Key West Downtown Vacation Rentals(159)
Ocean Breeze Suites-3 Bd, 3 Bath with loft Sleeps 10
- 3 Bedrooms,
- 3 Bathrooms, Sleeps 10
$695 -
$855
per night
2 - 4 night Minimum Stay
- 3 BR,
- 3 BA,
- Sleeps 10
Key West Condo in Truman Annex with Whirlpool Tub, 2 Bikes, & Access to Pool!
- 2 Bedrooms, Sleeps 4
$1,300 -
$1,950
per week
7 night Minimum Stay
- 2 BR,
- Sleeps 4
Private Luxury in Prestigious Casa Marina Neighborhood
- 3 Bedrooms,
- 3 Bathrooms,
- 1 Half Bath, Sleeps 7
$3,500 -
$8,800
per month
28 night Minimum Stay
- 3 BR,
- 3 BA,
- 1 HF BA,
- Sleeps 7
Walk to the beach!
- 1 Bedrooms,
- 1 Bathroom, Sleeps 2
$2,146 -
$2,884
per month
28 night Minimum Stay
- 1 BR,
- 1 BA,
- Sleeps 2
Full Month Discounts Now Available in Truman Annex, Key West
- 2 Bedrooms,
- 2 Bathrooms,
- 1 Half Bath, Sleeps 5
$1,750 -
$2,751
per week
7 night Minimum Stay
- 2 BR,
- 2 BA,
- 1 HF BA,
- Sleeps 5
Ocean Suite at the Galleon Resort
- 2 Bedrooms,
- 2 Bathrooms, Sleeps 8
$495 -
$695
per night
2 - 4 night Minimum Stay
- 2 BR,
- 2 BA,
- Sleeps 8
Key West Boat & Breakfast, Reef Sailing Trips, ASA sailing coming soon
- 2 Bedrooms,
- 2 Bathrooms, Sleeps 4
$320 -
$375
per night
2 - 3 night Minimum Stay
- 2 BR,
- 2 BA,
- Sleeps 4
'WINDOWS ON THE GULF @ THE ANNEX': Lavish Oceanfront 2BR/2.5BA Penthouse Condo..
- 2 Bedrooms,
- 2 Bathrooms,
- 1 Half Bath, Sleeps 6
$3,300 -
$5,500
per week
7 night Minimum Stay
- 2 BR,
- 2 BA,
- 1 HF BA,
- Sleeps 6
'VILLA BAHAMA @ THE FOUNDRY': Luxury 2BR/2.5BA Townhome in Truman Annex...
- 2 Bedrooms,
- 2 Bathrooms,
- 1 Half Bath, Sleeps 6
$1,950 -
$3,500
per week
7 night Minimum Stay
- 2 BR,
- 2 BA,
- 1 HF BA,
- Sleeps 6
'OLD TOWN OASIS @ TRUMAN ANNEX': Luxurious 2BR/2BA Condo + Oceanside Pool...
- 2 Bedrooms,
- 2 Bathrooms, Sleeps 6
$2,100 -
$3,800
per week
7 night Minimum Stay
- 2 BR,
- 2 BA,
- Sleeps 6
'GULFSIDE VISTAS @ TRUMAN ANNEX': Lavish Oceanfront 2BR/2.5BA Penthouse Condo...
- 2 Bedrooms,
- 2 Bathrooms,
- 1 Half Bath, Sleeps 5
$2,950 -
$5,000
per week
7 night Minimum Stay
- 2 BR,
- 2 BA,
- 1 HF BA,
- Sleeps 5
'PARADISE @ GARRISON BIGHT': Large 5BR/4BA Waterfront Home + Private Dock...
- 5 Bedrooms,
- 4 Bathrooms, Sleeps 14
$1,200 -
$1,800
per night
4 night Minimum Stay
- 5 BR,
- 4 BA,
- Sleeps 14
Tiki Beach Too, Charming Townhome, Old Town, Pool Access, great porch!
- 2 Bedrooms,
- 1 Bathroom, Sleeps 6
$1,195 -
$1,895
per week
7 night Minimum Stay
- 2 BR,
- 1 BA,
- Sleeps 6
'PUERTA CORALINA @ SOLARES HILL': Charming 2BR/3BA Cottage, 2 Master Suites...
- 2 Bedrooms,
- 3 Bathrooms, Sleeps 6
$350 -
$700
per night
4 night Minimum Stay
- 2 BR,
- 3 BA,
- Sleeps 6
'SOUTHERN STAR' @ THE SEAPORT' Renovated Historic 3BR/3BA Home with Pool...
- 3 Bedrooms,
- 3 Bathrooms, Sleeps 6
$7,000 -
$16,000
per month
28 night Minimum Stay
- 3 BR,
- 3 BA,
- Sleeps 6
'LA CASA AZUL @ SOLARES HILL': Elegantly Renovated 3BR/3BA Home + Heated Pool...
