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Vacation Rentals
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World
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Florida
>
Florida Keys
>
Lower Florida Keys
>
Key West
4
BR /
2
BA /
Sleeps
8
From $275/nt
Featured
2
BR /
2
BA /
Sleeps
6
From $265/nt
Featured
2
BR /
2
BA /
Sleeps
5
Featured
7
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7
BA /
Sleeps
12
From $9,500/wk
Featured
2
BR /
2
BA /
Sleeps
4
From $320/nt
Featured
Key West with Parking Included
(582)
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Availability Last Updated
Accepts Online Payments
Bedrooms: Least to Most
Bedrooms: Most to Least
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Price: Low to High
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Special Offers First
Ocean Breeze Suites-3 Bd, 3 Bath with loft Sleeps 10
3 Bedrooms,
3
Bathrooms
, Sleeps 10
$695 - $855
per night
Ocean Breeze Suites-3 Bd, 3 Bath with loft Sleeps 10
Book it Now!
2 - 4 night Minimum Stay
3
BR,
3
BA,
Sleeps
10
Lower Florida Keys
>
Key West Condo
#367100
(12)
Compare
Key West Condo in Truman Annex with Whirlpool Tub, 2 Bikes, & Access to Pool!
2 Bedrooms, Sleeps 4
$1,300 - $1,950
per week
Key West Condo in Truman Annex with Whirlpool Tub, 2 Bikes, & Access to Pool!
Book it Now!
7 night Minimum Stay
2
BR,
Sleeps
4
Lower Florida Keys
>
Key West Condo
#938538
(18)
Compare
Oceanfront Acre Heated Private Pool Sandy Area Dock 15 Min Key West
3 Bedrooms,
2
Bathrooms
, Sleeps 10
$1,800 - $2,900
per week
Oceanfront Acre Heated Private Pool Sandy Area Dock 15 Min Key West
7 night Minimum Stay
3
BR,
2
BA,
Sleeps
10
Lower Florida Keys
>
Key West House
#317093
(51)
Compare
Charming, Romantic, Funky, Cozy, Unique, Beautiful, Island Charm, Beach, Ocean
1 Bedrooms,
1
Bathroom
, Sleeps 2
$149 - $189
per night
Charming, Romantic, Funky, Cozy, Unique, Beautiful, Island Charm, Beach, Ocean
Book it Now!
2 - 3 night Minimum Stay
1
BR,
1
BA,
Sleeps
2
Lower Florida Keys
>
Key West Bungalow
#972748
(7)
Compare
Ocean Perch , Dock 80'Heated Pool Deep Channel Tennis 15 min Key West
2 Bedrooms,
2
Bathrooms
, Sleeps 6
$975 - $1,550
per week
Ocean Perch , Dock 80'Heated Pool Deep Channel Tennis 15 min Key West
7 night Minimum Stay
2
BR,
2
BA,
Sleeps
6
Lower Florida Keys
>
Key West House
#315267
(45)
Compare
STEPS FROM DUVAL! LUXURIOUS, SLEEPS 2-4, OLD TOWN
1 Bedrooms,
1
Bathroom
, Sleeps 4
STEPS FROM DUVAL! LUXURIOUS, SLEEPS 2-4, OLD TOWN
1
BR,
1
BA,
Sleeps
4
Lower Florida Keys
>
Key West Condo
#966039
(17)
Compare
Private Luxury in Prestigious Casa Marina Neighborhood
3 Bedrooms,
3
Bathrooms
,
1
Half Bath
, Sleeps 7
$3,500 - $8,800
per month
Private Luxury in Prestigious Casa Marina Neighborhood
28 night Minimum Stay
3
BR,
3
BA,
1
HF BA,
Sleeps
7
Lower Florida Keys
>
Key West House
#298674
(14)
Compare
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
Full Month Discounts Now Available in Truman Annex, Key West
7 night Minimum Stay
2
BR,
2
BA,
1
HF BA,
Sleeps
5
Lower Florida Keys
>
Key West Condo
#982960
(12)
Compare
'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
'GULFSIDE VISTAS @ TRUMAN ANNEX': Lavish Oceanfront 2BR/2.5BA Penthouse Condo...
