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Vacation Rentals
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>
Florida Keys
3
BR /
3
BA /
1
HF BA /
Sleeps
7
From $3,500/month
Featured
2
BR /
3
BA /
Sleeps
6
From $350/nt
Featured
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BR /
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1
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Sleeps
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Featured
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From $250/nt
Featured
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BR /
4
BA /
Sleeps
8
From $7,500/month
Featured
Florida Keys
(870)
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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
'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
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
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
'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
'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
Luxury Home with Pool, Hot Tub & 50' Dock. Spectacular Gulf View.
3 Bedrooms,
3
Bathrooms
, Sleeps 8
$2,300 - $3,500
per week
Luxury Home with Pool, Hot Tub & 50' Dock. Spectacular Gulf View.
7 night Minimum Stay
3
BR,
3
BA,
Sleeps
8
Central Florida Keys
>
Marathon House
#900688
(18)
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
World-Class Private Retreat Compound - Over 300' Waterfront- 152' Dock
7 Bedrooms,
6
Bathrooms
, Sleeps 14
$7,000
per week
World-Class Private Retreat Compound - Over 300' Waterfront- 152' Dock
Book it Now!
7 night Minimum Stay
7
BR,
6
BA,
Sleeps
14
Upper Florida Keys
>
Key Largo Estate
#3482337
Compare
Rock Lobster Bungalow!
2 Bedrooms,
2
Bathrooms
, Sleeps 4
$950 - $1,300
per week
Rock Lobster Bungalow!
7 night Minimum Stay
2
BR,
2
BA,
Sleeps
4
Central Florida Keys
>
Key Colony Beach Bungalow
#450095vb
(5)
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
'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
'SOUTHERNMOST COMFORT @ CASA EAST': Stunning 4BR/4.5BA Home w/ Cottage & Pool...
28 night Minimum Stay
4
BR,
4
BA,
1
HF BA,
Sleeps
8
Lower Florida Keys
>
Key West House
#990995
(11)
Compare
'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
'POOLSIDE RETREAT @ THE POOL': Poolside 2BR/2.5BA Villa with 2 Master Suites...
28 night Minimum Stay
3
BR,
2
BA,
1
HF BA,
Sleeps
6
Lower Florida Keys
>
Key West Villa
#390207
(3)
Compare
Sugarloaf Open Water Home With Beach, Dock and Swimming Canal
4 Bedrooms,
4
Bathrooms
, Sleeps 8
$8,000 - $10,000
per month
Sugarloaf Open Water Home With Beach, Dock and Swimming Canal
Book it Now!
28 night Minimum Stay
4
BR,
4
BA,
Sleeps
8
Lower Florida Keys
>
Sugarloaf Key House
#436830vb
(5)
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
'NATALIE'S BAHAMA CONCH' @ THE SANCTUARY': Lush 3BR/2.5BA Home, Pool...
3 Bedrooms,
2
Bathrooms
,
1
Half Bath
, Sleeps 8
$5,000 - $9,500
per month
'NATALIE'S BAHAMA CONCH' @ THE SANCTUARY': Lush 3BR/2.5BA Home, Pool...
28 night Minimum Stay
3
BR,
2
BA,
1
HF BA,
Sleeps
8
Lower Florida Keys
>
Key West House
#390203
(4)
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
'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
'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
'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
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
'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
'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
Quite, charming, elegant, tropical, a beautiful setting on the bay
5 Bedrooms,
3
Bathrooms
, Sleeps 16
$900
per night
Quite, charming, elegant, tropical, a beautiful setting on the bay
3 night Minimum Stay
5
BR,
3
BA,
Sleeps
16
Upper Florida Keys
>
Key Largo House
#338473
(23)
Compare
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Florida Keys
Central Florida Keys (228)
Lower Florida Keys (486)
Upper Florida Keys (156)