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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
7.6 out of 10, Good, (7 reviews)
"Host was great"
United States
Cindy H.
The price is £208
includes taxes & fees
1 Nov - 2 Nov
Island Home: 3-bedroom apartment in Bokeelia with hot tub, AC, water views, bbq

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, (4 reviews)
"Great location. Nice property. Clean and comfortable."
United States
Mary Ellen I.
The price is £273
includes taxes & fees
1 Nov - 2 Nov
Manatee Lookout Cottages - Boat to Beach, Dock, Pool, Kayaks, Direct Gulf Access

3. 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
8.8 out of 10, Excellent, (5 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 £172
includes taxes & fees
31 Oct - 1 Nov
Captain's Cottage: One-bedroom cottage with a spa in tropical Bokeelia, Florida

4. MALU LANI Inn & Marina

MALU LANI Inn & Marina
3.5 star property
Bokeelia
10.0 out of 10, Exceptional, (6 reviews)
"Beautiful property, peaceful, clean rental. Super responsive owner and all the things you need. Perfect location for boaters. Loved this stay and would definitely rent again! "
United States
April
The price is £287
includes taxes & fees
5 Nov - 6 Nov
MALU LANI Inn & Marina

5. 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 £194
includes taxes & fees
2 Nov - 3 Nov
Charming 1-bedroom apartment in Bokeelia with WiFi, AC, pool & heated spa

6. 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, (11 reviews)
"Property and house were beautiful, clean, quiet. Everything was top notch. Would definitely book again."
United States
Erik B.
The price is £331
includes taxes & fees
1 Nov - 2 Nov
3BR Coastal retreat in peaceful Bokeelia with pool, bikes, ping pong and fishing

7. 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 £155
includes taxes & fees
12 Nov - 13 Nov
The Oasis: A cosy one-bedroom house in tropical Bokeelia with air conditioning

8. 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 £139
includes taxes & fees
30 Oct - 31 Oct
The Salty Anchor - St. James City

9. 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 £162
includes taxes & fees
1 Nov - 2 Nov
Southernmost Inn King Suite on Canal

10. 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 £291
includes taxes & fees
2 Nov - 3 Nov
Casa Florida 🌴 waterfront home with boat ramp

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

NEW!! The “WATERSIDE” COTTAGE~With dockage
Bokeelia
10.0 out of 10, Exceptional, (52 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 £361
includes taxes & fees
1 Nov - 2 Nov
NEW!! The “WATERSIDE” COTTAGE~With dockage

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, (12 reviews)
"Nice place with good fishing in the canal. "
United States
Joshua A.
The price is £382
includes taxes & fees
1 Nov - 2 Nov
3-bedroom house in charming Saint James City with Canal Views!

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

Malu Lani Cottage at Pirates Cove Inn & Marina - Boat Slip Included
Bokeelia
The price is £311
includes taxes & fees
5 Nov - 6 Nov
Malu Lani Cottage at Pirates Cove Inn & Marina - Boat Slip Included

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, (97 reviews)
"Beautiful home easy access to gulf and awesome cool pool definitely will be back"
United States
Travis W.
The price is £405
includes taxes & fees
2 Nov - 3 Nov
Fisherman's Delight With Heated Salt Swimming Pool and a new Boat Lift

15. 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 £397
includes taxes & fees
8 Nov - 9 Nov
2-bedroom ground floor unit just steps from the gulf with a small private beach

16. Southernmost Inn Studio with a water view

Southernmost Inn Studio with a water view
St. James City
9.8 out of 10, Exceptional, (18 reviews)
"Everything was great we had a great time "
United States
Brigitte J.
The price is £149
includes taxes & fees
17 Nov - 18 Nov
Southernmost Inn Studio with a water view

17. 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 £200
includes taxes & fees
2 Nov - 3 Nov
Southernmost Inn Studio on the water

18. 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 £204
includes taxes & fees
1 Nov - 2 Nov
Southernmost Inn Canal Suite on Water

19. Matlacha Tiny Village

Matlacha Tiny Village
3.0 star property
Matlacha
8.8 out of 10, Excellent, (298 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 £167
includes taxes & fees
31 Oct - 1 Nov
Matlacha Tiny Village

20. Island Inn

Island Inn
3.5 star property
West End
9.4 out of 10, Exceptional, (1,165 reviews)
"Great location"
United States
Nicole
The price is £178
includes taxes & fees
8 Nov - 9 Nov
Island Inn
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 £69 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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