A waterfront with palm trees and a boat dock.

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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 £324
includes taxes & fees
1 Sept - 2 Sept
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
8.8 out of 10, Excellent, (296 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 £164
includes taxes & fees
1 Sept - 2 Sept
Matlacha Tiny Village

3. 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 £279
includes taxes & fees
3 Sept - 4 Sept
MALU LANI Inn & Marina

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 £237
includes taxes & fees
1 Sept - 2 Sept
Charming 1-bedroom apartment in Bokeelia with WiFi, AC, pool & heated spa

5. 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, (1,309 reviews)
"Great place"
United States
Nidia
The price is £133
includes taxes & fees
1 Sept - 2 Sept
The Suites at Fishermen’s Village

6. 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 £298
includes taxes & fees
1 Sept - 2 Sept
NEW!! The “WATERSIDE” COTTAGE~With dockage

7. Edison Beach House

Edison Beach House
3.5 star property
Fort Myers Beach
9.4 out of 10, Exceptional, (1,888 reviews)
"Our stay at Edison Beach House was amazing. The property owner is very sweet."
United States
Robin Marie
The price is £145
includes taxes & fees
1 Sept - 2 Sept
Edison Beach House

8. 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 £380
includes taxes & fees
2 Sept - 3 Sept
50’ of Dock for your boats. Hot tub, Boatlift, walk 2 restaurants Xtra parking.

9. 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 £282
includes taxes & fees
22 Sept - 23 Sept
Casa Florida 🌴 waterfront home with boat ramp

10. 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 £121
includes taxes & fees
1 Sept - 2 Sept
Studio with Patio - Turtle Cove - Welcome to our stunning, newly renovated studio condo!

11. 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)
"Host very responsive to questions! Really enjoyed the pool and on site amenities!"
United States
Doug M.
The price is £323
includes taxes & fees
1 Sept - 2 Sept
Ultra Modern Home w Heated Salt water Pool pet friendly

12. 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, (2 reviews)
"Absolutely beautiful room and amenities and the breakfast was delicious and with so many options. Loved the communication and cannot wait to come back! "
United States
Crissa
The price is £162
includes taxes & fees
1 Sept - 2 Sept
Hibiscus House Bed Breakfast Citrus Room

13. Island Inn

Island Inn
3.5 star property
West End
9.4 out of 10, Exceptional, (1,150 reviews)
"Wonderful room and stay. Beachfront!"
United States
Cindi
The price is £172
includes taxes & fees
1 Sept - 2 Sept
Island Inn

14. Luxe 3BR Waterfront Stay in Cape Coral

Luxe 3BR Waterfront Stay in Cape Coral
Mariner
10.0 out of 10, Exceptional, (12 reviews)
"We were pleased with our stay. "
United States
Jamie G.
The price is £220
includes taxes & fees
1 Sept - 2 Sept
Luxe 3BR Waterfront Stay in Cape Coral

15. 2 Queen Bed|Nsmk|Cape Coral FL

2 Queen Bed|Nsmk|Cape Coral FL
Caloosahatchee
10.0 out of 10, Exceptional, (150 reviews)
"Had a lovely time here!"
United States
Anonymous traveller
The price is £47
includes taxes & fees
1 Sept - 2 Sept
2 Queen Bed|Nsmk|Cape Coral FL

16. Perfect Getaway, Anytime of Year, Sunny, Clean, Spacious & Ideally Located!

Perfect Getaway, Anytime of Year, Sunny, Clean, Spacious & Ideally Located!
Pelican
10.0 out of 10, Exceptional, (36 reviews)
"Yes Great location . Close to stores and restaurants . Pool could have been better if Had a cover temp went down over nite."
United States
Rickie D.
The price is £318
includes taxes & fees
1 Sept - 2 Sept
Perfect Getaway, Anytime of Year, Sunny, Clean, Spacious & Ideally Located!

17. 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 £203
includes taxes & fees
1 Sept - 2 Sept
Cozy retreat, NE cape coral oasis 5 mins to restaurants and shopping plaza.

18. Sundial Beach Resort & Spa

Sundial Beach Resort & Spa
5.0 star property
Mid Island
8.6 out of 10, Excellent, (2,690 reviews)
"Great place"
United States
moti
The price is £369
includes taxes & fees
1 Sept - 2 Sept
Sundial Beach Resort & Spa

19. 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 £805
includes taxes & fees
12 Sept - 13 Sept
Matlacha/Cape Coral - Kokopelli House - a three-story Key West style residence

20. Beach Villa 2004 -Sublime Gulf Beach Villa

Beach Villa 2004 -Sublime Gulf Beach Villa
Captiva
9.8 out of 10, Exceptional, (26 reviews)
"Property was very clean, could see beautiful sunsets from the balcony. Beds were comfortable. "
United States
Theresa K.
The price is £582
includes taxes & fees
1 Sept - 2 Sept
Beach Villa 2004 -Sublime Gulf Beach Villa
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, apart-hotels, 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 favorite 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 depends 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 £76 per night. Entering your travel dates in the search wizard you might find 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?

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.