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

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
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Pine Island holiday homes

A room with a white door, a round table with chairs, and a small potted plant.

1. 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 €201
includes taxes & fees
26 Sept - 27 Sept
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.

2. 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, (10 reviews)
"Property and house were beautiful, clean, quiet. Everything was top notch. Would definitely book again."
United States
Erik B.
The price is €386
includes taxes & fees
4 Oct - 5 Oct
3BR Coastal retreat in peaceful Bokeelia with pool, bikes, ping pong and fishing
A spacious living room with a fireplace, two ceiling fans, a television, and a view of the outdoors.

3. 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 €371
includes taxes & fees
5 Oct - 6 Oct
Casa Florida 🌴 waterfront home with boat ramp
A sunlit room with a sofa, coffee table, and chairs, large windows with a view of a marina and palm trees.

4. 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, (11 reviews)
"Loved this place, right on the water, close to bars and restaurants."
United States
Brandon J.
The price is €447
includes taxes & fees
26 Sept - 27 Sept
3-bedroom house in charming Saint James City with Canal Views!
An aerial view of a coastal area with several small islands connected by bridges.

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

NEW!! The “WATERSIDE” COTTAGE~With dockage
Bokeelia
10.0 out of 10, Exceptional, (51 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 €415
includes taxes & fees
27 Sept - 28 Sept
NEW!! The “WATERSIDE” COTTAGE~With dockage
A covered swimming pool with a clear view of the surrounding area, including a body of water and greenery.

6. 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, (96 reviews)
"Beautiful home and warm pool conviently right on the canal with a boat lift! The host was very helpful!! We definitely will be back!! "
United States
Jennifer C.
The price is €430
includes taxes & fees
1 Oct - 2 Oct
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.

7. 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 €405
includes taxes & fees
4 Oct - 5 Oct
2-bedroom ground floor unit just steps from the gulf with a small private beach
A modern living room with a white sofa, a round coffee table, and a kitchen area in the background.

8. 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 €265
includes taxes & fees
26 Sept - 27 Sept
Waterfront Bungalow in Matlacha
A room with a large sliding glass door leading to a waterway, a bottle of wine, and two glasses on a small table.

9. New! Hidden- Speakeasy-penny floor. 3bd 3bath Boat dock & Walk 2 town FABULOUS

New! Hidden- Speakeasy-penny floor. 3bd 3bath Boat dock & Walk 2 town FABULOUS
Matlacha
10.0 out of 10, Exceptional, (15 reviews)
"Everything was great and the added amenities were a bonus. The little added things made our stay wonderful "
United States
Debra B.
New! Hidden- Speakeasy-penny floor. 3bd 3bath Boat dock & Walk 2 town FABULOUS

10. 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)
"Excellent!"
United States
Tim A.
The price is €389
includes taxes & fees
28 Sept - 29 Sept
50’ of Dock for your boats. Hot tub, Boatlift, walk 2 restaurants Xtra parking.
A spacious kitchen with white cabinets, a central island, a ceiling fan, and large windows.

11. Endless Summer Hideaway w/Pool/ocean access/5br

Endless Summer Hideaway w/Pool/ocean access/5br
Pelican
8.8 out of 10, Excellent, (25 reviews)
"Wonderful place to stay"
United States
Becky W.
The price is €319
includes taxes & fees
27 Sept - 28 Sept
Endless Summer Hideaway w/Pool/ocean access/5br
A spacious living room with a leather sofa, a recliner, and a coffee table. There is a large window with curtains, a dining area in the background, and a view of the outdoors.

12. 2621 SW 27th St. Cape Coral

2621 SW 27th St. Cape Coral
Pelican
9.4 out of 10, Exceptional, (24 reviews)
"Wonderful stay "
United States
Maite
2621 SW 27th St. Cape Coral
A modern living room with a large TV, a marble fireplace, a sofa, and a dining area with a bar.

