Simply Chic — Rates & Availability

Prime Vacations - Anna Maria Island4 bedrooms3 bathsSleeps 8

Check Availability & Book Direct

Rates as of October 9, 2026

Pricing Summary

Nightly Rate
$300–$1504 /night
Min Stay
7 nights
Next Available
Oct 9

12-Month Rate Calendar

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

October 2026$300–$300/night · 4% open
SuMoTuWeThFrSa
8 —9 $300 7n10 —
11 —12 —13 —14 —15 —16 —17 —
18 —19 —20 —21 —22 —23 —24 —
25 —26 —27 —28 —29 —30 —31 —
November 2026$320–$320/night · 23% open
SuMoTuWeThFrSa
1 —2 —3 —4 —5 —6 —7 —
8 —9 —10 —11 —12 —13 —14 $320 7n
15 $320 7n16 $320 7n17 $320 7n18 $320 7n19 $320 7n20 $320 7n21 —
22 —23 —24 —25 —26 —27 —28 —
29 —30 —
December 2026$300–$624/night · 68% open
SuMoTuWeThFrSa
1 —2 —3 —4 —5 $300 7n
6 $300 7n7 $300 7n8 $300 7n9 $300 7n10 $300 7n11 $300 7n12 $300 7n
13 $300 7n14 $300 7n15 $300 7n16 $300 7n17 $300 7n18 $300 7n19 $421 7n
20 $429 7n21 $446 7n22 $455 7n23 $522 7n24 $562 7n25 $624 7n26 —
27 —28 —29 —30 —31 —

No check-in: 6, 7, 8, 9, 10, 11, 13, 14, 15, 16, 17, 18, 20, 21, 22, 23, 24, 25

No check-out: 6, 7, 8, 9, 10, 11, 13, 14, 15, 16, 17, 18, 20, 21, 22, 23, 24

January 2027$300–$443/night · 90% open
SuMoTuWeThFrSa
1 —2 $396 7n
3 $338 7n4 $307 7n5 $300 7n6 $300 7n7 $300 7n8 $307 7n9 $319 7n
10 $303 7n11 $300 7n12 $300 7n13 $300 7n14 $309 7n15 $320 7n16 $313 7n
17 $300 7n18 $300 7n19 $300 7n20 $300 7n21 $303 7n22 $311 7n23 $418 7n
24 $403 7n25 $393 7n26 $391 7n27 $404 7n28 $425 7n29 $443 7n30 —
31 —

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

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

February 2027$910–$934/night · 7% open
SuMoTuWeThFrSa
1 —2 —3 —4 —5 —6 —
7 —8 —9 —10 —11 —12 —13 —
14 —15 —16 —17 —18 —19 —20 —
21 —22 —23 —24 —25 —26 —27 $934 7n
28 $910 7n

No check-in: 28

No check-out: 28

March 2027$910–$1504/night · 39% open
SuMoTuWeThFrSa
1 $913 7n2 $910 7n3 $927 7n4 $968 7n5 $1002 7n6 —
7 —8 —9 —10 —11 —12 —13 —
14 —15 —16 —17 —18 —19 —20 $1301 7n
21 $1300 7n22 $1319 7n23 $1354 7n24 $1408 7n25 $1471 7n26 $1504 7n27 —
28 —29 —30 —31 —

No check-in: 1, 2, 3, 4, 5, 21, 22, 23, 24, 25, 26

No check-out: 1, 2, 3, 4, 5, 21, 22, 23, 24, 25, 26

April 2027$597–$690/night · 47% open
SuMoTuWeThFrSa
1 —2 —3 —
4 —5 —6 —7 —8 —9 —10 —
11 —12 —13 —14 —15 —16 —17 $666 7n
18 $666 7n19 $666 7n20 $666 7n21 $666 7n22 $666 7n23 $597 7n24 $690 7n
25 $637 7n26 $637 7n27 $637 7n28 $637 7n29 $637 7n30 $689 7n

