This is the morning view of Pine Island Sound. Its pier juts out from the left side with wooden pylons standing up out of the water near the shore.

Holiday Homes in Pine Island

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Pine Island holiday homes

The Oasis: A cosy one-bedroom house in tropical Bokeelia with air conditioning

The Oasis: A cosy one-bedroom house in tropical Bokeelia with air conditioning
Bokeelia
The price is €166
includes taxes & fees
26 Jun - 27 Jun
The Oasis: A cosy one-bedroom house in tropical Bokeelia with air conditioning

NEW!! The “WATERSIDE” COTTAGE~With dockage

NEW!! The “WATERSIDE” COTTAGE~With dockage
Bokeelia
10.0 out of 10, Exceptional, (49 reviews)
"Great week spent at the Waterside Cottage! "
United States
Sandy S.
The price is €334
includes taxes & fees
9 Jul - 10 Jul
NEW!! The “WATERSIDE” COTTAGE~With dockage

Manatee Lookout Cottages - Boat to Beach, Pool, Kayaks, Pets, Direct Gulf Access

Manatee Lookout Cottages - Boat to Beach, Pool, Kayaks, Pets, Direct Gulf Access
Saint James City
10.0 out of 10, Exceptional, (1 review)
"The house was exactly as advertised. It was beautiful, clean, and easy to find. We really enjoyed our stay. 10/10 would recommend!"
United States
Bethany
The price is €300
includes taxes & fees
26 Jun - 27 Jun
Manatee Lookout Cottages - Boat to Beach, Pool, Kayaks, Pets, Direct Gulf Access

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 €349
includes taxes & fees
26 Jun - 27 Jun
Cozy 2-bedroom downstairs unit in a house in Saint James City Pine Island

3BR Coastal retreat in peaceful Bokeelia with pool, bikes, ping pong and fishing

3BR Coastal retreat in peaceful Bokeelia with pool, bikes, ping pong and fishing
Bokeelia
10.0 out of 10, Exceptional, (6 reviews)
"The home was absolutely perfect , clean, spacious, and very comfortable. Beautifully decorated , beds were cozy, and everything was exactly as described. The host was friendly and responsive, which made the stay stress-free. Great location and a perfect home base for our family trip.”"
United States
Kelly R.
The price is €373
includes taxes & fees
7 Jul - 8 Jul
3BR Coastal retreat in peaceful Bokeelia with pool, bikes, ping pong and fishing

Casa Florida 🌴 waterfront home with boat ramp

Casa Florida 🌴 waterfront home with boat ramp
Bokeelia
9.4 out of 10, Exceptional, (10 reviews)
"Nice place on canal, having everything you need . Enjoyed the stay. "
United States
John M.
The price is €396
includes taxes & fees
29 Jun - 30 Jun
Casa Florida 🌴 waterfront home with boat ramp

Fisherman's Delight With Heated Salt Swimming Pool and a new Boat Lift

Fisherman's Delight With Heated Salt Swimming Pool and a new Boat Lift
St James City
9.6 out of 10, Exceptional, (92 reviews)
"This home was great for my family we will try to rent again!!!!All-around great home and short vacation?????"
United States
Clint F.
The price is €423
includes taxes & fees
1 Jul - 2 Jul
Fisherman's Delight With Heated Salt Swimming Pool and a new Boat Lift

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, (9 reviews)
"Nice place with good fishing in the canal. "
United States
Joshua A.
The price is €457
includes taxes & fees
29 Jun - 30 Jun
3-bedroom house in charming Saint James City with Canal Views!

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
Bokeelia
6.4 out of 10, (6 reviews)
"It was a wonderful trip and we enjoyed the place. Perfect for our stay. Would have been better if the weather was above freezing ;) but it was awesome!"
United States
Diane F.
The price is €398
includes taxes & fees
26 Jun - 27 Jun
2-bedroom ground floor unit just steps from the gulf with a small private beach

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, (66 reviews)
"Overall was very clean and comfortable, we enjoyed our stay"
United States
Jennifer R.
The price is €213
includes taxes & fees
26 Jun - 27 Jun
Completely remodeled beautiful waterfront property on canal with dock

