Vacation Rentals by Owner

Key West Vacation Rentals Show this location only Back to top

•   Oceanfront Acre Heated Private Pool Sandy Area Dock 15 Min Key West 3BR+/2BA – Sleeps 10 – Private Homes, Unspecified #23604
  51
  $1800 - $2900 per week 7 night min stay

  View details
•   Ocean Perch , Dock 80'Heated Pool Deep Channel Tennis 15 Min Key West 2BR+/2BA – Sleeps 4-6 – Private Homes, Unspecified #49850
  45
  $975 - $1550 per week 7 night min stay

  View details
•   Truman Annex Best Location in Town 2BR+/2BA – Sleeps 4-6 – Truman Annex #67476
  6
  $1400 - $2200 per week 7 night min stay

  View details
•   'Casa Louisa @ Upper Duval': Historic Conch Cottage & Pool 1/2 Block Off Duval.. 3BR+/2BA – Sleeps 6-8 – Other Key West Properties #135603ha
  45
  $400 - $750 per night 4 night min stay

  View details
•   Ocean Breeze Suites-3 Bd, 3 Bath with Loft Sleeps 10 3BR/3BA – Sleeps 10 – Galleon #222110
  12
  $695 - $855 per night 2-4 night min stay

  View details
•   Sunset and Ocean View in Key West's Truman Annex with 2 Bikes and Pool Access 2BR+/1BA – Sleeps 4 – Truman Annex #236217
  61
  $1300 - $1950 per week 7 night min stay

  View details
•   'Old Town Oasis @ Truman Annex': Luxurious 2BR/2BA Condo + Oceanside Pool... 2BR+/2BA – Sleeps 4-6 – Truman Annex #71538
  23
  $2100 - $3800 per week 7 night min stay

  View details
•   Oceanfront Condominium - Key West Oceanfront at the Coral Reef 2BR/2BA – Sleeps 6 – 1800 Atlantic #107925
  34
  $199 - $495 per night

  View details
•   Charming Condo in Old Town Key West's Truman Annex 1BR/1BA – Sleeps 2 – Key West #297241
  32
  $1200 - $1850 per week 7 night min stay

  View details
•   Oceanfront Condominium - Key West's Crown Jewel 2BR+/2BA – Sleeps 4-6 – 1800 Atlantic #45706
  144
  $350-$440/nt - $2100-$3300/wk

  View details
•   Key West Boat & Breakfast, Reef Sailing Trips, Asa Sailing Coming Soon 2BR/2BA – Sleeps 4 – Private Homes, Historic Seaport #169864
  19
  $320 - $375 per night 2-3 night min stay

  View details
•   Truman Annex House, 2b/2.5b, Add 1b/1b Cottage=3BR/3.5BA, Pool 3BR/3.5BA – Sleeps 6 – Truman Annex #1614
  6
  $2150 - $5500 per wk

  View details
•   Wow Oceanside Voted #1 Key West's Best Luxury Penthouse Marina/Condo/Pool 3BR/2BA – Sleeps 6 – Oceanside Marina (formerly Kings Pointe) #154578
  22
  $1600-$3000/wk - WEEKLY RATES

  View details
•   'Poolside Retreat @ the Pool': Poolside 2BR/2.5BA Villa with 2 Master Suites... 3BR/2.5BA – Sleeps 4-6 – Key West Golf Club #104772
  3
  $3000 - $5750 per month 28 night min stay

  View details
•   Private Luxury in Prestigious Casa Marina Neighborhood 3BR/3.5BA – Sleeps 6-7 – Casa Marina #307081
  14
  $117 - $293 per night

  View details
•   Key West Condo in Truman Annex with Whirlpool Tub, 2 Bikes, & Access to Pool! 2BR/1BA – Sleeps 4 – Truman Annex #385544
  18
  $1300 - $1950 per week 7 night min stay

  View details
•   'La Provence @ the Sanctuary': 2 Master Suites, Spa Pool with Walled Yard... 2BR+/3BA – Sleeps 4-6 – Key West Golf Club #71542
  5
  $3000 - $6900 per month 28 night min stay

  View details
•   Steps from Duval $79-$129 Night - Free Bikes Included!!! Studio/1BA – Sleeps 2 – Private Homes, Old Town #140317
  19
  $79- $129/nt

  View details
•   Steps from Duval! Luxurious, Sleeps 2-4, Old Town 1BR+/1BA – Sleeps 2-4 – Private Homes, Old Town #365419
  17
  FROM $208/NIGHT

