Vacation Rentals by Owner

Key West Vacation Rentals Show this location only Back to top

•   Ocean Perch , Dock 80'Heated Pool Deep Channel Tennis 15 Min Key West 2BR+/2BA – Sleeps 4-6 – Private Homes, Unspecified #49850
  45
  $1400 - $1550 per week 7 night min stay

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

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•   Ocean Breeze Suites-3 Bd, 3 Bath with Loft Sleeps 10 3BR/3BA – Sleeps 10 – Galleon #222110
  12
  $5950 per week 2 night min stay

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

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•   Oceanfront Condominium - Key West Oceanfront at the Coral Reef 2BR/2BA – Sleeps 6 – 1800 Atlantic #107925
  34
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•   'Casa Louisa @ Upper Duval': Historic Conch Cottage & Pool 1/2 Block Off Duval.. 3BR+/2BA – Sleeps 6-8 – Other Key West Properties #135603ha
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•   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

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

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•   Private Luxury in Prestigious Casa Marina Neighborhood 3BR/3.5BA – Sleeps 6-7 – Casa Marina #307081
  14
  $233 per night

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

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•   '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
  $5750 per month 28 night min stay

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

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

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•   Bargain Rates in Truman Annex - Heart of Old Town, Key West 2BR/1BA – Sleeps 4-6 – Truman Annex #68720
  5
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•   Charming, Romantic, Funky, Cozy, Unique, Beautiful, Island Charm, Beach, Ocean 1BR/1BA – Sleeps 2 – Other Key West Properties #972748ha
  8
  $1253 per week 2-3 night min stay

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

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

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

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•   Ocean Suite at the Galleon Resort 2BR/2BA – Sleeps 8 – Galleon #378516
  4
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•   'Gulfside Vistas @ Truman Annex': Lavish Oceanfront 2BR/2.5BA Penthouse Condo... 2BR/2.5BA – Sleeps 4-5 – Other Key West Properties #904145ha
  19
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•   Carey's Conch Cottage Old Town, Key West, Private Heated Pool 1BR+/1.5BA – Sleeps 2-4 – Private Homes, Old Town #247863
  11
  $4500 per month 30 night min stay

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

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•   Key West 'Coral Hammock' - Poolside 3BR/3BA – Sleeps 6 – Key West Golf Club #105427
  6
  $1505 per week 5 night min stay

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•   Ocean Paradise 3BR+/4BA – Sleeps 8 – Truman Annex #216159
  6
  $5900 per week 7 night min stay

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•   'Puerta Coralina @ Solares Hill': Charming 2BR/3BA Cottage, 2 Master Suites... 2BR+/3BA – Sleeps 4-6 – Other Key West Properties #904144ha
  21
  $3600 per week 4 night min stay

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

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

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

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

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•   '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
  $2129 per night

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

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•   Southernmost Retreat: 1 Block from Duval in Old Town. 3BR/2BA – Sleeps 6 – Private Homes, Old Town #396516
  9
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•   Stunning Brand New Sleepafloat Houseboat in Paradise! 4BR/2BA – Sleeps 8 – Other Key West Properties #939677ha
  9
  $350 - $400 per night 2 night min stay

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•   Galleon Resort Efficiency Historic District 1BR/1BA – Sleeps 2 – Galleon #378522
  1
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•   Ocean Retreat 3BR/2.5BA – Sleeps 5 – Truman Annex #280619
  3
  $3900 per week 7 night min stay

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•   'Paradise @ Garrison Bight': Large 5BR/4BA Waterfront Home + Private Dock... 5BR+/4BA – Sleeps 14 – Other Key West Properties #390212ha
  25
  $1257 - $1700 per night

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•   'Cool Breeze @ the Annex': Meticulously Furnished 2BR/2.5BA Old Town Villa... 2BR+/2.5BA – Sleeps 6 – Other Key West Properties #390190ha
  5
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•   'Eden @ the Annex': 2BR/1.5BA Old Town Villa Near Beach & Sunset Pier... 2BR+/1.5BA – Sleeps 4-6 – Other Key West Properties #390205ha
  5
  $2500 per week 7 night min stay

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•   Luxury Spacious Townhouse Overlooking Pool W/ Water View & 2 Bikes 1BR/1BA – Sleeps 4 – Other Key West Properties #3472045ha
  8
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•   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

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

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

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

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

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

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

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•   Classic Conch-Steps from Hemingways and Lighthouse 3BR/4BA – Sleeps 6-10 – Private Homes, Old Town #454169
  0
  $5950 per week 3 night min stay

