Holiday Homes in Pine Island

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Our top choices for Pine Island holiday homes

Casa Florida 🌴 waterfront home with boat ramp

Casa Florida 🌴 waterfront home with boat ramp
Bokeelia
9.4 out of 10, Exceptional, (9)
"Nice place on canal, having everything you need . Enjoyed the stay. "
United States
John M.
The price is €438
includes taxes & fees
12 Jan - 13 Jan 2026
Casa Florida 🌴 waterfront home with boat ramp

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.
The price is €370
includes taxes & fees
4 Jan - 5 Jan 2026
NEW!! The “WATERSIDE” COTTAGE~With dockage

Newly remodeled, relaxing, romantic ground floor 1 bedroom waterfront getaway.

Newly remodeled, relaxing, romantic ground floor 1 bedroom waterfront getaway.
Bokeelia
9.8 out of 10, Exceptional, (18)
"Couldn’t be better!!! Highly recommend!!!"
United States
Luis K.
The price is €289
includes taxes & fees
24 Jan - 25 Jan 2026
Newly remodeled, relaxing, romantic ground floor 1 bedroom waterfront getaway.

Cozy 2-bedroom downstairs unit in a house in Saint James City Pine Island

Cozy 2-bedroom downstairs unit in a house in Saint James City Pine Island
Saint James City
The price is €294
includes taxes & fees
8 Jan - 9 Jan 2026
Cozy 2-bedroom downstairs unit in a house in Saint James City Pine Island

2-bedroom ground floor unit just steps from the gulf with a small private beach

2-bedroom ground floor unit just steps from the gulf with a small private beach
2.0 star property
Bokeelia
The price is €353
includes taxes & fees
5 Jan - 6 Jan 2026
2-bedroom ground floor unit just steps from the gulf with a small private beach

3-bedroom house in charming Saint James City with Canal Views!

3-bedroom house in charming Saint James City with Canal Views!
Saint James City
10.0 out of 10, Exceptional, (4)
"We had a great short stay this trip down to St James City. We love SJC and this house is a easy walk to our favorite restaurant. The best way I can describe this house is spa like. It is a very nice, comfortable house and if nothing else stay here for the shower! It had everything and was well equipped with just about anything you may need, down to the yoga mats. We had a few questions at check in and the host Britt was quick to respond and help us out. We like that the house is pet friendly as...
United States
Tracy L.
The price is €512
includes taxes & fees
4 Jan - 5 Jan 2026
3-bedroom house in charming Saint James City with Canal Views!

Tropical Getaway in St. James City – 3BR/2BA w/ Boat Ramp Access Nearby!

Tropical Getaway in St. James City – 3BR/2BA w/ Boat Ramp Access Nearby!
Manatee Bay
The price is €639
includes taxes & fees
24 Jan - 25 Jan 2026
Tropical Getaway in St. James City – 3BR/2BA w/ Boat Ramp Access Nearby!

Just Listed - Beautifully renovated waterfront 2 bedroom home

Just Listed - Beautifully renovated waterfront 2 bedroom home
Bokeelia
9.0 out of 10, Wonderful, (8)
"Me and one of my friends come to Florida once a year to fish with a couple of our good friends and this was the perfect place for us. The property was very nice, clean, communication with ownership was easy, and we had a great time. I would recommend this place to anyone looking for a fun weekend stay."
United States
Rex S.
The price is €454
includes taxes & fees
25 Dec - 26 Dec
Just Listed - Beautifully renovated waterfront 2 bedroom home

Charming 2-bedroom house in Englewood with WiFi and AC

Charming 2-bedroom house in Englewood with WiFi and AC
Englewood South
The price is €261
includes taxes & fees
27 Dec - 28 Dec
Charming 2-bedroom house in Englewood with WiFi and AC

Modern boho 2bed 2bath home, 8 mins to downtown cape and near beach.

Modern boho 2bed 2bath home, 8 mins to downtown cape and near beach.
Pelican
9.4 out of 10, Exceptional, (38)
"Everything was as listed! My husband and I had a great stay while visiting friends. Location was perfect and the space was super cozy! Would definitely recommend!"
United States
julie l.
The price is €227
includes taxes & fees
28 Dec - 29 Dec
Modern boho 2bed 2bath home, 8 mins to downtown cape and near beach.

