Upstay: Island Retreat w Private Pool & Bay View — Rates & Availability

Upstay4 bedrooms4 bathsSleeps 12

Check Availability & Book Direct

Rates as of October 8, 2026

Pricing Summary

Nightly Rate
$263–$2888 /night
Cleaning Fee
$249 per stay
Pet Fee
$100 per stay
Min Stay
2 nights
Next Available
Oct 10

12-Month Rate Calendar

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

October 2026$269–$809/night · 56% open
SuMoTuWeThFrSa
7 —8 —9 —
10 $809 2n11 —12 —13 $293 2n14 —15 —16 —
17 —18 $309 2n19 $301 2n20 $301 2n21 $297 2n22 $299 2n23 $430 2n
24 $416 2n25 $302 2n26 $296 2n27 $292 2n28 $269 2n29 $293 2n30 —
31 —
November 2026$263–$626/night · 100% open
SuMoTuWeThFrSa
1 $296 2n2 $282 2n3 $275 2n4 $275 2n5 $299 2n6 $457 2n7 $426 2n
8 $272 2n9 $263 2n10 $284 2n11 $307 2n12 $328 2n13 $434 2n14 $459 2n
15 $313 2n16 $288 2n17 $287 2n18 $263 2n19 $297 2n20 $452 2n21 $481 2n
22 $338 2n23 $352 2n24 $426 2n25 $555 2n26 $626 2n27 $626 2n28 $514 2n
29 $354 2n30 $322 2n
December 2026$299–$977/night · 100% open
SuMoTuWeThFrSa
1 $354 2n2 $299 2n3 $307 2n4 $371 2n5 $372 2n
6 $305 2n7 $328 2n8 $328 2n9 $317 2n10 $327 2n11 $383 2n12 $406 2n
13 $328 2n14 $336 2n15 $369 2n16 $367 2n17 $395 2n18 $430 3n19 $454 3n
20 $458 2n21 $548 2n22 $576 2n23 $657 2n24 $763 2n25 $780 3n26 $830 3n
27 $738 2n28 $747 2n29 $759 2n30 $957 2n31 $977 2n
January 2027$374–$899/night · 55% open
SuMoTuWeThFrSa
1 $899 3n2 $823 3n
3 $479 2n4 $402 2n5 $410 2n6 $433 2n7 $399 2n8 $477 2n9 $472 2n
10 $412 2n11 $374 2n12 $426 2n13 $398 2n14 $403 2n15 $534 3n16 $522 3n
17 $486 2n18 —19 —20 —21 —22 —23 —
24 —25 —26 —27 —28 —29 —30 —
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$566–$1674/night · 90% open
SuMoTuWeThFrSa
1 —2 —3 —4 $598 2n5 $623 3n6 $659 3n
7 $626 2n8 $609 2n9 $700 2n10 $760 2n11 $881 2n12 $995 3n13 $888 3n
14 $710 2n15 $796 2n16 $1294 3n17 $1290 3n18 $1292 3n19 $1129 3n20 $956 3n
21 $655 2n22 $574 2n23 $718 2n24 $766 2n25 $1027 3n26 $1627 3n27 $1674 3n
28 $1593 3n29 $566 2n30 $566 2n31 $566 2n
April 2027$566–$865/night · 100% open
SuMoTuWeThFrSa
1 $620 2n2 $653 3n3 $641 3n
4 $567 2n5 $566 2n6 $566 2n7 $566 2n8 $865 2n9 $721 3n10 $727 3n
11 $566 2n12 $566 2n13 $566 2n14 $566 2n15 $678 2n16 $713 3n17 $726 3n
18 $566 2n19 $566 2n20 $566 2n21 $593 2n22 $765 2n23 $718 3n24 $709 3n
25 $566 2n26 $566 2n27 $566 2n28 $765 2n29 $733 2n30 $687 3n
May 2027$566–$1536/night · 100% open
SuMoTuWeThFrSa
1 $679 3n
2 $566 2n3 $566 2n4 $566 2n5 $566 2n6 $701 2n7 $745 3n8 $745 3n
9 $980 2n10 $566 2n11 $566 2n12 $566 2n13 $701 2n14 $894 3n15 $894 3n
16 $804 2n17 $566 2n18 $566 2n19 $566 2n20 $928 2n21 $897 3n22 $976 3n
23 $703 2n24 $734 2n25 $597 2n26 $647 2n27 $928 3n28 $1522 3n29 $1536 3n
30 $1368 2n31 $795 2n
June 2027$701–$1630/night · 100% open
SuMoTuWeThFrSa
1 $701 2n2 $726 2n3 $861 2n4 $1155 3n5 $1153 3n
6 $791 2n7 $730 2n8 $738 2n9 $871 2n10 $935 2n11 $1338 3n12 $1369 3n
13 $1174 2n14 $936 2n15 $936 2n16 $937 2n17 $1630 3n18 $1518 3n19 $1532 3n
20 $1004 2n21 $995 2n22 $977 2n23 $1039 2n24 $1082 2n25 $1588 3n26 $1440 3n
27 $932 2n28 $793 2n29 $793 2n30 $1086 2n
July 2027$910–$2888/night · 100% open
SuMoTuWeThFrSa
1 $1183 3n2 $2772 3n3 $2787 3n
4 $2888 3n5 $1256 2n6 $1212 2n7 $1193 2n8 $1328 2n9 $1603 3n10 $1544 3n
11 $1139 2n12 $952 2n13 $910 2n14 $957 2n15 $1230 2n16 $1642 3n17 $1688 3n
18 $1134 2n19 $1152 2n20 $1136 2n21 $1138 2n22 $1296 2n23 $1672 3n24 $1598 3n
25 $1115 2n26 $1055 2n27 $1088 2n28 $1089 2n29 $1247 2n30 $1547 3n31 $1411 3n
August 2027$566–$1162/night · 100% open
SuMoTuWeThFrSa
1 $918 2n2 $832 2n3 $802 2n4 $795 2n5 $982 2n6 $1145 3n7 $1162 3n
8 $831 2n9 $752 2n10 $704 2n11 $687 2n12 $826 2n13 $1091 3n14 $1123 3n
15 $802 2n16 $918 2n17 $566 2n18 $566 2n19 $664 2n20 $957 3n21 $1002 3n
22 $698 2n23 $566 2n24 $566 2n25 $566 2n26 $584 2n27 $866 3n28 $872 3n
29 $790 2n30 $566 2n31 $566 2n
September 2027$566–$1367/night · 100% open
SuMoTuWeThFrSa
1 $566 2n2 $742 2n3 $1245 3n4 $1319 3n
5 $1367 3n6 $566 2n7 $566 2n8 $566 2n9 $742 2n10 $667 3n11 $745 3n
12 $897 2n13 $566 2n14 $566 2n15 $566 2n16 $693 2n17 $659 3n18 $661 3n
19 $693 2n20 $566 2n21 $566 2n22 $566 2n23 $693 2n24 $654 3n25 $654 3n
26 $693 2n27 $566 2n28 $566 2n29 $566 2n30 $566 2n

Rates updated: October 8, 2026