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

Upstay4 bedrooms4 bathsSleeps 12

Check Availability & Book Direct

Rates as of November 8, 2026

Pricing Summary

Nightly Rate
$225–$2338 /night
Cleaning Fee
$249 per stay
Min Stay
2 nights
Next Available
Nov 10

12-Month Rate Calendar

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

November 2026$225–$473/night · 79% open
SuMoTuWeThFrSa
7 —8 —9 —10 $225 2n11 $225 2n12 $225 2n13 $377 2n
14 $404 2n15 $268 2n16 $234 2n17 $233 2n18 $225 2n19 $238 2n20 $406 2n
21 $406 2n22 $264 2n23 —24 —25 $412 2n26 $471 2n27 $473 2n
28 $390 2n29 $231 2n30 $225 2n
December 2026$225–$589/night · 81% open
SuMoTuWeThFrSa
1 $243 2n2 $225 2n3 $225 2n4 $317 2n5 $315 2n
6 $225 2n7 $225 2n8 $225 2n9 $225 2n10 $225 2n11 $331 2n12 $356 2n
13 $284 2n14 $277 2n15 $308 2n16 $309 2n17 $323 2n18 $354 2n19 $373 2n
20 $376 2n21 $412 2n22 $444 2n23 $503 2n24 $579 2n25 $589 2n26 —
27 —28 —29 —30 —31 —
January 2027$327–$616/night · 45% open
SuMoTuWeThFrSa
1 —2 $616 2n
3 $403 2n4 $363 2n5 $329 2n6 $339 2n7 $338 2n8 —9 —
10 $355 2n11 $327 2n12 $360 2n13 $351 2n14 $357 2n15 $475 3n16 $455 3n
17 $407 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$485–$1505/night · 90% open
SuMoTuWeThFrSa
1 —2 —3 —4 $556 2n5 $578 3n6 $610 3n
7 $574 2n8 $545 2n9 $633 2n10 $694 2n11 $741 2n12 $853 3n13 $779 3n
14 $706 2n15 $783 2n16 $1088 3n17 $1088 3n18 $1132 3n19 $997 3n20 $863 3n
21 $587 2n22 $540 2n23 $662 2n24 $779 2n25 $927 3n26 $1482 3n27 $1505 3n
28 $1416 3n29 $486 2n30 $485 2n31 $492 2n
April 2027$485–$639/night · 100% open
SuMoTuWeThFrSa
1 $615 2n2 $613 3n3 $584 3n
4 $507 2n5 $485 2n6 $485 2n7 $485 2n8 $608 2n9 $629 3n10 $634 3n
11 $485 2n12 $485 2n13 $485 2n14 $485 2n15 $485 2n16 $639 3n17 $638 3n
18 $485 2n19 $485 2n20 $485 2n21 $485 2n22 $485 2n23 $617 3n24 $607 3n
25 $485 2n26 $485 2n27 $485 2n28 $485 2n29 $485 2n30 $572 3n
May 2027$485–$1308/night · 100% open
SuMoTuWeThFrSa
1 $579 3n
2 $485 2n3 $485 2n4 $485 2n5 $485 2n6 $485 2n7 $709 3n8 $709 3n
9 $933 2n10 $485 2n11 $485 2n12 $485 2n13 $667 2n14 $851 3n15 $851 3n
16 $765 2n17 $485 2n18 $485 2n19 $485 2n20 $883 2n21 $836 3n22 $836 3n
23 $607 2n24 $605 2n25 $516 2n26 $548 2n27 $883 3n28 $1308 3n29 $1287 3n
30 $1130 2n31 $704 2n
June 2027$657–$1456/night · 100% open
SuMoTuWeThFrSa
1 $699 2n2 $696 2n3 $774 2n4 $1029 3n5 $1054 3n
6 $699 2n7 $657 2n8 $657 2n9 $691 2n10 $787 2n11 $1138 3n12 $1137 3n
13 $987 2n14 $744 2n15 $824 2n16 $823 2n17 $1456 3n18 $1401 3n19 $1342 3n
20 $889 2n21 $878 2n22 $864 2n23 $989 2n24 $989 2n25 $1343 3n26 $1222 3n
27 $830 2n28 $755 2n29 $755 2n30 $1034 2n
July 2027$823–$2338/night · 100% open
SuMoTuWeThFrSa
1 $1122 3n2 $2338 3n3 $2297 3n
4 $2314 3n5 $1002 2n6 $960 2n7 $988 2n8 $1149 2n9 $1375 3n10 $1350 3n
11 $974 2n12 $845 2n13 $823 2n14 $867 2n15 $1119 2n16 $1432 3n17 $1413 3n
18 $980 2n19 $975 2n20 $966 2n21 $978 2n22 $1141 2n23 $1487 3n24 $1425 3n
25 $980 2n26 $953 2n27 $945 2n28 $954 2n29 $1140 2n30 $1427 3n31 $1318 3n
August 2027$485–$1096/night · 100% open
SuMoTuWeThFrSa
1 $834 2n2 $771 2n3 $846 2n4 $724 2n5 $898 2n6 $1096 3n7 $1058 3n
8 $763 2n9 $716 2n10 $627 2n11 $619 2n12 $749 2n13 $947 3n14 $937 3n
15 $763 2n16 $874 2n17 $494 2n18 $485 2n19 $571 2n20 $805 3n21 $822 3n
22 $651 2n23 $485 2n24 $485 2n25 $562 2n26 $545 2n27 $747 3n28 $765 3n
29 $752 2n30 $487 2n31 $485 2n
September 2027$485–$1095/night · 100% open
SuMoTuWeThFrSa
1 $485 2n2 $706 2n3 $1043 3n4 $1095 3n
5 $1079 3n6 $485 2n7 $485 2n8 $485 2n9 $706 2n10 $635 3n11 $709 3n
12 $854 2n13 $485 2n14 $485 2n15 $485 2n16 $660 2n17 $602 3n18 $602 3n
19 $660 2n20 $485 2n21 $485 2n22 $485 2n23 $660 2n24 $622 3n25 $622 3n
26 $660 2n27 $485 2n28 $485 2n29 $485 2n30 $523 2n
October 2027$485–$686/night · 100% open
SuMoTuWeThFrSa
1 $534 3n2 $660 3n
3 $523 2n4 $485 2n5 $485 2n6 $485 2n7 $485 2n8 $686 3n9 $671 3n
10 $632 2n11 $485 2n12 $485 2n13 $485 2n14 $485 2n15 $534 3n16 $534 3n
17 $485 2n18 $485 2n19 $485 2n20 $528 2n21 $528 2n22 $534 3n23 $534 3n
24 $485 2n25 $485 2n26 $485 2n27 $485 2n28 $485 2n29 $534 3n30 $534 3n
31 $485 2n

Rates updated: November 8, 2026