Pineapple Key — Rates & Availability

Anna Maria Vacations4 bedrooms2 bathsSleeps 8

Check Availability & Book Direct

Rates as of November 8, 2026

Pricing Summary

Nightly Rate
$200–$962 /night
Min Stay
7 nights
Next Available
Nov 30

12-Month Rate Calendar

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

November 2026$200–$200/night · 4% open
SuMoTuWeThFrSa
7 —8 —9 —10 —11 —12 —13 —
14 —15 —16 —17 —18 —19 —20 —
21 —22 —23 —24 —25 —26 —27 —
28 —29 —30 $200 7n
December 2026$200–$455/night · 81% open
SuMoTuWeThFrSa
1 $200 7n2 $200 7n3 $200 7n4 $200 7n5 $200 7n
6 $200 7n7 $200 7n8 $200 7n9 $200 7n10 $200 7n11 $200 7n12 $200 7n
13 $200 7n14 $200 7n15 $200 7n16 $200 7n17 $200 7n18 $200 7n19 $200 7n
20 $237 7n21 $219 7n22 $323 7n23 $330 7n24 $336 7n25 $455 7n26 —
27 —28 —29 —30 —31 —

No check-in: 20, 21, 22, 23, 24, 25

No check-out: 20, 21, 22, 23, 24, 25

January 2027$204–$378/night · 97% open
SuMoTuWeThFrSa
1 —2 $293 7n
3 $247 7n4 $225 7n5 $220 7n6 $204 7n7 $211 7n8 $212 7n9 $377 7n
10 $285 7n11 $285 7n12 $285 7n13 $285 7n14 $285 7n15 $378 7n16 $268 7n
17 $254 7n18 $249 7n19 $247 7n20 $243 7n21 $254 7n22 $263 7n23 $249 7n
24 $241 7n25 $235 7n26 $233 7n27 $239 7n28 $252 7n29 $262 7n30 $292 7n
31 $286 7n

No check-in: 3, 4, 5, 6, 7, 8, 10, 11, 12, 13, 14, 15, 17, 18, 19, 20, 21, 22, 24, 25, 26, 27, 28, 29, 31

No check-out: 3, 4, 5, 6, 7, 8, 10, 11, 12, 13, 14, 15, 17, 18, 19, 20, 21, 22, 24, 25, 26, 27, 28, 29, 31

February 2027$294–$495/night · 43% open
SuMoTuWeThFrSa
1 $294 7n2 $295 7n3 $317 7n4 $342 7n5 $356 7n6 $400 7n
7 $402 7n8 $408 7n9 $405 7n10 $428 7n11 $477 7n12 $495 7n13 —
14 —15 —16 —17 —18 —19 —20 —
21 —22 —23 —24 —25 —26 —27 —
28 —

No check-in: 1, 2, 3, 4, 5, 7, 8, 9, 10, 11, 12

No check-out: 1, 2, 3, 4, 5, 7, 8, 9, 10, 11, 12

March 2027$551–$962/night · 84% open
SuMoTuWeThFrSa
1 —2 —3 —4 —5 —6 $571 7n
7 $559 7n8 $551 7n9 $551 7n10 $570 7n11 $618 7n12 $640 7n13 $653 7n
14 $653 7n15 $653 7n16 $653 7n17 $653 7n18 $653 7n19 $653 7n20 $806 7n
21 $806 7n22 $806 7n23 $806 7n24 $806 7n25 $814 7n26 $831 7n27 $896 7n
28 $881 7n29 $874 7n30 $962 7n31 $962 7n

No check-in: 7, 8, 9, 10, 11, 12, 14, 15, 16, 17, 18, 19, 21, 22, 23, 24, 25, 26, 28, 29, 30, 31

No check-out: 7, 8, 9, 10, 11, 12, 14, 15, 16, 17, 18, 19, 21, 22, 23, 24, 25, 26, 28, 29, 30, 31

April 2027$372–$962/night · 77% open
SuMoTuWeThFrSa
1 $962 7n2 $962 7n3 —
4 —5 —6 —7 —8 —9 —10 $565 7n
11 $565 7n12 $565 7n13 $565 7n14 $565 7n15 $565 7n16 $565 7n17 $446 7n
18 $452 7n19 $442 7n20 $440 7n21 $433 7n22 $430 7n23 $433 7n24 $435 7n
25 $407 7n26 $388 7n27 $372 7n28 $372 7n29 $393 7n30 $417 7n

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

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

May 2027$286–$419/night · 100% open
SuMoTuWeThFrSa
1 $331 7n
2 $322 7n3 $316 7n4 $320 7n5 $312 7n6 $328 7n7 $333 7n8 $336 7n
9 $319 7n10 $341 7n11 $337 7n12 $344 7n13 $348 7n14 $356 7n15 $337 7n
16 $322 7n17 $286 7n18 $287 7n19 $291 7n20 $302 7n21 $313 7n22 $410 7n
23 $413 7n24 $417 7n25 $419 7n26 $379 7n27 $394 7n28 $397 7n29 $361 7n
30 $361 7n31 $361 7n