  View details
•   Bargain Rates in Truman Annex - Heart of Old Town, Key West 2BR/1BA – Sleeps 4-6 – Truman Annex #68720
  5
  $185 - $350 per night

  View details
•   Paradise Found*Luxury Oceanfront Key West 3/2 Oceanside Marina 3BR+/2BA – Sleeps 2-7 – Oceanside Marina (formerly Kings Pointe) #170889
  6
  $1,850-$2500/wk - $5000-$8000/mo

  View details
•   Charming, Romantic, Funky, Cozy, Unique, Beautiful, Island Charm, Beach, Ocean 1BR/1BA – Sleeps 2 – Other Key West Properties #972748ha
  8
  $149 - $189 per night 2-3 night min stay

  View details
•   Serendipity , Dluxe 3 BR, Ocnfrnt Condo 3BR+/2BA – Sleeps 6-8 – La Brisa #57418
  14
  From $1200/wk

  View details
•   Ocean Suite at the Galleon Resort 2BR/2BA – Sleeps 8 – Galleon #378516
  4
  $495 - $695 per night 2-4 night min stay

  View details
•   "Coconut Cabana" Old Town Tropical Bungalow 3BR/2BA – Sleeps 4-6 – Private Homes, Old Town #72848
  8
  $430-$580./nt - $2800-$5110./wk

  View details
•   'Windows on the Gulf @ the Annex': Lavish Oceanfront 2BR/2.5BA Penthouse Condo.. 2BR+/2.5BA – Sleeps 4-6 – Truman Annex #390177ha
  13
  $3300 - $5500 per week 7 night min stay

  View details
•   'Villa Bahama @ the Foundry': Luxury 2BR/2.5BA Townhome in Truman Annex... 2BR+/2.5BA – Sleeps 4-6 – Other Key West Properties #390213ha
  12
  $1950 - $3500 per week 7 night min stay

  View details
•   Carey's Conch Cottage Old Town, Key West, Private Heated Pool 1BR+/1.5BA – Sleeps 2-4 – Private Homes, Old Town #247863
  11
  $4500 - $6500 per month 30 night min stay

  View details
•   Private Yacht 3 Blocks from Duval Street & Sloppy Joe's 3BR/3BA – Sleeps 6 – Private Homes, Historic Seaport #390580
  21
  $595 - $650 per night 2-5 night min stay

  View details
•   Full Month Discounts Now Available in Truman Annex, Key West 2BR/2.5BA – Sleeps 4-5 – Truman Annex #406936
  12
  $1750 - $2751 per week 7 night min stay

  View details
•   Mojitoville: Pet-Friendly Old Town Cottage with Private Pool 3BR+/2BA – Sleeps 6-7 – Private Homes, Historic Seaport #54945
  0
  $4000- $7000/mo

  View details
•   Luxury Waterfront at the Galleon Resort in Old Town 2BR/2BA – Sleeps 8 – Galleon #233789
  5
  $343 - $600 per night

  View details
•   'Gulfside Vistas @ Truman Annex': Lavish Oceanfront 2BR/2.5BA Penthouse Condo... 2BR/2.5BA – Sleeps 4-5 – Other Key West Properties #904145ha
  19
  $2950 - $5000 per week 7 night min stay

  View details
•   'Paradise @ Garrison Bight': Large 5BR/4BA Waterfront Home + Private Dock... 5BR+/4BA – Sleeps 14 – Other Key West Properties #390212ha
  25
  $600 - $1800 per night

  View details
•   Ocean Paradise 3BR+/4BA – Sleeps 8 – Truman Annex #216159
  6
  $4900 - $6900 per week 7 night min stay

  View details
•   Key West 'Coral Hammock' - Poolside 3BR/3BA – Sleeps 6 – Key West Golf Club #105427
  6
  $140 - $215 per night 5 night min stay

  View details
•   'Puerta Coralina @ Solares Hill': Charming 2BR/3BA Cottage, 2 Master Suites... 2BR+/3BA – Sleeps 4-6 – Other Key West Properties #904144ha
  22
  $350 - $700 per night 4 night min stay

  View details
•   Steps to Duval! Luxurious, Sleeps 2-4, Old Town, Key West 1BR+/1BA – Sleeps 2-4 – Key West #433844
  9
  FROM $208/NIGHT

  View details
•   'Southern Star' @ the Seaport' Renovated Historic 3BR/3BA Home with Pool... 3BR/3BA – Sleeps 6 – Other Key West Properties #390182ha
  10
  $7000 - $16000 per month 28 night min stay

