Pineland Holiday Rentals

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Our top choices for Pineland holiday rentals

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, (2 reviews)
"The home was absolutely perfect , clean, spacious, and very comfortable. Beautifully decorated , beds were cozy, and everything was exactly as described. The host was friendly and responsive, which made the stay stress-free. Great location and a perfect home base for our family trip.”"
United States
Kelly R.
The price is AU$591
includes taxes & fees
7 May - 8 May
3BR Coastal retreat in peaceful Bokeelia with pool, bikes, ping pong and fishing

Tiny home glamping unit in pine island on a 6 acre property

Tiny home glamping unit in pine island on a 6 acre property
Saint James City
10.0 out of 10, Exceptional, (2 reviews)
"Wonderful setting, terrific host, just right for our one night stay!"
United States
A P.
The price is AU$195
includes taxes & fees
6 May - 7 May
Tiny home glamping unit in pine island on a 6 acre property

Heated Pool, 3 Mi to Dtwn: Cape Coral Escape!

Heated Pool, 3 Mi to Dtwn: Cape Coral Escape!
3.0 star property
Pelican
Heated Pool, 3 Mi to Dtwn: Cape Coral Escape!

Lakeside Retreat with Heated Pool

Lakeside Retreat with Heated Pool
Hancock
7.6 out of 10, Good, (37 reviews)
"The front door code lock worked when it wanted too. Forcing us to lock the front door and use the back door and walk around. Except when that door stopped working. Bugs found in the master bath in 2 different areas that we had to spray and wipe up. Yes, I understand its Florida but still. However the bed sheets were clean, lots of pillow choices, and towels to use. Property could use a refresh, its been beaten up a bit through the rentals but a good deal on price for what you receive. Pool...
United States
John
Lakeside Retreat with Heated Pool

Modern boho 2bed 2bath home, 8 mins to downtown cape and near beach.

Modern boho 2bed 2bath home, 8 mins to downtown cape and near beach.
Pelican
9.4 out of 10, Exceptional, (39 reviews)
"Very clean and loved the space. Very bright and homey. Loved how well equipped the kitchen was since I was there for Thanksgiving and had to cook a little. Not a far drive from some great spots such as Sanibel Island, Bonita Springs and the outlets for some great shopping. Host was great with communication. Would love to stay again next time I’m in the area. "
United States
Stacy D.
The price is AU$348
includes taxes & fees
2 May - 3 May
Modern boho 2bed 2bath home, 8 mins to downtown cape and near beach.

Water Front Boundary Vacation Home Villa close to beaches, golfing, Fishing

Water Front Boundary Vacation Home Villa close to beaches, golfing, Fishing
Oakland Hills
9.8 out of 10, Exceptional, (68 reviews)
"Had a great stay. Host was responsive and the home was very clean. Great location in a quiet residential area, but close enough to get to all activities in a short drive. Many grocery stores around too. We are pleased with our choice. "
United States
Delanie M.
The price is AU$444
includes taxes & fees
7 May - 8 May
Water Front Boundary Vacation Home Villa close to beaches, golfing, Fishing

SUNSHINE GETAWAY VACATION RENTALS

SUNSHINE GETAWAY VACATION RENTALS
Fort Myers
8.4 out of 10, Very good, (142 reviews)
"Easy location to get where we needed. Clean and spacious."
United States
Chris N.
The price is AU$366
includes taxes & fees
4 May - 5 May
SUNSHINE GETAWAY VACATION RENTALS

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)
"This property was exceptionally clean and beautifully decorated. We felt very at home here and would highly recommend!"
United States
Laura I.
The price is AU$398
includes taxes & fees
30 Apr - 1 May
Cozy retreat, NE cape coral oasis 5 mins to restaurants and shopping plaza.

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 AU$369
includes taxes & fees
5 May - 6 May
Hibiscus House Bed Breakfast Citrus Room

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, (61 reviews)
"Great place"
United States
Randy W.
The price is AU$354
includes taxes & fees
30 Apr - 1 May
Bright & Airy 2bed 2bath home near downtown/Weekly and monthly discounts!

