Florida Keys Luxury(364)
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
Kawama Yacht Club- Oceanfront Private Beach - Sunsets!
- 2 Bedrooms,
- 2 Bathrooms, Sleeps 8
$200 -
$300
per night
3 night Minimum Stay
- 2 BR,
- 2 BA,
- Sleeps 8
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
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
STEPS FROM DUVAL! LUXURIOUS, SLEEPS 2-4, OLD TOWN
- 1 Bedrooms,
- 1 Bathroom, Sleeps 4
- 1 BR,
- 1 BA,
- Sleeps 4
'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
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
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
Waterfront Luxury Home with An Incredible View on a Full Acre, Free Secured WiFi
- 4 Bedrooms,
- 3 Bathrooms, Sleeps 8
$2,400 -
$2,550
per week
7 night Minimum Stay
- 4 BR,
- 3 BA,
- Sleeps 8
'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
Seaglass-20 feet from the Gulf--Special Rate Aug. thru Dec. 20 !!!!!!
- 2 Bedrooms,
- 2 Bathrooms,
- 1 Half Bath, Sleeps 6
$1,195 -
$2,195
per week
7 - 14 night Minimum Stay
- 2 BR,
- 2 BA,
- 1 HF BA,
- Sleeps 6
Luxury New Home with Pool/Dock on the Atlantic Near Key West
- 2 Bedrooms,
- 3 Bathrooms, Sleeps 6
$250 -
$310
per night
3 night Minimum Stay
- 2 BR,
- 3 BA,
- Sleeps 6
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
World-Class Private Retreat Compound - Over 300' Waterfront- 152' Dock
- 7 Bedrooms,
- 6 Bathrooms, Sleeps 14
$7,000
per week
7 night Minimum Stay
- 7 BR,
- 6 BA,
- Sleeps 14
Oceanfront (Gulf) Condo, Fabulous Views, Heated Pool & Dock
- 2 Bedrooms,
- 2 Bathrooms,
- 1 Half Bath, Sleeps 6
$986 -
$1,586
per week
7 night Minimum Stay
- 2 BR,
- 2 BA,
- 1 HF BA,
- Sleeps 6
Beautiful Key Largo Town Home Fully Renovated Top to Bottom
- 2 Bedrooms,
- 2 Bathrooms, Sleeps 6
$180 -
$200
per night
3 night Minimum Stay
- 2 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
Ocean Reef Club Pool 36' Seawall Beach Golf Tennis
- 2 Bedrooms,
- 1 Bathroom, Sleeps 5
$185 -
$400
per night
2 - 7 night Minimum Stay
- 2 BR,
- 1 BA,
- Sleeps 5
'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
'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
Rock Lobster Bungalow!
- 2 Bedrooms,
- 2 Bathrooms, Sleeps 4
$950 -
$1,300
per week
7 night Minimum Stay
- 2 BR,
- 2 BA,
- Sleeps 4
Charming Condo in Old Town Key West's Truman Annex
- 1 Bedrooms,
- 1 Bathroom, Sleeps 2
- 1 BR,
- 1 BA,
- Sleeps 2
'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
'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
'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
A Magnificent, Luxurious 7 Bedrooms, 5 Bath Rent All or Part
- 8 Bedrooms,
- 5 Bathrooms, Sleeps 24
$1,200
per night
3 night Minimum Stay
- 8 BR,
- 5 BA,
- Sleeps 24
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
'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
Elegant Beach Home With Dockage and WIFI in Key Largo! Pet friendly!
- 4 Bedrooms,
- 3 Bathrooms, Sleeps 12
$350
per night
3 night Minimum Stay
- 4 BR,
- 3 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
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