Cozy Condo in Key West 1BR/1BA – Sleeps 2 – Galleria #138062
  26
  $120 OR $95

  View details
•   Papaya Place Pops with Color! 2BR+/2BA – Sleeps 4-6 – 1800 Atlantic #138915
  0
  $220-$305/nt - $1250-$1825/wk

  View details
•   Quiet and Beautiful Truman Annex 2 BR End-Unit Old Town 2BR+/1BA – Sleeps 4 – Truman Annex #420646
  14
  From $1100 - $1875 / week

  View details
•   Last Minute April Special $2200 Beach Condo 2 Pools One Month Min. 1BR+/1BA – Sleeps 2 – Seaside Resort #358407
  2
  From $1400/mo

  View details
•   Key West Truman Annex 2bed/3bath Sleeps 6 Min to Duval/Water 2BR/2.5BA – Sleeps 3-6 – Truman Annex #373185
  0
  From $1600/wk

  View details
•   Truman Annex - 1BR/1BA - Renovated Corner Unit with Great Reviews!!! 1BR+/1BA – Sleeps 2-4 – Truman Annex #50666
  19
  $1050- $5400/mo

  View details
•   Céad Míle Fáilte - a Thousand Welcomes to Our Innisfree 2BR/1BA – Sleeps 4 – Truman Annex #78945
  10
  $1400- $1900/wk

  View details
•   Conch Retreat in Key West Truman Annex with 2 Bikes 2BR/1BA – Sleeps 4 – Truman Annex #226298
  22
  $171 per night

  View details
•   Hemingway's Hideaway 2BR+/2.5BA – Sleeps 4 – Truman Annex #175251
  13
  $1855 per week 7 night min stay

  View details
•   Private & Peaceful Cottage Feel-with 7 Night Stay 1 Night Free 1BR/1BA – Sleeps 2-4 – Private Homes, Old Town #114836
  18
  From125 nt to 215 a nt for lodging

  View details
•   Villa Soleil-Enjoy America's Caribbean with Style and Comfort 2BR+/2.5BA – Sleeps 6 – Other Key West Properties #141421ha
  3
  $229 - $257 per night

  View details
•   Super Fun Key West Vacation Home on Canal, Swim Spa, More... 3BR+/2BA – Sleeps 7-8 – Key Haven #181624
  11
  $1850/wk - $4800/mo

  View details
•   An Artistic Hideaway in Paradise 1BR+/1BA – Sleeps 2-4 – Galleria #129956
  29
  $105 - $119 per night 1-2 night min stay

  View details
•   Chilmark South Tropical Key West Waterfront Condo 2BR+/2BA – Sleeps 6 – Truman Annex #165220
  5
  $2400- $3800/wk

  View details
•   Henry's Penthouse on the Ocean in Key West - Weekly / Nightly 2BR+/2BA – Sleeps 4-6 – Other Key West Properties #45061
  15
  $265-$425/nt - $1575-$2678/wk

  View details
•   Key West Gem - Large, Bright 2 BR Condo on Ocean W/ Olympic-Size Pool 2BR+/2BA – Sleeps 4-6 – 1800 Atlantic #420183
  10
  $205- $340/nt (depending on season)

  View details
•   Key West Cottage Charmer 2BR+/2BA – Sleeps 2-5 – Private Homes, Old Town #321956
  18
  $1700 - $7200

  View details
•   Carpe Diem- a Tropical Conch Cottage in Old Town Key West - 2BR/2BA – Sleeps 6 – Private Homes, Old Town #287462
  4
  $3300 - $6000 per month 30 night min stay

  View details
•   Island Rendezvous - Like Having Your Own Little Private Resort 6BR+/5BA – Sleeps 12-16 – Other Key West Properties #141726
  0
  $1100-$1250/nt - $7500-$5850/wk

  View details
•   Quiet Key West for Two! One Month Minimum Stay Required. 1BR+/1BA – Sleeps 2 – Other Key West Properties #127995
  1
  $1700- $3500/mo

  View details