This property allows you to book online with a credit card. After submitting a reservation request, the owner or manager has 24 hours to accept, at which time your card will be charged and you will receive an email confirmation
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Private Homes, Old Town Vacation Rentals Show this location only Back to top
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Private & Peaceful Cottage Feel-with 7 Night Stay 1 Night Free
1BR/1BA
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Sleeps 2-4
– Private Homes, Old Town #114836
From125 nt to 215 a nt for lodging
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Carpe Diem- a Tropical Conch Cottage in Old Town Key West -
2BR/2BA
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Sleeps 6
– Private Homes, Old Town #287462
$3300 - $6000 per month 30 night min stay
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Key West Cottage Charmer
2BR+/2BA
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Sleeps 2-5
– Private Homes, Old Town #321956
$1700 - $7200
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Charming 100+-Year-Old Conch Cottage in the Heart of Old Town
1BR/1BA
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Sleeps 1-2
– Private Homes, Old Town #37855
$1800- $3500/mo
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Private Home in Old Town, Key West Hideaway
2BR+/2BA
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Sleeps 4-6
– Private Homes, Old Town #281185
$300
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Fantasy Resort Villa - One-of-a-Kind Courtyard Villa
3BR+/3BA
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Sleeps 6-8
– Private Homes, Old Town #333274
From $3800. to $4300./wk
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Margaux's Hideaway - Two Story Luxury Home with Private Pool
3BR/3BA
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Sleeps 6
– Private Homes, Old Town #386583
$5300- $8200/mth
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Charming Bahamian Cottage 3bed/ 2.5 Pool, Easy Walk to Town
3BR/2.5BA
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Sleeps 5
– Private Homes, Old Town #390616
From $1600 - $7000.00
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Perfect Cottage with Private Pool and Garden-2bed/2bath
2BR+/2BA
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Sleeps 6-8
– Private Homes, Old Town #323986
$3500- $6500/mo +12.5% tax
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Private Historical Conch House with Pool 3 BR/2 BA, Old Town
3BR/2BA
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Sleeps 6
– Private Homes, Old Town #290390
$4000- $7500/mo
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Old Town Key West - Banyan Resort up to 4 Wks in a 1 BR Apt.
1BR+/1BA
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Sleeps 4
– Private Homes, Old Town #379877
$1200/wk - $2000/wk
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Architect's Personal Residence, Private Pool, 1 Blk. to Duval
2BR+/2.5BA
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Sleeps 4-6
– Private Homes, Old Town #105102
$368- $468/nt
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Charming Home with Great Old Town Flair!
3BR+/2BA
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Sleeps 6-8
– Private Homes, Old Town #35288
$4000 - $7000/mo
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Casa De Suenos (House of Dreams) Monthly Rental
1BR/1BA
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Sleeps 4
– Private Homes, Old Town #147469ha
$83 - $150 per night
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Isla Bella-Serene and "Green" Just Blocks from Duval Street
2BR+/2BA
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Sleeps 4-6
– Private Homes, Old Town #287243
$348- $428/nt
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Tropical Cottage on a Quiet Lane Available Summer
2BR/1.5BA
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Sleeps 2-4
– Private Homes, Old Town #434593
$3000 per month 30 night min stay
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Seaside Place 5 Bedroom 4 Bath Vacation House Old Town
5BR+/4BA
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Sleeps 12
– Private Homes, Old Town #364907
From $700/Night
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Elegant Key West Getaway
4BR/4.5BA
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Sleeps 7
– Private Homes, Old Town #276136
$4250- $9,000/mo
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Private Oriental Tropical Hideaway
1BR+/1BA
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Sleeps 2-4
– Private Homes, Old Town #382095
$110 - $185 per night 2-7 night min stay
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Beautiful Centrally Located Cottage-Condo - Monthly Rental
1BR+/1BA
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Sleeps 2
– Private Homes, Old Town #339927
From $2750/mo.
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2 BR House in Old Town Key West - Quiet
2BR+/1BA
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Sleeps 4
– Private Homes, Old Town #110480
$4000/mo Dollars
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Catherine House
2BR/2BA
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Sleeps 4
– Private Homes, Old Town #366746
From $290- $460/nt
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Relaxing, Quiet, Get-Away Close to Duval Street and the Beach
3BR+/2.5BA
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Sleeps 6-8
– Private Homes, Old Town #294667
From $2700/wk - $4000/mo
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"Concha Cabana" - Cutest Home North of Havana!