  View details
•   'Casa Blanca 1888 @ White': Historic 4BR/3BA Old Town Home + Very Large Pool.... 4BR+/3BA – Sleeps 10 – Other Key West Properties #390200ha
  11
  $7000 - $16000 per month 28 night min stay

  View details
•   Galleon Resort Efficiency in Old Town Studio/1BA – Sleeps 2 – Galleon #245665
  7
  $137 - $240 per night

  View details
•   Duval Compound, Private Pool, Parking, Roof Deck, Downtown Key West 6BR+/7BA – Sleeps 12-14 – Private Homes, DownTown #224704
  4
  $180 to $310 per room per night

  View details
•   Southernmost Retreat: 1 Block from Duval in Old Town. 3BR/2BA – Sleeps 6 – Private Homes, Old Town #396516
  9
  View details
•   'La Casa Azul @ Solares Hill': Elegantly Renovated 3BR/3BA Home + Heated Pool... 3BR/3BA – Sleeps 6 – Other Key West Properties #390185ha
  6
  $5500 - $15000 per month 28 night min stay

  View details
•   'Natalie'S Bahama Conch' @ the Sanctuary': Lush 3BR/2.5BA Home, Pool... 3BR+/2.5BA – Sleeps 6-8 – Other Key West Properties #390203ha
  4
  $5000 - $9500 per month 28 night min stay

  View details
•   'Hidden Treasure @ Casa East': Luxurious 3BR 3BA Villa & Huge Pool Near Beach... 3BR/3BA – Sleeps 6 – Other Key West Properties #390210ha
  7
  $5500 - $14000 per month 28 night min stay

  View details
•   'Conch Casa Grande @ the Annex': Enormous 7BR/7BA in Truman Annex... 7BR/7BA – Sleeps 12 – Truman Annex #390171ha
  12
  $1000 - $1843 per night

  View details
•   Luxury Spacious Townhouse Overlooking Pool W/ Water View & 2 Bikes 1BR/1BA – Sleeps 4 – Other Key West Properties #3472045ha
  8
  $185 - $328 per night

  View details
•   'Sunset Point @ Sunset Marina': Immaculate 3BR/2BA Waterfront Condo... 3BR/2BA – Sleeps 6-8 – Sunset Marina #293269
  0
  $4000 - $7700 per month 28 night min stay

  View details
•   'Flamingo Dreams @ Solares Hill': Pristine 3BR/2BA Conch Home in Old Town... 3BR/2BA – Sleeps 6 – Other Key West Properties #390211ha
  3
  $5500 - $14000 per month 28 night min stay

  View details
•   Galleon Resort Efficiency Historic District 1BR/1BA – Sleeps 2 – Galleon #378522
  1
  $219 - $299 per night 2-4 night min stay

  View details
•   'Noona'S Mansion-by-the-Sea @ the Annex' Sumptuous 7BR/5.5BA Home with Pool... 7BR/5.5BA – Sleeps 14 – Other Key West Properties #390202ha
  25
  $1300 - $2129 per night

  View details
•   Craig & Cindy's Truman Annex Key West Property 2BR+/2.5BA – Sleeps 4-6 – Truman Annex #108809
  2
  $1400- $2400/wk

  View details
•   'Cool Breeze @ the Annex': Meticulously Furnished 2BR/2.5BA Old Town Villa... 2BR+/2.5BA – Sleeps 6 – Truman Annex #390190ha
  6
  $1950 - $3200 per week 7 night min stay

  View details
•   Waterfront Luxury in Old Town Key West 1BR+/1BA – Sleeps 2-5 – Galleon #232060
  7
  $286 - $460 per night

  View details
•   Craig & Cindy's Key West Coral Hammock Rentals 3BR+/3BA – Sleeps 6-8 – Key West Golf Club #47580
  4
  $975- $1800/wk

  View details
•   Ocean Retreat 3BR/2.5BA – Sleeps 5 – Truman Annex #280619
  3
  $2900 - $4900 per week 7 night min stay

  View details
•   'Eden @ the Annex': 2BR/1.5BA Old Town Villa Near Beach & Sunset Pier... 2BR+/1.5BA – Sleeps 4-6 – Truman Annex #390205ha
  5
  $1650 - $2500 per week 7 night min stay

  View details
•   Tropical Key West Oasis Private Home 2BR/2 Bath W/ Pool, Weekly Rental 2BR+/2BA – Sleeps 4-6 – Private Homes, Old Town #420695
  21
  From $400/per night, From $2,800/per wk

