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Florida Keys with Air Conditioning
(2,596)
sort by
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Special Offers First
White Ibis Inn - Oceanview Estate. Summer Special!
4 Bedrooms,
3
Bathrooms
, Sleeps 14
$400 - $560
per night
White Ibis Inn - Oceanview Estate. Summer Special!
Book it Now!
5 night minimum stay
4
BR,
3
BA,
Sleeps
14
Lower Florida Keys
>
Cudjoe Key House
#951852
16 Reviews
Compare
Sunset and Ocean View in Key West's Truman Annex with 2 Bikes and Pool Access
2 Bedrooms,
1
Bathroom
, Sleeps 4
$1,100 - $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
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
(13)
Compare
Charming Condo in Old Town Key West's Truman Annex
1 Bedrooms,
1
Bathroom
, Sleeps 2
$1,000 - $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
$1,100 - $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
(19)
Compare
Kawama Yacht Club- Oceanfront Private Beach - Sunsets!
2 Bedrooms,
2
Bathrooms
, Sleeps 8
$125 - $300
per night
Kawama Yacht Club- Oceanfront Private Beach - Sunsets!
Book it Now!
3 night minimum stay
2
BR,
2
BA,
Sleeps
8
Upper Florida Keys
>
Key Largo Condo
#404942vb
(22)
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
(52)
Compare
Charming, Romantic, Funky, Cozy, Unique, Beautiful, Island Charm, Beach, Ocean
1 Bedrooms,
1
Bathroom
, Sleeps 2
$139 - $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
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
Marathon Luxury Waterfront Pool Home 75' Dock Fully Upgraded
2 Bedrooms,
2
Bathrooms
, Sleeps 6
$1,330 - $2,303
per week
Marathon Luxury Waterfront Pool Home 75' Dock Fully Upgraded
Book it Now!
7 night minimum stay
2
BR,
2
BA,
Sleeps
6
Central Florida Keys
>
Marathon House
#902566
(7)
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
(6)
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
(18)
Compare
'PUERTA CORALINA @ SOLARES HILL': Charming 2BR/3BA Cottage, 2 Master Suites...
2 Bedrooms,
3
Bathrooms
, Sleeps 6
$236 - $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
(24)
Compare
'GULFSIDE VISTAS @ TRUMAN ANNEX': Lavish Oceanfront 2BR/2.5BA Penthouse Condo...
2 Bedrooms,
2
Bathrooms
,
1
Half Bath
, Sleeps 5
$2,172 - $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
(21)
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
Private Yacht 3 blocks from Duval Street & Sloppy Joe's
3 Bedrooms, Sleeps 6
$450 - $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
Waterfront, Boat Ramp, Pool, Tennis, Golf, Fishing, Diving
1 Bedrooms,
1
Bathroom
, Sleeps 4
$64 - $135
per night
Waterfront, Boat Ramp, Pool, Tennis, Golf, Fishing, Diving
Book it Now!
2 - 3 night minimum stay
1
BR,
1
BA,
Sleeps
4
Central Florida Keys
>
Marathon Condo
#910616
(5)
Compare
'WINDOWS ON THE GULF @ THE ANNEX': Lavish Oceanfront 2BR/2.5BA Penthouse Condo..
2 Bedrooms,
2
Bathrooms
,
1
Half Bath
, Sleeps 6
$2,390 - $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
Oceanfront (Gulf) Condo, Fabulous Views, Heated Pool & Dock
2 Bedrooms,
2
Bathrooms
,
1
Half Bath
, Sleeps 6
$986 - $1,586
per week
Oceanfront (Gulf) Condo, Fabulous Views, Heated Pool & Dock
7 night minimum stay
2
BR,
2
BA,
1
HF BA,
Sleeps
6
Central Florida Keys
>
Marathon Condo
#113802
(95)
Compare
August Discounted! On the Ocean with Beach! Seaside Villa on Coco Plum
2 Bedrooms,
2
Bathrooms
, Sleeps 6
$1,000 - $1,695
per week
August Discounted! On the Ocean with Beach! Seaside Villa on Coco Plum
7 night minimum stay
2
BR,
2
BA,
Sleeps
6
Central Florida Keys
>
Marathon Condo
#40371vb
(36)
Compare
Luxury New Home with Pool/Dock on the Atlantic Near Key West
2 Bedrooms,
3
Bathrooms
, Sleeps 6
$194 - $310
per night
Luxury New Home with Pool/Dock on the Atlantic Near Key West
3 night minimum stay
2
BR,
3
BA,
Sleeps
6
Lower Florida Keys
>
Cudjoe Key House
#3020462
(21)
Compare
Location, Location, Location! Ocean View, Lagoon Beach Front
3 Bedrooms,
2
Bathrooms
, Sleeps 10
$360
per night
Location, Location, Location! Ocean View, Lagoon Beach Front
3 night minimum stay
3
BR,
2
BA,
Sleeps
10
Lower Florida Keys
>
Key West House Boat
#903627
(15)
Compare
'CONCH CASA GRANDE @ THE ANNEX': Enormous 7BR/7BA in Truman Annex...
7 Bedrooms,
7
Bathrooms
, Sleeps 12
$7,241 - $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
(13)
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
(9)
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
'SEA CAPTAIN'S HAVEN @ THE ANNEX': Immaculate Villa near Duval & Sunset Pier...
2 Bedrooms,
2
Bathrooms
,
1
Half Bath
, Sleeps 6
$2,052 - $3,700
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
(8)
Compare
Rare Penthouse 2 bed/2bath additional King in loft
2 Bedrooms,
2
Bathrooms
, Sleeps 8
$495 - $695
per night
Rare Penthouse 2 bed/2bath additional King in loft
Book it Now!
2 - 4 night minimum stay
2
BR,
2
BA,
Sleeps
8
Lower Florida Keys
>
Key West Condo
#929000
(4)
Compare
Penthouse Condo Sunsets at Key Largo, Kawama Yacht Club Tower
2 Bedrooms,
2
Bathrooms
, Sleeps 8
$950 - $2,095
per week
Penthouse Condo Sunsets at Key Largo, Kawama Yacht Club Tower
7 night minimum stay
2
BR,
2
BA,
Sleeps
8
Upper Florida Keys
>
Key Largo Condo
#233900
(33)
Compare
'EDEN @ THE ANNEX': 2BR/1.5BA Old Town Villa near Beach & Sunset Pier...
2 Bedrooms,
1
Bathroom
,
1
Half Bath
, Sleeps 6
$1,328 - $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
(7)
Compare
'CASA LOUISA @ UPPER DUVAL': Historic Conch Cottage & Pool 1/2 Block off Duval..
3 Bedrooms,
2
Bathrooms
, Sleeps 8
$286 - $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
(48)
Compare
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Florida Keys
Central Florida Keys (597)
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