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•   'Portside Mansion @ the Seaport': Lush 6BR/7BA 3-Building Home + Large Pool..... 6BR/6.5BA – Sleeps 12 – Other Key West Properties #390194ha
  7
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•   'Sunset Dreams @ Florida Bay': Luxury 3BR/2BA Waterfront Condo by Marina... 3BR+/2BA – Sleeps 6-8 – Other Key West Properties #390180ha
  2
  $7700 per month 28 night min stay

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•   Steps from Duval - Sleeps 2-4 1BR+/1BA – Sleeps 2-4 – Private Homes, Old Town #389224
  2
  $278 per night 4 night min stay

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•   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

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•   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

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•   High End Luxury House on Old Town Lane, Pool--Free Wireless Monthly Rentals Only 2BR/2BA – Sleeps 4 – Private Homes, Old Town #123424
  2
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•   'Casa Feliz @ the Seaport': Lushly Furnished 3BR/3.5BA Private Home + Pool... 3BR+/3BA – Sleeps 6-8 – Other Key West Properties #390195ha
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•   'La Casa Azul @ Solares Hill': Elegantly Renovated 3BR/3BA Home + Heated Pool... 3BR/3BA – Sleeps 6 – Other Key West Properties #390185ha
  6
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•   2013 Special Pricing Hemingway Style Cottage/Tropical Pool 3BR/2BA – Sleeps 2-8 – Private Homes, Old Town #306020
  13
  $5500- $9000/mo

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•   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

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•   Luxurious 'Old Town' Home - 3BR/3.5BA 3BR/3.5BA – Sleeps 6 – Private Homes, Old Town #432637
  3
  $695 per night 4 night min stay

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•   Luxury on Garrison Bight: 3 BR/3.5 BA Waterfront Home Sleeps 8 3BR/3.5BA – Sleeps 8 – Other Key West Properties #3475121ha
  1
  $695 per night 4 night min stay

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

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•   Sleeps 6 on Duval!! 2BR+/1.5BA – Sleeps 4-6 – Private Homes, Old Town #413282
  0
  $358 per night 4 night min stay

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•   Idyllic Courtyard and Location 1BR+/1BA – Sleeps 4 – Private Homes, Old Town #391927
  0
  $248 per night 4 night min stay

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•   'Octopus'S Garden @ Coral Hammock': 3BR/3BA Spacious Home W Pool & Gym 3BR+/3BA – Sleeps 6-8 – Other Key West Properties #3482727ha
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•   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

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

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•   Casa Marina Oasis 2BR+/2BA – Sleeps 4-6 – Other Key West Properties #3501277ha
  0
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•   'Caribbean Fling @ Southard': Delightful 2BR/1.5BA Island Cottage + Private Pool 2BR+/1.5BA – Sleeps 4-6 – Other Key West Properties #3556074ha
  1
  $7000 per month 28 night min stay

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•   On Duval Street! Sleeps 12 4BR/0BA – Sleeps 8-12 – Duval Square #458280
  0
  $700 per night 4 night min stay

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

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

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•   Condo in Historic 1928 Conch House, Walking Distance to Duval 1BR/2BA – Sleeps 2-4 – Private Homes, Old Town #460746
  2
  $2589 per month 30 night min stay

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•   3bdrm/2bath with Pool 3BR/2BA – Sleeps 6 – Private Homes, Old Town #439570
  0
  Per Month $6500- $10000

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•   This House is Sooo Perfect in Key West 2BR/2BA – Sleeps 4-5 – Private Homes, DownTown #443056
  0
  4500- 6500 pcm

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•   Estate Home on the Water with Private Pool and Dockage 4BR/4.5BA – Sleeps 8 – Key Haven #380616
  1
  5,250

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•   Stunning Interiors and Glorious Views at La Brisa 2BR/0BA – Sleeps 4 – La Brisa #443962
  0
  $4500- $6000/mo

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•   'Casa, Suite Casa @ Casa Marina': Lavish New Home W/ 4 Suites + Pool... 4BR/5BA – Sleeps 8-10 – Other Key West Properties #3485544ha
  2
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•   Sea Glass - Exquisite Key West Home and Cottage 4BR/4BA – Sleeps 8 – Private Homes, Old Town #476425
  0
  $6000 per month 28 night min stay

