A wooden pier extending into calm water with a clear sky and distant land.

Holiday Homes in Pine Island

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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Pine Island holiday homes

A view through a window of a residential area with a small tree, a body of water, and a building with a blue roof.

1. Manatee Lookout Cottages - Boat to Beach, Dock, Pool, Kayaks, Direct Gulf Access

Manatee Lookout Cottages - Boat to Beach, Dock, Pool, Kayaks, Direct Gulf Access
Saint James City
10.0 out of 10, Exceptional, (4 reviews)
"Great location. Nice property. Clean and comfortable."
United States
Mary Ellen I.
The price is NZ$602
includes taxes & fees
3 Nov - 4 Nov
Manatee Lookout Cottages - Boat to Beach, Dock, Pool, Kayaks, Direct Gulf Access
A room with a white door, a round table with chairs, and a small potted plant.

2. 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
10.0 out of 10, Exceptional, (1 review)
"The property was convenient to get to the boat, ramp and restaurants in the area. The property was exactly what I was looking for for a quick getway. The host was very nice and communicated with me about the property and check in was great."
United States
Michael W.
The price is NZ$338
includes taxes & fees
11 Nov - 12 Nov
The Oasis: A cosy one-bedroom house in tropical Bokeelia with air conditioning
A spacious patio with a dining table and chairs, a sofa, and a ceiling fan.

3. 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, (11 reviews)
"Great property, very clean and host was extremely helpful. Great quiet neighborhood with friendly neighbors."
United States
Neal G.
The price is NZ$710
includes taxes & fees
15 Nov - 16 Nov
3BR Coastal retreat in peaceful Bokeelia with pool, bikes, ping pong and fishing
A modern kitchen with white cabinets, stainless steel appliances, a wooden island, and a teal backsplash.

4. 1 bedroom apartment in Saint James City with AC -Tarpon Suite

1 bedroom apartment in Saint James City with AC -Tarpon Suite
Saint James City
The price is NZ$442
includes taxes & fees
3 Nov - 4 Nov
1 bedroom apartment in Saint James City with AC -Tarpon Suite
A spacious living room with a fireplace, two ceiling fans, a television, and a view of the outdoors.

5. Casa Florida 🌴 waterfront home with boat ramp

Casa Florida 🌴 waterfront home with boat ramp
Bokeelia
9.4 out of 10, Exceptional, (11 reviews)
"This is our second time staying at this location and we will definitely be back! It is so convenient to have the boat ramp at the house and we love the boat lift. The house and property itself has everything you need and is always clean! "
United States
Morgan P.
The price is NZ$700
includes taxes & fees
3 Nov - 4 Nov
Casa Florida 🌴 waterfront home with boat ramp
A spacious kitchen with white cabinets, a black backsplash, and a central island with bar stools.

6. 1 bedroom house in Saint James City with AC Snook Suite

1 bedroom house in Saint James City with AC Snook Suite
Saint James City
The price is NZ$318
includes taxes & fees
3 Nov - 4 Nov
1 bedroom house in Saint James City with AC Snook Suite
A modern kitchen with a central island, wooden cabinets, and a built-in oven.

7. NEW!! The “WATERSIDE” COTTAGE~With dockage

NEW!! The “WATERSIDE” COTTAGE~With dockage
Bokeelia
10.0 out of 10, Exceptional, (52 reviews)
"We had a great stay, was exactly as described. The host had great communication and gave great advice for the property and surrounding area."
United States
Jennifer D.
The price is NZ$782
includes taxes & fees
3 Nov - 4 Nov
NEW!! The “WATERSIDE” COTTAGE~With dockage
A sunlit room with a sofa, coffee table, and chairs, large windows with a view of a marina and palm trees.

8. 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, (12 reviews)
"Nice place with good fishing in the canal. "
United States
Joshua A.
The price is NZ$812
includes taxes & fees
3 Nov - 4 Nov
3-bedroom house in charming Saint James City with Canal Views!
A covered swimming pool with a clear view of the surrounding area, including a body of water and greenery.

9. 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, (97 reviews)
"Beautiful home easy access to gulf and awesome cool pool definitely will be back"
United States
Travis W.
The price is NZ$928
includes taxes & fees
1 Dec - 2 Dec
Fisherman's Delight With Heated Salt Swimming Pool and a new Boat Lift
A beach view from a covered area with a wooden deck and palm trees.

10. 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 NZ$906
includes taxes & fees
3 Nov - 4 Nov
2-bedroom ground floor unit just steps from the gulf with a small private beach
A kitchen with a wooden island, white cabinets, a fish-themed backsplash, and a sliding barn door.

