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Private Homes, Old Town Vacation Rentals Show this location only Back to top
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Steps from Duval! Luxurious, Sleeps 2-4, Old Town
1BR+/1BA
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Sleeps 2-4
– Private Homes, Old Town #365419
FROM $208/NIGHT
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Steps from Duval $79-$129 Night - Free Bikes Included!!!
Studio/1BA
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Sleeps 2
– Private Homes, Old Town #140317
$79- $129/nt
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Carey's Conch Cottage Old Town, Key West, Private Heated Pool
1BR+/1.5BA
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Sleeps 2-4
– Private Homes, Old Town #247863
$4500 - $6500 per month 30 night min stay
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"Coconut Cabana" Old Town Tropical Bungalow
3BR/2BA
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Sleeps 4-6
– Private Homes, Old Town #72848
$430-$580./nt - $2800-$5110./wk
- Southernmost Retreat: 1 Block from Duval in Old Town. 3BR/2BA – Sleeps 6 – Private Homes, Old Town #396516
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Tropical Key West Oasis Private Home 2BR/2 Bath W/ Pool, Weekly Rental
2BR+/2BA
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Sleeps 4-6
– Private Homes, Old Town #420695
From $400/per night, From $2,800/per wk
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Classic Conch-Steps from Hemingways and Lighthouse
3BR/4BA
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Sleeps 6-10
– Private Homes, Old Town #454169
$500 - $850 per night 3 night min stay
- High End Luxury House on Old Town Lane, Pool--Free Wireless Monthly Rentals Only 2BR/2BA – Sleeps 4 – Private Homes, Old Town #123424
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2013 Special Pricing Hemingway Style Cottage/Tropical Pool
3BR/2BA
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Sleeps 2-8
– Private Homes, Old Town #306020
$5500- $9000/mo
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Historic Compound in Old Key West
3BR+/2BA
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Sleeps 6-10
– Private Homes, Old Town #263076
Seasonal $375- $525
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Steps from Duval - Sleeps 2-4
1BR+/1BA
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Sleeps 2-4
– Private Homes, Old Town #389224
$198 - $388 per night 3-6 night min stay
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Chick-a-Pea's Cottage:Near Duval-Yet Private with the Comforts of Home
3BR/2.5BA
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Sleeps 6
– Private Homes, Old Town #449947
See Seasonal Rates
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Luxurious 'Old Town' Home - 3BR/3.5BA
3BR/3.5BA
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Sleeps 6
– Private Homes, Old Town #432637
$495 - $795 per night 3-6 night min stay
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'a Pearl on Petronia'- a Stunningly Renovated Conch Cottage
2BR/2.5BA
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Sleeps 4
– Private Homes, Old Town #371937
$6000- $10,000
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The Golden Heron
5BR+/4BA
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Sleeps 10-12
– Private Homes, Old Town #180397
$4,000- $14,000/mo
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Sleeps 6 on Duval!!
2BR+/1.5BA
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Sleeps 4-6
– Private Homes, Old Town #413282
$238 - $525 per night 3-6 night min stay
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Old Town Key West Condo - Monthly Rentals Only
2BR/2.5BA
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Sleeps 6
– Private Homes, Old Town #400281
$3000- $5000/mo
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Idyllic Courtyard and Location
1BR+/1BA
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Sleeps 4
– Private Homes, Old Town #391927
$178 - $348 per night 3-6 night min stay
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Condo in Historic 1928 Conch House, Walking Distance to Duval
1BR/2BA
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Sleeps 2-4
– Private Homes, Old Town #460746
$2500 - $3500 per month 30 night min stay
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3bdrm/2bath with Pool
3BR/2BA
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Sleeps 6
– Private Homes, Old Town #439570
Per Month $6500- $10000
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Sea Biscuit - Beautiful Home - Private Pool, Steps to Duval
3BR/3BA
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Sleeps 6
– Private Homes, Old Town #381900
weekly $2750 to $3300
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Petronia Palms, Just Off Duval St. Sleeps 6 Has a Large Pool! Hot-Tub
Studio/0BA
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Sleeps 6
– Private Homes, Old Town #442437
$1750 - $2250 per week 7-28 night min stay
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South Street Serenity - Summer Special 10% Off May-September!
3BR+/2.5BA
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Sleeps 8
– Private Homes, Old Town #411277
$5500- $9500
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Home 1/2 Block from Duval Street
1BR+/1BA
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Sleeps 4
– Private Homes, Old Town #439833
$389 - $429 per night 3-4 night min stay
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Beautiful House in the Best Location in Key West!
