Captiva Island holiday rentals
We found 2,339 holiday rentals — enter your dates for availability
Holiday rentals with weekly discounts – Captiva Island
Showing deals for:27 Nov - 4 Dec

Exceptional
(60 reviews)
Pet-Friendly / Family-Friendly Waterfront Vacation Rental + Free Boat Dockage!
Matlacha
S$1,556
for 7 nights, 1 room
S$222 per night
includes taxes & fees

Exceptional
(54 reviews)
Hidden Treasure - Near Beach-Pool- Private CuldeSac - Dock Rental - 10% Off Week
Captiva
S$6,497
for 7 nights, 1 home
S$928 per night
includes taxes & fees

Exceptional
(48 reviews)
Upgraded beach house located just steps away from the beach. Pool and Hot tub.
Captiva
S$5,686
for 7 nights, 1 home
S$812 per night
includes taxes & fees

Exceptional
(11 reviews)
Orange You Glad Cottage - A Fisherman’s Paradise in sunny Matlacha
Matlacha
S$1,691
for 7 nights, 1 cottage
S$242 per night
includes taxes & fees

Exceptional
(34 reviews)
Relax in Paradise: 2-Bedroom Island Retreat with private Pool & Golf Cart!
Captiva
S$4,727
for 7 nights, 1 home
S$675 per night
includes taxes & fees

Exceptional
(7 reviews)
Turtle House - Waterfront with Dock - Unbelievable Sunset View
Matlacha
S$2,490
for 7 nights, 1 home
S$356 per night
includes taxes & fees

Exceptional
(31 reviews)
Island Getaway Florida
Saint James City
S$3,347
for 7 nights, 1 home
S$478 per night
includes taxes & fees

Exceptional
(5 reviews)
Two minute walk to a soft sandy beach with some of the best shelling in the US.
Captiva
S$6,530
for 7 nights, 1 home
S$933 per night
includes taxes & fees

Exceptional
(61 reviews)
Private getaway on Pine Island. Full kitchen, lanai, deck. Beautiful yard.
Bokeelia
S$812
for 7 nights, 1 cottage
S$116 per night
includes taxes & fees
