3 vetted providers · updated 12:44 AM ET

Browse confirmed stays.

Every stay is an already-booked reservation with fixed dates and a fixed room. Filter the board, then book with the provider that holds it.

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Hotel

Month

Length of stay

Guests

Weekend

Sort by

Max nightly rate$3450+

88 stays match your filters

88 stays match your filters

Hotel

Month

Length of stay

Guests

Weekend

Sort by

Max nightly rate$3450+

88 stays match your filters

NEW TODAYTUE OCT 20 – WED 21 · 1 NIGHT · Check-in in 2 days
Old Key West
Deluxe Studio · Sleeps 4 · DVC Shop
$299 / night
$299
NEW TODAYTUE NOV 10 – THU 12 · 2 NIGHTS · 23 days out
Old Key West
1-Bedroom Villa - Standard View · Sleeps 5 · DVC Rental
$15 / pt· below board median
$437 / night
$874
NEW TODAYSUN NOV 15 – TUE 17 · 2 NIGHTS · 28 days out
Old Key West
Deluxe Studio · Sleeps 4 · DVC Request
$22 / pt· below board median
$286 / night
$572
NEW TODAYTUE DEC 15 – FRI 18 · 3 NIGHTS · 58 days out
Old Key West
3-Bedroom Grand Villa - Standard View · Sleeps 12 · DVC Rental
$27 / pt
$1,488 / night
$4,465
NEW TODAYMON JAN 4 – TUE 5 · 1 NIGHT · 78 days out
Old Key West
Deluxe Studio - Standard View · Sleeps 4 · DVC Rental
$27 / pt
$281 / night
$281
NEWTHU NOV 19 – FRI 20 · 1 NIGHT · 32 days out
Old Key West
Deluxe Studio - Standard View · Sleeps 4 · DVC Rental
$20 / pt· below board median
$270 / night
$270
NEWSAT NOV 28 – SUN 29 · 1 NIGHT · 41 days out
Old Key West
Deluxe Studio - Standard View · Sleeps 4 · DVC Rental
$27 / pt
$477 / night
$477
NEWTUE DEC 22 – SUN 27 · 5 NIGHTS · 65 days out
Old Key West
Two Bedroom · Sleeps 9 · DVC Request
$22 / pt· below board median
$1,122 / night
$5,610
FRI MAR 19 – WED 24 · 5 NIGHTS · 152 days out
Old Key West
Two Bedroom · Sleeps 9 · DVC Request
$22 / pt· below board median
$1,184 / night
$5,918
FRI MAY 14 – FRI 21 · 7 NIGHTS · 208 days out
Old Key West
Deluxe Studio · Sleeps 4 · DVC Shop
$271 / night
$1,896
SAT SEP 11 – TUE 14 · 3 NIGHTS · 328 days out
Old Key West
Deluxe Studio - Near Hospitality House · Sleeps 4 · DVC Shop
$393 / night
$1,178
MON JAN 4 – WED 6 · 2 NIGHTS · 78 days out
Old Key West
Deluxe Studio · Sleeps 4 · DVC Shop
$280 / night
$560
SAT JAN 2 – TUE 5 · 3 NIGHTS · 76 days out
Old Key West
Deluxe Studio · Sleeps 4 · DVC Shop
$363 / night
$1,088
SAT OCT 31 – SUN NOV 1 · 1 NIGHT · 13 days out
Old Key West
One Bedroom · Sleeps 5 · DVC Request
$21 / pt· below board medianPrice cut $34
$714 / night
$714
TUE NOV 24 – WED 25 · 1 NIGHT · 37 days out
Old Key West
Deluxe Studio · Sleeps 4 · DVC Shop
$299 / night
$299
SUN JUL 11 – SAT 17 · 6 NIGHTS · 266 days out
Old Key West
Deluxe Studio - Near Hospitality House · Sleeps 4 · DVC Rental
$27 / pt
$332 / night
$1,994
WED OCT 28 – THU 29 · 1 NIGHT · 10 days out
Old Key West
Deluxe Studio · Sleeps 4 · DVC Shop
$299 / night
$299
SUN MAY 23 – SAT 29 · 6 NIGHTS · 217 days out
Old Key West
Deluxe Studio - Standard View · Sleeps 4 · DVC Rental
$27 / pt
$304 / night
$1,825
SUN JUN 13 – SAT 19 · 6 NIGHTS · 238 days out
Old Key West
Deluxe Studio - Standard View · Sleeps 4 · DVC Rental