7 night Minimum Stay
2
BR,
2
BA,
1
HF BA,
Sleeps
5
Lower Florida Keys
>
Key West Condo
#904145
(19)
Compare
Ocean Suite at the Galleon Resort
2 Bedrooms,
2
Bathrooms
, Sleeps 8
$495 - $695
per night
Ocean Suite at the Galleon Resort
Book it Now!
2 - 4 night Minimum Stay
2
BR,
2
BA,
Sleeps
8
Lower Florida Keys
>
Key West Condo
#929000
(4)
Compare
Key West Boat & Breakfast, Reef Sailing Trips, ASA sailing coming soon
2 Bedrooms,
2
Bathrooms
, Sleeps 4
$320 - $375
per night
Key West Boat & Breakfast, Reef Sailing Trips, ASA sailing coming soon
2 - 3 night Minimum Stay
2
BR,
2
BA,
Sleeps
4
Lower Florida Keys
>
Key West Yacht
#229193
(19)
Compare
Luxury Spacious Townhouse overlooking Pool w/ water view & 2 Bikes
1 Bedrooms,
1
Bathroom
, Sleeps 4
$185 - $328
per night
Luxury Spacious Townhouse overlooking Pool w/ water view & 2 Bikes
3 - 5 night Minimum Stay
1
BR,
1
BA,
Sleeps
4
Lower Florida Keys
>
Key West Townhome
#3472045
(8)
Compare
'OLD TOWN OASIS @ TRUMAN ANNEX': Luxurious 2BR/2BA Condo + Oceanside Pool...
2 Bedrooms,
2
Bathrooms
, Sleeps 6
$2,100 - $3,800
per week
'OLD TOWN OASIS @ TRUMAN ANNEX': Luxurious 2BR/2BA Condo + Oceanside Pool...
7 night Minimum Stay
2
BR,
2
BA,
Sleeps
6
Lower Florida Keys
>
Key West Condo
#390175
(23)
Compare
Walk to the beach!
1 Bedrooms,
1
Bathroom
, Sleeps 2
$2,146 - $2,884
per month
Walk to the beach!
Book it Now!
28 night Minimum Stay
1
BR,
1
BA,
Sleeps
2
Lower Florida Keys
>
Key West Studio
#392129
2 Reviews
Compare
HGTV Featured Home - Boaters Paradise! Waterfront Key West Home
3 Bedrooms,
2
Bathrooms
, Sleeps 6
$6,409 - $7,196
per month
HGTV Featured Home - Boaters Paradise! Waterfront Key West Home
28 night Minimum Stay
3
BR,
2
BA,
Sleeps
6
Lower Florida Keys
>
Key West House
#277391
(32)
Compare
Oceanfront Condominium - Key West Oceanfront at the Coral Reef
2 Bedrooms,
2
Bathrooms
, Sleeps 6
$265 - $495
per night
Oceanfront Condominium - Key West Oceanfront at the Coral Reef
4 - 5 night Minimum Stay
2
BR,
2
BA,
Sleeps
6
Lower Florida Keys
>
Key West Condo
#154612
(34)
Compare
Special Offer
**SAVE** $350.00 OFF WEEKLY RATES (June 15 - June 22)
Salida del Sol - Waterfront Key West Resort Style Home w/Pool & Beach
2 Bedrooms,
2
Bathrooms
, Sleeps 6
$520 - $525
per night
Salida del Sol - Waterfront Key West Resort Style Home w/Pool & Beach
Book it Now!
3 night Minimum Stay
2
BR,
2
BA,
Sleeps
6
Lower Florida Keys
>
Key West House
#3498085
2 Reviews
Compare
'PUERTA CORALINA @ SOLARES HILL': Charming 2BR/3BA Cottage, 2 Master Suites...
2 Bedrooms,
3
Bathrooms
, Sleeps 6
$350 - $700
per night
'PUERTA CORALINA @ SOLARES HILL': Charming 2BR/3BA Cottage, 2 Master Suites...
4 night Minimum Stay
2
BR,
3
BA,
Sleeps
6
Lower Florida Keys
>
Key West House
#904144
(21)
Compare
'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
'VILLA BAHAMA @ THE FOUNDRY': Luxury 2BR/2.5BA Townhome in Truman Annex...
7 night Minimum Stay
2
BR,
2
BA,
1
HF BA,
Sleeps
6
Lower Florida Keys
>
Key West Villa
#390213
(12)
Compare
'CONCH CASA GRANDE @ THE ANNEX': Enormous 7BR/7BA in Truman Annex...
