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, (1 review)
"Wonderful setting, terrific host, just right for our one night stay!"
United States
A P.
The price is CA $148
CA $192 total
includes taxes & fees
Feb 9 - Feb 10
Tiny home glamping unit in pine island on a 6 acre property

Perfect 1-bedroom cottage with SPA in soothing Bokeelia, Florida

Perfect 1-bedroom cottage with SPA in soothing Bokeelia, Florida
Bokeelia
The price is CA $108
CA $325 total
includes taxes & fees
Mar 5 - Mar 6
Perfect 1-bedroom cottage with SPA in soothing Bokeelia, Florida

MALU LANI Inn & Marina

MALU LANI Inn & Marina
2.5 star property
Bokeelia
The price is CA $321
CA $481 total
includes taxes & fees
Feb 9 - Feb 10
MALU LANI Inn & Marina

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
10.0 out of 10, Exceptional, (12 reviews)
"Loved the quiet location. Pool /lanai was very relaxing. Everything was just as promised. "
United States
Ken K.
The price is CA $205
CA $430 total
includes taxes & fees
Feb 11 - Feb 12
Charming 1-bedroom apartment in Bokeelia with WiFi, AC, pool & heated spa

NEW!! The “WATERSIDE” COTTAGE~With dockage

NEW!! The “WATERSIDE” COTTAGE~With dockage
Bokeelia
10.0 out of 10, Exceptional, (44 reviews)
"My wife and I loved our stay at Waterside. The property was clean and well appointed. The area was nice and we loved walking up to the local watering hole for sunset views. I would recommend it highly. "
United States
Ron R.
The price is CA $277
CA $558 total
includes taxes & fees
Mar 1 - Mar 2
NEW!! The “WATERSIDE” COTTAGE~With dockage

Cozy 2-bedroom house in Bokeelia close to many amenities.

Cozy 2-bedroom house in Bokeelia close to many amenities.
Bokeelia
The price is CA $219
CA $534 total
includes taxes & fees
Feb 11 - Feb 12
Cozy 2-bedroom house in Bokeelia close to many amenities.

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 $222
CA $278 total
includes taxes & fees
Feb 9 - Feb 10
Glamping in pine island, Charming 1-bedroom cabin in welcoming Saint James City

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, (5 reviews)
"We had a great short stay this trip down to St James City. We love SJC and this house is a easy walk to our favorite restaurant. The best way I can describe this house is spa like. It is a very nice, comfortable house and if nothing else stay here for the shower! It had everything and was well equipped with just about anything you may need, down to the yoga mats. We had a few questions at check in and the host Britt was quick to respond and help us out. We like that the house is pet friendly as...
United States
Tracy L.
The price is CA $235
CA $662 total
includes taxes & fees
Feb 15 - Feb 16
3-bedroom house in charming Saint James City with Canal Views!

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 $293
CA $705 total
includes taxes & fees
Feb 9 - Feb 10
Casa Florida 🌴 waterfront home with boat ramp

Newly remodeled, relaxing, romantic ground floor 1 bedroom waterfront getaway.

Newly remodeled, relaxing, romantic ground floor 1 bedroom waterfront getaway.
Bokeelia
9.8 out of 10, Exceptional, (18 reviews)
"Couldn’t be better!!! Highly recommend!!!"
United States
Luis K.
The price is CA $274
CA $482 total
includes taxes & fees
Feb 27 - Feb 28
Newly remodeled, relaxing, romantic ground floor 1 bedroom waterfront getaway.

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 $286
CA $617 total
includes taxes & fees
Feb 10 - Feb 11
Cozy 2-bedroom downstairs unit in a house in Saint James City Pine Island

Tropical Getaway in St. James City – 3BR/2BA w/ Boat Ramp Access Nearby!

Tropical Getaway in St. James City – 3BR/2BA w/ Boat Ramp Access Nearby!
Manatee Bay
The price is CA $380
CA $1,053 total
includes taxes & fees
Feb 9 - Feb 10
Tropical Getaway in St. James City – 3BR/2BA w/ Boat Ramp Access Nearby!

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
The price is CA $220
CA $277 total
includes taxes & fees
Feb 9 - Feb 10
Glamping Cabin with a shared pool in the middle of best that nature has to offer

Just Listed - Beautifully renovated waterfront 2 bedroom home

Just Listed - Beautifully renovated waterfront 2 bedroom home
Bokeelia
9.0 out of 10, Wonderful, (8 reviews)
"Me and one of my friends come to Florida once a year to fish with a couple of our good friends and this was the perfect place for us. The property was very nice, clean, communication with ownership was easy, and we had a great time. I would recommend this place to anyone looking for a fun weekend stay."
United States
Rex S.
The price is CA $409
CA $723 total
includes taxes & fees
Feb 9 - Feb 10
Just Listed - Beautifully renovated waterfront 2 bedroom home

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
6.0 out of 10, (2 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 $330
CA $587 total
includes taxes & fees
Feb 23 - Feb 24
2-bedroom ground floor unit just steps from the gulf with a small private beach

Edison Beach House

Edison Beach House
3.5 star property
Fort Myers Beach
9.4 out of 10, Exceptional, (1,643 reviews)
"Staff is very friendly & accommodating. Location is great. Close to bars, restaurants, shopping and right on the beach. "
United States
Ellen
The price is CA $428
CA $523 total
includes taxes & fees
Feb 12 - Feb 13
Edison Beach House

The Suites at Fishermen’s Village- 2 Bedroom Suites

The Suites at Fishermen’s Village- 2 Bedroom Suites
3.0 star property
Punta Gorda Isles
9.8 out of 10, Exceptional, (1,096 reviews)
"Wonderful staff, clean and updated rooms, great location."
United States
Shawn
The price is CA $393
CA $440 total
includes taxes & fees
Feb 22 - Feb 23
The Suites at Fishermen’s Village- 2 Bedroom Suites

Matlacha Tiny Village

Matlacha Tiny Village
3.0 star property
Matlacha
8.8 out of 10, Excellent, (274 reviews)
"The property was super cute and clean! It also had just about anything you could need!"
United States
Wyatt
The price is CA $171
CA $293 total
includes taxes & fees
Feb 9 - Feb 10
Matlacha Tiny Village

Sundial Beach Resort & Spa

Sundial Beach Resort & Spa
5.0 star property
Mid Island
8.6 out of 10, Excellent, (2,598 reviews)
"Room was clean and was cleaned in the middle of our stay and staff was great."
United States
Glen
The price is CA $778
CA $942 total
includes taxes & fees
Feb 11 - Feb 12
Sundial Beach Resort & Spa

GullWing Beach Resort

GullWing Beach Resort
3.5 star property
South Island
9.4 out of 10, Exceptional, (932 reviews)
"The view of the beach was spectacular. "
United States
Carol
GullWing Beach Resort
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.