$27 / pt
$332 / night
$1,994
SUN MAR 14 – FRI 19 · 5 NIGHTS · 147 days out
Old Key West
Deluxe Studio · Sleeps 4 · DVC Request
$22 / pt· below board median
$330 / night
$1,650
WED NOV 25 – THU 26 · 1 NIGHT · 38 days out
Old Key West
Deluxe Studio · Sleeps 4 · DVC Request
$22 / pt· below board median
$330 / night
$330
TUE OCT 27 – FRI 30 · 3 NIGHTS · 9 days out
Old Key West
Two Bedroom · Sleeps 9 · DVC Request
$22 / pt· below board median
$858 / night
$2,574
FRI SEP 3 – WED 8 · 5 NIGHTS · 320 days out
Old Key West
Deluxe Studio - Near Hospitality House · Sleeps 4 · DVC Shop
$371 / night
$1,855
SUN MAY 2 – MON 3 · 1 NIGHT · 196 days out
Old Key West
Deluxe Studio - Standard View · Sleeps 4 · DVC Rental
$27 / pt
$281 / night
$281
WED APR 21 – MON 26 · 5 NIGHTS · 185 days out
Old Key West
Two Bedroom · Sleeps 9 · DVC Request
$22 / pt· below board median
$986 / night
$4,928
TUE JUN 1 – FRI 4 · 3 NIGHTS · 226 days out
Old Key West
Deluxe Studio - Standard View · Sleeps 4 · DVC Rental
$27 / pt
$281 / night
$842
SUN JUN 20 – FRI 25 · 5 NIGHTS · 245 days out
Old Key West
Deluxe Studio - Standard View · Sleeps 4 · DVC Rental
$27 / pt
$309 / night
$1,544
SUN JUL 18 – FRI 23 · 5 NIGHTS · 273 days out
Old Key West
Deluxe Studio - Near Hospitality House · Sleeps 4 · DVC Rental
$27 / pt
$309 / night
$1,544
SUN SEP 5 – FRI 10 · 5 NIGHTS · 322 days out
Old Key West
Deluxe Studio - Near Hospitality House · Sleeps 4 · DVC Rental
$27 / pt
$253 / night
$1,264
SAT AUG 21 – SAT 28 · 7 NIGHTS · 307 days out
Old Key West
Deluxe Studio - Near Hospitality House · Sleeps 4 · DVC Shop
$410 / night
$2,871
SUN NOV 29 – MON 30 · 1 NIGHT · 42 days out
Old Key West
Deluxe Studio · Sleeps 4 · DVC Shop
$429 / night
$429
SUN DEC 13 – THU 17 · 4 NIGHTS · 56 days out
Old Key West
Deluxe Studio · Sleeps 4 · DVC Shop
$460 / night
$1,840
THU JAN 21 – FRI 22 · 1 NIGHT · 95 days out
Old Key West
Deluxe Studio · Sleeps 4 · DVC Shop
$335 / night
$335
SAT FEB 20 – THU 25 · 5 NIGHTS · 125 days out
Old Key West
Deluxe Studio · Sleeps 4 · DVC Shop
$427 / night
$2,133
SAT NOV 28 – SUN 29 · 1 NIGHT · 41 days out
Old Key West
Deluxe Studio · Sleeps 4 · DVC Shop
$357 / night
$357
WED APR 7 – TUE 13 · 6 NIGHTS · 171 days out
Old Key West
Deluxe Studio · Sleeps 4 · DVC Request
$22 / pt· below board median
$359 / night
$2,156
THU MAY 27 – SAT 29 · 2 NIGHTS · 221 days out
Old Key West
Deluxe Studio - Near Hospitality House · Sleeps 4 · DVC Rental
$27 / pt
$351 / night
$702
FRI FEB 19 – THU 25 · 6 NIGHTS · 124 days out
Old Key West
Deluxe Studio - Standard View · Sleeps 4 · DVC Rental
$27 / pt
$459 / night
$2,752
THU DEC 24 – FRI 25 · 1 NIGHT · 67 days out
Old Key West
Deluxe Studio - Near Hospitality House · Sleeps 4 · DVC Shop
$462 / night
$462
SAT AUG 14 – SAT 21 · 7 NIGHTS · 300 days out
Old Key West
Deluxe Studio - Near Hospitality House · Sleeps 4 · DVC Shop
$410 / night
$2,871
THU OCT 29 – WED NOV 4 · 6 NIGHTS · 11 days out
Old Key West
Two Bedroom · Sleeps 9 · DVC Request
$22 / pt· below board median
$895 / night
$5,368
THU OCT 29 – FRI 30 · 1 NIGHT · 11 days out
Old Key West
Deluxe Studio · Sleeps 4 · DVC Shop
