Pineapple Key — Rates & Availability

Anna Maria Vacations4 bedrooms2 bathsSleeps 8

Check Availability & Book Direct

Rates as of September 11, 2026

Pricing Summary

Nightly Rate
$200–$200 /night
Min Stay
7 nights
Next Available
Oct 10

12-Month Rate Calendar

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

September 20260% open
SuMoTuWeThFrSa
11 —12 —13 —14 —15 —
16 —17 —18 —19 —20 —21 —22 —
23 —24 —25 —26 —27 —28 —29 —
30 —
October 2026$200–$200/night · 48% open
SuMoTuWeThFrSa
1 —2 —3 —
4 —5 —6 —7 —8 —9 —10 $200 7n
11 $200 7n12 $200 7n13 $200 7n14 $200 7n15 $200 7n16 $200 7n17 —
18 —19 —20 —21 —22 —23 —24 $200 7n
25 $200 7n26 $200 7n27 $200 7n28 $200 7n29 $200 7n30 $200 7n31 $200 7n
November 2026$200–$200/night · 77% open
SuMoTuWeThFrSa
1 $200 7n2 $200 7n3 $200 7n4 $200 7n5 $200 7n6 $200 7n7 $200 7n
8 $200 7n9 $200 7n10 $200 7n11 $200 7n12 $200 7n13 $200 7n14 $200 7n
15 $200 7n16 $200 7n17 $200 7n18 $200 7n19 $200 7n20 $200 7n21 —
22 —23 —24 —25 —26 —27 —28 $200 7n
29 $200 7n30 $200 7n

No check-in: 1, 2, 3, 4, 5, 6, 8, 9, 10, 11, 12, 13, 15, 16, 17, 18, 19, 20, 29, 30

No check-out: 1, 2, 3, 4, 5, 6, 8, 9, 10, 11, 12, 13, 15, 16, 17, 18, 19, 20, 29, 30

December 2026$200–$200/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 $200 7n21 $200 7n22 $200 7n23 $200 7n24 $200 7n25 $200 7n26 —
27 —28 —29 —30 —31 —

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

January 2027$200–$200/night · 97% open
SuMoTuWeThFrSa
1 —2 $200 7n
3 $200 7n4 $200 7n5 $200 7n6 $200 7n7 $200 7n8 $200 7n9 $200 7n
10 $200 7n11 $200 7n12 $200 7n13 $200 7n14 $200 7n15 $200 7n16 $200 7n
17 $200 7n18 $200 7n19 $200 7n20 $200 7n21 $200 7n22 $200 7n23 $200 7n
24 $200 7n25 $200 7n26 $200 7n27 $200 7n28 $200 7n29 $200 7n30 $200 7n
31 $200 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$200–$200/night · 43% open
SuMoTuWeThFrSa
1 $200 7n2 $200 7n3 $200 7n4 $200 7n5 $200 7n6 $200 7n
7 $200 7n8 $200 7n9 $200 7n10 $200 7n11 $200 7n12 $200 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$200–$200/night · 84% open
SuMoTuWeThFrSa
1 —2 —3 —4 —5 —6 $200 7n
7 $200 7n8 $200 7n9 $200 7n10 $200 7n11 $200 7n12 $200 7n13 $200 7n
14 $200 7n15 $200 7n16 $200 7n17 $200 7n18 $200 7n19 $200 7n20 $200 7n
21 $200 7n22 $200 7n23 $200 7n24 $200 7n25 $200 7n26 $200 7n27 $200 7n
28 $200 7n29 $200 7n30 $200 7n31 $200 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$200–$200/night · 77% open
SuMoTuWeThFrSa
1 $200 7n2 $200 7n3 —
4 —5 —6 —7 —8 —9 —10 $200 7n
11 $200 7n12 $200 7n13 $200 7n14 $200 7n15 $200 7n16 $200 7n17 $200 7n
18 $200 7n19 $200 7n20 $200 7n21 $200 7n22 $200 7n23 $200 7n24 $200 7n
25 $200 7n26 $200 7n27 $200 7n28 $200 7n29 $200 7n30 $200 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$200–$200/night · 100% open
SuMoTuWeThFrSa
1 $200 7n
2 $200 7n3 $200 7n4 $200 7n5 $200 7n6 $200 7n7 $200 7n8 $200 7n
9 $200 7n10 $200 7n11 $200 7n12 $200 7n13 $200 7n14 $200 7n15 $200 7n
16 $200 7n17 $200 7n18 $200 7n19 $200 7n20 $200 7n21 $200 7n22 $200 7n
23 $200 7n24 $200 7n25 $200 7n26 $200 7n27 $200 7n28 $200 7n29 $200 7n
30 $200 7n31 $200 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$200–$200/night · 77% open
SuMoTuWeThFrSa
1 $200 7n2 $200 7n3 $200 7n4 $200 7n5 —
6 —7 —8 —9 —10 —11 —12 $200 7n
13 $200 7n14 $200 7n15 $200 7n16 $200 7n17 $200 7n18 $200 7n19 $200 7n
20 $200 7n21 $200 7n22 $200 7n23 $200 7n24 $200 7n25 $200 7n26 $200 7n
27 $200 7n28 $200 7n29 $200 7n30 $200 7n

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

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

July 2027$200–$200/night · 97% open
SuMoTuWeThFrSa
1 $200 7n2 $200 7n3 $200 7n
4 $200 7n5 $200 7n6 $200 7n7 $200 7n8 $200 7n9 $200 7n10 $200 7n
11 $200 7n12 $200 7n13 $200 7n14 $200 7n15 $200 7n16 $200 7n17 $200 7n
18 $200 7n19 $200 7n20 $200 7n21 $200 7n22 $200 7n23 $200 7n24 $200 7n
25 $200 7n26 $200 7n27 $200 7n28 $200 7n29 $200 7n30 $200 7n31 —

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

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

August 2027$200–$200/night · 81% open
SuMoTuWeThFrSa
1 —2 —3 —4 —5 —6 —7 $200 7n
8 $200 7n9 $200 7n10 $200 7n11 $200 7n12 $200 7n13 $200 7n14 $200 7n
15 $200 7n16 $200 7n17 $200 7n18 $200 7n19 $200 7n20 $200 7n21 $200 7n
22 $200 7n23 $200 7n24 $200 7n25 $200 7n26 $200 7n27 $200 7n28 $200 7n
29 $200 7n30 $200 7n31 $200 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

Rates updated: September 11, 2026