A waterfront with palm trees and a boat dock.

Pineland Holiday Rentals

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Check prices for these dates

In two weeks
4 Sept - 6 Sept
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

Our top choices for Pineland holiday rentals

Dining

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)
"We had a wonderful stay. Beautiful home with a peaceful view. Great communication with the host. A nice quiet neighborhood. Would stay again. "
United States
Shauna
The price is HK$1,233
HK$3,377 total
includes taxes & fees
25 Aug - 26 Aug
3BR Coastal retreat in peaceful Bokeelia with pool, bikes, ping pong and fishing
Pool

2. 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$2,469 total
includes taxes & fees
20 Aug - 21 Aug
Charming 1-bedroom apartment in Bokeelia with WiFi, AC, pool & heated spa
Exterior

3. Matlacha Tiny Village

Matlacha Tiny Village
3.0 star property
Matlacha
8.8 out of 10, Excellent, (295 reviews)
"We had a wonderful visit July 26th-28th. Check in was so easy. We stayed in the flamingo. The flamingo is so cute and charming. We had a wonderful time just relaxing and fishing off the dock with the grandkids. We love the kayaks. Tiny village is the perfect place for a little getaway and we can’t wait to book again."
United States
Heather
The price is HK$863
HK$1,551 total
includes taxes & fees
20 Aug - 21 Aug
Matlacha Tiny Village
Sun-loungers, beach towels

4. 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$1,490
HK$3,108 total
includes taxes & fees
1 Sept - 2 Sept
NEW!! The “WATERSIDE” COTTAGE~With dockage
Exterior

5. North Captiva Steps to Gulf Beaches Last Minute Offers Beach + Golf Cart + Club

North Captiva Steps to Gulf Beaches Last Minute Offers Beach + Golf Cart + Club
North Captiva
10.0 out of 10, Exceptional, (35 reviews)
"Amazing stay!Beds were comfortable, kitchen was well stocked. We would stay here again and again. "
United States
Tanya J.
The price is HK$994
HK$10,276 total
includes taxes & fees
20 Aug - 21 Aug
North Captiva Steps to Gulf Beaches Last Minute Offers Beach + Golf Cart + Club
Marina

6. 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, (41 reviews)
"I can't imagine a better place to stay and relax. They had everything you needed and more.I hope to come back in the future."
United States
George G.
The price is HK$1,482
HK$3,790 total
includes taxes & fees
20 Aug - 21 Aug
50’ of Dock for your boats. Hot tub, Boatlift, walk 2 restaurants Xtra parking.
Coffee/tea maker, fridge, microwave, oven

7. Warm & Welcoming Rancher

Warm & Welcoming Rancher
Mariner
8.0 out of 10, Very good, (3 reviews)
"It was in the ideal location (close to our grandchildren)."
United States
Timothy
The price is HK$642
HK$2,787 total
includes taxes & fees
20 Aug - 21 Aug
Warm & Welcoming Rancher
TV

8. 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, (14 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$821
HK$3,660 total
includes taxes & fees
20 Aug - 21 Aug
Bayside Villa 4224: Bright Corner Unit with Stunning Bay Views
Beach nearby

9. 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$1,043
HK$4,049 total
includes taxes & fees
20 Aug - 21 Aug
Captiva Villa 3213 | Chic Residence | Great Amenities | Walk to the Beach
Smart TV

10. 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, (19 reviews)
"Loved the property. "
United States
ONE LEGACY
The price is HK$1,334
HK$3,652 total
includes taxes & fees
20 Aug - 21 Aug
Ultra Modern Home w Heated Salt water Pool pet friendly
Balcony view

11. The Suites at Fishermen’s Village- 2 Bedroom Suites

The Suites at Fishermen’s Village- 2 Bedroom Suites
3.0 star property
Punta Gorda Isles
9.8 out of 10, Exceptional, (1,301 reviews)
"Great location and love the shops being under us. Great view and food options."
United States
Nathaniel
The price is HK$1,194
HK$1,337 total
includes taxes & fees
26 Aug - 27 Aug
The Suites at Fishermen’s Village- 2 Bedroom Suites
Beach nearby

12. Bayside Villa 4118 | Spacious Harbourview Residence | Sleeps 6 | Walk to the Beach

Bayside Villa 4118 | Spacious Harbourview Residence | Sleeps 6 | Walk to the Beach
Captiva
9.2 out of 10, Wonderful, (19 reviews)
"Wonderful property. My family of 6 enjoyed our stay, though I would say it probably fits 4 better than 6. The pull outs were actually fairly comfortable. Short walk to the beach. We rented bikes which made it very convienient."
United States
Jeremy S.
The price is HK$980
HK$3,739 total
includes taxes & fees
20 Aug - 21 Aug
Bayside Villa 4118 | Spacious Harbourview Residence | Sleeps 6 | Walk to the Beach
Beach

