A waterfront with palm trees and a boat dock.

Pineland Holiday Rentals

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Pineland holiday rentals

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

1. 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 S$273
includes taxes & fees
15 Oct - 16 Oct
Matlacha Tiny Village
A beach with a prominent dead tree trunk, sandy shore, and calm sea.

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 S$478
includes taxes & fees
21 Oct - 22 Oct
MALU LANI Inn & Marina
A beach with a view of the ocean and a sunset.

3. Island Inn

Island Inn
3.5 star property
West End
9.4 out of 10, Exceptional, (1,162 reviews)
"Great location"
United States
Nicole
The price is S$353
includes taxes & fees
17 Oct - 18 Oct
Island Inn
A beach with a thatched-roof structure, palm trees, and a view of the sea.

4. The Suites at Fishermen’s Village

The Suites at Fishermen’s Village
3.0 star property
Punta Gorda Isles
9.8 out of 10, Exceptional, (1,344 reviews)
"Stay here every time I visit Florida. Highly recommend"
United States
Dawn
The price is S$246
includes taxes & fees
25 Oct - 26 Oct
The Suites at Fishermen’s Village
A modern living room with a flat-screen TV, a floor lamp, a dining table, and a sofa.

5. Lazy Cuckoo Inn

Lazy Cuckoo Inn
2.0 star property
Fort Myers Beach
8.8 out of 10, Excellent, (301 reviews)
"Great place!"
United States
Bruce
The price is S$119
includes taxes & fees
25 Oct - 26 Oct
Lazy Cuckoo Inn
A beach view from a balcony with a pool, palm trees, and a building with a balcony.

6. Edison Beach House

Edison Beach House
3.5 star property
Fort Myers Beach
9.4 out of 10, Exceptional, (1,939 reviews)
"Great stay."
United States
Angie
The price is S$307
includes taxes & fees
18 Oct - 19 Oct
Edison Beach House
A pool area with lounge chairs and umbrellas, a beach with umbrellas and lounge chairs, and palm trees.

7. Sundial Beach Resort & Spa

Sundial Beach Resort & Spa
5.0 star property
Mid Island
8.6 out of 10, Excellent, (2,714 reviews)
"Love the resort and great access to beach"
United States
Lisa Renee
The price is S$595
includes taxes & fees
14 Oct - 15 Oct
Sundial Beach Resort & Spa
A spacious living room with a grey sofa, striped armchair, and a woven coffee table. Large windows offer a view of a tropical garden.

8. Driftwood Inn

Driftwood Inn
4.0 star property
Mid Island
10.0 out of 10, Exceptional, (11 reviews)
"This was our second stay at Driftwood Inn and we enjoyed it as much this time as the last! Property is immaculately cleaned, comfortable and has everything we need. The beach is a short walk away and the included cart, umbrellas and beach chairs make it easy to enjoy your time relaxing in the sun. Highly recommend this property for your beach time!"
United States
Heather
The price is S$602
includes taxes & fees
18 Oct - 19 Oct
Driftwood Inn
A bedroom with a bed, a nightstand, a lamp, and a window with blinds.

9. Lakeside Oasis Fort Myers

Lakeside Oasis Fort Myers
2.0 star property
Iona
The price is S$310
includes taxes & fees
17 Oct - 18 Oct
Lakeside Oasis Fort Myers
A balcony with wicker chairs and a glass table, overlooking a colorful building with a metal roof.

10. Harbour House at the Inn 308

Harbour House at the Inn 308
3.0 star property
Fort Myers Beach
The price is S$641
includes taxes & fees
27 Oct - 28 Oct
Harbour House at the Inn 308
A living room with a sectional sofa, a rug, a framed picture, and a door leading to another room.

11. Fort Myers Escape Near Downtown & Beach w/ Parking

Fort Myers Escape Near Downtown & Beach w/ Parking
3.0 star property
Fort Myers
The price is S$436
includes taxes & fees
14 Oct - 15 Oct
Fort Myers Escape Near Downtown & Beach w/ Parking
A modern kitchen with white cabinets, a dining area with a wooden table and chairs, and a view of a pool through a glass door.

12. Dreams Away - Sleeps 10 Pool Golf Fun

Dreams Away - Sleeps 10 Pool Golf Fun
2.0 star property
Oakland Hills
The price is S$556
includes taxes & fees
22 Oct - 23 Oct
Dreams Away - Sleeps 10 Pool Golf Fun
A living room with a ceiling fan, a sofa with nautical-themed pillows, a coffee table, and a rug with a starfish design.

13. 3 Mi to Fort Myers Beach! Family Getaway w/ Pool

3 Mi to Fort Myers Beach! Family Getaway w/ Pool
3.0 star property
Iona
The price is S$564
includes taxes & fees
4 Nov - 5 Nov
3 Mi to Fort Myers Beach! Family Getaway w/ Pool
A modern kitchen with white cabinetry, a central island, and stainless steel appliances.

14. Riverfront Home w Private Dock Pool Beaches

Riverfront Home w Private Dock Pool Beaches
2.0 star property
McGregor
The price is S$1,119
includes taxes & fees
14 Oct - 15 Oct
Riverfront Home w Private Dock Pool Beaches
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 Pineland Hotel Reviews

Pink Shell Beach Resort and Marina

Pink Shell Beach Resort and Marina

10/10 Excellent
"Maggie was very nice. She answered all of our questions and was extremely helpful. Great!"
Gleydis 3-night trip
Posted 1 hour ago
Pink Shell Beach Resort and Marina

Frequently asked questions

Can I find holiday rentals in Pineland?

Yes, there are holiday rentals close to the most popular sights in Pineland, or you can select a more secluded option if you're looking for a relaxing stay.

How many holiday rentals are there in Pineland?

Expedia has 9 holiday rentals for your stay in Pineland.

What can I see and do in Pineland?

While exploring the area, visit family-friendly sights like Sun Splash Water Park, or get outside and enjoy nature at Calusa Heritage Trail. In the wider area, you’ll find Randell Research Center and Useppa Island.

What are holiday rentals like in Pineland?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Pineland. Holiday rentals feature extras like laundry facilities and kitchens so you'll have a home away from home. If you're concerned about cleanliness, holiday rentals can offer a sense of privacy away from shared hotel lifts and lobbies packed with people while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental a great choice for families.