- 3 Bedrooms,
- 3 Bathrooms, Sleeps 6
$5,500 -
$15,000
per month
28 night Minimum Stay
- 3 BR,
- 3 BA,
- Sleeps 6
'CASA BLANCA 1888 @ WHITE': Historic 4BR/3BA Old Town Home + Very Large Pool....
- 4 Bedrooms,
- 3 Bathrooms, Sleeps 10
$7,000 -
$16,000
per month
28 night Minimum Stay
- 4 BR,
- 3 BA,
- Sleeps 10
'FLAMINGO DREAMS @ SOLARES HILL': Pristine 3BR/2BA Conch Home in Old Town...
- 3 Bedrooms,
- 2 Bathrooms, Sleeps 6
$5,500 -
$14,000
per month
28 night Minimum Stay
- 3 BR,
- 2 BA,
- Sleeps 6
'CONCH CASA GRANDE @ THE ANNEX': Enormous 7BR/7BA in Truman Annex...
- 7 Bedrooms,
- 7 Bathrooms, Sleeps 12
$9,500 -
$12,900
per week
7 night Minimum Stay
- 7 BR,
- 7 BA,
- Sleeps 12
'SEA CAPTAIN'S HAVEN @ THE ANNEX': Immaculate Villa near Duval & Sunset Pier...
- 2 Bedrooms,
- 2 Bathrooms,
- 1 Half Bath, Sleeps 6
$2,100 -
$3,600
per week
7 night Minimum Stay
- 2 BR,
- 2 BA,
- 1 HF BA,
- Sleeps 6
'NOONA'S MANSION-by-the-SEA @ THE ANNEX' Sumptuous 7BR/5.5BA Home with Pool...
- 7 Bedrooms,
- 5 Bathrooms,
- 1 Half Bath, Sleeps 14
$11,000 -
$14,900
per week
7 night Minimum Stay
- 7 BR,
- 5 BA,
- 1 HF BA,
- Sleeps 14
'COOL BREEZE @ THE ANNEX': Meticulously Furnished 2BR/2.5BA Old Town Villa...
- 2 Bedrooms,
- 2 Bathrooms,
- 1 Half Bath, Sleeps 6
$1,950 -
$3,200
per week
7 night Minimum Stay
- 2 BR,
- 2 BA,
- 1 HF BA,
- Sleeps 6
Southernmost Retreat: 1 Block from Duval in Old Town.
- 3 Bedrooms,
- 2 Bathrooms, Sleeps 6
- 3 BR,
- 2 BA,
- Sleeps 6
'EDEN @ THE ANNEX': 2BR/1.5BA Old Town Villa near Beach & Sunset Pier...
- 2 Bedrooms,
- 1 Bathroom,
- 1 Half Bath, Sleeps 6
$1,650 -
$2,500
per week
7 night Minimum Stay
- 2 BR,
- 1 BA,
- 1 HF BA,
- Sleeps 6
'AVALYNN HOUSE @ THE ANNEX': Incredibly Spacious 5BR Home, Large Pool..
- 5 Bedrooms,
- 3 Bathrooms,
- 1 Half Bath, Sleeps 12
$8,000 -
$11,900
per week
7 night Minimum Stay
- 5 BR,
- 3 BA,
- 1 HF BA,
- Sleeps 12
'CASA FELIZ @ THE SEAPORT': Lushly Furnished 3BR/3.5BA Private Home + Pool...
- 3 Bedrooms,
- 3 Bathrooms, Sleeps 8
$6,600 -
$15,000
per month
28 night Minimum Stay
- 3 BR,
- 3 BA,
- Sleeps 8
'CASA PLUMERIA @ OLD TOWN SOUTH': 4BR/3.5BA Home & Guest Cottage + Pool...
- 4 Bedrooms,
- 3 Bathrooms,
- 1 Half Bath, Sleeps 10
$6,000 -
$14,000
per month
28 night Minimum Stay
- 4 BR,
- 3 BA,
- 1 HF BA,
- Sleeps 10
'BELLA PETRONIA @ THE MEADOWS: 3BR/3.5BA Private Home With Pool & Jacuzzi...
- 3 Bedrooms,
- 3 Bathrooms,
- 1 Half Bath, Sleeps 6
$5,000 -
$14,000
per month
28 night Minimum Stay
- 3 BR,
- 3 BA,
- 1 HF BA,
- Sleeps 6
'VILLA PARADISO @ CASA MARINA': Airy & Spacious Villa + Large Pool..
- 2 Bedrooms,
- 2 Bathrooms, Sleeps 6
$4,000 -
$7,700
per month
28 night Minimum Stay
- 2 BR,
- 2 BA,
- Sleeps 6
'HEAVENLY ZEN @ THE SEAPORT': Lavish 4BR/3BA Old Town Home + Pool....
- 4 Bedrooms,
- 3 Bathrooms, Sleeps 8
$11,000 -
$19,000
per month
28 night Minimum Stay
- 4 BR,
- 3 BA,
- Sleeps 8
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