$429 / night
$429
SAT AUG 7 – SAT 14 · 7 NIGHTS · 293 days out
Old Key West
Deluxe Studio - Near Hospitality House · Sleeps 4 · DVC Shop
$410 / night
$2,871
SAT JUL 3 – SAT 10 · 7 NIGHTS · 258 days out
Old Key West
Deluxe Studio · Sleeps 4 · DVC Shop
$298 / night
$2,088
SAT JUL 10 – SAT 17 · 7 NIGHTS · 265 days out
Old Key West
Deluxe Studio - Near Hospitality House · Sleeps 4 · DVC Shop
$298 / night
$2,088
SAT JUL 31 – SAT AUG 7 · 7 NIGHTS · 286 days out
Old Key West
Deluxe Studio - Near Hospitality House · Sleeps 4 · DVC Shop
$298 / night
$2,088
FRI FEB 5 – SUN 7 · 2 NIGHTS · 110 days out
Old Key West
Deluxe Studio · Sleeps 4 · DVC Shop
$448 / night
$896
SAT JUL 3 – TUE 6 · 3 NIGHTS · 258 days out
Old Key West
One Bedroom · Sleeps 5 · DVC Request
$22 / pt· below board median
$601 / night
$1,804
SUN JUL 25 – FRI 30 · 5 NIGHTS · 280 days out
Old Key West
Deluxe Studio - Near Hospitality House · Sleeps 4 · DVC Shop
$363 / night
$1,815
SAT FEB 6 – SUN 7 · 1 NIGHT · 111 days out
Old Key West
Deluxe Studio - Near Hospitality House · Sleeps 4 · DVC Rental
$27 / pt
$449 / night
$449
SUN MAY 23 – WED 26 · 3 NIGHTS · 217 days out
Old Key West
Deluxe Studio - Near Hospitality House · Sleeps 4 · DVC Shop
$360 / night
$1,080
THU DEC 24 – SAT JAN 2 · 9 NIGHTS · 67 days out
Old Key West
One Bedroom · Sleeps 5 · DVC Request
$22 / pt· below board median
$895 / night
$8,052
FRI MAR 19 – SUN 21 · 2 NIGHTS · 152 days out
Old Key West
Deluxe Studio - Near Hospitality House · Sleeps 4 · DVC Shop
$494 / night
$988
SUN JUL 4 – FRI 9 · 5 NIGHTS · 259 days out
Old Key West
Deluxe Studio · Sleeps 4 · DVC Shop
$374 / night
$1,870
SUN AUG 1 – FRI 6 · 5 NIGHTS · 287 days out
Old Key West
Deluxe Studio - Near Hospitality House · Sleeps 4 · DVC Shop
$374 / night
$1,870
SAT MAR 13 – FRI 19 · 6 NIGHTS · 146 days out
Old Key West
Deluxe Studio · Sleeps 4 · DVC Shop
$486 / night
$2,914
SAT JUL 24 – SAT 31 · 7 NIGHTS · 279 days out
Old Key West
Deluxe Studio - Near Hospitality House · Sleeps 4 · DVC Shop
$410 / night
$2,871
SUN MAY 23 – SUN 30 · 7 NIGHTS · 217 days out
Old Key West
Deluxe Studio · Sleeps 4 · DVC Shop
$320 / night
$2,240
SUN APR 25 – FRI 30 · 5 NIGHTS · 189 days out
Old Key West
Deluxe Studio - Near Hospitality House · Sleeps 4 · DVC Rental
$27 / pt
$421 / night
$2,106
WED DEC 23 – SAT 26 · 3 NIGHTS · 66 days out
Old Key West
Deluxe Studio - Standard View · Sleeps 4 · DVC Rental
$27 / pt
$543 / night
$1,629
SAT NOV 21 – SAT 28 · 7 NIGHTS · 34 days out
Old Key West
Deluxe Studio - Near Hospitality House · Sleeps 4 · DVC Shop
Price cut $420
$435 / night
$3,045
SUN DEC 27 – SUN JAN 3 · 7 NIGHTS · 70 days out
Old Key West
Deluxe Studio - Near Hospitality House · Sleeps 4 · DVC Shop
Price cut $414
$552 / night
$3,864
SAT JAN 9 – SAT 16 · 7 NIGHTS · 83 days out
Old Key West
Deluxe Studio - Near Hospitality House · Sleeps 4 · DVC Shop
$368 / night
$2,574
SAT FEB 6 – SAT 13 · 7 NIGHTS · 111 days out
Old Key West
Deluxe Studio - Near Hospitality House · Sleeps 4 · DVC Shop
$410 / night
$2,871
SAT FEB 13 – SAT 20 · 7 NIGHTS · 118 days out
Old Key West
