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
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Pine Island vacation rentals

A bedroom with a bed, a nightstand with a lamp, a TV, and a view of a balcony.

1. 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
8.4 out of 10, Very good, (6 reviews)
"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.
$190 nightly
The price is $210
Sep 28 - Sep 29
Total with taxes and fees
Island Home: 3-bedroom apartment in Bokeelia with hot tub, AC, water views, bbq
An infinity pool with chairs and tables, a palm tree, and a sunset view.

2. Manatee Lookout Cottages - Boat to Beach, Dock, Pool, Kayaks, Direct Gulf Access

Manatee Lookout Cottages - Boat to Beach, Dock, Pool, Kayaks, 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
$306 nightly
The price is $338
Oct 1 - Oct 2
Total with taxes and fees
Manatee Lookout Cottages - Boat to Beach, Dock, Pool, Kayaks, Direct Gulf Access
A beach with a prominent dead tree trunk, sandy shore, and calm sea.

3. 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
$335 nightly
The price is $364
Oct 27 - Oct 28
Total with taxes and fees
MALU LANI Inn & Marina
A pool with a metal railing, surrounded by lush greenery and a covered area with a metal frame.

4. 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
$220 nightly
The price is $243
Sep 28 - Sep 29
Total with taxes and fees
Charming 1-bedroom apartment in Bokeelia with WiFi, AC, pool & heated spa
A room with a white door, a round table with chairs, and a small potted plant.

5. 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
10.0 out of 10, Exceptional, (1 review)
"The property was convenient to get to the boat, ramp and restaurants in the area. The property was exactly what I was looking for for a quick getway. The host was very nice and communicated with me about the property and check in was great."
United States
Michael W.
$198 nightly
The price is $218
Sep 28 - Sep 29
Total with taxes and fees
The Oasis: A cosy one-bedroom house in tropical Bokeelia with air conditioning
A hot tub with water bubbling, a life ring on the door, and a sign prohibiting chemicals.

6. 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.
$181 nightly
The price is $200
Sep 30 - Oct 1
Total with taxes and fees
Captain's Cottage: One-bedroom cottage with a spa in tropical Bokeelia, Florida
A waterfront property with a wooden deck, a marina with boats, and a clear view of the water.

7. Southernmost Inn Studio with a water view

Southernmost Inn Studio with a water view
St. James City
9.8 out of 10, Exceptional, (17 reviews)
"The location on the water was awesome. Beautiful! "
United States
Lori F.
$177 nightly
The price is $195
Sep 28 - Sep 29
Total with taxes and fees
Southernmost Inn Studio with a water view
A spacious living room with a fireplace, two ceiling fans, a television, and a view of the outdoors.

8. Casa Florida 🌴 waterfront home with boat ramp

Casa Florida 🌴 waterfront home with boat ramp
Bokeelia
9.4 out of 10, Exceptional, (11 reviews)
"This is our second time staying at this location and we will definitely be back! It is so convenient to have the boat ramp at the house and we love the boat lift. The house and property itself has everything you need and is always clean! "
United States
Morgan P.
$324 nightly
The price is $359
Sep 29 - Sep 30
Total with taxes and fees
Casa Florida 🌴 waterfront home with boat ramp
A beach with a thatched-roof structure, palm trees, and a calm sea.

9. The Salty Anchor - St. James City

The Salty Anchor - St. James City
Saint James City
10.0 out of 10, Exceptional, (1 review)
"Perfect accomodations for my work trip. Excellent"
United States
Brent B.
$165 nightly
The price is $182
Sep 28 - Sep 29
Total with taxes and fees
The Salty Anchor - St. James City
A spacious patio with a dining table and chairs, a sofa, and a ceiling fan.

10. 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, (10 reviews)
"Property and house were beautiful, clean, quiet. Everything was top notch. Would definitely book again."
United States
Erik B.
$356 nightly
The price is $394
Oct 7 - Oct 8
Total with taxes and fees
3BR Coastal retreat in peaceful Bokeelia with pool, bikes, ping pong and fishing
An aerial view of a coastal area with several small islands connected by bridges.

11. NEW!! The “WATERSIDE” COTTAGE~With dockage

NEW!! The “WATERSIDE” COTTAGE~With dockage
Bokeelia
10.0 out of 10, Exceptional, (51 reviews)
"We had a great stay, was exactly as described. The host had great communication and gave great advice for the property and surrounding area."
United States
Jennifer D.
$399 nightly
The price is $442
Sep 28 - Sep 29
Total with taxes and fees
NEW!! The “WATERSIDE” COTTAGE~With dockage
A sunlit room with a sofa, coffee table, and chairs, large windows with a view of a marina and palm trees.

