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Our top choices for Pine Island holiday rentals

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 £153
includes taxes & fees
16 Sept - 17 Sept
Island Home: 3-bedroom apartment in Bokeelia with hot tub, AC, water views, bbq

2. 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 £281
includes taxes & fees
1 Oct - 2 Oct
MALU LANI Inn & Marina

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 £190
includes taxes & fees
15 Sept - 16 Sept
Charming 1-bedroom apartment in Bokeelia with WiFi, AC, pool & heated spa

4. 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 £152
includes taxes & fees
15 Sept - 16 Sept
Captain's Cottage: One-bedroom cottage with a spa in tropical Bokeelia, Florida

5. 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 £137
includes taxes & fees
15 Sept - 16 Sept
The Salty Anchor - St. James City

6. 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 £169
includes taxes & fees
15 Sept - 16 Sept
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

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 £322
includes taxes & fees
18 Sept - 19 Sept
3BR Coastal retreat in peaceful Bokeelia with pool, bikes, ping pong and fishing

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.
The price is £292
includes taxes & fees
15 Sept - 16 Sept
Casa Florida 🌴 waterfront home with boat ramp

9. 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 £354
includes taxes & fees
16 Sept - 17 Sept
NEW!! The “WATERSIDE” COTTAGE~With dockage

10. 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 £273
includes taxes & fees
15 Sept - 16 Sept
Southernmost Inn Studio on the water

11. 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 £393
includes taxes & fees
17 Sept - 18 Sept
3-bedroom house in charming Saint James City with Canal Views!

12. 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 £363
includes taxes & fees
14 Oct - 15 Oct
Fisherman's Delight With Heated Salt Swimming Pool and a new Boat Lift

13. 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 £340
includes taxes & fees
15 Sept - 16 Sept
2-bedroom ground floor unit just steps from the gulf with a small private beach

14. 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 £226
includes taxes & fees
15 Sept - 16 Sept
Southernmost Inn Studio with a water view

15. 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 £270
includes taxes & fees
15 Sept - 16 Sept
Southernmost Inn King Suite on Canal

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.
The price is £302
includes taxes & fees
15 Sept - 16 Sept
Southernmost Inn Canal Suite on Water

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 £165
includes taxes & fees
15 Sept - 16 Sept
Matlacha Tiny Village

18. 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 traveller
The price is £51
includes taxes & fees
15 Sept - 16 Sept
2 Queen Bed|Nsmk|Cape Coral FL

19. Bayside Villa 4224: Bright Corner Unit with Stunning Bay Views

Bayside Villa 4224: Bright Corner Unit with Stunning Bay Views
Captiva
8.8 out of 10, Excellent, (15 reviews)
"Clean property, easy access. Good kitchen supplies. It was nice to be staying on the island and close to the beach."
United States
Louis
The price is £333
includes taxes & fees
15 Sept - 16 Sept
Bayside Villa 4224: Bright Corner Unit with Stunning Bay Views

20. Captiva Villa 3213 | Chic Residence | Great Amenities | Walk to the Beach

Captiva Villa 3213 | Chic Residence | Great Amenities | Walk to the Beach
Captiva
9.0 out of 10, Wonderful, (19 reviews)
"Great villa for 2 people. The place was clean, well stocked and comfortable. The pool was lovely. Check in / check out was seamless. Would definitely book again."
United States
Connie A.
Captiva Villa 3213 | Chic Residence | Great Amenities | 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

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, apart-hotels, 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 £62 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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