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Pine Island Holiday Rentals

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Our top choices for Pine Island holiday 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 NZ$302
includes taxes & fees
22 July - 23 July
Tiny home glamping unit in pine island on a 6 acre property

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 NZ$328
includes taxes & fees
23 July - 24 July
The Oasis: A cosy one-bedroom house in tropical Bokeelia with air conditioning

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 NZ$598
includes taxes & fees
16 July - 17 July
Manatee Lookout Cottages - Boat to Beach, Pool, Kayaks, Pets, Direct Gulf Access

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 NZ$693
includes taxes & fees
16 July - 17 July
Cozy 2-bedroom downstairs unit in a house in Saint James City Pine Island

The Salty Anchor - St. James City

The Salty Anchor - St. James City
Saint James City
The price is NZ$313
includes taxes & fees
16 July - 17 July
The Salty Anchor - St. James City

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$766
includes taxes & fees
14 Aug - 15 Aug
2-bedroom ground floor unit just steps from the gulf with a small private beach

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$700
includes taxes & fees
29 July - 30 July
MALU LANI Inn & Marina

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 NZ$651
includes taxes & fees
14 Aug - 15 Aug
NEW!! The “WATERSIDE” COTTAGE~With dockage

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 NZ$831
includes taxes & fees
27 July - 28 July
Fisherman's Delight With Heated Salt Swimming Pool and a new Boat Lift

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 NZ$410
includes taxes & fees
17 July - 18 July
Private location on island time

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$364
includes taxes & fees
13 Aug - 14 Aug
Captain's Cottage: One-bedroom cottage with a spa in tropical Bokeelia, Florida

Island Oasis- Olde Florida Keys atmosphere

Island Oasis- Olde Florida Keys atmosphere
Saint 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 NZ$548
includes taxes & fees
14 Aug - 15 Aug
Island Oasis- Olde Florida Keys atmosphere

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$537
includes taxes & fees
14 Aug - 15 Aug
Charming 1-bedroom apartment in Bokeelia with WiFi, AC, pool & heated spa

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 NZ$618
includes taxes & fees
11 Aug - 12 Aug
Studio on the water

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 NZ$272
includes taxes & fees
10 Aug - 11 Aug
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, (9 reviews)
"Nice place with good fishing in the canal. "
United States
Joshua A.
The price is NZ$868
includes taxes & fees
17 July - 18 July
3-bedroom house in charming Saint James City with Canal Views!

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, (8 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 NZ$747
includes taxes & fees
20 July - 21 July
3BR Coastal retreat in peaceful Bokeelia with pool, bikes, ping pong and fishing

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 NZ$378
includes taxes & fees
9 Aug - 10 Aug
Island Home: 3-bedroom apartment in Bokeelia with hot tub, AC, water views, bbq

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 NZ$378
includes taxes & fees
12 Aug - 13 Aug
Glamping Cabin with a shared pool in the middle of best that nature has to offer

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 NZ$669
includes taxes & fees
4 Aug - 5 Aug
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

Find out more about Pine Island

Everything you need to know about Pine Island holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Pine Island holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Pine Island holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Pine Island holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Pine Island. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Pine Island holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Pine Island holiday rentals we have selected for you start as low as NZ$123 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Pine Island rentals

At Expedia, we put the best Pine Island holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Pine Island rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Pine Island holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Pine Island. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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