7 Bedrooms,
7
Bathrooms
, Sleeps 12
$9,500 - $12,900
per week
'CONCH CASA GRANDE @ THE ANNEX': Enormous 7BR/7BA in Truman Annex...
7 night Minimum Stay
7
BR,
7
BA,
Sleeps
12
Lower Florida Keys
>
Key West House
#390171
(12)
Compare
'CASA LOUISA @ UPPER DUVAL': Historic Conch Cottage & Pool 1/2 Block off Duval..
3 Bedrooms,
2
Bathrooms
, Sleeps 8
$400 - $750
per night
'CASA LOUISA @ UPPER DUVAL': Historic Conch Cottage & Pool 1/2 Block off Duval..
4 night Minimum Stay
3
BR,
2
BA,
Sleeps
8
Lower Florida Keys
>
Key West Cottage
#135603
(45)
Compare
'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
'NOONA'S MANSION-by-the-SEA @ THE ANNEX' Sumptuous 7BR/5.5BA Home with Pool...
7 night Minimum Stay
7
BR,
5
BA,
1
HF BA,
Sleeps
14
Lower Florida Keys
>
Key West House
#390202
(25)
Compare
Sunset and Ocean View in Key West's Truman Annex with 2 Bikes and Pool Access
2 Bedrooms,
1
Bathroom
, Sleeps 4
Sunset and Ocean View in Key West's Truman Annex with 2 Bikes and Pool Access
2
BR,
1
BA,
Sleeps
4
Lower Florida Keys
>
Key West Condo
#244472
(61)
Compare
'HIDDEN TREASURE @ CASA EAST': Luxurious 3BR 3BA Villa & Huge Pool near Beach...
3 Bedrooms,
3
Bathrooms
, Sleeps 6
$5,500 - $14,000
per month
'HIDDEN TREASURE @ CASA EAST': Luxurious 3BR 3BA Villa & Huge Pool near Beach...
28 night Minimum Stay
3
BR,
3
BA,
Sleeps
6
Lower Florida Keys
>
Key West House
#390210
(7)
Compare
'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
'SEA CAPTAIN'S HAVEN @ THE ANNEX': Immaculate Villa near Duval & Sunset Pier...
7 night Minimum Stay
2
BR,
2
BA,
1
HF BA,
Sleeps
6
Lower Florida Keys
>
Key West Villa
#996654
(7)
Compare
Stunning Brand New SleepAfloat HOUSEBOAT in Paradise!
4 Bedrooms,
2
Bathrooms
, Sleeps 8
$275 - $400
per night
Stunning Brand New SleepAfloat HOUSEBOAT in Paradise!
2 night Minimum Stay
4
BR,
2
BA,
Sleeps
8
Lower Florida Keys
>
Key West House Boat
#939677
(9)
Compare
Galleon Resort Efficiency Historic District
1 Bedrooms,
1
Bathroom
, Sleeps 2
$219 - $299
per night
Galleon Resort Efficiency Historic District
Book it Now!
2 - 4 night Minimum Stay
1
BR,
1
BA,
Sleeps
2
Lower Florida Keys
>
Key West Condo
#931332
1 Review
Compare
'PARADISE @ GARRISON BIGHT': Large 5BR/4BA Waterfront Home + Private Dock...
5 Bedrooms,
4
Bathrooms
, Sleeps 14
$1,200 - $1,800
per night
'PARADISE @ GARRISON BIGHT': Large 5BR/4BA Waterfront Home + Private Dock...
4 night Minimum Stay
5
BR,
4
BA,
Sleeps
14
Lower Florida Keys
>
Key West Townhome
#390212
(25)
Compare
'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
'AVALYNN HOUSE @ THE ANNEX': Incredibly Spacious 5BR Home, Large Pool..
7 night Minimum Stay
5
BR,
3
BA,
1
HF BA,
Sleeps
12
Lower Florida Keys
>
Key West House
#996261
(8)
Compare
'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
'COOL BREEZE @ THE ANNEX': Meticulously Furnished 2BR/2.5BA Old Town Villa...
7 night Minimum Stay
2
BR,
2
BA,
1
HF BA,
Sleeps
6
Lower Florida Keys
>
Key West Villa
#390190
(5)
Compare
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