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

Pine Island Vacation Rentals

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Check prices for these dates

In two weeks
Jul 24 - Jul 26
In two months
Sep 4 - Sep 6
In three months
Oct 2 - Oct 4
In four months
Oct 30 - Nov 1

Our top choices for Pine Island vacation rentals

Outdoor dining

Tiny home glamping unit in pine island on a 6 acre property

Tiny home glamping unit in pine island on a 6 acre property
Saint James City
10.0 out of 10, Exceptional, (2 reviews)
"Wonderful setting, terrific host, just right for our one night stay!"
United States
A P.
The price is ￥22,150
￥27,932 total
includes taxes & fees
Jul 13 - Jul 14
Tiny home glamping unit in pine island on a 6 acre property
Dining

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 ￥14,406
￥35,989 total
includes taxes & fees
Jul 13 - Jul 14
The Oasis: A cosy one-bedroom house in tropical Bokeelia with air conditioning
Outdoor dining

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, (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 ￥18,432
￥56,765 total
includes taxes & fees
Jul 13 - Jul 14
Manatee Lookout Cottages - Boat to Beach, Pool, Kayaks, Pets, Direct Gulf Access
Interior

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 ￥27,486
￥64,802 total
includes taxes & fees
Jul 15 - Jul 16
Cozy 2-bedroom downstairs unit in a house in Saint James City Pine Island
Beach

The Salty Anchor - St. James City

The Salty Anchor - St. James City
Saint James City
The price is ￥13,824
￥27,662 total
includes taxes & fees
Jul 13 - Jul 14
The Salty Anchor - St. James City
Interior

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 ￥41,875
￥72,964 total
includes taxes & fees
Jul 13 - Jul 14
2-bedroom ground floor unit just steps from the gulf with a small private beach
Private beach nearby, motor boating, fishing

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 ￥32,045
￥64,703 total
includes taxes & fees
Jul 14 - Jul 15
MALU LANI Inn & Marina
Sun loungers, beach towels

NEW!! The “WATERSIDE” COTTAGE~With dockage

NEW!! The “WATERSIDE” COTTAGE~With dockage
Bokeelia
10.0 out of 10, Exceptional, (50 reviews)
"Great week spent at the Waterside Cottage! "
United States
Sandy S.
The price is ￥27,647
￥59,019 total
includes taxes & fees
Aug 10 - Aug 11
NEW!! The “WATERSIDE” COTTAGE~With dockage
A heated pool

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, (93 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 ￥31,209
￥79,005 total
includes taxes & fees
Jul 13 - Jul 14
Fisherman's Delight With Heated Salt Swimming Pool and a new Boat Lift
Exterior

Private location on island time

Private location on island time
Bokeelia
4.6 out of 10, (4 reviews)
"Host did not provide information for entry into the property. Had to get a hotel and wait for a refund. "
United States
Landa P.
The price is ￥18,917
￥38,817 total
includes taxes & fees
Jul 13 - Jul 14
Private location on island time
Terrace/patio

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 ￥12,951
￥36,170 total
includes taxes & fees
Jul 13 - Jul 14
Captain's Cottage: One-bedroom cottage with a spa in tropical Bokeelia, Florida
Beach

Island Oasis- Olde Florida Keys atmosphere

Island Oasis- Olde Florida Keys atmosphere
St James City
10.0 out of 10, Exceptional, (4 reviews)
"The family and I had such a great time. Everything was so nice and clean, and very easy to get in contact with. We went boating, kayaking, and my son was able to fish every night. Would definitely recommend and would love to come back. Thank you"
United States
Monique S.
The price is ￥21,018
￥51,952 total
includes taxes & fees
Jul 13 - Jul 14
Island Oasis- Olde Florida Keys atmosphere
Pool

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 ￥24,252
￥50,889 total
includes taxes & fees
Jul 19 - Jul 20
Charming 1-bedroom apartment in Bokeelia with WiFi, AC, pool & heated spa
Terrace/patio

Studio on the water

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 ￥30,396
￥58,548 total
includes taxes & fees
Jul 13 - Jul 14
Studio on the water
Outdoor pool

Glamping in pine island, Charming 1-bedroom cabin in welcoming Saint James City

Glamping in pine island, Charming 1-bedroom cabin in welcoming Saint James City
Saint James City
8.0 out of 10, Very Good, (1 review)
"It was very cozy. We loved the location and little patio. It was nice and quiet. We would definitely stay again.We had 2 small suggestions. A mirror somewhere for getting ready and having a bit more space between the toilet and door. It is quite tight with thee door closed.Otherwise it was perfect! Thank you"
United States
Jason C.
The price is ￥20,048
￥25,587 total
includes taxes & fees
Aug 10 - Aug 11
Glamping in pine island, Charming 1-bedroom cabin in welcoming Saint James City
Terrace/patio

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 ￥36,815
￥89,993 total
includes taxes & fees
Jul 17 - Jul 18
3-bedroom house in charming Saint James City with Canal Views!
Dining

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, (7 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 ￥25,424
￥68,812 total
includes taxes & fees
Jul 20 - Jul 21
3BR Coastal retreat in peaceful Bokeelia with pool, bikes, ping pong and fishing
3 bedrooms, free WiFi, bed sheets

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
4.0 out of 10, (1 review)
"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 ￥12,951
￥36,008 total
includes taxes & fees
Aug 3 - Aug 4
Island Home: 3-bedroom apartment in Bokeelia with hot tub, AC, water views, bbq
Pool

Glamping Cabin with a shared pool in the middle of best that nature has to offer

Glamping Cabin with a shared pool in the middle of best that nature has to offer
Saint James City
9.0 out of 10, Wonderful, (2 reviews)
"Perfect place for a stay on the island. Highly recommended "
United States
David B.
The price is ￥28,941
￥35,827 total
includes taxes & fees
Jul 13 - Jul 14
Glamping Cabin with a shared pool in the middle of best that nature has to offer
Living area

Casa Florida 🌴 waterfront home with boat ramp

Casa Florida 🌴 waterfront home with boat ramp
Bokeelia
9.4 out of 10, Exceptional, (11 reviews)
"Nice place on canal, having everything you need . Enjoyed the stay. "
United States
John M.
The price is ￥18,160
￥62,124 total
includes taxes & fees
Aug 4 - Aug 5
Casa Florida 🌴 waterfront home with boat ramp
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

Sanibel Island Beach Resort

Sanibel Island Beach Resort

10/10 Excellent
"Good"
Oreste 1-night trip
Posted 5 hours ago
Sanibel Island Beach Resort

Find out more about Pine Island

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