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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 /
4
BA /
Sleeps
8
From $7,500/month
Featured
3
BR /
3
BA /
Sleeps
8
From $1,850/wk
Featured
4
BR /
4
BA /
Sleeps
8
From $6,000/month
Featured
6
BR /
7
BA /
Sleeps
14
Featured
3
BR /
2
BA /
Sleeps
7
From $5,500/month
Featured
Key West
(389)
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
Sunset and Ocean View in Key West's Truman Annex with 2 Bikes and Pool Access
2 Bedrooms,
1
Bathroom
, Sleeps 4
$1,300 - $1,950
per week
Sunset and Ocean View in Key West's Truman Annex with 2 Bikes and Pool Access
Book it Now!
7 night Minimum Stay
2
BR,
1
BA,
Sleeps
4
Lower Florida Keys
>
Key West Condo
#244472
(61)
Compare
Charming Condo in Old Town Key West's Truman Annex
1 Bedrooms,
1
Bathroom
, Sleeps 2
$1,200 - $1,850
per week
Charming Condo in Old Town Key West's Truman Annex
Book it Now!
7 night Minimum Stay
1
BR,
1
BA,
Sleeps
2
Lower Florida Keys
>
Key West Condo
#290407
(32)
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
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
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
(8)
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
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
(33)
Compare
Private Yacht 3 blocks from Duval Street & Sloppy Joe's
3 Bedrooms, Sleeps 6
$575 - $650
per night
Private Yacht 3 blocks from Duval Street & Sloppy Joe's
2 - 5 night Minimum Stay
3
BR,
Sleeps
6
Lower Florida Keys
>
Key West Yacht
#390580vb
(21)
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
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
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
(3)
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
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
Tropical Key West Oasis Private Home 2BR/2 Bath w/ Pool, Weekly Rental
2 Bedrooms,
2
Bathrooms
, Sleeps 6
Tropical Key West Oasis Private Home 2BR/2 Bath w/ Pool, Weekly Rental
2
BR,
2
BA,
Sleeps
6
Lower Florida Keys
>
Key West House
#420695vb
(21)
Compare
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
Carey's Conch Cottage Old Town, Key West, Private Heated Pool
30 night Minimum Stay
1
BR,
1
BA,
1
HF BA,
Sleeps
4
Lower Florida Keys
>
Key West Cottage
#247863vb
(11)
Compare
Casa Marina Oasis
2 Bedrooms,
2
Bathrooms
, Sleeps 6
$4,000 - $7,000
per month
Casa Marina Oasis
28 night Minimum Stay
2
BR,
2
BA,
Sleeps
6
Lower Florida Keys
>
Key West House
#3501277
Compare
Paradise Found*Luxury Oceanfront Key West 3/2 Oceanside Marina
3 Bedrooms,
2
Bathrooms
, Sleeps 7
Paradise Found*Luxury Oceanfront Key West 3/2 Oceanside Marina
3
BR,
2
BA,
Sleeps
7
Lower Florida Keys
>
Key West Condo
#170889vb
(6)
Compare
Real World MTV House---Not Just a House Your Own Private Resort
10 Bedrooms,
5
Bathrooms
,
1
Half Bath
, Sleeps 24
$1,500 - $2,000
per night
Real World MTV House---Not Just a House Your Own Private Resort
4 night Minimum Stay
10
BR,
5
BA,
1
HF BA,
Sleeps
24
Lower Florida Keys
>
Key West House
#326563
(14)
Compare
Chick-A-Pea's Cottage:Near Duval-yet private with the comforts of home
3 Bedrooms,
2
Bathrooms
,
1
Half Bath
, Sleeps 6
Chick-A-Pea's Cottage:Near Duval-yet private with the comforts of home
3
BR,
2
BA,
1
HF BA,
Sleeps
6
Lower Florida Keys
>
Key West House
#449947vb
(5)
Compare
Luxury Waterfront at the Galleon Resort in Old Town
2 Bedrooms,
2
Bathrooms
, Sleeps 8
$400 - $600
per night
Luxury Waterfront at the Galleon Resort in Old Town
3 - 4 night Minimum Stay
2
BR,
2
BA,
Sleeps
8
Lower Florida Keys
>
Key West Condo
#161268
(5)
Compare
Luxury on Garrison Bight: 3 BR/3.5 BA Waterfront Home Sleeps 8
3 Bedrooms,
3
Bathrooms
,
1
Half Bath
, Sleeps 8
$495 - $795
per night
Luxury on Garrison Bight: 3 BR/3.5 BA Waterfront Home Sleeps 8
3 - 6 night Minimum Stay
3
BR,
3
BA,
1
HF BA,
Sleeps
8
Lower Florida Keys
>
Key West House
#3475121
1 Review
Compare
Condo In Historic 1928 Conch House, Walking Distance To Duval
1 Bedrooms,
2
Bathrooms
, Sleeps 4
$2,500 - $3,500
per month
Condo In Historic 1928 Conch House, Walking Distance To Duval
30 night Minimum Stay
1
BR,
2
BA,
Sleeps
4
Lower Florida Keys
>
Key West Condo
#460746vb
2 Reviews
Compare
Bargain Rates in Truman Annex - Heart of Old Town, Key West
2 Bedrooms,
1
Bathroom
, Sleeps 6
$225 - $350
per night
Bargain Rates in Truman Annex - Heart of Old Town, Key West
5 night Minimum Stay
2
BR,
1
BA,
Sleeps
6
Lower Florida Keys
>
Key West Condo
#184913
(5)
Compare
Galleon Resort Efficiency in Old Town
Studio,
1
Bathroom
, Sleeps 2
$160 - $240
per night
Galleon Resort Efficiency in Old Town
3 - 4 night Minimum Stay
Studio,
1
BA,
Sleeps
2
Lower Florida Keys
>
Key West Studio
#169027
(7)
Compare
516 Louisa Street
2 Bedrooms,
1
Bathroom
,
1
Half Bath
, Sleeps 4
$350 - $650
per night
516 Louisa Street
3 - 5 night Minimum Stay
2
BR,
1
BA,
1
HF BA,
Sleeps
4
Lower Florida Keys
>
Key West House
#3483364
Compare
6 bedrooms w/ Pool, Hot Tub, Parking & Huge Roof Deck on Duval Street
6 Bedrooms,
7
Bathrooms
, Sleeps 14
6 bedrooms w/ Pool, Hot Tub, Parking & Huge Roof Deck on Duval Street
6
BR,
7
BA,
Sleeps
14
Lower Florida Keys
>
Key West Villa
#228157
(4)
Compare
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