Carefree Cay — Rates & Availability

Prime Vacations - Anna Maria Island3 bedrooms2.5 bathsSleeps 6

Check Availability & Book Direct

Rates as of September 23, 2026

Pricing Summary

Nightly Rate
$251–$1207 /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.

September 20260% open
SuMoTuWeThFrSa
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$251–$303/night · 23% open
SuMoTuWeThFrSa
1 2 3 4 5
6 7 8 9 10 11 12 $295 5n
13 $267 5n14 $255 5n15 $251 5n16 $259 5n17 $280 5n18 $303 5n19
20 21 22 23 24 25 26
27 28 29 30 31
January 2027$580–$599/night · 6% 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 $580 5n
31 $599 5n
February 2027$604–$721/night · 18% open
SuMoTuWeThFrSa
1 $610 5n2 $604 5n3 $632 5n4 $678 5n5 $721 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$1112–$1207/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 $1207 7n
28 $1183 7n29 $1173 7n30 $1147 7n31 $1112 7n

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

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

April 2027$645–$1131/night · 100% open
SuMoTuWeThFrSa
1 $1131 7n2 $1106 7n3 $1010 7n
4 $961 7n5 $1031 7n6 $889 7n7 $924 7n8 $886 7n9 $843 7n10 $759 5n
11 $723 5n12 $679 5n13 $645 5n14 $735 5n15 $743 5n16 $748 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, 4, 5, 6, 7, 8, 9

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

May 2027$623–$1124/night · 100% open
SuMoTuWeThFrSa
1 $719 5n
2 $689 5n3 $669 5n4 $659 5n5 $742 5n6 $701 5n7 $691 5n8 $731 5n
9 $658 5n10 $658 5n11 $658 5n12 $644 5n13 $687 5n14 $680 5n15 $704 5n
16 $680 5n17 $658 5n18 $623 5n19 $633 5n20 $1069 5n21 $1067 5n22 $942 5n
23 $1124 5n24 $727 5n25 $714 5n26 $688 5n27 $704 5n28 $755 5n29 $721 7n
30 $724 7n31 $732 7n

No check-in: 30, 31

No check-out: 30, 31

June 2027$706–$933/night · 100% open
SuMoTuWeThFrSa
1 $771 7n2 $706 7n3 $730 7n4 $763 7n5 $780 7n
6 $753 7n7 $755 7n8 $771 7n9 $790 7n10 $816 7n11 $836 7n12 $815 7n
13 $793 7n14 $786 7n15 $790 7n16 $793 7n17 $829 7n18 $824 7n19 $873 7n
20 $847 7n21 $824 7n22 $835 7n23 $837 7n24 $856 7n25 $933 7n26 $839 7n
27 $828 7n28 $829 7n29 $831 7n30 $854 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$763–$984/night · 100% open
SuMoTuWeThFrSa
1 $956 7n2 $962 7n3 $965 7n
4 $961 7n5 $864 7n6 $845 7n7 $841 7n8 $854 7n9 $873 7n10 $984 7n
11 $935 7n12 $913 7n13 $900 7n14 $926 7n15 $953 7n16 $949 7n17 $839 7n
18 $820 7n19 $794 7n20 $784 7n21 $790 7n22 $831 7n23 $845 7n24 $814 7n
25 $794 7n26 $775 7n27 $763 7n28 $766 7n29 $783 7n30 $793 7n31 $776 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$424–$883/night · 100% open
SuMoTuWeThFrSa
1 $834 7n2 $809 7n3 $792 7n4 $785 7n5 $801 7n6 $804 7n7 $883 7n
8 $847 7n9 $776 7n10 $711 7n11 $612 7n12 $619 7n13 $617 7n14 $612 5n
15 $577 5n16 $533 5n17 $532 5n18 $532 5n19 $685 5n20 $685 5n21 $538 5n
22 $494 5n23 $466 5n24 $455 5n25 $461 5n26 $477 5n27 $694 5n28 $696 5n
29 $662 5n30 $431 5n31 $424 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

Rates updated: September 23, 2026