Matlacha Tiny Village

Matlacha Tiny Village
3.0 star property
Matlacha
8.8 out of 10, Excellent, (286 reviews)
"Super cute place!! Super clean and comfortable."
United States
Francesca
The price is AU$440
includes taxes & fees
5 May - 6 May
Matlacha Tiny Village

Stunning Luxury villa Sandpiper across the street from the beach!

Stunning Luxury villa Sandpiper across the street from the beach!
East End
9.0 out of 10, Wonderful, (47 reviews)
"Lovely and clean place to stay. Short walk to the beach."
United States
AMANDA S.
The price is AU$689
includes taxes & fees
4 May - 5 May
Stunning Luxury villa Sandpiper across the street from the beach!

Waterfront Condo with Pool & Boat Slip

Waterfront Condo with Pool & Boat Slip
Caloosahatchee
10.0 out of 10, Exceptional, (45 reviews)
"Everything about this stay was wonderful, if you want a comfortable, quiet, excellant vacation pick this resort. "
United States
Harry
The price is AU$502
includes taxes & fees
3 May - 4 May
Waterfront Condo with Pool & Boat Slip

Caribbean Tiki Hut relaxation. Enjoy the Islands & Boca Grande without the costs

Caribbean Tiki Hut relaxation. Enjoy the Islands & Boca Grande without the costs
Englewood
10.0 out of 10, Exceptional, (52 reviews)
"Apartment was very clean! Lots of outdoor seating options. Nice beach chairs to take to the beach."
United States
Apryl H.
The price is AU$419
includes taxes & fees
4 May - 5 May
Caribbean Tiki Hut relaxation. Enjoy the Islands & Boca Grande without the costs

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, (35 reviews)
"Was a nice place."
United States
Michael B.
The price is AU$403
includes taxes & fees
18 May - 19 May
Modern Luxurious Condo, King Bed Suite, Waterfront + Pool, Near Downtown

Bright & Cozy Townhome · Pool & Near Downtown

Bright & Cozy Townhome · Pool & Near Downtown
3.5 star property
Fort Myers
The price is AU$489
includes taxes & fees
30 Apr - 1 May
Bright & Cozy Townhome · Pool & Near Downtown

Ellis' Hideaway! Cozy 2-bedroom pool home with WiFi, AC in enjoyable Cape Coral

Ellis' Hideaway! Cozy 2-bedroom pool home with WiFi, AC in enjoyable Cape Coral
Caloosahatchee
10.0 out of 10, Exceptional, (25 reviews)
"Great host, perfect amenities!We would definitely come back!"
United States
Eva Marianne T.
The price is AU$427
includes taxes & fees
11 May - 12 May
Ellis' Hideaway! Cozy 2-bedroom pool home with WiFi, AC in enjoyable Cape Coral

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, (17 reviews)
"Couldn’t been better"
United States
Louis
The price is AU$438
includes taxes & fees
4 May - 5 May
Charming 1-bedroom apartment in Bokeelia with WiFi, AC, pool & heated spa

Enjoy a 3-bedroom vacation home in Yacht Club - Special January & February.

Enjoy a 3-bedroom vacation home in Yacht Club - Special January & February.
Caloosahatchee
9.6 out of 10, Exceptional, (120 reviews)
"We loved our stay"
United States
Nathaniel H.
The price is AU$553
includes taxes & fees
3 May - 4 May
Enjoy a 3-bedroom vacation home in Yacht Club - Special January & February.

Lakeside Haven with Heated Pool

Lakeside Haven with Heated Pool
Hancock
9.2 out of 10, Wonderful, (45 reviews)
"Fun great location"
United States
William H.
The price is AU$604
includes taxes & fees
11 May - 12 May
Lakeside Haven with Heated Pool
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$133 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?

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.