12. 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, (11 reviews)
"Loved this place, right on the water, close to bars and restaurants."
United States
Brandon J.
$413 nightly
The price is $458
Oct 2 - Oct 3
Total with taxes and fees
3-bedroom house in charming Saint James City with Canal Views!
A coastal scene with a dock, a building with a blue facade, and palm trees.

13. Malu Lani Cottage at Pirates Cove Inn & Marina - Boat Slip Included

Malu Lani Cottage at Pirates Cove Inn & Marina - Boat Slip Included
Bokeelia
$354 nightly
The price is $392
Oct 5 - Oct 6
Total with taxes and fees
Malu Lani Cottage at Pirates Cove Inn & Marina - Boat Slip Included
A covered swimming pool with a clear view of the surrounding area, including a body of water and greenery.

14. 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, (96 reviews)
"Beautiful home and warm pool conviently right on the canal with a boat lift! The host was very helpful!! We definitely will be back!! "
United States
Jennifer C.
$415 nightly
The price is $460
Oct 1 - Oct 2
Total with taxes and fees
Fisherman's Delight With Heated Salt Swimming Pool and a new Boat Lift
A wooden deck leading to a glass door, a pool, and a white building with a covered patio area.

15. Southernmost Inn Studio on the water

Southernmost Inn Studio on the water
Saint James City
9.0 out of 10, Wonderful, (22 reviews)
"Very Cozy Stay.. Great Area"
United States
Tremayne F.
$227 nightly
The price is $251
Sep 28 - Sep 29
Total with taxes and fees
Southernmost Inn Studio on the water
A wooden deck with a table and chairs overlooking a marina with boats and buildings.

16. Southernmost Inn Canal Suite on Water

Southernmost Inn Canal Suite on Water
Saint James City
9.8 out of 10, Exceptional, (16 reviews)
"Great location, plenty of space. "
United States
Tracy L.
$238 nightly
The price is $263
Sep 28 - Sep 29
Total with taxes and fees
Southernmost Inn Canal Suite on Water
A beach view from a covered area with a wooden deck and palm trees.

17. 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.
$382 nightly
The price is $423
Sep 28 - Sep 29
Total with taxes and fees
2-bedroom ground floor unit just steps from the gulf with a small private beach
A wooden deck with a table and chairs overlooking a body of water, palm trees, and a house in the background.

18. Southernmost Inn King Suite on Canal

Southernmost Inn King Suite on Canal
Saint James City
10.0 out of 10, Exceptional, (19 reviews)
"Great spot. We have stayed multiple times, love the location. Everything has been great and look forward to going back! "
United States
Tracy L.
$188 nightly
The price is $207
Oct 1 - Oct 2
Total with taxes and fees
Southernmost Inn King Suite on Canal
A beachside area with colorful beach houses, a dock, and a sandy beach.

19. Matlacha Tiny Village

Matlacha Tiny Village
3.0 star property
Matlacha
9.0 out of 10, Wonderful, (297 reviews)
"So cute and clean nice dock to sit and relax or fish. Kayaks available to use free as well with life jackets paddles, etc. well equipped rental we can’t wait to go again! Great communication with hosts."
United States
Lori
$222 nightly
The price is $239
Sep 30 - Oct 1
Total with taxes and fees
Matlacha Tiny Village
A balcony with a pool, chairs, and a view of a water body and buildings.

20. 2 Queen Bed|Nsmk|Cape Coral FL

2 Queen Bed|Nsmk|Cape Coral FL
Caloosahatchee
10.0 out of 10, Exceptional, (151 reviews)
"Had a lovely time here!"
United States
Anonymous traveler
$61 nightly
The price is $68
Sep 28 - Sep 29
Total with taxes and fees
2 Queen Bed|Nsmk|Cape Coral FL
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
"We had a great stay! The location is spectacular. We loved the beach, enjoyed the pool and the restaurant was fantastic. We’re already planning our next trip back. Only feedback about our room was the air conditioner is loud. It’s to be expected with those units but otherwise, it was a great little vacation!"
Melanie 2-night trip
Posted 3 hours ago
Sanibel Island Beach Resort

Find out more about Pine Island

Everything you need to know about Pine Island vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Pine Island vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Pine Island vacation 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 low season months. For more hustle and bustle, you may prefer to visit Pine Island in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $85 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Pine Island rentals

At Expedia, we put the best Pine Island vacation 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 vacation.

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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