A waterfront with palm trees and a boat dock.

Pineland Holiday Rentals

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Pineland holiday rentals

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

1. 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 HK$1,234
HK$3,340 total
includes taxes & fees
6 Oct - 7 Oct
3BR Coastal retreat in peaceful Bokeelia with pool, bikes, ping pong and fishing
A beachside area with colorful beach houses, a dock, and a sandy beach.

2. 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 HK$1,038
HK$1,746 total
includes taxes & fees
5 Oct - 6 Oct
Matlacha Tiny Village
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 HK$1,177
HK$1,954 total
includes taxes & fees
5 Oct - 6 Oct
Charming 1-bedroom apartment in Bokeelia with WiFi, AC, pool & heated spa
A beach with a view of the ocean and a sunset.

4. Island Inn

Island Inn
3.5 star property
West End
9.4 out of 10, Exceptional, (1,160 reviews)
"Great location"
United States
Nicole
The price is HK$1,602
HK$1,786 total
includes taxes & fees
5 Oct - 6 Oct
Island Inn
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, (300 reviews)
"Great place!"
United States
Bruce
The price is HK$447
HK$753 total
includes taxes & fees
1 Nov - 2 Nov
Lazy Cuckoo Inn
A beach with a thatched-roof structure, palm trees, and a view of the sea.

6. 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, (1,338 reviews)
"Excellent,clean y quiet"
United States
Carmen
The price is HK$1,375
HK$1,540 total
includes taxes & fees
30 Oct - 31 Oct
The Suites at Fishermen’s Village
A spacious living room with a fireplace, two ceiling fans, a television, and a view of the outdoors.

7. 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 HK$1,028
HK$3,234 total
includes taxes & fees
3 Nov - 4 Nov
Casa Florida 🌴 waterfront home with boat ramp
A balcony with a pool, chairs, and a view of a water body and buildings.

8. 2 Queen Bed|Nsmk|Cape Coral FL

2 Queen Bed|Nsmk|Cape Coral FL
Caloosahatchee
10.0 out of 10, Exceptional, (153 reviews)
"Had a lovely time here!"
United States
Anonymous traveller
The price is HK$473
HK$527 total
includes taxes & fees
5 Oct - 6 Oct
2 Queen Bed|Nsmk|Cape Coral FL
A narrow hallway with a checkered rug, a hanging light fixture, a potted plant, a mirror, a wooden shelf with plants, a coffee maker, and a microwave.

9. Comfort in the Cape

Comfort in the Cape
Caloosahatchee
10.0 out of 10, Exceptional, (4 reviews)
"Great place, lovely people"
United States
Kayla L.
The price is HK$416
HK$883 total
includes taxes & fees
5 Oct - 6 Oct
Comfort in the Cape
A spacious living room with a flat-screen TV, a sofa, a coffee table, and a balcony with a view of the beach.

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

Bayside Villa 4224: Bright Corner Unit with Stunning Bay Views
Captiva
9.0 out of 10, Wonderful, (16 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 HK$814
HK$3,606 total
includes taxes & fees
8 Oct - 9 Oct
Bayside Villa 4224: Bright Corner Unit with Stunning Bay Views
A beach view from a balcony with a pool, palm trees, and a building with a balcony.

11. Edison Beach House

Edison Beach House
3.5 star property
Fort Myers Beach
9.4 out of 10, Exceptional, (1,924 reviews)
"Great stay."
United States
Angie
The price is HK$1,298
HK$1,753 total
includes taxes & fees
12 Oct - 13 Oct
Edison Beach House
An aerial view of a coastal area with several small islands connected by bridges.

12. 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 HK$1,962
HK$3,658 total
includes taxes & fees
5 Oct - 6 Oct
NEW!! The “WATERSIDE” COTTAGE~With dockage
A balcony with a pool, chairs, and a view of a water body and buildings.