Studio/0BA
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Sleeps 6-8
– Private Homes, Old Town #448222
$4900 - $9520 per month 28 night min stay
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Secret Villa - a Key West Hidden Gem
3BR+/3BA
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Sleeps 6-8
– Private Homes, Old Town #425095
$4200- $5530 US
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Summertime Special 10% Off June-September!
4BR/4.5BA
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Sleeps 8
– Private Homes, Old Town #426633
$8000- $17000
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'Casa Amorita' - Affordable Luxury in the Heart of Old Town
1BR/1BA
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Sleeps 3
– Private Homes, Old Town #443385
$2,400 - $4,400 monthly
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10% Summer Discount - Available Now
2BR+/0BA
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Sleeps 6
– Private Homes, Old Town #473461
$6000 - $9510 per month 30 night min stay
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Old Town Cottages
3BR/0BA
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Sleeps 6-8
– Private Homes, Old Town #453776
seasonal $695- $1050.
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Secluded, Private, Tropical Retreat in Old Town, Key West.
2BR/1BA
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Sleeps 4-6
– Private Homes, Old Town #453779
$325- $475 per night
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Key West Lazy Lane Vacation Rental Accommodations & Cottages
1BR+/1BA
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Sleeps 2-6
– Private Homes, Old Town #6429
$85-$400/nt - $800- $1800/wk
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Key West Jasmine House - Tropical Inn with Private Spa
4BR/4BA
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Sleeps 8
– Private Homes, Old Town #27325
$85-$840/nt - $800- $3900/wk
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"The Real Deal" Key West, Only 1 Block Off Duval on Southard
1BR/1BA
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Sleeps 1-4
– Private Homes, Old Town #117148
From $215/nt or $1,393-$1,799/wk
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The Mermaids House - Old Town, Historic Bahama Conch House
2BR/1.5BA
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Sleeps 4
– Private Homes, Old Town #129511
$225 - $300 per night 3 night min stay
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Casa Amor - 3BR Residence 2 Blocks from Duval Street
3BR+/2.5BA
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Sleeps 6-8
– Private Homes, Old Town #177596
$8,500- 11,000.00
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Casa De Cuba a Beach House - Cuban Flair Steps from Duval
3BR/2BA
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Sleeps 6
– Private Homes, Old Town #98473
$510-$680/nt - $3360-$4520/wk
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Harbor Inn Condominium
2BR+/2BA
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Sleeps 4
– Private Homes, Old Town #82650
$1450- $2050/wk
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Tropical Retreat in a Key West Conch Cottage
2BR/1BA
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Sleeps 4
– Private Homes, Old Town #360092
$3000- $4500/mo
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The Hollinsed House "Caribbean Suite" - Large 2 Bedroom
2BR+/1BA
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Sleeps 4
– Private Homes, Old Town #118424
From $249/nt/ $1495 wk (Summer)
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Bahama Gardens - Historic Key West Old Town, Near Duval /Beach
4BR+/1.5BA
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Sleeps 6-8
– Private Homes, Old Town #142507
$3,000. - $9,000.
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Villa Tropicale - Secluded Tropical Villa
4BR+/5BA
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Sleeps 8-9
– Private Homes, Old Town #125695
$710- 1228/nt
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A Royal Home with 4 Master Suites & an Attic Suite
4BR/4.75BA
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Sleeps 6-10
– Private Homes, Old Town #123121
$1250 per night 5 night min stay
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Ashe Splashe-Award Winning Historic Restoration
3BR+/3BA
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Sleeps 6
– Private Homes, Old Town #177438
$4500- $8500/mo
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Captain's Mansion - April Availability
3BR/3.5BA
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Sleeps 6
– Private Homes, Old Town #99427
$7000- $11,000/mo
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'Southard Comfort' @ Old Town: a Dazzling Key West Conch House
3BR/2.5BA
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Sleeps 6
– Private Homes, Old Town #122535
From $321/nt - $2250/wk - $6000/mo
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New Potter's Cottage -Private Pool, Quiet, Yet Steps Off Duval
2BR+/2BA
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Sleeps 5
– Private Homes, Old Town #340360
$314 - $400 per night
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XXX Special,(Quiet)House with Guest Cottage,Close to Duval St
3BR+/3.5BA
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Sleeps 6-8
– Private Homes, Old Town #103479
$5800- $10,200/mo
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Dos Casas-4 BR Compound in Beautiful Old Town Key West
4BR/2BA
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Sleeps 8
– Private Homes, Old Town #76082
$5500 - 9500/mo
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Southard House - Lovely Home in the Heart of Old Town
4BR+/4BA
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Sleeps 8
– Private Homes, Old Town #256054
$730- $1100/nt
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Petronia Palms, Just Off Duval St. Safe! and Has a Large Pool!