No check-in: 2, 3, 4, 5, 6, 7, 9, 10, 11, 12, 13, 14, 16, 17, 18, 19, 20, 21, 23, 24, 25, 26, 27, 28, 30, 31

No check-out: 2, 3, 4, 5, 6, 7, 9, 10, 11, 12, 13, 14, 16, 17, 18, 19, 20, 21, 23, 24, 25, 26, 27, 28, 30, 31

June 2027$405–$617/night · 77% open
SuMoTuWeThFrSa
1 $405 7n2 $405 7n3 $405 7n4 $484 7n5 —
6 —7 —8 —9 —10 —11 —12 $617 7n
13 $617 7n14 $617 7n15 $617 7n16 $617 7n17 $617 7n18 $617 7n19 $456 7n
20 $434 7n21 $424 7n22 $421 7n23 $426 7n24 $440 7n25 $452 7n26 $454 7n
27 $447 7n28 $443 7n29 $449 7n30 $461 7n

No check-in: 1, 2, 3, 4

No check-out: 1, 2, 3, 4

July 2027$392–$827/night · 97% open
SuMoTuWeThFrSa
1 $534 7n2 $538 7n3 $565 7n
4 $563 7n5 $490 7n6 $477 7n7 $476 7n8 $484 7n9 $495 7n10 $635 7n
11 $596 7n12 $596 7n13 $596 7n14 $596 7n15 $596 7n16 $636 7n17 $827 7n
18 $827 7n19 $827 7n20 $827 7n21 $827 7n22 $827 7n23 $827 7n24 $424 7n
25 $410 7n26 $399 7n27 $392 7n28 $394 7n29 $404 7n30 $408 7n31 —

No check-in: 4, 5, 6, 7, 8, 9

No check-out: 4, 5, 6, 7, 8, 9

August 2027$229–$419/night · 81% open
SuMoTuWeThFrSa
1 —2 —3 —4 —5 —6 —7 $413 7n
8 $419 7n9 $391 7n10 $382 7n11 $369 7n12 $365 7n13 $356 7n14 $301 7n
15 $283 7n16 $281 7n17 $281 7n18 $262 7n19 $264 7n20 $281 7n21 $281 7n
22 $272 7n23 $258 7n24 $253 7n25 $229 7n26 $237 7n27 $258 7n28 $306 7n
29 $298 7n30 $293 7n31 $288 7n

No check-in: 15, 16, 17, 18, 19, 20, 22, 23, 24, 25, 26, 27, 29, 30, 31

No check-out: 15, 16, 17, 18, 19, 20, 22, 23, 24, 25, 26, 27, 29, 30, 31

September 2027$200–$430/night · 100% open
SuMoTuWeThFrSa
1 $289 7n2 $430 7n3 $429 7n4 $275 7n
5 $271 7n6 $264 7n7 $260 7n8 $220 7n9 $235 7n10 $235 7n11 $245 7n
12 $215 7n13 $200 7n14 $200 7n15 $200 7n16 $207 7n17 $221 7n18 $276 7n
19 $272 7n20 $272 7n21 $271 7n22 $271 7n23 $274 7n24 $280 7n25 $217 7n
26 $208 7n27 $201 7n28 $200 7n29 $204 7n30 $215 7n

No check-in: 1, 2, 3, 5, 6, 7, 8, 9, 10, 12, 13, 14, 15, 16, 17, 19, 20, 21, 22, 23, 24, 26, 27, 28, 29, 30

No check-out: 1, 2, 3, 5, 6, 7, 8, 9, 10, 12, 13, 14, 15, 16, 17, 19, 20, 21, 22, 23, 24, 26, 27, 28, 29, 30

October 2027$207–$269/night · 100% open
SuMoTuWeThFrSa
1 $222 7n2 $211 7n
3 $208 7n4 $209 7n5 $207 7n6 $217 7n7 $237 7n8 $248 7n9 $255 7n
10 $255 7n11 $253 7n12 $247 7n13 $247 7n14 $263 7n15 $268 7n16 $269 7n
17 $258 7n18 $256 7n19 $252 7n20 $254 7n21 $255 7n22 $265 7n23 $235 7n
24 $230 7n25 $230 7n26 $230 7n27 $230 7n28 $230 7n29 $230 7n30 $219 7n
31 $210 7n

No check-in: 1, 3, 4, 5, 6, 7, 8, 10, 11, 12, 13, 14, 15, 17, 18, 19, 20, 21, 22, 24, 25, 26, 27, 28, 29, 31

No check-out: 1, 3, 4, 5, 6, 7, 8, 10, 11, 12, 13, 14, 15, 17, 18, 19, 20, 21, 22, 24, 25, 26, 27, 28, 29, 31

Rates updated: November 8, 2026