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•   'Paradise Perfected @ Smathers Beach': Handsome Beach House + Pool... 3BR/2BA – Sleeps 6-8 – Other Key West Properties #3545074ha
  0
  $14000 per month 28 night min stay

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•   Charming Gated Community Just Off Duval 1BR/2BA – Sleeps 2 – Private Homes, DownTown #391946
  0
  $4000- $6000 p/m

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

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•   Sea Biscuit - Beautiful Home - Private Pool, Steps to Duval 3BR/3BA – Sleeps 6 – Private Homes, Old Town #381900
  2
  weekly $2750 to $3300

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•   Luxury Townhouse Key West Gated Community. Easy Walk to Downtown 2BR/2.5BA – Sleeps 6 – Truman Annex #453182
  0
  $1750/wk - $8250/mo

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•   10% Summer Discount - Available Now 2BR+/0BA – Sleeps 6 – Private Homes, Old Town #473461
  0
  $9480 per month 30 night min stay

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•   516 Louisa Street 2BR/1.5BA – Sleeps 2-4 – Other Key West Properties #3483364ha
  0
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•   Ocean Out Your Windows!? Intown Key West? Yes! Studio Studio/1BA – Sleeps 2 – Casa Marina #41312
  20
  $1886 per week 5 night min stay

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•   Key West Lazy Lane Vacation Rental Accommodations & Cottages 1BR+/1BA – Sleeps 2-6 – Private Homes, Old Town #6429
  22
  $85-$400/nt - $800- $1800/wk

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•   Direct Oceanfront 50% Off May Free High Speed Wifi & Hbo 3BR/2.5BA – Sleeps 6 – 1800 Atlantic #35327
  22
  $375/nt (low)- $550/nt (high)

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•   Key West Jasmine House - Tropical Inn with Private Spa 4BR/4BA – Sleeps 8 – Private Homes, Old Town #27325
  26
  $85-$840/nt - $800- $3900/wk

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•   Casa De Cuba a Beach House - Cuban Flair Steps from Duval 3BR/2BA – Sleeps 6 – Private Homes, Old Town #98473
  6
  $510-$680/nt - $3360-$4520/wk

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•   Luxury and Spacious Condo on Duval Steet 2BR+/2BA – Sleeps 4-6 – Key West Cuban Club #178773
  28
  Starting at $295.00/nt 2 - 6 guests

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•   'Avalynn House @ the Annex': Elegant 5BR/3.5BA Home & Lagoon Pool... 5BR+/3.5BA – Sleeps 10-12 – Private Homes, Unspecified #168095
  8
  $8000-11,500/wk, $30,000-$40,000/mo

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•   "The Real Deal" Key West, Only 1 Block Off Duval on Southard 1BR/1BA – Sleeps 1-4 – Private Homes, Old Town #117148
  80
  From $215/nt or $1,393-$1,799/wk

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•   Location, Location, Location! Ocean View, Lagoon Beach Front 3BR/2BA – Sleeps 10 – Key West Harbour Yacht Club #342886
  14
  $360 per night 3 night min stay

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•   The Mermaids House - Old Town, Historic Bahama Conch House 2BR/1.5BA – Sleeps 4 – Private Homes, Old Town #129511
  26
  $2000 per week 3 night min stay

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•   Casa Amor - 3BR Residence 2 Blocks from Duval Street 3BR+/2.5BA – Sleeps 6-8 – Private Homes, Old Town #177596
  13
  $8,500- 11,000.00

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•   Luxury Yacht - Lagoon 440 Sailing Catamaran 3BR+/3BA – Sleeps 6-8 – Key West Harbour Yacht Club #290130
  9
  $295 per night 2 night min stay

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•   Tropical Island Get-Away, Garden Level Condo in Truman Annex 2BR+/1BA – Sleeps 4 – Truman Annex #55381
  8
  $1050-$1900/wk - $2800/mo

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•   Luxurious Truman Annex 4 BR/3 Full BA (Private Pool) 4BR/3BA – Sleeps 8 – Truman Annex #219779
  24
  $2900- $4900/wk

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•   Henry's Piece of Paradise on the Ocean in Key West - Weekly 2BR/2BA – Sleeps 2-5 – 1800 Atlantic #20873
  13
  $245-$405/nt - $1544-$2552/wk

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•   Beautiful Truman Annex End Unit Townhouse with Side Courtyard 2BR+/2.5BA – Sleeps 4-6 – Truman Annex #140996
  12
  $1800- $2100/wk

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