Deluxe Studio - Near Hospitality House · Sleeps 4 · DVC Shop
$481 / night
$3,366
SAT JAN 30 – SAT FEB 6 · 7 NIGHTS · 104 days out
Old Key West
Deluxe Studio · Sleeps 4 · DVC Shop
$432 / night
$3,024
SAT FEB 20 – SAT 27 · 7 NIGHTS · 125 days out
Old Key West
Deluxe Studio - Near Hospitality House · Sleeps 4 · DVC Shop
$500 / night
$3,503
SUN FEB 28 – SAT MAR 6 · 6 NIGHTS · 133 days out
Old Key West
Deluxe Studio - Near Hospitality House · Sleeps 4 · DVC Shop
$486 / night
$2,914
SUN FEB 28 – SUN MAR 7 · 7 NIGHTS · 133 days out
Old Key West
Deluxe Studio - Near Hospitality House · Sleeps 4 · DVC Shop
$500 / night
$3,503
SAT JAN 23 – SAT 30 · 7 NIGHTS · 97 days out
Old Key West
Deluxe Studio · Sleeps 4 · DVC Shop
$368 / night
$2,574
SAT MAR 6 – SAT 13 · 7 NIGHTS · 139 days out
Old Key West
Deluxe Studio - Near Hospitality House · Sleeps 4 · DVC Shop
$500 / night
$3,503
SAT MAR 13 – SAT 20 · 7 NIGHTS · 146 days out
Old Key West
Deluxe Studio - Near Hospitality House · Sleeps 4 · DVC Shop
$500 / night
$3,503
SAT MAR 20 – SAT 27 · 7 NIGHTS · 153 days out
Old Key West
Deluxe Studio - Near Hospitality House · Sleeps 4 · DVC Shop
$686 / night
$4,805
SAT APR 3 – SAT 10 · 7 NIGHTS · 167 days out
Old Key West
Deluxe Studio - Near Hospitality House · Sleeps 4 · DVC Shop
$500 / night
$3,503
FRI NOV 27 – MON 30 · 3 NIGHTS · 40 days out
Old Key West
Deluxe Studio · Sleeps 4 · DVC Shop
$425 / night
$1,274
SAT APR 10 – SAT 17 · 7 NIGHTS · 174 days out
Old Key West
Deluxe Studio - Near Hospitality House · Sleeps 4 · DVC Shop
$500 / night
$3,503
SAT APR 17 – SAT 24 · 7 NIGHTS · 181 days out
Old Key West
Deluxe Studio - Near Hospitality House · Sleeps 4 · DVC Shop
$500 / night
$3,503
SUN APR 25 – SUN MAY 2 · 7 NIGHTS · 189 days out
Old Key West
Deluxe Studio - Near Hospitality House · Sleeps 4 · DVC Shop
$478 / night
$3,348
SAT APR 24 – SAT MAY 1 · 7 NIGHTS · 188 days out
Old Key West
Deluxe Studio - Near Hospitality House · Sleeps 4 · DVC Shop
$500 / night
$3,503
TUE JAN 5 – MON 11 · 6 NIGHTS · 79 days out
Old Key West
Deluxe Studio · Sleeps 4 · DVC Shop
$363 / night
$2,176
SAT MAY 1 – SAT 8 · 7 NIGHTS · 195 days out
Old Key West
Deluxe Studio · Sleeps 4 · DVC Shop
$345 / night
$2,418
SAT MAY 8 – SAT 15 · 7 NIGHTS · 202 days out
Old Key West
Deluxe Studio - Near Hospitality House · Sleeps 4 · DVC Shop
$345 / night
$2,418
SUN JAN 3 – MON 4 · 1 NIGHT · 77 days out
Old Key West
Deluxe Studio · Sleeps 4 · DVC Shop
$230 / night
$230
SAT JUN 26 – SAT JUL 3 · 7 NIGHTS · 251 days out
Old Key West
Deluxe Studio - Near Hospitality House · Sleeps 4 · DVC Shop
$410 / night
$2,871
SUN FEB 28 – TUE MAR 2 · 2 NIGHTS · 133 days out
Old Key West
Deluxe Studio · Sleeps 4 · DVC Shop
$420 / night
$840
SAT JUL 3 – WED 7 · 4 NIGHTS · 258 days out
Old Key West
Deluxe Studio - Near Hospitality House · Sleeps 4 · DVC Shop
$417 / night
$1,666
SAT JUL 17 – SAT 24 · 7 NIGHTS · 272 days out
Old Key West
Deluxe Studio - Near Hospitality House · Sleeps 4 · DVC Shop
$398 / night
$2,784
MON MAR 1 – SAT 6 · 5 NIGHTS · 134 days out
Old Key West
One Bedroom · Sleeps 5 · DVC Request
$22 / pt· below board median
$704 / night
$3,520