1BR+/1BA
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Sleeps 4
– Private Homes, Old Town #208439
$3100- $7500/mo
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Petronia Palms, Just Off Duval St.Safe! and Has a Large Pool!
1BR+/1BA
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Sleeps 4
– Private Homes, Old Town #219051
From $3000/mo
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Brass Palm Villa - Luxurious Tropical Private Home
3BR/2.5BA
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Sleeps 6
– Private Homes, Old Town #314995
$5500- $8200/mo
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Abaco Dreams 3BR/2BA Old Town Private Paradise Key West
3BR/2BA
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Sleeps 6
– Private Homes, Old Town #151361
From $550/nt - $3500/wk
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Hollinsed House - Stay in "Eve's Paradise"
2BR+/1.75BA
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Sleeps 6
– Private Homes, Old Town #144522
$4000- $5000/mo
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Beautiful Private Home in Old Town; Great Nightly/Weekly Rates
1BR+/1BA
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Sleeps 2-4
– Private Homes, Old Town #243086
From $258/nt
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'Southard Comfort' -- Famous Old Town Conch Cottage
2BR+/2BA
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Sleeps 6
– Private Homes, Old Town #243222
$4750- $8000/mo
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Family Reunion - 3 Homes and a Cottage in Pool Garden Compound
12BR+/10BA
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Sleeps 22-28
– Private Homes, Old Town #202539
From $7,950/wk - $11,450/wk
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Havana Hideaway, Downtown, Pool, Parking, 1 Block Off Duval
2BR+/2.5BA
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Sleeps 4-6
– Private Homes, Old Town #220196
$368- $408/nt
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Luxury Private Home, Center of Old Town, Designer Furnished
3BR+/3BA
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Sleeps 8
– Private Homes, Old Town #225232
$12,000- Month
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Key West Golf Course
3BR/2.5BA
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Sleeps 3-6
– Private Homes, Old Town #179222
$4500 per month 30 night min stay
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Petronia Palms for Budget Minded by Duval St Has a Large Pool!
Studio/1BA
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Sleeps 1-2
– Private Homes, Old Town #265376
$2500- $4000/mo
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Petronia Palms, Just Off Duval St.Safe! and Has a Large Pool!
1BR+/1BA
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Sleeps 2-4
– Private Homes, Old Town #249689
$3200- $6500/mo All
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Steps from the Beach and Duval - Sleeps 4
1BR+/1BA
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Sleeps 2-4
– Private Homes, Old Town #412106
$188 - $368 per night 3-6 night min stay
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Private Cottage 2 Blocks from Duval Street!
1BR+/1BA
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Sleeps 2-4
– Private Homes, Old Town #411925
$208 - $419 per night 3-6 night min stay
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Historic 'Tobago House' in-Ground Private Spa, Lush Gardens
2BR/2BA
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Sleeps 2-4
– Private Homes, Old Town #301138
From $3,500- $5,750/month
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Supermodel Home - Old Town Hideaway, Pool, Perfect Location
2BR/2BA
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Sleeps 4-5
– Private Homes, Old Town #185246
$226- $486/nt/mo
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The Hollinsed House "Victorian Delights" - Large 1 Bedroom
1BR+/1BA
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Sleeps 2-4
– Private Homes, Old Town #400912
From $189/nt/ $1095 wk (Summer)
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Absolute Dream Cottage, with Private Hot Tub, Walk Everywhere!
Studio/1BA
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Sleeps 2
– Private Homes, Old Town #267650
From $198/nt
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The Hollinsed House "Poolside Suite" - Deluxe King Studio
1BR/1BA
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Sleeps 2
– Private Homes, Old Town #400907
From $169/nt/ $995 wk (Summer)
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Beautiful 4 Bedroom Home with Pool
4BR/3BA
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Sleeps 8
– Private Homes, Old Town #466412
$5000 - $9500 per month 28 night min stay
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The Hollinsed House "Michael's Retreat" - Large 1 Bedroom
1BR+/1BA
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Sleeps 2-4
– Private Homes, Old Town #400911
From $189/nt/ $1095 wk (Summer)
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Heavenly Hideout at Key West Mile Zero ~ Rainbow's End
4BR/4BA
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Sleeps 8
– Private Homes, Old Town #445226
$575-$775/nt - $3400-$2400/wk
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4 Bed/4 Bath Retreat at the End of the Road
4BR/4BA
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Sleeps 6-8
– Private Homes, Old Town #474319
$7500 - $12000 per month 30 night min stay
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The Hollinsed House "Shangrila Suite" - Deluxe Queen Studio
1BR/1BA
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Sleeps 2
– Private Homes, Old Town #400909
From $159/nt/ $895 wk (Summer)
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Absolutely Paradise
3BR/2.5BA
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Sleeps 6
– Private Homes, Old Town #347826
From $408/nt - $2856/wk
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Victoria House 5 Bedroom Beauty Key West Rental
5BR/5.5BA
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Sleeps 12
– Private Homes, Old Town #251638
$865-$1225/nt - $5800-$8300/wk
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Secluded Getaway Just Off Duval
3BR+/3BA
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Sleeps 6-8
– Private Homes, Old Town #346291
$450 - $720/nt.