1BR/1BA
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Sleeps 2
– Private Homes, Old Town #395871
From $2,200 to $3,950/mo.
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Summertime Special 10% Off June-September!
3BR/2.5BA
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Sleeps 6
– Private Homes, Old Town #440374
$9800 per month 28 night min stay
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Southernmost City Historic Vacation Home II
2BR/2.5BA
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Sleeps 4-6
– Private Homes, Old Town #449895
from $3000/month
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The 'Shark Tank' 5 BR, 5 BA Luxury Weekly Only Beach Home in Old Town
5BR/5BA
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Sleeps 10-12
– Private Homes, Old Town #444503
$9000 per week 7 night min stay
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Old Town Conch Cottage Close to All the Action!
2BR/1BA
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Sleeps 4
– Private Homes, Old Town #435844
$4980 per month 30 night min stay
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Ellen's Retreat - Tropical Living, 28 Days Minimum Stay.
3BR/2BA
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Sleeps 2-6
– Private Homes, Old Town #422831
$5488 - $9520 per month 28 night min stay
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Tropical Paradise Surrounds 2BR 2BA Old Town Cottage
2BR/2BA
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Sleeps 4
– Private Homes, Old Town #308865
$2200- $5000/mo
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Great Taste - Great Location - Newly Restored 2 Bedroom - Pool
2BR/2BA
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Sleeps 4
– Private Homes, Old Town #252753
$4000- $6000/mo
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Garden Studio in Historic Old Town
Studio/1BA
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Sleeps 2
– Private Homes, Old Town #330201
$2500- $4000/mo
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Downtown Historic District
2BR/2BA
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Sleeps 4-6
– Private Homes, Old Town #466457
$200 - $300 per night 2 night min stay
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Turtle House: Paradise Retreat in Charming Old Town Key West
2BR+/2BA
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Sleeps 4
– Private Homes, Old Town #384490
From $4500.00 to $6000.00/mo
- 616 Caroline #6 1BR/1BA – Sleeps 1-2 – Private Homes, Old Town #914435ha
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Caribbean Soul - Clean, Spacious & Centrally Located
3BR/3BA
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Sleeps 6
– Private Homes, Old Town #395078ha
$150 - $300 per night
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Enjoy Historic Bahama Village
2BR/2BA
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Sleeps 4
– Private Homes, Old Town #368346ha
$117 - $150 per night
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Casa Verde ~ Darling Cigar Cottage in Old Town Key West!
4BR/2.5BA
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Sleeps 6
– Private Homes, Old Town #3005607ha
$5600 per month 28 night min stay
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Private & Peaceful Cottage Feel-with 7 Night Stay 1 Night Free
1BR/1BA
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Sleeps 2-4
– Private Homes, Old Town #114836
Overview of Private Homes, Old Town Vacation Rentals
Experience Tropical Living at Old Town Key West Vacation Rentals
Key West is the most southern city in the continental United States and offers fabulous sunny skies; year-round temperate weather; salty sea breezes; blue-green, crystal-clear waters; and pure white sand shores. Why wouldn't you want to visit? The tropical landscaping and Victorian charm of Old Town Key West resort rentals is waiting, so hop on a boat, in a car, or on a plane and experience the beauty, relaxation, and nightlife that makes Key West travel so popular.
Old Town Key West Vacation Rentals Feature American History in a Beautiful Setting
Visit Fort Zachary Taylor Park, or Fort Zach, to see the biggest collection of Civil War cannons ever found at one place. Tour the fort and learn the history of this structure that was built in the 1800s to help defend the Southern US Coastline and was then named a historic landmark in the 1970s. This park close to most Old Town Key West vacation rentals also has a raved-about beach complete with a refreshment stand.
Old Town Key West Resort Rentals Offer Fun for All Ages
Head to the soft sandy shores and warm water surrounding Old Town Key West vacation rentals for fantastic swimming, snorkeling, fishing, kite flying, Frisbee tossing, sand-castle building, or just plain relaxing. Check out the mangrove fields, or the old Gato Cigar Factory, which now houses county offices. At nearby Duvall Street, follow in Hemingway's footsteps and eat at Sloppy Joe's Bar, or check out the oldest bar for blues in the US, The Green Parrot. There are also themed restaurants like Jimmy Buffet's Margaritaville and Hard Rock Café, which are good places for families. The Historic Seaport is worth a stroll for adults and kids alike, and a nightly sunset gathering takes place in Mallory Square to celebrate the oranges and pinks spanning the sky above Old Town Key West vacation rentals.