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Vacation Rentals
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>
Florida Keys
>
Lower Florida Keys
>
Key West
2
BR /
3
BA /
Sleeps
6
From $350/nt
Featured
3
BR /
2
BA /
Sleeps
6
Featured
3
BR /
3
BA /
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Sleeps
6
From $495/nt
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Sleeps
6
From $3,000/month
Featured
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BR /
2
BA /
Sleeps
10
From $360/nt
Featured
Key West Downtown Vacation Rentals
(159)
sort by
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Availability Last Updated
Accepts Online Payments
Bedrooms: Least to Most
Bedrooms: Most to Least
Price: High to Low
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
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
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
(5)
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
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
'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
'WINDOWS ON THE GULF @ THE ANNEX': Lavish Oceanfront 2BR/2.5BA Penthouse Condo..
7 night Minimum Stay
2
BR,
2
BA,
1
HF BA,
Sleeps
6
Lower Florida Keys
>
Key West Condo
#390177
(13)
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
'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
'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
'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
Tiki Beach Too, Charming Townhome, Old Town, Pool Access, great porch!
2 Bedrooms,
1
Bathroom
, Sleeps 6
$1,195 - $1,895
per week
Tiki Beach Too, Charming Townhome, Old Town, Pool Access, great porch!
Book it Now!
7 night Minimum Stay
2
BR,
1
BA,
Sleeps
6
Lower Florida Keys
>
Key West Townhome
#3539485
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
(22)
Compare
'SOUTHERN STAR' @ THE SEAPORT' Renovated Historic 3BR/3BA Home with Pool...
3 Bedrooms,
3
Bathrooms
, Sleeps 6
$7,000 - $16,000
per month
'SOUTHERN STAR' @ THE SEAPORT' Renovated Historic 3BR/3BA Home with Pool...
28 night Minimum Stay
3
BR,
3
BA,
Sleeps
6
Lower Florida Keys
>
Key West House
#390182
(10)
Compare
'LA CASA AZUL @ SOLARES HILL': Elegantly Renovated 3BR/3BA Home + Heated Pool...
3 Bedrooms,
3
Bathrooms
, Sleeps 6
$5,500 - $15,000
per month
'LA CASA AZUL @ SOLARES HILL': Elegantly Renovated 3BR/3BA Home + Heated Pool...
28 night Minimum Stay
3
BR,
3
BA,
Sleeps
6
Lower Florida Keys
>
Key West House
#390185
(6)
Compare
'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
'CASA BLANCA 1888 @ WHITE': Historic 4BR/3BA Old Town Home + Very Large Pool....
28 night Minimum Stay
4
BR,
3
BA,
Sleeps
10
Lower Florida Keys
>
Key West House
#390200
(11)
Compare
'FLAMINGO DREAMS @ SOLARES HILL': Pristine 3BR/2BA Conch Home in Old Town...
3 Bedrooms,
2
Bathrooms
, Sleeps 6
$5,500 - $14,000
per month
'FLAMINGO DREAMS @ SOLARES HILL': Pristine 3BR/2BA Conch Home in Old Town...
28 night Minimum Stay
3
BR,
2
BA,
Sleeps
6
Lower Florida Keys
>
Key West House
#390211
(3)
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
'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
'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
'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
(6)
Compare
Southernmost Retreat: 1 Block from Duval in Old Town.
3 Bedrooms,
2
Bathrooms
, Sleeps 6
Southernmost Retreat: 1 Block from Duval in Old Town.
3
BR,
2
BA,
Sleeps
6
Lower Florida Keys
>
Key West House
#959155
(9)
Compare
'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
'EDEN @ THE ANNEX': 2BR/1.5BA Old Town Villa near Beach & Sunset Pier...
7 night Minimum Stay
2
BR,
1
BA,
1
HF BA,
Sleeps
6
Lower Florida Keys
>
Key West Villa
#390205
(5)
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
'CASA FELIZ @ THE SEAPORT': Lushly Furnished 3BR/3.5BA Private Home + Pool...
3 Bedrooms,
3
Bathrooms
, Sleeps 8
$6,600 - $15,000
per month
'CASA FELIZ @ THE SEAPORT': Lushly Furnished 3BR/3.5BA Private Home + Pool...
28 night Minimum Stay
3
BR,
3
BA,
Sleeps
8
Lower Florida Keys
>
Key West House
#390195
(5)
Compare
'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
'CASA PLUMERIA @ OLD TOWN SOUTH': 4BR/3.5BA Home & Guest Cottage + Pool...
28 night Minimum Stay
4
BR,
3
BA,
1
HF BA,
Sleeps
10
Lower Florida Keys
>
Key West House
#390189
(4)
Compare
'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
'BELLA PETRONIA @ THE MEADOWS: 3BR/3.5BA Private Home With Pool & Jacuzzi...
28 night Minimum Stay
3
BR,
3
BA,
1
HF BA,
Sleeps
6
Lower Florida Keys
>
Key West House
#390197
(6)
Compare
'VILLA PARADISO @ CASA MARINA': Airy & Spacious Villa + Large Pool..
2 Bedrooms,
2
Bathrooms
, Sleeps 6
$4,000 - $7,700
per month
'VILLA PARADISO @ CASA MARINA': Airy & Spacious Villa + Large Pool..
28 night Minimum Stay
2
BR,
2
BA,
Sleeps
6
Lower Florida Keys
>
Key West Villa
#915976
(3)
Compare
'HEAVENLY ZEN @ THE SEAPORT': Lavish 4BR/3BA Old Town Home + Pool....
4 Bedrooms,
3
Bathrooms
, Sleeps 8
$11,000 - $19,000
per month
'HEAVENLY ZEN @ THE SEAPORT': Lavish 4BR/3BA Old Town Home + Pool....
28 night Minimum Stay
4
BR,
3
BA,
Sleeps
8
Lower Florida Keys
>
Key West House
#390201
(5)
Compare
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