Tradewinds Key West Style #9 — Rates & Availability

Prime Vacations - Anna Maria Island1 bedroom1 bathSleeps 4

Check Availability & Book Direct

Rates as of September 22, 2026

Pricing Summary

Nightly Rate
$125–$567 /night
Min Stay
2 nights
Next Available
Sep 22

12-Month Rate Calendar

Each date shows: day · nightly rate · minimum stay (e.g. 2n = 2-night minimum). “—” = booked.

September 2026$125–$125/night · 44% open
SuMoTuWeThFrSa
22 $125 2n23 $125 2n24 25 26
27 28 29 $125 2n30 $125 2n
October 2026$135–$171/night · 58% open
SuMoTuWeThFrSa
1 $135 2n2 $150 2n3 $150 2n
4 $135 2n5 $135 2n6 $135 2n7 $135 2n8 $135 2n9 $154 2n10 $164 2n
11 12 13 14 15 $136 2n16 $171 2n17 $170 2n
18 $135 2n19 $135 2n20 21 22 23 24 $146 2n
25 $135 2n26 27 28 29 30 31 $155 3n
November 2026$135–$236/night · 80% open
SuMoTuWeThFrSa
1 $135 3n2 $135 3n3 $135 3n4 $135 3n5 $157 3n6 $182 3n7 $190 3n
8 $171 3n9 $167 3n10 $148 3n11 $148 3n12 $144 3n13 $167 3n14 $158 3n
15 $135 3n16 $135 3n17 $135 3n18 $135 3n19 $135 3n20 $177 3n21 $236 3n
22 $210 3n23 $214 3n24 25 26 27 28
29 30 $135 4n
December 2026$135–$430/night · 100% open
SuMoTuWeThFrSa
1 $135 4n2 $135 4n3 $135 4n4 $135 4n5 $148 4n
6 $135 4n7 $135 4n8 $135 4n9 $135 4n10 $135 4n11 $136 4n12 $189 4n
13 $166 4n14 $135 4n15 $135 4n16 $135 4n17 $135 4n18 $135 4n19 $194 7n
20 $167 7n21 $167 7n22 $175 7n23 $188 7n24 $217 7n25 $281 7n26 $314 7n
27 $281 7n28 $380 7n29 $373 7n30 $430 7n31 $430 7n

No check-in: 20, 21, 22, 23, 24, 25, 27, 28, 29, 30, 31

No check-out: 20, 21, 22, 23, 24, 27, 28, 29, 30, 31

January 2027$181–$368/night · 32% open
SuMoTuWeThFrSa
1 $364 7n2
3 4 5 6 7 8 9
10 11 12 13 14 15 16
17 18 19 20 21 22 23 $218 4n
24 $184 4n25 $181 4n26 $279 4n27 $279 4n28 $279 4n29 $324 4n30 $368 4n
31 $341 4n

No check-in: 1

February 2027$295–$508/night · 100% open
SuMoTuWeThFrSa
1 $325 4n2 $325 4n3 $325 4n4 $325 4n5 $362 4n6 $345 4n
7 $295 4n8 $295 4n9 $295 4n10 $295 4n11 $295 4n12 $382 4n13 $420 5n
14 $420 5n15 $420 5n16 $359 5n17 $359 5n18 $359 5n19 $420 5n20 $441 5n
21 $406 5n22 $406 5n23 $406 5n24 $406 5n25 $406 5n26 $508 5n27 $475 5n
28 $404 5n
March 2027$363–$567/night · 100% open
SuMoTuWeThFrSa
1 $388 5n2 $377 5n3 $366 5n4 $390 5n5 $503 5n6 $428 5n
7 $367 5n8 $363 5n9 $366 5n10 $369 5n11 $373 5n12 $446 5n13 $463 5n
14 $393 5n15 $398 5n16 $391 5n17 $546 5n18 $567 5n19 $382 5n20 $482 5n
21 $421 5n22 $404 5n23 $407 5n24 $414 5n25 $436 5n26 $499 5n27 $493 5n
28 $426 5n29 $458 5n30 $398 5n31 $379 5n
April 2027$183–$541/night · 100% open
SuMoTuWeThFrSa
1 $360 5n2 $541 5n3 $493 5n
4 $396 5n5 $461 5n6 $409 5n7 $405 5n8 $402 5n9 $436 5n10 $266 4n
11 $226 4n12 $237 4n13 $233 4n14 $242 4n15 $258 4n16 $282 4n17 $293 4n
18 $260 4n19 $245 4n20 $245 4n21 $203 4n22 $205 4n23 $224 4n24 $238 4n
25 $201 4n26 $192 4n27 $183 4n28 $228 4n29 $228 4n30 $265 4n
May 2027$166–$414/night · 100% open
SuMoTuWeThFrSa
1 $255 4n
2 $183 4n3 $175 4n4 $173 4n5 $172 4n6 $208 4n7 $263 4n8 $274 4n
9 $228 4n10 $214 4n11 $214 4n12 $217 4n13 $294 4n14 $305 4n15 $254 4n
16 $189 4n17 $181 4n18 $180 4n19 $166 4n20 $173 4n21 $200 4n22 $414 4n
23 $414 4n24 $181 4n25 $184 4n26 $187 4n27 $227 4n28 $302 4n29 $306 7n
30 $266 7n31 $237 7n