13. Cape Coral FL | King bed

Cape Coral FL | King bed
Caloosahatchee
10.0 out of 10, Exceptional, (196 reviews)
"Views of the lake from this hotel are wonderful. The pool was enjoyable as well."
United States
Anonymous traveller
The price is HK$495
HK$552 total
includes taxes & fees
5 Oct - 6 Oct
Cape Coral FL | King bed
A modern kitchen with white cabinetry, a central island, and a dining area with a sofa and table.

14. 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 HK$1,240
HK$4,744 total
includes taxes & fees
5 Oct - 6 Oct
Bayside Villa 5110 | Upscale Bayfront Residence | In-unit laundry | Walk to the Beach
A coastal resort with a long sandy beach, multiple white buildings, and lush greenery.

15. 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.
The price is HK$1,311
HK$4,567 total
includes taxes & fees
5 Oct - 6 Oct
Captiva Villa 3213 | Chic Residence | Great Amenities | Walk to the Beach
A room with a glass table, a ceiling fan, and a view of a palm tree and water.

16. 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.
The price is HK$1,240
HK$4,050 total
includes taxes & fees
5 Oct - 6 Oct
Bayside Villa 4208 | Stunning Harbourview Residence| Walk to the Beach
A beach with a single seashell in the foreground and two people in the background.

17. Coastal Chic Cottage "Sandpiper" minutes to the beach! Free bikes

Coastal Chic Cottage "Sandpiper" minutes to the beach! Free bikes
West End
9.0 out of 10, Wonderful, (23 reviews)
"Loved our stay at the cottage. It was a perfect getaway for 2. Short walk to a quiet beach. Convenient to restaurants and Ding Darling.We will be back!"
United States
Catherine B.
The price is HK$1,099
HK$3,115 total
includes taxes & fees
5 Oct - 6 Oct
Coastal Chic Cottage "Sandpiper" minutes to the beach! Free bikes
A modern kitchen with a central island, a dining area with chairs, a TV mounted on the wall, and a balcony with outdoor furniture.

18. Beach Villa 2426 | Stunning Beachfront Residence on Captiva Island

Beach Villa 2426 | Stunning Beachfront Residence on Captiva Island
Captiva
9.6 out of 10, Exceptional, (26 reviews)
"There were a few minor issues, but for the most part, our stay was enjoyable. "
United States
Ronald
The price is HK$1,679
HK$6,084 total
includes taxes & fees
5 Oct - 6 Oct
Beach Villa 2426 | Stunning Beachfront Residence on Captiva Island
A wooden deck with a table and chairs overlooking a body of water, palm trees, and a house in the background.

19. 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 HK$926
HK$1,643 total
includes taxes & fees
5 Oct - 6 Oct
Southernmost Inn King Suite on Canal
A waterfront hotel with a pool, lounge chairs, and palm trees.

20. Waterfront Condo with Pool & Boat Slip

Waterfront Condo with Pool & Boat Slip
Caloosahatchee
10.0 out of 10, Exceptional, (48 reviews)
"This place was great! Brian is an amazing host!"
United States
Byon W.
The price is HK$639
HK$2,630 total
includes taxes & fees
5 Oct - 6 Oct
Waterfront Condo with Pool & Boat Slip
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

Margaritaville Beach Resort Fort Myers

Margaritaville Beach Resort Fort Myers

10/10 Excellent
"Lo único malo de ese momento fue que la máquina de hielo no servía"
fabiola 1-night trip
Posted 3 hours ago
Margaritaville Beach Resort Fort Myers

Find out more about Pineland

Search for holiday rentals in Pineland on Expedia! You can easily find your home rentals, villas, holiday apartments in Pineland using one of the methods below:

  • View our selection of featured holiday rentals in Pineland
  • Use the map to find apartments and other holiday homes in the Pineland neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Pineland while they last

Look no further and take a look at our great range of rental properties in Pineland!

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.

What are some of the best holiday rentals that Pineland has to offer?

Tiki Hut Paradise 4-bedroom Bokeelia House w Golf Cart Tesla Charger Island Time: This highly rated holiday home rental in Pineland has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

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.