Carefree Cay — Rates & Availability

Prime Vacations - Anna Maria Island3 bedrooms2.5 bathsSleeps 6

Check Availability & Book Direct

Rates as of July 29, 2026

Pricing Summary

Nightly Rate
$280–$1235 /night
Min Stay
5 nights
Next Available
Dec 12

12-Month Rate Calendar

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

July 20260% open
SuMoTuWeThFrSa
29 —30 —31 —
August 20260% 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 —28 —29 —
30 —31 —
September 20260% 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 —28 —29 —30 —
October 20260% 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 —28 —29 —30 —31 —
November 20260% 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 —28 —
29 —30 —
December 2026$280–$612/night · 42% open
SuMoTuWeThFrSa
1 —2 —3 —4 —5 —
6 —7 —8 —9 —10 —11 —12 $295 5n
13 $280 5n14 $280 5n15 $280 5n16 $280 5n17 $299 5n18 $325 5n19 —
20 —21 —22 —23 —24 —25 —26 $612 7n
27 $612 7n28 $612 7n29 $612 7n30 $612 7n31 $612 7n

No check-in: 27, 28, 29, 30, 31

No check-out: 27, 28, 29, 30, 31

January 2027$501–$612/night · 10% open
SuMoTuWeThFrSa
1 $612 7n2 —
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 —28 —29 —30 $501 5n
31 $530 5n

No check-in: 1

February 2027$521–$612/night · 18% open
SuMoTuWeThFrSa
1 $527 5n2 $521 5n3 $546 5n4 $585 5n5 $612 5n6 —
7 —8 —9 —10 —11 —12 —13 —
14 —15 —16 —17 —18 —19 —20 —
21 —22 —23 —24 —25 —26 —27 —
28 —
March 2027$1079–$1235/night · 16% 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 $1235 7n
28 $1197 7n29 $1187 7n30 $1131 7n31 $1079 7n

No check-in: 28, 29, 30, 31

No check-out: 28, 29, 30, 31

April 2027$565–$1134/night · 100% open
SuMoTuWeThFrSa
1 $1134 7n2 $1125 7n3 $1013 7n
4 $612 7n5 $612 7n6 $612 7n7 $612 7n8 $612 7n9 $612 7n10 $612 5n
11 $612 5n12 $612 5n13 $612 5n14 $612 5n15 $612 5n16 $612 5n17 $612 5n
18 $612 5n19 $612 5n20 $612 5n21 $612 5n22 $612 5n23 $612 5n24 $612 5n
25 $578 5n26 $565 5n27 $565 5n28 $565 5n29 $565 5n30 $612 5n

No check-in: 1, 2, 4, 5, 6, 7, 8, 9

No check-out: 1, 2, 4, 5, 6, 7, 8, 9

May 2027$469–$612/night · 100% open
SuMoTuWeThFrSa
1 $509 5n
2 $489 5n3 $476 5n4 $469 5n5 $505 5n6 $507 5n7 $516 5n8 $548 5n
9 $497 5n10 $494 5n11 $494 5n12 $483 5n13 $526 5n14 $521 5n15 $540 5n
16 $527 5n17 $500 5n18 $470 5n19 $498 5n20 $612 5n21 $612 5n22 $612 5n
23 $612 5n24 $606 5n25 $595 5n26 $601 5n27 $612 5n28 $612 5n29 $612 7n
30 $612 7n31 $612 7n

No check-in: 30, 31

No check-out: 30, 31

June 2027$612–$612/night · 100% open
SuMoTuWeThFrSa
1 $612 7n2 $612 7n3 $612 7n4 $612 7n5 $612 7n
6 $612 7n7 $612 7n8 $612 7n9 $612 7n10 $612 7n11 $612 7n12 $612 7n
13 $612 7n14 $612 7n15 $612 7n16 $612 7n17 $612 7n18 $612 7n19 $612 7n
20 $612 7n21 $612 7n22 $612 7n23 $612 7n24 $612 7n25 $612 7n26 $612 7n
27 $612 7n28 $612 7n29 $612 7n30 $612 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

Rates updated: July 29, 2026