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

Upstay4 bedrooms4 bathsSleeps 12

Check Availability & Book Direct

Rates as of September 20, 2026

Pricing Summary

Nightly Rate
$256–$2710 /night
Cleaning Fee
$249 per stay
Pet Fee
$100 per stay
Min Stay
2 nights
Next Available
Sep 20

12-Month Rate Calendar

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

September 2026$256–$305/night · 64% open
SuMoTuWeThFrSa
20 $256 2n21 $260 2n22 $305 2n23 $260 2n24
25 26 27 28 $268 2n29 $262 2n30 $263 2n
October 2026$263–$667/night · 81% open
SuMoTuWeThFrSa
1 $263 2n2 3
4 $298 2n5 $306 2n6 $289 2n7 $303 2n8 $329 2n9 $630 2n10 $667 2n
11 $498 2n12 $284 2n13 $271 2n14 15 16 17
18 $343 2n19 $306 2n20 $305 2n21 $293 2n22 $319 2n23 $456 2n24 $434 2n
25 $299 2n26 $273 2n27 $270 2n28 $275 2n29 $302 2n30 $399 2n31 $382 2n
November 2026$273–$649/night · 100% open
SuMoTuWeThFrSa
1 $307 2n2 $284 2n3 $274 2n4 $273 2n5 $293 2n6 $410 2n7 $409 2n
8 $294 2n9 $277 2n10 $313 2n11 $338 2n12 $356 2n13 $444 2n14 $465 2n
15 $350 2n16 $322 2n17 $321 2n18 $338 2n19 $341 2n20 $487 2n21 $508 2n
22 $413 2n23 $435 2n24 $506 2n25 $637 3n26 $649 3n27 $646 3n28 $550 3n
29 $356 2n30 $337 2n
December 2026$307–$973/night · 100% open
SuMoTuWeThFrSa
1 $375 2n2 $316 2n3 $334 2n4 $405 2n5 $398 2n
6 $328 2n7 $313 2n8 $315 2n9 $307 2n10 $323 2n11 $383 2n12 $402 2n
13 $325 2n14 $321 2n15 $357 2n16 $356 2n17 $378 2n18 $412 3n19 $438 3n
20 $438 2n21 $534 2n22 $580 2n23 $667 2n24 $776 3n25 $802 3n26 $848 3n
27 $726 2n28 $738 2n29 $753 2n30 $965 3n31 $973 3n
January 2027$369–$883/night · 55% open
SuMoTuWeThFrSa
1 $883 3n2 $814 3n
3 $465 2n4 $388 2n5 $398 2n6 $424 2n7 $403 2n8 $472 2n9 $460 2n
10 $407 2n11 $369 2n12 $420 2n13 $394 2n14 $403 2n15 $523 3n16 $507 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$539–$1698/night · 90% open
SuMoTuWeThFrSa
1 2 3 4 $578 2n5 $602 3n6 $648 3n
7 $616 2n8 $594 2n9 $695 2n10 $749 2n11 $869 2n12 $978 3n13 $855 3n
14 $637 2n15 $757 2n16 $1279 3n17 $1267 3n18 $1284 3n19 $1116 3n20 $1038 3n
21 $659 2n22 $574 2n23 $716 2n24 $755 2n25 $1026 3n26 $1664 3n27 $1698 3n
28 $1605 3n29 $539 2n30 $539 2n31 $539 2n
April 2027$539–$964/night · 100% open
SuMoTuWeThFrSa
1 $954 2n2 $964 3n3 $964 3n
4 $563 2n5 $539 2n6 $539 2n7 $539 2n8 $823 2n9 $711 3n10 $706 3n
11 $539 2n12 $539 2n13 $539 2n14 $539 2n15 $645 2n16 $702 3n17 $711 3n
18 $539 2n19 $539 2n20 $539 2n21 $564 2n22 $728 2n23 $733 3n24 $714 3n
25 $539 2n26 $539 2n27 $539 2n28 $728 2n29 $698 2n30 $663 3n
May 2027$539–$1531/night · 100% open
SuMoTuWeThFrSa
1 $646 3n
2 $539 2n3 $539 2n4 $539 2n5 $539 2n6 $667 2n7 $709 3n8 $709 3n
9 $933 2n10 $539 2n11 $539 2n12 $539 2n13 $667 2n14 $851 3n15 $851 3n
16 $765 2n17 $539 2n18 $539 2n19 $539 2n20 $883 2n21 $872 3n22 $961 3n
23 $667 2n24 $595 2n25 $566 2n26 $606 2n27 $883 3n28 $1459 3n29 $1531 3n
30 $1348 2n31 $825 2n
June 2027$726–$1561/night · 100% open
SuMoTuWeThFrSa
1 $799 2n2 $789 2n3 $847 2n4 $1147 3n5 $1134 3n
6 $784 2n7 $726 2n8 $734 2n9 $779 2n10 $911 2n11 $1289 3n12 $1289 3n
13 $1098 2n14 $772 2n15 $744 2n16 $793 2n17 $1561 3n18 $1458 3n19 $1493 3n
20 $976 2n21 $955 2n22 $953 2n23 $989 2n24 $1075 2n25 $1539 3n26 $1353 3n
27 $887 2n28 $755 2n29 $755 2n30 $1034 2n
July 2027$878–$2710/night · 100% open
SuMoTuWeThFrSa
1 $1135 3n2 $2575 3n3 $2584 3n
4 $2710 3n5 $1176 2n6 $1123 2n7 $1126 2n8 $1285 2n9 $1562 3n10 $1501 3n
11 $1046 2n12 $924 2n13 $878 2n14 $929 2n15 $1176 2n16 $1543 3n17 $1599 3n
18 $1084 2n19 $1059 2n20 $1073 2n21 $1071 2n22 $1222 2n23 $1580 3n24 $1511 3n
25 $1071 2n26 $1037 2n27 $1037 2n28 $1038 2n29 $1219 2n30 $1501 3n31 $1366 3n
August 2027$539–$1103/night · 100% open
SuMoTuWeThFrSa
1 $893 2n2 $807 2n3 $763 2n4 $753 2n5 $920 2n6 $1080 3n7 $1085 3n
8 $824 2n9 $745 2n10 $872 2n11 $864 2n12 $847 2n13 $1090 3n14 $1103 3n
15 $763 2n16 $874 2n17 $539 2n18 $539 2n19 $634 2n20 $883 3n21 $922 3n
22 $651 2n23 $539 2n24 $641 2n25 $632 2n26 $610 2n27 $821 3n28 $863 3n
29 $752 2n30 $539 2n31 $539 2n

Rates updated: September 20, 2026