13. Cozy retreat, NE cape coral oasis 5 mins to restaurants and shopping plaza.

Cozy retreat, NE cape coral oasis 5 mins to restaurants and shopping plaza.
Diplomat
9.4 out of 10, Exceptional, (23 reviews)
"Very clean property and close to shopping and restaurants. "
United States
Kristen M.
The price is HK$741
HK$2,119 total
includes taxes & fees
24 Aug - 25 Aug
Cozy retreat, NE cape coral oasis 5 mins to restaurants and shopping plaza.
Property amenity

14. Island Inn

Island Inn
3.5 star property
West End
9.4 out of 10, Exceptional, (1,147 reviews)
"Wonderful room and stay. Beachfront!"
United States
Cindi
The price is HK$1,561
HK$1,740 total
includes taxes & fees
31 Aug - 1 Sept
Island Inn
Beach nearby

15. Captiva Villa 3221 | Coastal Residence | Great Amenities | Walk to the Beach

Captiva Villa 3221 | Coastal Residence | Great Amenities | Walk to the Beach
Captiva
7.8 out of 10, Good, (10 reviews)
"Property was perfect for an extended weekend getaway. Great location near a beautiful beach."
United States
Janice S.
The price is HK$863
HK$3,513 total
includes taxes & fees
20 Aug - 21 Aug
Captiva Villa 3221 | Coastal Residence | Great Amenities | Walk to the Beach
On the beach

16. The Chic Shack: Elevated Beachfront Luxury & Designer Views at Beach Villa 2414

The Chic Shack: Elevated Beachfront Luxury & Designer Views at Beach Villa 2414
Captiva
9.4 out of 10, Exceptional, (32 reviews)
"Such cute condo in a great location with amazing sunsets."
United States
Doug H.
The price is HK$1,159
HK$4,551 total
includes taxes & fees
20 Aug - 21 Aug
The Chic Shack: Elevated Beachfront Luxury & Designer Views at Beach Villa 2414
Coffee/tea maker, fridge, microwave, oven

17. Modern Luxurious Condo, King Bed Suite, Waterfront + Pool, Near Downtown

Modern Luxurious Condo, King Bed Suite, Waterfront + Pool, Near Downtown
Caloosahatchee
9.2 out of 10, Wonderful, (40 reviews)
"Great stay here! Clean and spacious. Loved the amenities and the location ease of access."
United States
Brianna L.
The price is HK$642
HK$2,287 total
includes taxes & fees
27 Aug - 28 Aug
Modern Luxurious Condo, King Bed Suite, Waterfront + Pool, Near Downtown
Beach

18. Bayside Villa 5114 | Gorgeous Residence | Sleeps 5 | Walk to the Beach

Bayside Villa 5114 | Gorgeous Residence | Sleeps 5 | Walk to the Beach
Captiva
9.2 out of 10, Wonderful, (19 reviews)
"Very nice property & the property manager was easy to reach with questions and very responsive. Would definitely stay here again!"
United States
Jenny B.
The price is HK$980
HK$3,739 total
includes taxes & fees
20 Aug - 21 Aug
Bayside Villa 5114 | Gorgeous Residence | Sleeps 5 | Walk to the Beach
TV, offices

19. Harbour Tower 414 | Gorgeous Residence with Panoramic Water Views and Secluded Beach

Harbour Tower 414 | Gorgeous Residence with Panoramic Water Views and Secluded Beach
Punta Rassa
9.6 out of 10, Exceptional, (20 reviews)
"Was even better in person than the pictures. The communication with the owners was fantastic and the place was absolutely perfect. The private beach was amazing and loved the staff! We are booking again and is an absolute gem to stay at! Had a manatee swim next to us in the ocean and saw dolphins at sunset! Even a Mama Stingray and her baby swam by! Loved this perfect vacation!"
United States
Misti G.
The price is HK$1,020
HK$5,718 total
includes taxes & fees
22 Aug - 23 Aug
Harbour Tower 414 | Gorgeous Residence with Panoramic Water Views and Secluded Beach
Terrace/patio

20. Tiki Life ! Relax and Enjoy w/m discount! Close to beaches without the costs!!

Tiki Life ! Relax and Enjoy w/m discount! Close to beaches without the costs!!
Englewood
10.0 out of 10, Exceptional, (50 reviews)
"Very clean everything you need great location!"
United States
Laura B.
The price is HK$699
HK$2,367 total
includes taxes & fees
20 Aug - 21 Aug
Tiki Life ! Relax and Enjoy w/m discount! Close to beaches without the costs!!
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

Lani Kai Beachfront Resort

Lani Kai Beachfront Resort

10/10 Excellent
"Very nice"
LOUIS L 4-night trip
Posted 1 hour ago
Lani Kai Beachfront Resort

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?

North Captiva Point House - Boat/Water Taxi Only **NEWLY RENOVATED **: This holiday home rental outside of Pineland is located on the beach, and has a balcony, a BBQ and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

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.