Winter Rentals in Greater Fort Myers

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Hyatt Vacation Club At Coconut Cove

Bonita Springs, Florida

Dec 14–20, 2025 (6 nights)
Studio/1 bath, sleeps 4
$1,054 ($176/night)

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Hyatt Vacation Club At Coconut Cove

Bonita Springs, Florida

Dec 15–19, 2025 (4 nights)
2 bed/2 bath, sleeps 8
$887 ($222/night)

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Hyatt Vacation Club At Coconut Cove

Bonita Springs, Florida

Dec 16–20, 2025 (4 nights)
2 bed/2 bath, sleeps 8
$998 ($249/night)

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Hurricane House

Sanibel Island, Florida

Dec 19–26, 2025 (7 nights)
2 bed/2 bath, sleeps 6
$2,204 ($315/night)

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Hurricane House

Sanibel Island, Florida

Dec 19–26, 2025 (7 nights)
2 bed/2 bath, sleeps 6
$2,204 ($315/night)

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Hyatt Vacation Club At Coconut Cove

Bonita Springs, Florida

Dec 20–24, 2025 (4 nights)
Studio/1 bath, sleeps 4
$555 ($139/night)

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Hyatt Vacation Club At Coconut Cove

Bonita Springs, Florida

Dec 20–24, 2025 (4 nights)
2 bed/2 bath, sleeps 8
$1,110 ($278/night)

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Seawatch On-the-Beach Resort

Fort Myers Beach, Florida

Dec 20–27, 2025 (7 nights)
1 bed/2 bath, sleeps 4
$1,550 ($221/night)

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Shell Island Beach Club

Sanibel Island, Florida

Dec 20–27, 2025 (7 nights)
2 bed/2 bath, sleeps 6
$2,641 ($377/night)

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Shell Island Beach Club

Sanibel Island, Florida

Dec 20–27, 2025 (7 nights)
2 bed/2 bath, sleeps 6
$1,358 ($194/night)

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Hyatt Vacation Club At Coconut Cove

Bonita Springs, Florida

Dec 20–27, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$2,309 ($330/night)

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Hyatt Vacation Club At Coconut Cove

Bonita Springs, Florida

Dec 23–28, 2025 (5 nights)
2 bed/2 bath, sleeps 8
$2,205 ($441/night)

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Tortuga Beach Club

Sanibel Island, Florida

Dec 26, 2025 – Jan 2, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$3,295 ($471/night)

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The Cottages at South Seas Island Resort

Captiva, Florida

Jan 2–9, 2026 (7 nights)
3 bed/2 bath, sleeps 8
$2,314 ($331/night)

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Tortuga Beach Club

Sanibel Island, Florida

Jan 2–9, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$3,949 ($564/night)

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The Cottages at South Seas Island Resort

Captiva, Florida

Jan 2–9, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$5,475 ($782/night)

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Shell Island Beach Club

Sanibel Island, Florida

Jan 3–10, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$1,358 ($194/night)

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Hyatt Vacation Club At Coconut Cove

Bonita Springs, Florida

Jan 4–11, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,096 ($299/night)

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Hyatt Vacation Club At Coconut Cove

Bonita Springs, Florida

Jan 4–11, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,932 ($276/night)

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Hyatt Vacation Club At Coconut Cove

Bonita Springs, Florida

Jan 11–17, 2026 (6 nights)
2 bed/2 bath, sleeps 8
$1,660 ($277/night)

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Plantation Beach Club at South Seas Island Resort

Captiva, Florida

Jan 16–23, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$2,096 ($299/night)

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Hyatt Vacation Club At Coconut Cove

Bonita Springs, Florida

Jan 17–24, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$3,077 ($440/night)

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Plantation Beach Club at South Seas Island Resort

Captiva, Florida

Jan 23–30, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$2,085 ($298/night)

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Hyatt Vacation Club At Coconut Cove

Bonita Springs, Florida

Jan 24–31, 2026 (7 nights)
Studio/1 bath, sleeps 4
$2,423 ($346/night)

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Hyatt Vacation Club At Coconut Cove

Bonita Springs, Florida

Jan 25 – Feb 1, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$3,268 ($467/night)

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Plantation Beach Club at South Seas Island Resort

Captiva, Florida

Jan 30 – Feb 6, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$2,085 ($298/night)

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Tortuga Beach Club

Sanibel Island, Florida

Jan 30 – Feb 13, 2026 (14 nights)
2 bed/2 bath, sleeps 6
$7,650 ($546/night)

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Hyatt Vacation Club At Coconut Cove

Bonita Springs, Florida

Feb 1–8, 2026 (7 nights)
Studio/1 bath, sleeps 4
$1,440 ($206/night)

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Hyatt Vacation Club At Coconut Cove

Bonita Springs, Florida

Feb 7–14, 2026 (7 nights)
Studio/1 bath, sleeps 4
$1,932 ($276/night)

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Hyatt Vacation Club At Coconut Cove

Bonita Springs, Florida

Feb 8–15, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$3,513 ($502/night)

Hyatt Vacation Club At Coconut Cove

Bonita Springs, Florida

Feb 8–15, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$3,458 ($494/night)

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DiamondHead Beach Resort

Fort Myers Beach, Florida

Feb 13–20, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$3,022 ($432/night)

Hyatt Vacation Club At Coconut Cove

Bonita Springs, Florida

Feb 14–21, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$4,069 ($581/night)

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Hyatt Vacation Club At Coconut Cove

Bonita Springs, Florida

Feb 15–22, 2026 (7 nights)
Studio/1 bath, sleeps 4
$1,905 ($272/night)

Shell Island Beach Club

Sanibel Island, Florida

Feb 21–28, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$2,532 ($362/night)

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Hyatt Vacation Club At Coconut Cove

Bonita Springs, Florida

Feb 22 – Mar 1, 2026 (7 nights)
Studio/1 bath, sleeps 4
$1,905 ($272/night)

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Tortuga Beach Club

Sanibel Island, Florida

Feb 27 – Mar 6, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$5,175 ($739/night)

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Hyatt Vacation Club At Coconut Cove

Bonita Springs, Florida

Feb 28 – Mar 7, 2026 (7 nights)
Studio/1 bath, sleeps 4
$1,932 ($276/night)

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Hyatt Vacation Club At Coconut Cove

Bonita Springs, Florida

Feb 28 – Mar 7, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$3,731 ($533/night)

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Hyatt Vacation Club At Coconut Cove

Bonita Springs, Florida

Feb 28 – Mar 7, 2026 (7 nights)
Studio/1 bath, sleeps 4
$1,813 ($259/night)

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Hyatt Vacation Club At Coconut Cove

Bonita Springs, Florida

Feb 28 – Mar 7, 2026 (7 nights)
Studio/1 bath, sleeps 4
$1,877 ($268/night)