Key West Luxury(153)
Charming Condo in Old Town Key West's Truman Annex
- 1 Bedrooms,
- 1 Bathroom, Sleeps 2
$1,200 -
$1,850
per week
7 night minimum stay
- 1 BR,
- 1 BA,
- Sleeps 2
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
Charming, Romantic, Funky, Cozy, Unique, Beautiful, Island Charm, Beach, Ocean
- 1 Bedrooms,
- 1 Bathroom, Sleeps 2
$149 -
$189
per night
2 - 3 night minimum stay
- 1 BR,
- 1 BA,
- Sleeps 2
Location, Location, Location! Ocean View, Lagoon Beach Front
- 3 Bedrooms,
- 2 Bathrooms, Sleeps 10
$360
per night
3 night minimum stay
- 3 BR,
- 2 BA,
- Sleeps 10
STEPS FROM DUVAL! LUXURIOUS, SLEEPS 2-4, OLD TOWN
- 1 Bedrooms,
- 1 Bathroom, Sleeps 4
- 1 BR,
- 1 BA,
- Sleeps 4
'CONCH CASA GRANDE @ THE ANNEX': Enormous 7BR/7BA in Truman Annex...
- 7 Bedrooms,
- 7 Bathrooms, Sleeps 12
$8,000 -
$12,900
per week
7 night minimum stay
- 7 BR,
- 7 BA,
- Sleeps 12
'HIDDEN TREASURE @ CASA EAST': Luxurious 3BR 3BA Villa & Huge Pool near Beach...
- 3 Bedrooms,
- 3 Bathrooms, Sleeps 6
$5,500 -
$14,000
per month
28 night minimum stay
- 3 BR,
- 3 BA,
- Sleeps 6
Oceanfront Condominium - Key West Oceanfront at the Coral Reef
- 2 Bedrooms,
- 2 Bathrooms, Sleeps 6
$265 -
$495
per night
4 - 5 night minimum stay
- 2 BR,
- 2 BA,
- Sleeps 6
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
'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
Luxury Spacious Townhouse overlooking Pool w/ water view & 2 Bikes
- 1 Bedrooms,
- 1 Bathroom, Sleeps 4
$185 -
$328
per night
3 - 5 night minimum stay
- 1 BR,
- 1 BA,
- Sleeps 4
Salida del Sol - Waterfront Key West Resort Style Home w/Pool & Beach
- 2 Bedrooms,
- 2 Bathrooms, Sleeps 6
$520 -
$525
per night
3 night minimum stay
- 2 BR,
- 2 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
'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
'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
'COOL BREEZE @ THE ANNEX': Meticulously Furnished 2BR/2.5BA Old Town Villa...
- 2 Bedrooms,
- 2 Bathrooms,
- 1 Half Bath, Sleeps 6
$1,950 -
$3,300
per week
7 night minimum stay
- 2 BR,
- 2 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
'SOUTHERNMOST COMFORT @ CASA EAST': Stunning 4BR/4.5BA Home w/ Cottage & Pool...
- 4 Bedrooms,
- 4 Bathrooms,
- 1 Half Bath, Sleeps 8
$9,000 -
$17,000
per month
28 night minimum stay
- 4 BR,
- 4 BA,
- 1 HF BA,
- Sleeps 8
'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
'SEA CAPTAIN'S HAVEN @ THE ANNEX': Immaculate Villa near Duval & Sunset Pier...
- 2 Bedrooms,
- 2 Bathrooms,
- 1 Half Bath, Sleeps 6
$2,100 -
$3,700
per week
7 night minimum stay
- 2 BR,
- 2 BA,
- 1 HF BA,
- Sleeps 6
'AZURE AFTERNOON @ OCEANSIDE MARINA': 3BR/2BA Oceanfront Condo + Pool & Spa...
- 3 Bedrooms,
- 2 Bathrooms, Sleeps 6
$1,950 -
$2,950
per week
7 night minimum stay
- 3 BR,
- 2 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
'PORTSIDE MANSION @ THE SEAPORT': Lush 6BR/7BA 3-Building Home + Large Pool.....
- 6 Bedrooms,
- 2 Bathrooms,
- 1 Half Bath, Sleeps 12
$20,000 -
$38,000
per month
28 night minimum stay
- 6 BR,
- 2 BA,
- 1 HF BA,
- Sleeps 12
'LA PROVENCE @ THE SANCTUARY': 2 Master Suites, Spa Pool with Walled Yard...
- 2 Bedrooms,
- 3 Bathrooms, Sleeps 6
$3,000 -
$6,900
per month
28 night minimum stay
- 2 BR,
- 3 BA,
- Sleeps 6
'PROMENADE TO PARADISE @ THE ANNEX': Spacious 2BR/2BA Waterfront Condo...
- 2 Bedrooms,
- 2 Bathrooms, Sleeps 6
$2,300 -
$4,000
per week
7 night minimum stay
- 2 BR,
- 2 BA,
- Sleeps 6
'POOLSIDE RETREAT @ THE POOL': Poolside 2BR/2.5BA Villa with 2 Master Suites...
- 3 Bedrooms,
- 2 Bathrooms,
- 1 Half Bath, Sleeps 6
$3,000 -
$5,750
per month
28 night minimum stay
- 3 BR,
- 2 BA,
- 1 HF BA,
- Sleeps 6
'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
Carey's Conch Cottage Old Town, Key West, Private Heated Pool
- 1 Bedrooms,
- 1 Bathroom,
- 1 Half Bath, Sleeps 4
$4,500 -
$6,500
per month
30 night minimum stay
- 1 BR,
- 1 BA,
- 1 HF BA,
- Sleeps 4
'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
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