Charming 2-bedroom house in Englewood with WiFi and AC

Charming 2-bedroom house in Englewood with WiFi and AC
Englewood South
10.0 out of 10, Exceptional, (3 reviews)
"Cute, clean, comfortable beds. Perfect for our needs."
United States
Sharon K.
The price is €219
includes taxes & fees
26 Jun - 27 Jun
Charming 2-bedroom house in Englewood with WiFi and AC

WaterView 176B Sunny Vacation home 3 bdr, 2 ba Close to Gulf, Beaches

WaterView 176B Sunny Vacation home 3 bdr, 2 ba Close to Gulf, Beaches
Oakland Hills
10.0 out of 10, Exceptional, (24 reviews)
"Ammenities were great.Everything you need.Bring a carry on and check inWill stay again."
United States
Keenan F.
The price is €284
includes taxes & fees
8 Jul - 9 Jul
WaterView 176B Sunny Vacation home 3 bdr, 2 ba Close to Gulf, Beaches

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
9.4 out of 10, Exceptional, (23 reviews)
"Very clean property and close to shopping and restaurants. "
United States
Kristen M.
The price is €239
includes taxes & fees
6 Jul - 7 Jul
Cozy retreat, NE cape coral oasis 5 mins to restaurants and shopping plaza.

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
8.8 out of 10, Excellent, (11 reviews)
"Very convenient location for us"
United States
Julia M.
The price is €217
includes taxes & fees
29 Jun - 30 Jun
Cozy Home-Centrally located-pet friendly 10min from airport & 2min from FGCU

Harbor House, renovated luxury waterfront- 30 ft private dock

Harbor House, renovated luxury waterfront- 30 ft private dock
Edgewater
9.8 out of 10, Exceptional, (28 reviews)
"We had a great stay. Very clean home with new comforts!"
United States
Robert D.
The price is €402
includes taxes & fees
26 Jun - 27 Jun
Harbor House, renovated luxury waterfront- 30 ft private dock

Huge Pool, Close to Beach - Bikes, Beach Gear, Everything You Need!

Huge Pool, Close to Beach - Bikes, Beach Gear, Everything You Need!
Caloosahatchee
10.0 out of 10, Exceptional, (38 reviews)
"We had a great stay and the house is great. "
United States
Craig L.
The price is €328
includes taxes & fees
8 Jul - 9 Jul
Huge Pool, Close to Beach - Bikes, Beach Gear, Everything You Need!

Waterfront Condo with Pool & Boat Slip

Waterfront Condo with Pool & Boat Slip
Caloosahatchee
10.0 out of 10, Exceptional, (11 reviews)
"The property was amazing. Everything was clean and perfect for our great little vacation."
United States
Amy G.
The price is €361
includes taxes & fees
26 Jun - 27 Jun
Waterfront Condo with Pool & Boat Slip

2-bedroom pool house with golf cart in Englewood, close to the beaches!

2-bedroom pool house with golf cart in Englewood, close to the beaches!
Grove City
10.0 out of 10, Exceptional, (10 reviews)
"Everything was great, including the host"
United States
Fred
The price is €306
includes taxes & fees
29 Jun - 30 Jun
2-bedroom pool house with golf cart in Englewood, close to the beaches!

coastal chic cottage "Heron" minutes to the beach! JULY SAVINGS!

coastal chic cottage "Heron" minutes to the beach! JULY SAVINGS!
West End
9.2 out of 10, Wonderful, (43 reviews)
"Very responsive host. The cottage was roomy and comfortable and had everything you needed to cook. The bikes were nice and an added bonus. Beach was a couple of hundred yards. Nice neighborhood. We would stay here again. "
United States
Geo K.
The price is €522
includes taxes & fees
6 Jul - 7 Jul
coastal chic cottage "Heron" minutes to the beach! JULY SAVINGS!

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, (2 reviews)
"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 €228
includes taxes & fees
2 Jul - 3 Jul
Hibiscus House Bed Breakfast Citrus Room
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Pine Island Hotel Reviews

Find out more about Pine Island

Pine Island Holiday Homes information

Number of reviews
423
Accommodation
1122 Holiday Homes
Lowest Price
€166
Highest Price
€522

Explore a world of travel with Expedia