  View details
•   'Southernmost Comfort @ Casa East': Stunning 4BR/4.5BA Home W/ Cottage & Pool... 4BR/4.5BA – Sleeps 8 – Other Key West Properties #990995ha
  11
  $300 - $567 per night

  View details
•   Stunning Brand New Sleepafloat Houseboat in Paradise! 4BR/2BA – Sleeps 8 – Other Key West Properties #939677ha
  9
  $275 - $400 per night 2 night min stay

  View details
•   Bahama House - Tropical Retreat W/ Private Heated Pool/Hot Tub 3BR+/3.5BA – Sleeps 6-8 – Private Homes, DownTown #220940
  0
  $180 to $310 per room per night (3 rooms

  View details
•   Salida Del Sol - Waterfront Key West Resort Style Home W/Pool & Beach 2BR/2BA – Sleeps 6 – Private Homes, Unspecified #3498085ha
  3
  $520 - $525 per night 3 night min stay

  View details
•   'Casa Feliz @ the Seaport': Lushly Furnished 3BR/3.5BA Private Home + Pool... 3BR+/3BA – Sleeps 6-8 – Other Key West Properties #390195ha
  5
  $6600 - $15000 per month 28 night min stay

  View details
•   'Casa Plumeria @ Old Town South': 4BR/3.5BA Home & Guest Cottage + Pool... 4BR+/3.5BA – Sleeps 10 – Other Key West Properties #390189ha
  4
  $6000 - $14000 per month 28 night min stay

  View details
•   'Bella Petronia @ the Meadows: 3BR/3.5BA Private Home with Pool & Jacuzzi... 3BR+/3.5BA – Sleeps 6 – Other Key West Properties #390197ha
  6
  $5000 - $14000 per month 28 night min stay

  View details
•   Classic Conch-Steps from Hemingways and Lighthouse 3BR/4BA – Sleeps 6-10 – Private Homes, Old Town #454169
  0
  $500 - $850 per night 3 night min stay

  View details
•   'Heavenly Zen @ the Seaport': Lavish 4BR/3BA Old Town Home + Pool.... 4BR/3BA – Sleeps 8 – Other Key West Properties #390201ha
  5
  $367 - $633 per night

  View details
•   'Azure Afternoon @ Oceanside Marina': 3BR/2BA Oceanfront Condo + Pool & Spa... 3BR/2BA – Sleeps 6 – Other Key West Properties #390173ha
  3
  $1850 - $2950 per week 7 night min stay

  View details
•   'Tropical Jewel @ the Seaport': 2BR/2BA Lovely Old Town Cottage + Pool... 3BR+/2BA – Sleeps 7 – Other Key West Properties #390191ha
  1
  $5500 - $11000 per month 28 night min stay

  View details
•   'Portside Mansion @ the Seaport': Lush 6BR/7BA 3-Building Home + Large Pool..... 6BR/6.5BA – Sleeps 12 – Other Key West Properties #390194ha
  7
  $667 - $1267 per night

  View details
•   'Sunset Dreams @ Florida Bay': Luxury 3BR/2BA Waterfront Condo by Marina... 3BR+/2BA – Sleeps 6-8 – Other Key West Properties #390180ha
  2
  $4000 - $7700 per month 28 night min stay

  View details
•   'Top O' the Town @ the Historic Seaport': 3BR/3.5BA Five Star Luxury Condo... 3BR/3.5BA – Sleeps 6-8 – Other Key West Properties #390196ha
  1
  $5500 - $14000 per month 28 night min stay

  View details
•   Dreaming on Duval 5BR/4BA – Sleeps 10-11 – Private Homes, DownTown #286622
  4
  From $900/nt - $2100./nt.

  View details
•   Hidden Beach - the Perfect Place to Stay in Key West 1BR/1.5BA – Sleeps 2 – Other Key West Properties #266139
  7
  265- 420 dollars/night

  View details
•   Tiki Beach Too, Charming Townhome, Old Town, Pool Access, Great Porch! 2BR/1BA – Sleeps 4-6 – Truman Annex #3539485ha
  0
  $1195 - $1895 per week 7 night min stay

  View details
•   Duval St. Luxury Penthouse (Private Pool, Parking, Roof Deck) 3BR+/2.5BA – Sleeps 8 – Private Homes, DownTown #217650
  1
  $180 to $310 per room per night

  View details
•   High End Luxury House on Old Town Lane, Pool--Free Wireless Monthly Rentals Only 2BR/2BA – Sleeps 4 – Private Homes, Old Town #123424
  2
  View details
•   Steps from Duval - Sleeps 2-4 1BR+/1BA – Sleeps 2-4 – Private Homes, Old Town #389224
  2
  $198 - $388 per night 3-6 night min stay

