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

Pine Island Holiday Rentals

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Our top choices for Pine Island holiday rentals

1. Island Home: 3-bedroom apartment in Bokeelia with hot tub, AC, water views, bbq

Island Home: 3-bedroom apartment in Bokeelia with hot tub, AC, water views, bbq
Bokeelia
7.6 out of 10, Good, (7 reviews)
"This was a nice property, as in pictures. It was secluded and view from back porch to a lake/pond is great with a morning coffee or late night cocktail. Location is easily accessible to local venues. Publix and liquor store at end of street, and gas station across street. The Host does need to correct some issues and she does reply. Overall stay was great and we did a weekend in Matlacha (Matt LaShay.. LOL) ."
United States
Cynthia P.
The price is NZ$406
includes taxes & fees
22 Oct - 23 Oct
Island Home: 3-bedroom apartment in Bokeelia with hot tub, AC, water views, bbq

2. 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, (3 reviews)
"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 NZ$631
includes taxes & fees
17 Oct - 18 Oct
Manatee Lookout Cottages - Boat to Beach, Dock, Pool, Kayaks, Direct Gulf Access

3. MALU LANI Inn & Marina

MALU LANI Inn & Marina
3.5 star property
Bokeelia
10.0 out of 10, Exceptional, (6 reviews)
"Overall, very friendly Gave me advice about the area Told me what live bands were playing that night Very fun definitely will be back"
United States
Kyle
The price is NZ$665
includes taxes & fees
15 Oct - 16 Oct
MALU LANI Inn & Marina

4. Charming 1-bedroom apartment in Bokeelia with WiFi, AC, pool & heated spa

Charming 1-bedroom apartment in Bokeelia with WiFi, AC, pool & heated spa
Bokeelia
9.8 out of 10, Exceptional, (18 reviews)
"peaceful and quiet in a great place to getaway"
United States
Louis
The price is NZ$433
includes taxes & fees
26 Oct - 27 Oct
Charming 1-bedroom apartment in Bokeelia with WiFi, AC, pool & heated spa

5. 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)
"Property and house were beautiful, clean, quiet. Everything was top notch. Would definitely book again."
United States
Erik B.
The price is NZ$820
includes taxes & fees
1 Nov - 2 Nov
3BR Coastal retreat in peaceful Bokeelia with pool, bikes, ping pong and fishing

6. 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 NZ$823
includes taxes & fees
14 Oct - 15 Oct
NEW!! The “WATERSIDE” COTTAGE~With dockage

7. Southernmost Inn Canal Suite on Water

Southernmost Inn Canal Suite on Water
Saint James City
9.8 out of 10, Exceptional, (16 reviews)
"Great location, plenty of space. "
United States
Tracy L.
The price is NZ$481
includes taxes & fees
14 Oct - 15 Oct
Southernmost Inn Canal Suite on Water

8. Captain's Cottage: One-bedroom cottage with a spa in tropical Bokeelia, Florida

Captain's Cottage: One-bedroom cottage with a spa in tropical Bokeelia, Florida
Bokeelia
8.6 out of 10, Excellent, (4 reviews)
"The cottage was very cute inside, and had everything we needed. Be sure that you have your entrance information ahead of time as cell service is limited in the area."
United States
Lisa E.
The price is NZ$373
includes taxes & fees
14 Oct - 15 Oct
Captain's Cottage: One-bedroom cottage with a spa in tropical Bokeelia, Florida

9. The Salty Anchor - St. James City

The Salty Anchor - St. James City
Saint James City
10.0 out of 10, Exceptional, (1 review)
"Perfect accomodations for my work trip. Excellent"
United States
Brent B.
The Salty Anchor - St. James City

10. 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)
"Nice place with good fishing in the canal. "
United States
Joshua A.
The price is NZ$923
includes taxes & fees
2 Nov - 3 Nov
3-bedroom house in charming Saint James City with Canal Views!

11. 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$337
includes taxes & fees
15 Oct - 16 Oct
The Oasis: A cosy one-bedroom house in tropical Bokeelia with air conditioning

12. 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)
"This is a beautiful home, nicely decorated and well maintained, on a canal on Pine Island. The canal provided easy access to waterways making Sanibel and Captiva Islands a short trip away. There was plenty of room to park our boat trailer during our stay. Check-in was easy and the host was quick to respond to a couple of questions we had upon arrival. We enjoyed our stay and look forward to returning."
United States
Becky W.
The price is NZ$785
includes taxes & fees
7 Nov - 8 Nov
Fisherman's Delight With Heated Salt Swimming Pool and a new Boat Lift

13. 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$702
includes taxes & fees
14 Oct - 15 Oct
Casa Florida 🌴 waterfront home with boat ramp

14. Malu Lani Cottage at Pirates Cove Inn & Marina - Boat Slip Included

Malu Lani Cottage at Pirates Cove Inn & Marina - Boat Slip Included
Bokeelia
The price is NZ$732
includes taxes & fees
26 Oct - 27 Oct
Malu Lani Cottage at Pirates Cove Inn & Marina - Boat Slip Included

15. 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$790
includes taxes & fees
14 Oct - 15 Oct
2-bedroom ground floor unit just steps from the gulf with a small private beach

16. Southernmost Inn Studio on the water

Southernmost Inn Studio on the water
Saint James City
9.0 out of 10, Wonderful, (22 reviews)
"Very Cozy Stay.. Great Area"
United States
Tremayne F.
The price is NZ$449
includes taxes & fees
11 Nov - 12 Nov
Southernmost Inn Studio on the water

17. Southernmost Inn Studio with a water view

Southernmost Inn Studio with a water view
St. James City
9.8 out of 10, Exceptional, (18 reviews)
"Everything was great we had a great time "
United States
Brigitte J.
Southernmost Inn Studio with a water view

18. Southernmost Inn King Suite on Canal

Southernmost Inn King Suite on Canal
Saint James City
10.0 out of 10, Exceptional, (19 reviews)
"Great spot. We have stayed multiple times, love the location. Everything has been great and look forward to going back! "
United States
Tracy L.
The price is NZ$369
includes taxes & fees
14 Oct - 15 Oct
Southernmost Inn King Suite on Canal

19. Matlacha Tiny Village

Matlacha Tiny Village
3.0 star property
Matlacha
9.0 out of 10, Wonderful, (297 reviews)
"So cute and clean nice dock to sit and relax or fish. Kayaks available to use free as well with life jackets paddles, etc. well equipped rental we can’t wait to go again! Great communication with hosts."
United States
Lori
The price is NZ$380
includes taxes & fees
15 Oct - 16 Oct
Matlacha Tiny Village

20. Island Inn

Island Inn
3.5 star property
West End
9.4 out of 10, Exceptional, (1,162 reviews)
"Great location"
United States
Nicole
The price is NZ$550
includes taxes & fees
30 Oct - 31 Oct
Island Inn
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

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Pine Island holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Pine Island. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Pine Island. Seeing all the best attractions is bound to make you fall in love with Pine Island. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Pine Island short-term rentals, that won’t be hard to do.

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