13. Ultra Modern Home w Heated Salt water Pool pet friendly

Ultra Modern Home w Heated Salt water Pool pet friendly
Mariner
10.0 out of 10, Exceptional, (21 reviews)
"Host very responsive to questions! Really enjoyed the pool and on site amenities!"
United States
Doug M.
The price is €382
includes taxes & fees
1 Oct - 2 Oct
Ultra Modern Home w Heated Salt water Pool pet friendly
A beach with calm water, palm trees, and a clear sky.

14. Gulf access home with heated pool & dock

Gulf access home with heated pool & dock
Caloosahatchee
9.0 out of 10, Wonderful, (88 reviews)
"We thoroughly enjoyed our week long stay! It was very clean and comfortable. The hosts were easy to communicate with. We would highly recommend this property for a relaxing vacation. "
United States
Laurie B.
The price is €400
includes taxes & fees
5 Oct - 6 Oct
Gulf access home with heated pool & dock
A wooden TV stand with a flat-screen TV displaying a beach scene, flanked by two potted plants.

15. RARE FIND COASTAL COZY BRIGHT 2BR 2BATH HOME! 10MINS AWAY TO THE BEACH!

RARE FIND COASTAL COZY BRIGHT 2BR 2BATH HOME! 10MINS AWAY TO THE BEACH!
Hancock
9.6 out of 10, Exceptional, (18 reviews)
"Had a great time. Cute decor!! House was very clean and a nice quiet neighborhood!!Thank you"
United States
Jennifer A.
The price is €216
includes taxes & fees
27 Sept - 28 Sept
RARE FIND COASTAL COZY BRIGHT 2BR 2BATH HOME! 10MINS AWAY TO THE BEACH!
A swimming pool with a covered area, surrounded by palm trees and a herringbone-patterned patio.

16. Enjoy a 3-bedroom vacation home in Yacht Club - Special January & February.

Enjoy a 3-bedroom vacation home in Yacht Club - Special January & February.
Caloosahatchee
9.6 out of 10, Exceptional, (122 reviews)
"Close to restaurants and the beach. Nice house overall."
United States
Paul L.
The price is €394
includes taxes & fees
2 Oct - 3 Oct
Enjoy a 3-bedroom vacation home in Yacht Club - Special January & February.
A beach with clear turquoise water, a sandy shore, and a line of trees in the background.

17. 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 €222
includes taxes & fees
27 Sept - 28 Sept
Cozy retreat, NE cape coral oasis 5 mins to restaurants and shopping plaza.
A swimming pool with a glass enclosure, surrounded by outdoor furniture and a view of greenery.

18. 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, (42 reviews)
"We had a great stay and the house is great. "
United States
Craig L.
The price is €385
includes taxes & fees
25 Oct - 26 Oct
Huge Pool, Close to Beach - Bikes, Beach Gear, Everything You Need!
An indoor swimming pool with a view of the water, lounge chairs, and potted plants.

19. Waterfront Home: Private Pool & Stunning Sea Views

Waterfront Home: Private Pool & Stunning Sea Views
Pelican
10.0 out of 10, Exceptional, (8 reviews)
"Home was spotless. Loved the layout and view "
United States
Jo-Ann
The price is €412
includes taxes & fees
6 Oct - 7 Oct
Waterfront Home: Private Pool & Stunning Sea Views
A beach with a single seashell in the foreground and two people in the background.

20. 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, (44 reviews)
"This was my second stay . It’s so amazing and the location is perfect !!!! We will be back !"
United States
EMILY B.
The price is €422
includes taxes & fees
6 Oct - 7 Oct
coastal chic cottage "Heron" minutes to the beach! JULY SAVINGS!
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Pine Island Hotel Reviews

Lani Kai Beachfront Resort

Lani Kai Beachfront Resort

10/10 Excellent
"Everything you’d expect and then some! Will travel again soon!"
Lora Lee 1-night trip
Posted 2 hours ago
Lani Kai Beachfront Resort

Find out more about Pine Island

Pine Island Holiday Homes information

Number of reviews
582
Accommodation
1149 Holiday Homes
Lowest Price
€201
Highest Price
€447

Explore a world of travel with Expedia