Carefree Cay — Rates & Availability

Prime Vacations - Anna Maria Island3 bedrooms2.5 bathsSleeps 6

Check Availability & Book Direct

Rates as of November 8, 2026

Pricing Summary

Nightly Rate
$245–$1295 /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.

November 20260% 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 —
December 2026$245–$295/night · 23% open
SuMoTuWeThFrSa
1 —2 —3 —4 —5 —
6 —7 —8 —9 —10 —11 —12 $295 5n
13 $250 5n14 $245 5n15 $245 5n16 $245 5n17 $261 5n18 $284 5n19 —
20 —21 —22 —23 —24 —25 —26 —
27 —28 —29 —30 —31 —
January 2027$503–$503/night · 3% 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 $503 4n
31 —
February 20270% 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 —
March 2027$1185–$1295/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 $1295 7n
28 $1272 7n29 $1261 7n30 $1233 7n31 $1185 7n

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

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

April 2027$676–$1184/night · 100% open
SuMoTuWeThFrSa
1 $1184 7n2 $1172 7n3 $1023 5n
4 $961 5n5 $1031 5n6 $889 5n7 $924 5n8 $886 5n9 $843 5n10 $787 5n
11 $751 5n12 $710 5n13 $676 5n14 $772 5n15 $780 5n16 $785 5n17 $793 5n
18 $819 5n19 $819 5n20 $819 5n21 $819 5n22 $819 5n23 $819 5n24 $860 5n
25 $753 5n26 $753 5n27 $753 5n28 $753 5n29 $753 5n30 $822 5n

No check-in: 1, 2

No check-out: 1, 2

May 2027$623–$1124/night · 100% open
SuMoTuWeThFrSa
1 $744 5n
2 $716 5n3 $695 5n4 $684 5n5 $779 5n6 $715 5n7 $738 5n8 $767 5n
9 $691 5n10 $691 5n11 $691 5n12 $647 5n13 $670 5n14 $697 5n15 $687 5n
16 $672 5n17 $623 5n18 $624 5n19 $634 5n20 $1069 5n21 $1067 5n22 $942 5n
23 $1124 5n24 $727 5n25 $714 5n26 $688 5n27 $697 5n28 $755 5n29 $683 7n
30 $674 7n31 $682 7n

No check-in: 30, 31

No check-out: 30, 31

June 2027$663–$933/night · 100% open
SuMoTuWeThFrSa
1 $720 7n2 $663 7n3 $685 7n4 $724 7n5 $764 7n
6 $743 7n7 $738 7n8 $748 7n9 $766 7n10 $801 7n11 $820 7n12 $808 7n
13 $776 7n14 $804 7n15 $798 7n16 $819 7n17 $846 7n18 $855 7n19 $883 7n
20 $840 7n21 $822 7n22 $815 7n23 $824 7n24 $853 7n25 $933 7n26 $836 7n
27 $825 7n28 $818 7n29 $829 7n30 $851 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$760–$960/night · 100% open
SuMoTuWeThFrSa
1 $946 7n2 $953 7n3 $956 7n
4 $952 7n5 $861 7n6 $841 7n7 $838 7n8 $853 7n9 $871 7n10 $960 7n
11 $906 7n12 $875 7n13 $873 7n14 $890 7n15 $924 7n16 $930 7n17 $845 7n
18 $818 7n19 $793 7n20 $783 7n21 $789 7n22 $816 7n23 $825 7n24 $821 7n
25 $794 7n26 $773 7n27 $760 7n28 $763 7n29 $781 7n30 $790 7n31 $774 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$423–$839/night · 100% open
SuMoTuWeThFrSa
1 $839 7n2 $808 7n3 $791 7n4 $792 7n5 $797 7n6 $794 7n7 $829 7n
8 $743 7n9 $672 7n10 $619 7n11 $602 7n12 $612 7n13 $609 7n14 $602 5n
15 $567 5n16 $532 5n17 $532 5n18 $532 5n19 $685 5n20 $685 5n21 $564 5n
22 $546 5n23 $518 5n24 $507 5n25 $459 5n26 $476 5n27 $694 5n28 $696 5n
29 $662 5n30 $431 5n31 $423 5n

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$389–$586/night · 100% open
SuMoTuWeThFrSa
1 $433 5n2 $491 5n3 $565 5n4 $586 5n
5 $578 5n6 $490 5n7 $482 5n8 $407 5n9 $437 5n10 $435 5n11 $491 5n
12 $431 5n13 $395 5n14 $389 5n15 $395 5n16 $416 5n17 $445 5n18 $501 5n
19 $508 5n20 $493 5n21 $508 5n22 $493 5n23 $468 5n24 $488 5n25 $479 5n
26 $460 5n27 $444 5n28 $436 5n29 $451 5n30 $476 5n
October 2027$449–$641/night · 100% open
SuMoTuWeThFrSa
1 $493 5n2 $456 5n
3 $451 5n4 $458 5n5 $449 5n6 $491 5n7 $528 5n8 $550 5n9 $553 5n
10 $553 5n11 $549 5n12 $535 5n13 $554 5n14 $570 5n15 $608 5n16 $641 5n
17 $581 5n18 $581 5n19 $581 5n20 $581 5n21 $581 5n22 $641 5n23 $641 5n
24 $581 5n25 $581 5n26 $581 5n27 $581 5n28 $575 5n29 $486 5n30 $475 5n
31 $456 5n

Rates updated: November 8, 2026