Tradewinds Key West Style #9 — Rates & Availability

Prime Vacations - Anna Maria Island1 bedroom1 bathSleeps 4

Check Availability & Book Direct

Rates as of November 7, 2026

Pricing Summary

Nightly Rate
$135–$567 /night
Next Available
Nov 11

12-Month Rate Calendar

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

November 2026$135–$200/night · 29% open
SuMoTuWeThFrSa
7 —8 —9 —10 —11 $13512 —13 —
14 —15 —16 —17 —18 —19 $135 2n20 $175 2n
21 $200 2n22 $200 2n23 $200 2n24 —25 —26 —27 —
28 —29 —30 $135 2n
December 2026$135–$450/night · 100% open
SuMoTuWeThFrSa
1 $135 2n2 $135 2n3 $135 2n4 $155 2n5 $155 2n
6 $135 2n7 $135 2n8 $135 2n9 $135 2n10 $135 2n11 $155 2n12 $161 2n
13 $139 2n14 $135 2n15 $135 2n16 $135 2n17 $135 2n18 $155 2n19 $175 3n
20 $175 3n21 $175 3n22 $175 4n23 $175 4n24 $300 4n25 $300 4n26 $335 4n
27 $325 4n28 $395 4n29 $450 4n30 $450 4n31 $450 4n
January 2027$173–$450/night · 32% open
SuMoTuWeThFrSa
1 $450 4n2 —
3 —4 —5 —6 —7 —8 —9 —
10 —11 —12 —13 —14 —15 —16 —
17 —18 —19 —20 —21 —22 —23 $214 4n
24 $176 4n25 $173 4n26 $248 4n27 $248 4n28 $248 4n29 $289 4n30 $327 4n
31 $303 4n
February 2027$237–$369/night · 100% open
SuMoTuWeThFrSa
1 $237 4n2 $237 4n3 $237 4n4 $237 4n5 $265 4n6 $279 4n
7 $239 4n8 $239 4n9 $239 4n10 $239 4n11 $254 4n12 $310 4n13 $356 5n
14 $356 5n15 $356 5n16 $324 5n17 $305 5n18 $321 5n19 $369 5n20 $336 5n
21 $285 5n22 $285 5n23 $285 5n24 $285 5n25 $285 5n26 $356 5n27 $300 5n
28 $256 5n
March 2027$270–$567/night · 100% open
SuMoTuWeThFrSa
1 $272 5n2 $270 5n3 $277 5n4 $289 5n5 $334 5n6 $363 5n
7 $349 5n8 $345 5n9 $348 5n10 $350 5n11 $354 5n12 $423 5n13 $463 5n
14 $393 5n15 $398 5n16 $391 5n17 $546 5n18 $567 5n19 $450 5n20 $425 5n
21 $425 5n22 $425 5n23 $425 5n24 $425 5n25 $425 5n26 $425 5n27 $449 5n
28 $388 5n29 $417 5n30 $363 5n31 $345 5n
April 2027$179–$493/night · 100% open
SuMoTuWeThFrSa
1 $323 5n2 $493 5n3 $448 5n
4 $360 5n5 $419 5n6 $372 5n7 $368 5n8 $365 5n9 $396 5n10 $284 4n
11 $241 4n12 $261 4n13 $257 4n14 $267 4n15 $284 4n16 $311 4n17 $323 4n
18 $287 4n19 $270 4n20 $270 4n21 $212 4n22 $217 4n23 $239 4n24 $228 4n
25 $195 4n26 $186 4n27 $179 4n28 $228 4n29 $228 4n30 $265 4n
May 2027$160–$403/night · 100% open
SuMoTuWeThFrSa
1 $255 4n
2 $178 4n3 $166 4n4 $166 4n5 $165 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 $160 4n20 $166 4n21 $194 4n22 $403 4n
23 $403 4n24 $175 4n25 $177 4n26 $179 4n27 $221 4n28 $294 4n29 $298 7n
30 $259 7n31 $230 7n

No check-in: 30, 31

No check-out: 30, 31

June 2027$208–$373/night · 100% open
SuMoTuWeThFrSa
1 $225 7n2 $235 7n3 $246 7n4 $373 7n5 $345 7n
6 $286 7n7 $285 7n8 $281 7n9 $208 7n10 $219 7n11 $245 7n12 $268 7n
13 $237 7n14 $230 7n15 $225 7n16 $223 7n17 $230 7n18 $262 7n19 $256 7n
20 $217 7n21 $209 7n22 $211 7n23 $213 7n24 $223 7n25 $262 7n26 $278 5n
27 $239 5n28 $231 5n29 $231 5n30 $237 5n

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

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

July 2027$205–$318/night · 84% open
SuMoTuWeThFrSa
1 —2 —3 —
4 —5 —6 $265 4n7 $260 4n8 $279 4n9 $318 4n10 $251 7n
11 $224 7n12 $217 7n13 $214 7n14 $216 7n15 $224 7n16 $261 7n17 $271 7n
18 $213 7n19 $205 7n20 $207 7n21 $212 7n22 $216 7n23 $276 7n24 $286 7n
25 $247 7n26 $239 7n27 $236 7n28 $228 7n29 $233 7n30 $213 7n31 $205 7n

No check-in: 11, 12, 13, 14, 15, 16, 18, 19, 20, 21, 22, 23, 25, 26, 27, 28, 29, 30

No check-out: 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 $179 7n2 $172 7n3 $172 7n4 $164 7n5 $167 7n6 $200 7n7 $187 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

September 2027$135–$312/night · 100% open
SuMoTuWeThFrSa
1 $135 4n2 $183 4n3 $299 4n4 $312 4n
5 $168 4n6 $135 4n7 $135 4n8 $135 4n9 $135 4n10 $135 4n11 $135 4n
12 $155 4n13 $155 4n14 $155 4n15 $155 4n16 $135 4n17 $135 4n18 $145 4n
19 $135 4n20 $135 4n21 $135 4n22 $209 4n23 $141 4n24 $146 4n25 $146 4n
26 $141 4n27 $138 4n28 $154 4n29 $135 4n30 $135 4n
October 2027$135–$230/night · 100% open
SuMoTuWeThFrSa
1 $188 4n2 $171 4n
3 $171 4n4 $171 4n5 $171 4n6 $171 4n7 $171 4n8 $171 4n9 $167 4n
10 $135 4n11 $135 4n12 $140 4n13 $147 4n14 $154 4n15 $190 4n16 $230 4n
17 $176 4n18 $173 4n19 $168 4n20 $168 4n21 $168 4n22 $185 4n23 $173 4n
24 $135 4n25 $155 4n26 $155 4n27 $155 4n28 $160 4n29 $184 4n30 $144 4n
31 $135 4n

Rates updated: November 7, 2026