Pine Island Vacation Rentals

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Our top choices for Pine Island vacation rentals

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 CA $163
CA $209 total
includes taxes & fees
May 18 - May 19
Tiny home glamping unit in pine island on a 6 acre property

The Salty Anchor - St. James City

The Salty Anchor - St. James City
Saint James City
The price is CA $117
CA $234 total
includes taxes & fees
May 11 - May 12
The Salty Anchor - St. James City

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
7.0 out of 10, Good, (2 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 CA $110
CA $309 total
includes taxes & fees
May 11 - May 12
Captain's Cottage: One-bedroom cottage with a spa in tropical Bokeelia, Florida

MALU LANI Inn & Marina

MALU LANI Inn & Marina
3.5 star property
Bokeelia
10.0 out of 10, Exceptional, (6 reviews)
"Beautiful property, peaceful, clean rental. Super responsive owner and all the things you need. Perfect location for boaters. Loved this stay and would definitely rent again! "
United States
April
The price is CA $278
CA $555 total
includes taxes & fees
May 14 - May 15
MALU LANI Inn & Marina

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 CA $233
CA $548 total
includes taxes & fees
May 13 - May 14
Cozy 2-bedroom downstairs unit in a house in Saint James City Pine Island

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 CA $164
CA $210 total
includes taxes & fees
May 12 - May 13
Glamping in pine island, Charming 1-bedroom cabin in welcoming Saint James City

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, (17 reviews)
"Couldn’t been better"
United States
Louis
The price is CA $205
CA $430 total
includes taxes & fees
May 11 - May 12
Charming 1-bedroom apartment in Bokeelia with WiFi, AC, pool & heated spa

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 CA $178
CA $439 total
includes taxes & fees
May 11 - May 12
Island Oasis- Olde Florida Keys atmosphere

Casa Florida 🌴 waterfront home with boat ramp

Casa Florida 🌴 waterfront home with boat ramp
Bokeelia
9.4 out of 10, Exceptional, (9 reviews)
"Nice place on canal, having everything you need . Enjoyed the stay. "
United States
John M.
The price is CA $184
CA $576 total
includes taxes & fees
May 13 - May 14
Casa Florida 🌴 waterfront home with boat ramp

Soak up Paradise and Relax in Heated Pool/Spa Home surrounded by Happy Wildlife

Soak up Paradise and Relax in Heated Pool/Spa Home surrounded by Happy Wildlife
Bokeelia
9.8 out of 10, Exceptional, (47 reviews)
"Hosts were very helpful and informative. Clean and well equipped house. We loved the pool and hot tub!"
United States
Rosemary L.
The price is CA $274
CA $643 total
includes taxes & fees
Jun 1 - Jun 2
Soak up Paradise and Relax in Heated Pool/Spa Home surrounded by Happy Wildlife

NEW!! The “WATERSIDE” COTTAGE~With dockage

NEW!! The “WATERSIDE” COTTAGE~With dockage
Bokeelia
10.0 out of 10, Exceptional, (48 reviews)
"Cute home that was perfect to spend time there as well as go sightseeing. If you stay here be sure to go down to the end of the street to meet UNO.Pictures are very acurate"
United States
Janice F.
The price is CA $260
CA $542 total
includes taxes & fees
Jun 1 - Jun 2
NEW!! The “WATERSIDE” COTTAGE~With dockage

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, (8 reviews)
"The house was perfect for our family over the holidays!"
United States
Sarah B.
The price is CA $231
CA $661 total
includes taxes & fees
May 11 - May 12
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, (5 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 CA $300
CA $549 total
includes taxes & fees
May 11 - May 12
2-bedroom ground floor unit just steps from the gulf with a small private beach

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, (3 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 CA $215
CA $583 total
includes taxes & fees
May 16 - May 17
3BR Coastal retreat in peaceful Bokeelia with pool, bikes, ping pong and fishing

Waterfront Gulf Access-Private Dock & Pier. Near beach. See Dolphins daily!

Waterfront Gulf Access-Private Dock & Pier. Near beach. See Dolphins daily!
Saint James City
8.0 out of 10, Very good, (1 review)
"The pictures and description of the property were accurate. The host and hostess tried to think of everything and be very accommodating. I did not give it 5 stars as their was an ant issue in the kitchen and the primary bathroom. Also, we were not able to control the thermostat. We were told it was tricky and they could control it remotely, and they did. We could see it go up during the day, and down at night. Also, the information provided for the stay did not include instruction on how to...
United States
Mary c.
The price is CA $280
CA $760 total
includes taxes & fees
May 11 - May 12
Waterfront Gulf Access-Private Dock & Pier. Near beach. See Dolphins daily!

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 CA $160
CA $331 total
includes taxes & fees
May 11 - May 12
Private location on island time

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 CA $245
CA $306 total
includes taxes & fees
May 11 - May 12
Glamping Cabin with a shared pool in the middle of best that nature has to offer

StudioRes by Marriott Fort Myers Airport

StudioRes by Marriott Fort Myers Airport
3.0 star property
Fort Myers
9.4 out of 10, Exceptional, (54 reviews)
"Great hotel and free clean and friendly staff"
United States
cynthia
The price is CA $115
CA $128 total
includes taxes & fees
May 17 - May 18
StudioRes by Marriott Fort Myers Airport
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 vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation 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 or room. 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 vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . 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 . 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 vacation rental 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 vacation 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 short-term rentals, that won’t be hard to do.