Gorgeous relaxing 2BD Near Ft. Myers Beach

Gorgeous relaxing 2BD Near Ft. Myers Beach
Iona
10.0 out of 10, Exceptional, (4)
"Great place to stay by Fort Myers Beach."
United States
Gabriel O.
The price is €215
includes taxes & fees
27 Dec - 28 Dec
Gorgeous relaxing 2BD Near Ft. Myers Beach

Hibiscus House Bed Breakfast Citrus Room

Hibiscus House Bed Breakfast Citrus Room
2.0 star property
Fort Myers River District
10.0 out of 10, Exceptional, (1)
"Absolutely beautiful room and amenities and the breakfast was delicious and with so many options. Loved the communication and cannot wait to come back! "
United States
Crissa
The price is €194
includes taxes & fees
28 Dec - 29 Dec
Hibiscus House Bed Breakfast Citrus Room

Hibiscus House Bed & Breakfast Inn Turtle Room Bed-ADA

Hibiscus House Bed & Breakfast Inn Turtle Room Bed-ADA
Fort Myers River District
10.0 out of 10, Exceptional, (3)
"Perhaps one of the best places I have stayed in fort Myers. "
United States
Shane R.
The price is €163
includes taxes & fees
3 Jan - 4 Jan 2026
Hibiscus House Bed & Breakfast Inn Turtle Room Bed-ADA

Cozy Home-Centrally located-pet friendly 10min from airport & 2min from FGCU

Cozy Home-Centrally located-pet friendly 10min from airport & 2min from FGCU
San Carlos Park
8.6 out of 10, Excellent, (10)
"Very convenient location for us"
United States
Julia M.
The price is €203
includes taxes & fees
5 Jan - 6 Jan 2026
Cozy Home-Centrally located-pet friendly 10min from airport & 2min from FGCU

Completely remodeled beautiful waterfront property on canal with dock

Completely remodeled beautiful waterfront property on canal with dock
Port Charlotte
9.6 out of 10, Exceptional, (61)
"Had an extended Prospect Wire tournament in the area with my oldest son. The house was PERFECT! The remodel was done really well. The kitchen had everything we needed, the bedrooms were very comfortable and clean. We needed an extra night at the last minute and the host was extremely accommodating with our schedule and our needs. I would recommend this place for anyone looking for a great stay at a great house."
United States
Jason M.
The price is €266
includes taxes & fees
27 Dec - 28 Dec
Completely remodeled beautiful waterfront property on canal with dock

Cozy retreat, NE cape coral oasis 5 mins to restaurants and shopping plaza.

Cozy retreat, NE cape coral oasis 5 mins to restaurants and shopping plaza.
Diplomat
9.2 out of 10, Wonderful, (22)
"Great host. House was exactly as advertised. Would absolutely stay again!"
United States
Andrew S.
The price is €239
includes taxes & fees
28 Dec - 29 Dec
Cozy retreat, NE cape coral oasis 5 mins to restaurants and shopping plaza.

So Coastal! A family and pet friendly home

So Coastal! A family and pet friendly home
Iona
9.6 out of 10, Exceptional, (5)
"Property was very clean and updated. Nice screened in porch, kitchen and bath. Host was very responsive and check in process was easy. "
United States
Jeffery L.
The price is €170
includes taxes & fees
3 Jan - 4 Jan 2026
So Coastal! A family and pet friendly home

Hidden Secret Waterfront Retreat

Hidden Secret Waterfront Retreat
2.0 star property
Hancock
10.0 out of 10, Exceptional, (3)
"The pool was very nice, and the seating by the canal was amazing, it was so relaxing, and the owner was quick to respond and very friendly!"
United States
bethany r.
The price is €305
includes taxes & fees
2 Jan - 3 Jan 2026
Hidden Secret Waterfront Retreat

Bright & Airy 2bed 2bath home near downtown/Weekly and monthly discounts!

Bright & Airy 2bed 2bath home near downtown/Weekly and monthly discounts!
Pelican
9.6 out of 10, Exceptional, (54)
"Every time excellent in every way!!!"
United States
Kim G.
The price is €236
includes taxes & fees
30 Dec - 31 Dec
Bright & Airy 2bed 2bath home near downtown/Weekly and monthly discounts!

HEATED POOL-LANAI-BBQ-5 Mi to BEACH-WASHER/DRYER-TENNIS-GOLF-BLISSFUL RETREAT

HEATED POOL-LANAI-BBQ-5 Mi to BEACH-WASHER/DRYER-TENNIS-GOLF-BLISSFUL RETREAT
Rotonda Heights
9.8 out of 10, Exceptional, (7)
"Clean and spacious house worth every penny"
United States
Milica B.
The price is €388
includes taxes & fees
2 Jan - 3 Jan 2026
HEATED POOL-LANAI-BBQ-5 Mi to BEACH-WASHER/DRYER-TENNIS-GOLF-BLISSFUL 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 Pine Island Hotel Reviews

Find out more about Pine Island

Pine Island Holiday Homes information

Number of reviews
284
Accommodation
1087 Holiday Homes
Lowest Price
€163
Highest Price
€665

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