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 AU$595
includes taxes & fees
24 Sept - 25 Sept
3BR Coastal retreat in peaceful Bokeelia with pool, bikes, ping pong and fishing

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 AU$533
includes taxes & fees
15 Oct - 16 Oct
MALU LANI Inn & Marina

3. 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 AU$312
includes taxes & fees
29 Sept - 30 Sept
Matlacha Tiny Village

4. 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 AU$353
includes taxes & fees
24 Sept - 25 Sept
Charming 1-bedroom apartment in Bokeelia with WiFi, AC, pool & heated spa

5. 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 AU$644
includes taxes & fees
24 Sept - 25 Sept
NEW!! The “WATERSIDE” COTTAGE~With dockage

6. 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 AU$571
includes taxes & fees
5 Oct - 6 Oct
Casa Florida 🌴 waterfront home with boat ramp

7. 50’ of Dock for your boats. Hot tub, Boatlift, walk 2 restaurants Xtra parking.

50’ of Dock for your boats. Hot tub, Boatlift, walk 2 restaurants Xtra parking.
Matlacha
10.0 out of 10, Exceptional, (42 reviews)
"Excellent!"
United States
Tim A.
The price is AU$581
includes taxes & fees
23 Sept - 24 Sept
50’ of Dock for your boats. Hot tub, Boatlift, walk 2 restaurants Xtra parking.

8. Studio with Patio - Turtle Cove - Welcome to our stunning, newly renovated studio condo!

Studio with Patio - Turtle Cove - Welcome to our stunning, newly renovated studio condo!
Matlacha
9.8 out of 10, Exceptional, (9 reviews)
"This is a wonderful property with a fantastic manager -Stacey. It is beautiful with great amenities and a great location."
United States
David H.
The price is AU$227
includes taxes & fees
24 Sept - 25 Sept
Studio with Patio - Turtle Cove - Welcome to our stunning, newly renovated studio condo!

9. 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, (1,326 reviews)
"Great place"
United States
Nidia
The price is AU$251
includes taxes & fees
4 Oct - 5 Oct
The Suites at Fishermen’s Village

10. Island Inn

Island Inn
3.5 star property
West End
9.4 out of 10, Exceptional, (1,156 reviews)
"Great location"
United States
Nicole
The price is AU$317
includes taxes & fees
23 Sept - 24 Sept
Island Inn

11. Edison Beach House

Edison Beach House
3.5 star property
Fort Myers Beach
9.4 out of 10, Exceptional, (1,917 reviews)
"Great stay."
United States
Angie
The price is AU$277
includes taxes & fees
23 Sept - 24 Sept
Edison Beach House

12. Matlacha/Cape Coral - Kokopelli House - a three-story Key West style residence

Matlacha/Cape Coral - Kokopelli House - a three-story Key West style residence
Matlacha
9.8 out of 10, Exceptional, (64 reviews)
"Great stay, would definitely go back! "
United States
Chad N.
The price is AU$1,478
includes taxes & fees
23 Sept - 24 Sept
Matlacha/Cape Coral - Kokopelli House - a three-story Key West style residence

13. Ultra Modern Home w Heated Salt water Pool pet friendly

Ultra Modern Home w Heated Salt water Pool pet friendly
Mariner
10.0 out of 10, Exceptional, (21 reviews)
"Host very responsive to questions! Really enjoyed the pool and on site amenities!"
United States
Doug M.
The price is AU$643
includes taxes & fees
23 Sept - 24 Sept
Ultra Modern Home w Heated Salt water Pool pet friendly

14. Marina Villa 603 | Spacious Coastal Residence | Great Amenities | Walk to the Beach

Marina Villa 603 | Spacious Coastal Residence | Great Amenities | Walk to the Beach
Captiva
8.6 out of 10, Excellent, (13 reviews)
"We stayed with our 2 grandchildren and loved the location and the full kitchen. "
United States
Cheryl G.
Marina Villa 603 | Spacious Coastal Residence | Great Amenities | Walk to the Beach

15. Lazy Cuckoo Inn

Lazy Cuckoo Inn
2.0 star property
Fort Myers Beach
8.8 out of 10, Excellent, (299 reviews)
"Great place!"
United States
Bruce
The price is AU$124
includes taxes & fees
1 Oct - 2 Oct
Lazy Cuckoo Inn

16. Hibiscus House Bed Breakfast Citrus Room

Hibiscus House Bed Breakfast Citrus Room
2.0 star property
Fort Myers River District
10.0 out of 10, Exceptional, (3 reviews)
"Quiet, staff friendly, breakfast beautifully presented. Staff very helpful."
United States
Ann
The price is AU$317
includes taxes & fees
23 Sept - 24 Sept
Hibiscus House Bed Breakfast Citrus Room

17. Sundial Beach Resort & Spa

Sundial Beach Resort & Spa
5.0 star property
Mid Island
8.6 out of 10, Excellent, (2,700 reviews)
"Excellent place for children"
United States
Jaime E
The price is AU$623
includes taxes & fees
23 Sept - 24 Sept
Sundial Beach Resort & Spa

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 AU$96
includes taxes & fees
23 Sept - 24 Sept
2 Queen Bed|Nsmk|Cape Coral FL

19. 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.
Bayside Villa 5110 | Upscale Bayfront Residence | In-unit laundry | Walk to the Beach

20. Bright & Airy 2bed 2bath home near downtown/Weekly and monthly discounts!

Bright & Airy 2bed 2bath home near downtown/Weekly and monthly discounts!
Pelican
9.6 out of 10, Exceptional, (63 reviews)
"House was very clean and looked just like advertised. Had a very comfortable stay and property is close to everything you need. Will definitely come back."
United States
Jennifer B.
The price is AU$335
includes taxes & fees
23 Sept - 24 Sept
Bright & Airy 2bed 2bath home near downtown/Weekly and monthly discounts!
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

Everything you need to know about Pineland 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 Pineland holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, 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 Pineland holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Pineland holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Pineland. 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 depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Pineland 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 Pineland holiday rentals we have selected for you start as low as AU$124 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Pineland rentals

At Expedia, we put the best Pineland 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 Pineland 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 Pineland 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 Pineland. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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.