A waterfront with palm trees and a boat dock.

Pineland Vacation Rentals

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Check prices for these dates

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

Our top choices for Pineland vacation rentals

A spacious patio with a dining table and chairs, a sofa, and a ceiling fan.

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
$391 nightly
The price is $431
Aug 25 - Aug 26
Total with taxes and fees
3BR Coastal retreat in peaceful Bokeelia with pool, bikes, ping pong and fishing
A pool with a metal railing, surrounded by lush greenery and a covered area with a metal frame.

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
$285 nightly
The price is $314
Aug 22 - Aug 23
Total with taxes and fees
Charming 1-bedroom apartment in Bokeelia with WiFi, AC, pool & heated spa
A beachside area with colorful beach houses, a dock, and a sandy beach.

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
$185 nightly
The price is $198
Sep 9 - Sep 10
Total with taxes and fees
Matlacha Tiny Village
An aerial view of a coastal area with several small islands connected by bridges.

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.
$327 nightly
The price is $361
Sep 7 - Sep 8
Total with taxes and fees
NEW!! The “WATERSIDE” COTTAGE~With dockage
A multi-level house with a white exterior, a staircase, and a deck area.

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.
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.
$452 nightly
The price is $497
Aug 23 - Aug 24
Total with taxes and fees
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
$323 nightly
The price is $355
Aug 22 - Aug 23
Total with taxes and fees
Warm & Welcoming Rancher
A spacious living room with a flat-screen TV, a sofa, a coffee table, and a balcony with a view of the beach.

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
$422 nightly
The price is $465
Aug 22 - Aug 23
Total with taxes and fees
Bayside Villa 4224: Bright Corner Unit with Stunning Bay Views
A coastal resort with a long sandy beach, multiple white buildings, and lush greenery.

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.
$467 nightly
The price is $516
Aug 23 - Aug 24
Total with taxes and fees
Captiva Villa 3213 | Chic Residence | Great Amenities | Walk to the Beach
A modern living room with a large TV, a marble fireplace, a sofa, and a dining area with a bar.

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
$413 nightly
The price is $455
Aug 30 - Aug 31
Total with taxes and fees
Ultra Modern Home w Heated Salt water Pool pet friendly
A beach with a thatched-roof structure, palm trees, and a view of the sea.

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
$175 nightly
The price is $196
Sep 1 - Sep 2
Total with taxes and fees
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.
Bayside Villa 4118 | Spacious Harbourview Residence | Sleeps 6 | Walk to the Beach
A beach with clear turquoise water, a sandy shore, and a line of trees in the background.

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.
$246 nightly
The price is $270
Aug 24 - Aug 25
Total with taxes and fees
Cozy retreat, NE cape coral oasis 5 mins to restaurants and shopping plaza.
A beach with a view of the ocean and a sunset.

14. Island Inn

Island Inn
3.5 star property
West End
9.4 out of 10, Exceptional, (1,148 reviews)
"Wonderful room and stay. Beachfront!"
United States
Cindi
$199 nightly
The price is $222
Aug 31 - Sep 1
Total with taxes and fees
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.
$407 nightly
The price is $448
Aug 23 - Aug 24
Total with taxes and fees
Captiva Villa 3221 | Coastal Residence | Great Amenities | Walk to the Beach
An aerial view of a resort with multiple buildings, a beach, and a mangrove area.

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.
$544 nightly
The price is $599
Aug 24 - Aug 25
Total with taxes and fees
The Chic Shack: Elevated Beachfront Luxury & Designer Views at Beach Villa 2414
A modern kitchen with a central island, stainless steel appliances, and a decorative backsplash.

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.
$265 nightly
The price is $292
Aug 27 - Aug 28
Total with taxes and fees
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.
$433 nightly
The price is $477
Aug 23 - Aug 24
Total with taxes and fees
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)
"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.
$642 nightly
The price is $707
Aug 23 - Aug 24
Total with taxes and fees
Harbour Tower 414 | Gorgeous Residence with Panoramic Water Views and Secluded Beach
A beachfront property with a covered patio, palm trees, and a wooden deck.

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)
"The stay was, as usual, very nice! I can’t say enough about how wonderful the management team is here!! Outstanding!! See you next year!!"
United States
Chris N.
$273 nightly
The price is $302
Aug 22 - Aug 23
Total with taxes and fees
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

Edison Beach House

Edison Beach House

10/10 Excellent
"B"
Danilo 2-night trip
Posted 11 hours ago
Edison Beach House

Find out more about Pineland

Everything you need to know about Pineland vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Pineland vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Pineland vacation 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 low season months. For more hustle and bustle, you may prefer to visit Pineland in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $196 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Pineland rentals

At Expedia, we put the best Pineland vacation 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 vacation.

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 vacation rentals in Pineland?

Yes, you can find vacation rentals close to well known points of interest in Pineland, or you can select a secluded option if you're looking for relaxation.

What are some of the best vacation rentals in Pineland?

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

How many vacation rentals are there in Pineland?

Expedia has 9 vacation 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 larger area, you’ll find Randell Research Center and Useppa Island.

What are vacation rentals like in Pineland?

Vacation rentals are privately owned properties you can book for a couple days or more in Pineland. Vacation rentals offer extras like laundry facilities and kitchens so your stay will be comfortable. If you're concerned about a clean environment, vacation rentals can offer a sense of safety away from shared hotel elevators and busy reception areas while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive option for family gatherings.