Pine Island Vacation Rentals from $80: Search Short-Term Rentals

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Our top choices for Pine Island vacation rentals

An infinity pool with chairs and tables, a palm tree, and a sunset view.

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

Saint James City

Bethany

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

2. Island Home: 3-bedroom apartment in Bokeelia with hot tub, AC, water views, bbq

Bokeelia

"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) ."

Cynthia P.

$185 nightly

Aug 31 - Sep 1

Total with taxes and fees

A beach with a prominent dead tree trunk, sandy shore, and calm sea.

3. MALU LANI Inn & Marina

Bokeelia

Kyle

$340 nightly

Sep 3 - Sep 4

Total with taxes and fees

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

Bokeelia

Louis

$286 nightly

Aug 31 - Sep 1

Total with taxes and fees

A hot tub with water bubbling, a life ring on the door, and a sign prohibiting chemicals.

5. Captain's Cottage: One-bedroom cottage with a spa in tropical Bokeelia, Florida

Bokeelia

Lisa E.

$179 nightly

Aug 31 - Sep 1

Total with taxes and fees

A room with a white door, a round table with chairs, and a small potted plant.

6. The Oasis: A cosy one-bedroom house in tropical Bokeelia with air conditioning

Bokeelia

Michael W.

$190 nightly

Aug 31 - Sep 1

Total with taxes and fees

A spacious patio with a dining table and chairs, a sofa, and a ceiling fan.

7. 3BR Coastal retreat in peaceful Bokeelia with pool, bikes, ping pong and fishing

Bokeelia

Shauna

$360 nightly

Sep 9 - Sep 10

Total with taxes and fees

A beach with a thatched-roof structure, palm trees, and a calm sea.

8. The Salty Anchor - St. James City

Saint James City

Brent B.

$165 nightly

Aug 31 - Sep 1

Total with taxes and fees

An outdoor patio area with wicker furniture, a green sofa, and a staircase leading to an upper level.

9. Canalfront St James City Home w/ Unique View

Saint James City

$310 nightly

Sep 7 - Sep 8

Total with taxes and fees

10. Boat Dock & Patio: Canal-Front St James City Home!

St. James City

Casey W.

$318 nightly

Sep 7 - Sep 8

Total with taxes and fees

An aerial view of a coastal area with several small islands connected by bridges.

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

Bokeelia

Jennifer D.

$337 nightly

Sep 1 - Sep 2

Total with taxes and fees

A spacious living room with a fireplace, two ceiling fans, a television, and a view of the outdoors.

12. Casa Florida 🌴 waterfront home with boat ramp

Bokeelia

Morgan P.

$347 nightly

Sep 22 - Sep 23

Total with taxes and fees

A sunlit room with a sofa, coffee table, and chairs, large windows with a view of a marina and palm trees.

13. 3-bedroom house in charming Saint James City with Canal Views!

Saint James City

Joshua A.

$514 nightly

Aug 31 - Sep 1

Total with taxes and fees

A wooden deck leading to a glass door, a pool, and a white building with a covered patio area.

14. Studio on the water

Saint James City

Tremayne F.

$328 nightly

Aug 31 - Sep 1

Total with taxes and fees

A covered swimming pool with a clear view of the surrounding area, including a body of water and greenery.

15. Fisherman's Delight With Heated Salt Swimming Pool and a new Boat Lift

St James City

Jennifer C.

$462 nightly

Aug 31 - Sep 1

Total with taxes and fees

A beach view from a covered area with a wooden deck and palm trees.

16. 2-bedroom ground floor unit just steps from the gulf with a small private beach

Bokeelia

Diane F.

$410 nightly

Aug 31 - Sep 1

Total with taxes and fees

A waterfront property with a wooden deck, a marina with boats, and a clear view of the water.

17. Studio with a water view

St. James City

Lori F.

$271 nightly

Aug 31 - Sep 1

Total with taxes and fees

A wooden deck with a table and chairs overlooking a body of water, palm trees, and a house in the background.

18. King Suite on Canal

Saint James City

Tracy L.

$324 nightly

Aug 31 - Sep 1

Total with taxes and fees

A wooden deck with a table and chairs overlooking a marina with boats and buildings.

19. Canal Suite with Water views

Saint James City

Tracy L.

$381 nightly

Aug 31 - Sep 1

Total with taxes and fees

A beachside area with colorful beach houses, a dock, and a sandy beach.

20. Matlacha Tiny Village

Matlacha

Lori

$207 nightly

Sep 9 - Sep 10

Total with taxes and fees

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Top Pine Island Hotel Reviews

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

10/10 Excellent

"Perfect"

Hyatt Vacation Club at Coconut Cove, Bonita Springs

8/10 Good

"I would love to give this resort 5- stars but the a/c issue with my unit is the deduction of the star. The property is immaculate. The landscaping, club house, pool area, lazy river is a 10/10. The unit I was in had issues with the a/c and would not cool down. It progressively got worse each night. I reached out to the front desk and maintenance came by. He shared that this was the fifth time that a service call was made to this unit. Management had refused to repair unit. Maintenance came by and brought me a portable unit for the bedroom. I ended up cutting my trip short by a night."

Lani Kai Beachfront Resort

8/10 Good

"I had a wonderful experience…except that both mattresses in our room were sagging; one more than the other. Mine being the one with the largest dip in it. It also made a lot of noise when I moved. Next time I will definitely request a firm mattress!!! Everything else, and I literally mean EVERYTHING, was exceptional! I enjoyed every minute, from the check-in process to the check-out process. I will definitely return!"

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 $80 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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Check prices for these dates

Our top choices for Pine Island vacation rentals

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

2. Island Home: 3-bedroom apartment in Bokeelia with hot tub, AC, water views, bbq

3. MALU LANI Inn & Marina

4. Charming 1-bedroom apartment in Bokeelia with WiFi, AC, pool & heated spa

5. Captain's Cottage: One-bedroom cottage with a spa in tropical Bokeelia, Florida

6. The Oasis: A cosy one-bedroom house in tropical Bokeelia with air conditioning

7. 3BR Coastal retreat in peaceful Bokeelia with pool, bikes, ping pong and fishing

8. The Salty Anchor - St. James City

9. Canalfront St James City Home w/ Unique View

10. Boat Dock & Patio: Canal-Front St James City Home!

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

12. Casa Florida 🌴 waterfront home with boat ramp

13. 3-bedroom house in charming Saint James City with Canal Views!

14. Studio on the water

15. Fisherman's Delight With Heated Salt Swimming Pool and a new Boat Lift

16. 2-bedroom ground floor unit just steps from the gulf with a small private beach

17. Studio with a water view

18. King Suite on Canal

19. Canal Suite with Water views

20. Matlacha Tiny Village

Find vacation rentals that suit your style

Top Pine Island Hotel Reviews

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

Find out more about Pine Island

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