  View details
•   Luxurious Garden Home Paradise with Pool in Midtown Key West 2BR+/1BA – Sleeps 6 – Private Homes, Mid Town #355596
  4
  View details
•   Upscale Vacation Rentals in Old Town Key West 1BR+/1BA – Sleeps 0-4 – Villas Key West #261612
  0
  $215- $325/nt

  View details
•   Historic Compound in Old Key West 3BR+/2BA – Sleeps 6-10 – Private Homes, Old Town #263076
  0
  Seasonal $375- $525

  View details
•   2013 Special Pricing Hemingway Style Cottage/Tropical Pool 3BR/2BA – Sleeps 2-8 – Private Homes, Old Town #306020
  13
  $5500- $9000/mo

  View details
•   'a Pearl on Petronia'- a Stunningly Renovated Conch Cottage 2BR/2.5BA – Sleeps 4 – Private Homes, Old Town #371937
  0
  $6000- $10,000

  View details
•   Luxurious 'Old Town' Home - 3BR/3.5BA 3BR/3.5BA – Sleeps 6 – Private Homes, Old Town #432637
  3
  $495 - $795 per night 3-6 night min stay

  View details
•   The Golden Heron 5BR+/4BA – Sleeps 10-12 – Private Homes, Old Town #180397
  1
  $4,000- $14,000/mo

  View details
•   'Octopus'S Garden @ Coral Hammock': 3BR/3BA Spacious Home W Pool & Gym 3BR+/3BA – Sleeps 6-8 – Other Key West Properties #3482727ha
  2
  $1850 - $2750 per week 7 night min stay

  View details
•   Close to Duval Street, But Quiet and Secluded 2BR+/2BA – Sleeps 4-6 – Villas Key West #258224
  0
  $275- $525/nt

  View details
•   Luxury on Garrison Bight: 3 BR/3.5 BA Waterfront Home Sleeps 8 3BR/3.5BA – Sleeps 8 – Other Key West Properties #3475121ha
  1
  $495 - $795 per night 3-6 night min stay

  View details
•   'Promenade to Paradise @ the Annex': Spacious 2BR/2BA Waterfront Condo... 2BR+/2BA – Sleeps 4-6 – Other Key West Properties #3554697ha
  0
  $2100 - $3800 per week 7 night min stay

  View details
•   Sleeps 6 on Duval!! 2BR+/1.5BA – Sleeps 4-6 – Private Homes, Old Town #413282
  0
  $238 - $525 per night 3-6 night min stay

  View details
•   Chick-a-Pea's Cottage:Near Duval-Yet Private with the Comforts of Home 3BR/2.5BA – Sleeps 6 – Private Homes, Old Town #449947
  5
  See Seasonal Rates

  View details
•   Old Town Key West Condo - Monthly Rentals Only 2BR/2.5BA – Sleeps 6 – Private Homes, Old Town #400281
  2
  $3000- $5000/mo

  View details
•   'Casa Oliviana @ Solares Hill': Stunning Restored 6BR/6BA Old Town Home & Pool.. 6BR/6BA – Sleeps 14 – Other Key West Properties #996857ha
  2
  $500 - $867 per night

  View details
•   Casa Marina Oasis 2BR+/2BA – Sleeps 4-6 – Other Key West Properties #3501277ha
  0
  $133 - $233 per night

  View details
•   The Ultimate Place to Stay in Key West. 4BR/5.5BA – Sleeps 8 – Other Key West Properties #262527
  2
  $8,750- $10,000/wk

  View details
•   Idyllic Courtyard and Location 1BR+/1BA – Sleeps 4 – Private Homes, Old Town #391927
  0
  $178 - $348 per night 3-6 night min stay

  View details
•   Enchanted Garden Compound in Best Old Town Location 4BR/3.5BA – Sleeps 8 – Private Homes, DownTown #261246
  0
  $15,000 to $25,000/month

  View details
•   Craig & Cindy Key West Beachside Resort Condo 2BR+/2.5BA – Sleeps 2-6 – BeachSide #261487
  2
  $1200- $2350/wk

  View details
•   'Caribbean Fling @ Southard': Delightful 2BR/1.5BA Island Cottage + Private Pool 2BR+/1.5BA – Sleeps 4-6 – Other Key West Properties #3556074ha
  1
  $4000 - $7000 per month 28 night min stay

  View details