A welcome sign to Captiva surrounded by tropical vegetation.

Captiva Island Holiday Rentals

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Our top choices for Captiva Island holiday rentals

1. Island Inn

Island Inn
3.5 star property
West End
9.4 out of 10, Exceptional, (1,168 reviews)
"Great location"
United States
Nicole
The price is NZ$546
includes taxes & fees
8 Nov - 9 Nov
Island Inn

2. Sundial Beach Resort & Spa

Sundial Beach Resort & Spa
5.0 star property
Mid Island
8.6 out of 10, Excellent, (2,718 reviews)
"Love the resort and great access to beach"
United States
Lisa Renee
The price is NZ$771
includes taxes & fees
8 Dec - 9 Dec
Sundial Beach Resort & Spa

3. Edison Beach House

Edison Beach House
3.5 star property
Fort Myers Beach
9.4 out of 10, Exceptional, (1,961 reviews)
"Great stay."
United States
Angie
The price is NZ$400
includes taxes & fees
8 Nov - 9 Nov
Edison Beach House

4. Matlacha Tiny Village

Matlacha Tiny Village
3.0 star property
Matlacha
9.0 out of 10, Wonderful, (299 reviews)
"So cute and clean nice dock to sit and relax or fish. Kayaks available to use free as well with life jackets paddles, etc. well equipped rental we can’t wait to go again! Great communication with hosts."
United States
Lori
The price is NZ$398
includes taxes & fees
10 Nov - 11 Nov
Matlacha Tiny Village

5. Driftwood Inn

Driftwood Inn
4.0 star property
Mid Island
10.0 out of 10, Exceptional, (11 reviews)
"Great place to stay on sanibel"
United States
Terri
The price is NZ$818
includes taxes & fees
9 Nov - 10 Nov
Driftwood Inn

6. GullWing Beach Resort

GullWing Beach Resort
3.5 star property
South Island
9.6 out of 10, Exceptional, (987 reviews)
"Gullwing is an excellent beach front condo property. Very well maintained, friendly staff and close to amenities."
United States
Jennifer
The price is NZ$968
includes taxes & fees
2 Dec - 3 Dec
GullWing Beach Resort

7. Lazy Cuckoo Inn

Lazy Cuckoo Inn
2.0 star property
Fort Myers Beach
8.8 out of 10, Excellent, (307 reviews)
"Great place!"
United States
Bruce
The price is NZ$175
includes taxes & fees
9 Nov - 10 Nov
Lazy Cuckoo Inn

8. MALU LANI Inn & Marina

MALU LANI Inn & Marina
3.5 star property
Bokeelia
10.0 out of 10, Exceptional, (6 reviews)
"Beautiful property, peaceful, clean rental. Super responsive owner and all the things you need. Perfect location for boaters. Loved this stay and would definitely rent again! "
United States
April
The price is NZ$698
includes taxes & fees
17 Nov - 18 Nov
MALU LANI Inn & Marina

9. Flamingo Inn

Flamingo Inn
3.0 star property
Mid Island
8.0 out of 10, Very good, (1,028 reviews)
"Cute, clean, beachside inn. Will definitely be back!"
United States
Emily
The price is NZ$339
includes taxes & fees
14 Nov - 15 Nov
Flamingo Inn

10. Harbour House at the Inn 308

Harbour House at the Inn 308
3.0 star property
Fort Myers Beach
The price is NZ$928
includes taxes & fees
11 Nov - 12 Nov
Harbour House at the Inn 308

11. 3 Mi to Fort Myers Beach! Family Getaway w/ Pool

3 Mi to Fort Myers Beach! Family Getaway w/ Pool
3.0 star property
Iona
The price is NZ$787
includes taxes & fees
1 Dec - 2 Dec
3 Mi to Fort Myers Beach! Family Getaway w/ Pool

12. Lakeside Oasis

Lakeside Oasis
2.0 star property
Iona
The price is NZ$447
includes taxes & fees
20 Nov - 21 Nov
Lakeside Oasis

13. Riverfront Home w Private Dock Pool Beaches

Riverfront Home w Private Dock Pool Beaches
2.0 star property
McGregor
The price is NZ$1,804
includes taxes & fees
30 Nov - 1 Dec
Riverfront Home w Private Dock Pool Beaches

14. Private Pool! Game Room! Very Close to Downtown!

Private Pool! Game Room! Very Close to Downtown!
3.0 star property
Hancock
The price is NZ$970
includes taxes & fees
8 Nov - 9 Nov
Private Pool! Game Room! Very Close to Downtown!

15. Beach Days & Backyard Nights! Fort Myers Retreat

Beach Days & Backyard Nights! Fort Myers Retreat
3.0 star property
Harlem Heights
The price is NZ$600
includes taxes & fees
23 Nov - 24 Nov
Beach Days & Backyard Nights! Fort Myers Retreat
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Captiva Island Hotel Reviews

Find out more about Captiva Island

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Captiva Island holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Captiva Island. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Captiva Island. Seeing all the best attractions is bound to make you fall in love with Captiva Island. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Captiva Island short-term rentals, that won’t be hard to do.

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