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.
The price is CA $101
CA $301 total
includes taxes & fees
Sep 28 - Sep 29
Island Home: 3-bedroom apartment in Bokeelia with hot tub, AC, water views, bbq
A hot tub with water bubbling, a life ring on the door, and a sign prohibiting chemicals.

2. 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 CA $88
CA $284 total
includes taxes & fees
Sep 27 - Sep 28
Captain's Cottage: One-bedroom cottage with a spa in tropical Bokeelia, Florida
A pool with a metal railing, surrounded by lush greenery and a covered area with a metal frame.

3. 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 CA $212
CA $352 total
includes taxes & fees
Sep 27 - Sep 28
Charming 1-bedroom apartment in Bokeelia with WiFi, AC, pool & heated spa
A wooden deck with a table and chairs overlooking a body of water, palm trees, and a house in the background.

4. 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.
The price is CA $167
CA $296 total
includes taxes & fees
Oct 1 - Oct 2
Southernmost Inn King Suite on Canal
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.
The price is CA $126
CA $315 total
includes taxes & fees
Sep 27 - Sep 28
The Oasis: A cosy one-bedroom house in tropical Bokeelia with air conditioning
A beach with a thatched-roof structure, palm trees, and a calm sea.

6. 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.
The price is CA $134
CA $257 total
includes taxes & fees
Sep 27 - Sep 28
The Salty Anchor - St. James City
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

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.
The price is CA $198
CA $572 total
includes taxes & fees
Oct 7 - Oct 8
3BR Coastal retreat in peaceful Bokeelia with pool, bikes, ping pong and fishing
A beach with a prominent dead tree trunk, sandy shore, and calm sea.

8. 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 CA $252
CA $534 total
includes taxes & fees
Oct 6 - Oct 7
MALU LANI Inn & Marina
A spacious living room with a fireplace, two ceiling fans, a television, and a view of the outdoors.

9. 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.
The price is CA $177
CA $574 total
includes taxes & fees
Sep 30 - Oct 1
Casa Florida 🌴 waterfront home with boat ramp
A sunlit room with a sofa, coffee table, and chairs, large windows with a view of a marina and palm trees.

10. 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.
The price is CA $252
CA $700 total
includes taxes & fees
Sep 27 - Sep 28
3-bedroom house in charming Saint James City with Canal Views!
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.
The price is CA $354
CA $661 total
includes taxes & fees
Sep 27 - Sep 28
NEW!! The “WATERSIDE” COTTAGE~With dockage
A waterfront property with a wooden deck, a marina with boats, and a clear view of the water.

12. 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.
The price is CA $151
CA $277 total
includes taxes & fees
Sep 27 - Sep 28
Southernmost Inn Studio with a water view
A wooden deck leading to a glass door, a pool, and a white building with a covered patio area.

13. 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.
The price is CA $151
CA $365 total
includes taxes & fees
Sep 27 - Sep 28
Southernmost Inn Studio on the water
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.
The price is CA $273
CA $684 total
includes taxes & fees
Oct 1 - Oct 2
Fisherman's Delight With Heated Salt Swimming Pool and a new Boat Lift
A wooden deck with a table and chairs overlooking a marina with boats and buildings.

15. 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.
The price is CA $167
CA $385 total
includes taxes & fees
Sep 27 - Sep 28
Southernmost Inn Canal Suite on Water
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

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 CA $366
CA $633 total
includes taxes & fees
Sep 27 - Sep 28
2-bedroom ground floor unit just steps from the gulf with a small private beach
A beachside area with colorful beach houses, a dock, and a sandy beach.

17. 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
The price is CA $187
CA $315 total
includes taxes & fees
Sep 29 - Sep 30
Matlacha Tiny Village
A beach with a view of the ocean and a sunset.

18. Island Inn

Island Inn
3.5 star property
West End
9.4 out of 10, Exceptional, (1,156 reviews)
"Great location"
United States
Nicole
The price is CA $289
CA $322 total
includes taxes & fees
Sep 28 - Sep 29
Island Inn
A modern kitchen with white cabinetry, a central island, and a dining area with a sofa and table.

19. Bayside Villa 5110 | Upscale Bayfront Residence | In-unit laundry | Walk to the Beach

Bayside Villa 5110 | Upscale Bayfront Residence | In-unit laundry | Walk to the Beach
Captiva
9.6 out of 10, Exceptional, (23 reviews)
"Well kept condo."
United States
Joseph S.
The price is CA $221
CA $831 total
includes taxes & fees
Sep 27 - Sep 28
Bayside Villa 5110 | Upscale Bayfront Residence | In-unit laundry | Walk to the Beach
A room with a glass table, a ceiling fan, and a view of a palm tree and water.

20. Bayside Villa 4208 | Stunning Harbourview Residence| Walk to the Beach

Bayside Villa 4208 | Stunning Harbourview Residence| Walk to the Beach
Captiva
9.2 out of 10, Wonderful, (31 reviews)
"Very nice condo overlooking waterway. Nice pool and easy in and out. "
United States
William B.
Bayside Villa 4208 | Stunning Harbourview Residence| Walk to the Beach
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
"Our room was clean and tidy when we arrived and service came every other day for cleaning and linen change, etc. The staff was cordial and helpful every step of the way. The on-site restaurant was very good, particularly their grilled mahi-mahi and their onion rings! Other items on the menu were equally as good if not better than a couple of the local establishments. Our parking was convenient to our room, and our room was just a few steps from the pool and the beach. Our stay was a full week that, unfortunately, flew by way too fast!"
Judith 7-night trip
Posted 2 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, 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 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 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Pine Island vacation rentals we have selected for you start as low as CA $118 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 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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