A waterfront with palm trees and a boat dock.

Holiday Rentals in Pineland

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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)
"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 €402
includes taxes & fees
14 Sept - 15 Sept
3BR Coastal retreat in peaceful Bokeelia with pool, bikes, ping pong and fishing

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 €276
includes taxes & fees
30 Aug - 31 Aug
Charming 1-bedroom apartment in Bokeelia with WiFi, AC, pool & heated spa

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 €171
includes taxes & fees
20 Aug - 21 Aug
Matlacha Tiny Village

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 €347
includes taxes & fees
14 Sept - 15 Sept
NEW!! The “WATERSIDE” COTTAGE~With dockage

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 €1,138
includes taxes & fees
19 Aug - 20 Aug
North Captiva Steps to Gulf Beaches Last Minute Offers Beach + Golf Cart + Club

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 €405
includes taxes & fees
19 Aug - 20 Aug
50’ of Dock for your boats. Hot tub, Boatlift, walk 2 restaurants Xtra parking.

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 €307
includes taxes & fees
19 Aug - 20 Aug
Warm & Welcoming Rancher

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 €391
includes taxes & fees
19 Aug - 20 Aug
Bayside Villa 4224: Bright Corner Unit with Stunning Bay Views

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 €437
includes taxes & fees
19 Aug - 20 Aug
Captiva Villa 3213 | Chic Residence | Great Amenities | Walk to the Beach

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 €400
includes taxes & fees
14 Sept - 15 Sept
Ultra Modern Home w Heated Salt water Pool pet friendly

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 €135
includes taxes & fees
2 Sept - 3 Sept
The Suites at Fishermen’s Village- 2 Bedroom Suites

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 €383
includes taxes & fees
19 Aug - 20 Aug
Bayside Villa 4118 | Spacious Harbourview Residence | Sleeps 6 | Walk to the 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 €235
includes taxes & fees
19 Aug - 20 Aug
Cozy retreat, NE cape coral oasis 5 mins to restaurants and shopping plaza.

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 €192
includes taxes & fees
24 Aug - 25 Aug
Island Inn

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 €378
includes taxes & fees
19 Aug - 20 Aug
Captiva Villa 3221 | Coastal Residence | Great Amenities | Walk to 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 €523
includes taxes & fees
19 Aug - 20 Aug
The Chic Shack: Elevated Beachfront Luxury & Designer Views at Beach Villa 2414

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 €257
includes taxes & fees
27 Aug - 28 Aug
Modern Luxurious Condo, King Bed Suite, Waterfront + Pool, Near Downtown

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 €400
includes taxes & fees
19 Aug - 20 Aug
Bayside Villa 5114 | Gorgeous Residence | Sleeps 5 | Walk to the Beach

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)
"The condo is perfect! Perfect size. Perfect location. Perfect everything! The location is a quiet secluded location with time for relaxation. It also allows for a lot of fun with a quick ride to Fort Myers Beach and Sanibel. "
United States
Sabrina F.
Harbour Tower 414 | Gorgeous Residence with Panoramic Water Views and Secluded Beach

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 €266
includes taxes & fees
27 Aug - 28 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

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 €135 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 10 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.