11. 1 bedroom apartment in Saint James City with AC Redfish Suite

1 bedroom apartment in Saint James City with AC Redfish Suite
Saint James City
The price is NZ$442
includes taxes & fees
3 Nov - 4 Nov
1 bedroom apartment in Saint James City with AC Redfish Suite
Private kitchen

12. 2 bedroom house with AC in Saint James City Cabana Suite

2 bedroom house with AC in Saint James City Cabana Suite
Saint James City
The price is NZ$474
includes taxes & fees
3 Nov - 4 Nov
2 bedroom house with AC in Saint James City Cabana Suite
A modern living room with a white sofa, a round coffee table, and a kitchen area in the background.

13. Waterfront Bungalow in Matlacha

Waterfront Bungalow in Matlacha
Matlacha
10.0 out of 10, Exceptional, (7 reviews)
"Great place and convenient location "
United States
Clinton N.
The price is NZ$634
includes taxes & fees
3 Nov - 4 Nov
Waterfront Bungalow in Matlacha
A modern kitchen with white cabinetry, a central island, a stainless steel refrigerator, and a chandelier.

14. 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, (63 reviews)
"House was very clean and looked just like advertised. Had a very comfortable stay and property is close to everything you need. Will definitely come back."
United States
Jennifer B.
The price is NZ$405
includes taxes & fees
4 Nov - 5 Nov
Bright & Airy 2bed 2bath home near downtown/Weekly and monthly discounts!
A modern kitchen with white cabinetry, stainless steel appliances, and a central island.

15. 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, (42 reviews)
"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 NZ$410
includes taxes & fees
3 Nov - 4 Nov
Modern boho 2bed 2bath home, 8 mins to downtown cape and near beach.
A multi-level house with a white exterior, a staircase, and a deck area.

16. North Captiva Steps to Gulf Beaches Last Minute Offers Beach + Golf Cart + Club

North Captiva Steps to Gulf Beaches Last Minute Offers Beach + Golf Cart + Club
North Captiva Island
10.0 out of 10, Exceptional, (37 reviews)
"Amazing stay!Beds were comfortable, kitchen was well stocked. We would stay here again and again. "
United States
Tanya J.
The price is NZ$1,673
includes taxes & fees
3 Nov - 4 Nov
North Captiva Steps to Gulf Beaches Last Minute Offers Beach + Golf Cart + Club
A wooden dock with colorful Adirondack chairs, a marina with boats, and a clear blue sky.

17. 50’ of Dock for your boats. Hot tub, Boatlift, walk 2 restaurants Xtra parking.

50’ of Dock for your boats. Hot tub, Boatlift, walk 2 restaurants Xtra parking.
Matlacha
10.0 out of 10, Exceptional, (42 reviews)
"Our stay was absolutely wonderful. The home was perfect, beautifully decorated, and had everything we needed. It felt comfortable, peaceful, and welcoming from the moment we arrived. Every detail was thoughtfully prepared, making it easy to relax and enjoy our vacation. There's a lot of space for your boat or jet skis, we will definitely go back."
United States
Jocelyn F.
The price is NZ$834
includes taxes & fees
7 Nov - 8 Nov
50’ of Dock for your boats. Hot tub, Boatlift, walk 2 restaurants Xtra parking.
An indoor swimming pool with a view of the water, lounge chairs, and potted plants.

18. Waterfront Home: Private Pool & Stunning Sea Views

Waterfront Home: Private Pool & Stunning Sea Views
Pelican
10.0 out of 10, Exceptional, (8 reviews)
"Overall, was a wonderful stay and a beautiful home. "
United States
Kyra S.
The price is NZ$796
includes taxes & fees
17 Nov - 18 Nov
Waterfront Home: Private Pool & Stunning Sea Views
A modern kitchen with white cabinets, stainless steel appliances, and a grey countertop.

19. Sunny Cape Coral Escape: Warmth Awaits!

Sunny Cape Coral Escape: Warmth Awaits!
Hancock
8.4 out of 10, Very good, (19 reviews)
"Older home with nice improvements and more improvements are happening."
United States
Frank S.
The price is NZ$566
includes taxes & fees
3 Nov - 4 Nov
Sunny Cape Coral Escape: Warmth Awaits!
A modern living room with a dining area, a grey sofa, a coffee table, and a wall clock.

20. Lakeside Oasis Fort Myers

Lakeside Oasis Fort Myers
2.0 star property
Iona
The price is NZ$444
includes taxes & fees
5 Nov - 6 Nov
Lakeside Oasis Fort Myers
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

DiamondHead Beach Resort

DiamondHead Beach Resort

10/10 Excellent
"The staff was very hospitable. The location was perfect for us. The hotel restaurants and offerings were excellent!"
Heidi 9-night trip
Posted 2 hours ago
DiamondHead Beach Resort

Find out more about Pine Island

Pine Island Holiday Homes information

Number of reviews
352
Accommodation
1146 Holiday Homes
Lowest Price
NZ$318
Highest Price
NZ$1,673

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