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Sophisticated Elegance on Fleming Street (Pool, Parking)
3BR/2.5BA
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Sleeps 6
– Private Homes, Old Town #128058
$9000- $15,000/mo
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Quintessential Charming Hideaway
2BR+/2BA
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Sleeps 4-6
– Private Homes, Old Town #238475
$3000- $6000 monthly
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"Tranquility " at Ann Street Gardens Steps from Duval
1BR/1BA
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Sleeps 2
– Private Homes, Old Town #98557
$230-$310/nt - $1540-$2030/wk
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Hollinsed House - Key West Old Town - Great Location!!
Studio/1BA
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Sleeps 2
– Private Homes, Old Town #255530
$148-$228/nt - $959- $1400/wk
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Historic 4 /3 Luxury Beach Home in Key West
4BR/3BA
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Sleeps 4-8
– Private Homes, Old Town #116745
$5600 per week 7 night min stay
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Colony Cabanas - Tropical Bungalow in the Heart of Old Town
1BR+/1BA
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Sleeps 2-3
– Private Homes, Old Town #137869
$190- $320/nt
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Old Town Bali Hideaway for 2, Just Steps from Duval
Studio/1BA
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Sleeps 2
– Private Homes, Old Town #82634
$210-$280/nt - $1400-$1820/wk
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Modern Luxury and Privacy Just Steps from Duval
2BR+/2BA
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Sleeps 6
– Private Homes, Old Town #302200
$425/nt and Up
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Sophisticated Southard Street Charmer
3BR/3BA
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Sleeps 6
– Private Homes, Old Town #176314
$4800 to $10,000 per month
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Amelia's Hideaway - Hidden Courtyard Villa with Private Pool
4BR/3.5BA
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Sleeps 8-10
– Private Homes, Old Town #137983
$750-$850/nt - $4000-$5100/wk
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Fleming Street Townhouse in the Sky!
2BR+/2.5BA
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Sleeps 4-6
– Private Homes, Old Town #289989
$3500- $5500/mo
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Designer Dream 2BR/2BA with Heated Pool
2BR/2BA
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Sleeps 2-4
– Private Homes, Old Town #190172
$4000- $7000/mo
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Old Town Historic Eyebrow -One Block to Duval-Private Pool/Spa
4BR+/4BA
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Sleeps 8
– Private Homes, Old Town #150378
3490/wk
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The Meeting Point - Key West - Elegant and Grand
11BR/0BA
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Sleeps 24-26
– Private Homes, Old Town #457272
from $2100/night
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Cute, Clean, Cozy and Close to All
1BR/1BA
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Sleeps 2-3
– Private Homes, Old Town #250411
$135-$225/nt - $895- $1500/wk
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Tropical Dreaming - 2 Bedroom Home - Private Pool
2BR/2.5BA
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Sleeps 4-6
– Private Homes, Old Town #251642
$340-$470/nt - $2100-$3000/wk
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The Kingfisher - Historic Old Town Luxury Home (Monthly Only)
3BR/2.5BA
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Sleeps 6
– Private Homes, Old Town #430740
$6000- $10000/mo
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Quiet Lane Retreat in the Heart of Old Town
2BR+/1.5BA
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Sleeps 6
– Private Homes, Old Town #425235
$2500- $6000/mo.
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Egret Cottage: 1 Bedroom Cottage Old Town Key West
1BR+/1BA
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Sleeps 4
– Private Homes, Old Town #92567
$1050- $1550/wk
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Summer Rates from $3000/Month - Louisa Bella
2BR+/1BA
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Sleeps 4-6
– Private Homes, Old Town #101530
$3000- $6500/mo
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Sailor House, Luxurious Two Bedroom 1/2 Block from Duval St.
2BR+/1.5BA
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Sleeps 4-6
– Private Homes, Old Town #321456
$265- $399/nt plus 12.5% tax
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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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Steps from Duval! Luxurious, Sleeps 2-4, Old Town
1BR+/1BA
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Sleeps 2-4
– Private Homes, Old Town #365419
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.