Find Historic Hotels in Pine Island, FL

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Our top choices for Pine Island historic hotels

Pool
NEW!! The “WATERSIDE” COTTAGE~With dockage

NEW!! The “WATERSIDE” COTTAGE~With dockage

Bokeelia
10.0 out of 10, Exceptional, (41)
"My wife and I loved our stay at Waterside. The property was clean and well appointed. The area was nice and we loved walking up to the local watering hole for sunset views. I would recommend it highly. "
United States
Ron R.
$334 nightly
The price is $368
Dec 10 - Dec 11
Total with taxes and fees
NEW!! The “WATERSIDE” COTTAGE~With dockage
Pool
The Banyan Hotel Fort Myers, Tapestry Collection by Hilton

The Banyan Hotel Fort Myers, Tapestry Collection by Hilton

3.5 star property
Downtown Historic District
8.6 out of 10, Excellent, (835)
"Staff was friendly. "
United States
Jennifer
$155 nightly
The price is $173
Dec 22 - Dec 23
Total with taxes and fees
The Banyan Hotel Fort Myers, Tapestry Collection by Hilton
Outdoor dining
Pet-Friendly / Family-Friendly Waterfront Vacation Rental + Free Boat Dockage!

Pet-Friendly / Family-Friendly Waterfront Vacation Rental + Free Boat Dockage!

Matlacha
9.4 out of 10, Exceptional, (49)
"The atmosphere and art very local"
United States
Cindy
$170 nightly
The price is $187
Dec 10 - Dec 11
Total with taxes and fees
Pet-Friendly / Family-Friendly Waterfront Vacation Rental + Free Boat Dockage!
On the beach
Gulf Views - No Stairs - Directly “On the Beach” - Jensen's "On the Gulf" - Cozy Suite 1

Gulf Views - No Stairs - Directly “On the Beach” - Jensen's "On the Gulf" - Cozy Suite 1

Captiva
7.8 out of 10, Good, (12)
"Loved being right on the beach! Such a great little place!"
United States
Bryant
$484 nightly
The price is $508
Dec 10 - Dec 11
Total with taxes and fees
Gulf Views - No Stairs - Directly “On the Beach” - Jensen's "On the Gulf" - Cozy Suite 1
Property grounds
Newly remodeled Parrot Nest Toucan Cottage! Walk to beach, shops, restaurants!

Newly remodeled Parrot Nest Toucan Cottage! Walk to beach, shops, restaurants!

East End
9.6 out of 10, Exceptional, (46)
"Great place "
United States
Christine
$313 nightly
The price is $332
Dec 15 - Dec 16
Total with taxes and fees
Newly remodeled Parrot Nest Toucan Cottage! Walk to beach, shops, restaurants!
Exterior
Newly Renovated Charlotte Harbor - Sunset Inn #7

Newly Renovated Charlotte Harbor - Sunset Inn #7

Port Charlotte
10.0 out of 10, Exceptional, (5)
"Super cute small place!"
United States
Kayla
$200 nightly
The price is $215
Jan 6 - Jan 7, 2026
Total with taxes and fees
Newly Renovated Charlotte Harbor - Sunset Inn #7
Sun loungers, beach towels
SUNSHINE GETAWAY VACATION RENTALS

SUNSHINE GETAWAY VACATION RENTALS

Fort Myers
8.4 out of 10, Very Good, (137)
"Easy location to get where we needed. Clean and spacious."
United States
Chris N.
$238 nightly
The price is $263
Dec 23 - Dec 24
Total with taxes and fees
SUNSHINE GETAWAY VACATION RENTALS
Beach
Sunshine Getaway Vacation Rentals!

Sunshine Getaway Vacation Rentals!

Fort Myers
8.2 out of 10, Very Good, (69)
"The property is as described and everything needed is there for a wonderful stay. The host is available for any questions and responds very quickly. Thank you for a great stay"
United States
Shell B.
$252 nightly
The price is $278
Jan 1 - Jan 2, 2026
Total with taxes and fees
Sunshine Getaway Vacation Rentals!
Beach nearby, sun loungers, beach towels
Gorgeous Blue Lagoon. An oasis just 2 min walk from the beach.

Gorgeous Blue Lagoon. An oasis just 2 min walk from the beach.

Mid Island
10.0 out of 10, Exceptional, (101)
"Was a great family vacation! Short walk to the beach and had all the chairs and cart available to use, pool was awesome for the kids!!"
United States
Chase H.
$494 nightly
The price is $545
Dec 11 - Dec 12
Total with taxes and fees
Gorgeous Blue Lagoon. An oasis just 2 min walk from the beach.
On the beach
Historic Captiva PO Cottage Garden Suite Steps to Beach Casual Lux Décor - Jensen's "On the Gulf" 7

Historic Captiva PO Cottage Garden Suite Steps to Beach Casual Lux Décor - Jensen's "On the Gulf" 7

3.0 star property
Captiva
8.0 out of 10, Very Good, (10)
"We loved being able to walk out to the beach without having to drive and the availability of beach chairs and umbrellas to carry with us. We also loved being able to walk to restaurants and the local grocery store nearby. Our room was pretty, comfortable and clean. It was a wonderful vacation! Thank you! "
United States
Barbara
$554 nightly
The price is $582
Dec 11 - Dec 12
Total with taxes and fees
Historic Captiva PO Cottage Garden Suite Steps to Beach Casual Lux Décor - Jensen's "On the Gulf" 7
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 Pine Island Hotel Reviews

Hyatt Place Fort Myers/at The Forum

Hyatt Place Fort Myers/at The Forum

10/10 Excellent
"All good. Breakfast great. "
Craig R 3-night trip
Posted 19 hours ago
Hyatt Place Fort Myers/at The Forum

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