A waterfront with palm trees and a boat dock.

Pineland Holiday Rentals

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Our top choices for Pineland holiday rentals

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 NZ$765
includes taxes & fees
6 Oct - 7 Oct
3BR Coastal retreat in peaceful Bokeelia with pool, bikes, ping pong and fishing

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 NZ$396
includes taxes & fees
5 Oct - 6 Oct
Matlacha Tiny Village

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 NZ$447
includes taxes & fees
5 Oct - 6 Oct
Charming 1-bedroom apartment in Bokeelia with WiFi, AC, pool & heated spa

4. Island Inn

Island Inn
3.5 star property
West End
9.4 out of 10, Exceptional, (1,159 reviews)
"Great location"
United States
Nicole
The price is NZ$405
includes taxes & fees
5 Oct - 6 Oct
Island Inn

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 NZ$161
includes taxes & fees
3 Nov - 4 Nov
Lazy Cuckoo Inn

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, (1,337 reviews)
"Excellent,clean y quiet"
United States
Carmen
The price is NZ$349
includes taxes & fees
30 Oct - 31 Oct
The Suites at Fishermen’s Village

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 NZ$690
includes taxes & fees
5 Oct - 6 Oct
Casa Florida 🌴 waterfront home with boat ramp

8. 2 Queen Bed|Nsmk|Cape Coral FL

2 Queen Bed|Nsmk|Cape Coral FL
Caloosahatchee
10.0 out of 10, Exceptional, (152 reviews)
"Had a lovely time here!"
United States
Anonymous traveller
The price is NZ$120
includes taxes & fees
5 Oct - 6 Oct
2 Queen Bed|Nsmk|Cape Coral FL

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 NZ$200
includes taxes & fees
5 Oct - 6 Oct
Comfort in the Cape

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 NZ$820
includes taxes & fees
5 Oct - 6 Oct
Bayside Villa 4224: Bright Corner Unit with Stunning Bay Views

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 NZ$398
includes taxes & fees
12 Oct - 13 Oct
Edison Beach House

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 NZ$837
includes taxes & fees
5 Oct - 6 Oct
NEW!! The “WATERSIDE” COTTAGE~With dockage

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 NZ$125
includes taxes & fees
5 Oct - 6 Oct
Cape Coral FL | King bed

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 NZ$1,078
includes taxes & fees
5 Oct - 6 Oct
Bayside Villa 5110 | Upscale Bayfront Residence | In-unit laundry | Walk to the Beach

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 NZ$1,038
includes taxes & fees
5 Oct - 6 Oct
Captiva Villa 3213 | Chic Residence | Great Amenities | Walk to the Beach

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 NZ$921
includes taxes & fees
5 Oct - 6 Oct
Bayside Villa 4208 | Stunning Harbourview Residence| Walk to the Beach

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 NZ$709
includes taxes & fees
5 Oct - 6 Oct
Coastal Chic Cottage "Sandpiper" minutes to the beach! Free bikes

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 NZ$1,361
includes taxes & fees
5 Oct - 6 Oct
Beach Villa 2426 | Stunning Beachfront Residence on Captiva Island

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 NZ$371
includes taxes & fees
5 Oct - 6 Oct
Southernmost Inn King Suite on Canal

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 NZ$594
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

Find out more about Pineland

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Pineland holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Pineland. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Pineland. Seeing all the best attractions is bound to make you fall in love with Pineland. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Pineland short-term rentals, that won’t be hard to do.

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.