No check-in: 18, 19, 20, 21, 22, 23, 25, 26, 27, 28, 29, 30

No check-out: 18, 19, 20, 21, 22, 23, 25, 26, 27, 28, 29, 30

May 2027$485–$747/night · 55% open
SuMoTuWeThFrSa
1 —
2 —3 —4 —5 —6 —7 —8 $496 7n
9 $493 7n10 $493 7n11 $485 7n12 $493 7n13 $485 7n14 $499 7n15 —
16 —17 —18 —19 —20 —21 —22 $704 7n
23 $710 7n24 $715 7n25 $721 7n26 $622 7n27 $634 7n28 $747 7n29 $731 7n
30 $668 7n31 $714 7n

No check-in: 9, 10, 11, 12, 13, 14, 23, 24, 25, 26, 27, 28, 30, 31

No check-out: 9, 10, 11, 12, 13, 14, 23, 24, 25, 26, 27, 28, 30, 31

June 2027$631–$834/night · 100% open
SuMoTuWeThFrSa
1 $712 7n2 $715 7n3 $742 7n4 $808 7n5 $797 7n
6 $730 7n7 $723 7n8 $725 7n9 $725 7n10 $732 7n11 $796 7n12 $654 7n
13 $643 7n14 $637 7n15 $631 7n16 $642 7n17 $649 7n18 $667 7n19 $696 7n
20 $686 7n21 $696 7n22 $664 7n23 $669 7n24 $677 7n25 $769 7n26 $791 7n
27 $803 7n28 $810 7n29 $823 7n30 $834 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$515–$914/night · 100% open
SuMoTuWeThFrSa
1 $904 7n2 $914 7n3 $825 7n
4 $826 7n5 $804 7n6 $793 7n7 $810 7n8 $821 7n9 $829 7n10 $669 7n
11 $636 7n12 $621 7n13 $618 7n14 $631 7n15 $649 7n16 $646 7n17 $657 7n
18 $629 7n19 $629 7n20 $629 7n21 $629 7n22 $644 7n23 $636 7n24 $665 7n
25 $662 7n26 $653 7n27 $635 7n28 $628 7n29 $629 7n30 $623 7n31 $515 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$300–$536/night · 100% open
SuMoTuWeThFrSa
1 $503 7n2 $493 7n3 $484 7n4 $488 7n5 $489 7n6 $490 7n7 $536 7n
8 $498 7n9 $467 7n10 $452 7n11 $437 7n12 $437 7n13 $427 7n14 $438 7n
15 $427 7n16 $419 7n17 $411 7n18 $413 7n19 $414 7n20 $421 7n21 $322 7n
22 $300 7n23 $300 7n24 $300 7n25 $300 7n26 $300 7n27 $320 7n28 $300 7n
29 $300 7n30 $300 7n31 $300 7n

No check-in: 1, 2, 3, 4, 5, 6, 8, 9, 10, 11, 12, 13, 15, 16, 17, 18, 19, 20, 22, 23, 24, 25, 26, 27, 29, 30, 31

No check-out: 1, 2, 3, 4, 5, 6, 8, 9, 10, 11, 12, 13, 15, 16, 17, 18, 19, 20, 22, 23, 24, 25, 26, 27, 29, 30, 31

September 2027$300–$421/night · 100% open
SuMoTuWeThFrSa
1 $300 7n2 $300 7n3 $335 7n4 $390 7n
5 $411 7n6 $357 7n7 $357 7n8 $357 7n9 $357 7n10 $397 7n11 $377 7n
12 $339 7n13 $339 7n14 $339 7n15 $339 7n16 $339 7n17 $374 7n18 $421 7n
19 $381 7n20 $381 7n21 $381 7n22 $381 7n23 $381 7n24 $418 7n25 $372 7n
26 $367 7n27 $364 7n28 $361 7n29 $367 7n30 $371 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

Rates updated: October 9, 2026