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
2.0 star 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 ¥14,686
¥19,514 total
includes taxes & fees
Feb 1 - Feb 2
Tiny home glamping unit in pine island on a 6 acre property

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, (10 reviews)
"Loved the quiet location. Pool /lanai was very relaxing. Everything was just as promised. "
United States
Ken K.
The price is ¥23,535
¥39,068 total
includes taxes & fees
Jan 15 - Jan 16
Charming 1-bedroom apartment in Bokeelia with WiFi, AC, pool & heated spa

MALU LANI Inn & Marina

MALU LANI Inn & Marina
2.5 star property
Bokeelia
The price is ¥36,872
¥55,233 total
includes taxes & fees
Jan 28 - Jan 29
MALU LANI Inn & Marina

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
The price is ¥20,711
¥26,231 total
includes taxes & fees
Jan 11 - Jan 12
Glamping in pine island, Charming 1-bedroom cabin in welcoming Saint James City

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 ¥24,966
¥68,947 total
includes taxes & fees
Jan 12 - Jan 13
Casa Florida 🌴 waterfront home with boat ramp

NEW!! The “WATERSIDE” COTTAGE~With dockage

NEW!! The “WATERSIDE” COTTAGE~With dockage
Bokeelia
10.0 out of 10, Exceptional, (42 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 ¥35,303
¥65,153 total
includes taxes & fees
Jan 12 - Jan 13
NEW!! The “WATERSIDE” COTTAGE~With dockage

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 ¥31,578
¥53,083 total
includes taxes & fees
Jan 22 - Jan 23
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 ¥23,999
¥57,271 total
includes taxes & fees
Jan 11 - Jan 12
Cozy 2-bedroom downstairs unit in a house in Saint James City Pine Island

MALU LANI Inn & Marina "Pelicans Porch" Unit 4

MALU LANI Inn & Marina "Pelicans Porch" Unit 4
2.0 star property
Bokeelia
The price is ¥31,066
¥53,341 total
includes taxes & fees
Jan 21 - Jan 22
MALU LANI Inn & Marina "Pelicans Porch" Unit 4

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
2.0 star property
Bokeelia
The price is ¥36,236
¥65,114 total
includes taxes & fees
Jan 23 - Jan 24
2-bedroom ground floor unit just steps from the gulf with a small private beach

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 ¥43,618
¥120,796 total
includes taxes & fees
Jan 31 - Feb 1
Tropical Getaway in St. James City – 3BR/2BA w/ Boat Ramp Access Nearby!

Blue Crab Key Condo! Two Bedroom Two Bathroom!

Blue Crab Key Condo! Two Bedroom Two Bathroom!
Bokeelia
The price is ¥39,382
¥87,042 total
includes taxes & fees
Jan 16 - Jan 17
Blue Crab Key Condo! Two Bedroom Two Bathroom!

Gulf getaway! Boat dock, HEATED saltwater pool

Gulf getaway! Boat dock, HEATED saltwater pool
Saint James City
10.0 out of 10, Exceptional, (37 reviews)
"Great stay"
United States
Shawn H.
Gulf getaway! Boat dock, HEATED saltwater pool

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 ¥46,913
¥82,335 total
includes taxes & fees
Jan 11 - Jan 12
Just Listed - Beautifully renovated waterfront 2 bedroom home

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, (1,070 reviews)
"Excellent location and comfortable. Spacious rooms with full kitchens. "
United States
Janet
The price is ¥35,330
¥39,570 total
includes taxes & fees
Feb 1 - Feb 2
The Suites at Fishermen’s Village- 2 Bedroom Suites

StudioRes Fort Myers Airport

StudioRes Fort Myers Airport
3.0 star property
Fort Myers
9.2 out of 10, Wonderful, (24 reviews)
"Loved stay here!!! "
United States
Melissa
The price is ¥20,668
¥23,044 total
includes taxes & fees
Jan 19 - Jan 20
StudioRes Fort Myers Airport

Matlacha Tiny Village

Matlacha Tiny Village
3.0 star property
Matlacha
8.8 out of 10, Excellent, (271 reviews)
"Super clean! Super cute and easy for two. It is close to the road so we hear traffic, but the white noise helped with that. Communication was flawless! Would stay again. "
United States
Rhonda
The price is ¥18,655
¥32,642 total
includes taxes & fees
Jan 11 - Jan 12
Matlacha Tiny Village

Edison Beach House

Edison Beach House
3.5 star property
Fort Myers Beach
9.4 out of 10, Exceptional, (1,610 reviews)
"Location, staff, room with view…all were excellent. Will stay again!"
United States
Leah
Edison Beach House

Delightful Luxury Suite In The Heart Of Fort Myers

Delightful Luxury Suite In The Heart Of Fort Myers
Daniels Corridor
9.6 out of 10, Exceptional, (45 reviews)
"This is a great place, the owners are so nice and helpful with everything great place to stay. We were very pleased with this beautiful place. Shopping, restaurants and over all cool and clean place. "
United States
Hugo B.
The price is ¥10,591
¥28,068 total
includes taxes & fees
Jan 17 - Jan 18
Delightful Luxury Suite In The Heart Of Fort Myers
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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