No check-in: 30, 31

No check-out: 30, 31

June 2027$209–$382/night · 100% open
SuMoTuWeThFrSa
1 $231 7n2 $240 7n3 $253 7n4 $382 7n5 $355 7n
6 $293 7n7 $292 7n8 $289 7n9 $212 7n10 $222 7n11 $250 7n12 $247 7n
13 $213 7n14 $211 7n15 $209 7n16 $209 7n17 $218 7n18 $248 7n19 $261 7n
20 $226 7n21 $218 7n22 $217 7n23 $225 7n24 $238 7n25 $279 7n26 $272 7n
27 $241 7n28 $231 7n29 $229 7n30 $234 7n

No check-in: 1, 2, 3, 4, 6, 7, 8, 9, 10, 11, 13, 14, 15, 16, 17, 18, 20, 21, 22, 23, 24, 25, 27, 28, 29, 30

No check-out: 1, 2, 3, 4, 6, 7, 8, 9, 10, 11, 13, 14, 15, 16, 17, 18, 20, 21, 22, 23, 24, 25, 27, 28, 29, 30

July 2027$204–$305/night · 100% open
SuMoTuWeThFrSa
1 $274 7n2 $303 7n3 $305 7n
4 $276 7n5 $240 7n6 $235 7n7 $238 7n8 $252 7n9 $284 7n10 $291 7n
11 $245 7n12 $244 7n13 $241 7n14 $249 7n15 $259 7n16 $304 7n17 $264 7n
18 $215 7n19 $207 7n20 $204 7n21 $207 7n22 $215 7n23 $269 7n24 $286 7n
25 $247 7n26 $239 7n27 $236 7n28 $228 7n29 $233 7n30 $219 7n31 $215 7n

No check-in: 1, 2, 4, 5, 6, 7, 8, 9, 11, 12, 13, 14, 15, 16, 18, 19, 20, 21, 22, 23, 25, 26, 27, 28, 29, 30

No check-out: 1, 2, 4, 5, 6, 7, 8, 9, 11, 12, 13, 14, 15, 16, 18, 19, 20, 21, 22, 23, 25, 26, 27, 28, 29, 30

August 2027$135–$289/night · 100% open
SuMoTuWeThFrSa
1 $183 7n2 $176 7n3 $172 7n4 $169 7n5 $172 7n6 $200 7n7 $191 7n
8 $163 7n9 $156 7n10 $155 7n11 $155 7n12 $158 7n13 $177 7n14 $189 4n
15 $135 4n16 $135 4n17 $135 4n18 $135 4n19 $135 4n20 $184 4n21 $176 4n
22 $151 4n23 $163 4n24 $163 4n25 $163 4n26 $163 4n27 $233 4n28 $269 4n
29 $289 4n30 $135 4n31 $135 4n

No check-in: 1, 2, 3, 4, 5, 6, 8, 9, 10, 11, 12, 13

No check-out: 1, 2, 3, 4, 5, 6, 8, 9, 10, 11, 12, 13

Rates updated: September 22, 2026