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Pineland Vacation Rentals

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Check prices for these dates

In two weeks
Sep 12 - Sep 14
In one month
Sep 26 - Sep 28
In two months
Oct 24 - Oct 26
In three months
Nov 21 - Nov 23

Vacation Rentals in Pineland

Our top choices for Pineland vacation rentals

Edison Beach House
Apartment, Multiple Beds, Partial Ocean View | Beach/ocean view

Edison Beach House

3.5 star property
9.4 out of 10, Exceptional, (1476)
"Our family had a great time there. Staff was nice, location is great."
The price is ￥27,098
￥30,214 total
includes taxes & fees
Sep 1 - Sep 2
Edison Beach House
The Suites at Fishermen’s Village- 2 Bedroom Suites
Outdoor pool

The Suites at Fishermen’s Village- 2 Bedroom Suites

3.0 star property
9.8 out of 10, Exceptional, (970)
"Great stay"
The price is ￥23,380
￥26,185 total
includes taxes & fees
Sep 9 - Sep 10
The Suites at Fishermen’s Village- 2 Bedroom Suites
Sundial Beach Resort & Spa
Daily cooked-to-order breakfast for a fee

Sundial Beach Resort & Spa

5.0 star property
8.6 out of 10, Excellent, (2575)
"Very nice Resort. Not a 5 star but they are remodeling. Easy access to the beautiful beach. Resturants were very good. Service was excellent. We went off season so there was not may people on the property which we liked."
The price is ￥46,736
￥71,487 total
includes taxes & fees
Sep 7 - Sep 8
Sundial Beach Resort & Spa
Island Inn
Luxury Suite, Sea View | Beach/ocean view

Island Inn

3.5 star property
9.4 out of 10, Exceptional, (1100)
"Right on the beach!"
The price is ￥32,252
￥35,962 total
includes taxes & fees
Sep 3 - Sep 4
Island Inn
North Captiva Point House - Boat/Water Taxi Only **NEWLY RENOVATED **
Terrace/patio

North Captiva Point House - Boat/Water Taxi Only **NEWLY RENOVATED **

9.6 out of 10, Exceptional, (97)
"Everything was perfect."
North Captiva Point House - Boat/Water Taxi Only **NEWLY RENOVATED **
Landing Apartments near North Fort Myers
Apartment, 1 Bedroom | Private kitchen | Full-size fridge, microwave, oven, stovetop

Landing Apartments near North Fort Myers

4.0 star property
9.4 out of 10, Exceptional, (39)
"Overall a great experience."
Landing Apartments near North Fort Myers
Lazy Cuckoo Inn
Grand Studio Suite, Kitchenette | Living area | Smart TV

Lazy Cuckoo Inn

2.0 star property
9.0 out of 10, Wonderful, (214)
"Perfect place to stay"
The price is ￥11,663
￥17,766 total
includes taxes & fees
Sep 4 - Sep 5
Lazy Cuckoo Inn
Matlacha Tiny Village
Dock

Matlacha Tiny Village

3.0 star property
8.8 out of 10, Excellent, (263)
"Very nice place with all necesary accommodations for a Pleasant stay. "
The price is ￥14,447
￥27,155 total
includes taxes & fees
Sep 1 - Sep 2
Matlacha Tiny Village
“BEACHFRONT” LUXURY ISLAND HOME. PRIVATE SWIM SPA~DOCK FISHING~GolfCart STUNNING
On the beach, sun loungers, beach towels

“BEACHFRONT” LUXURY ISLAND HOME. PRIVATE SWIM SPA~DOCK FISHING~GolfCart STUNNING

10.0 out of 10, Exceptional, (5)
"This property is amazing! Beautiful views and great fishing right off the dock. My wife and I stayed for our belated anniversary and we couldnt have been happier. We will be back."
“BEACHFRONT” LUXURY ISLAND HOME. PRIVATE SWIM SPA~DOCK FISHING~GolfCart STUNNING
PALM BREEZE - SWIM UP TO THE BAR! Integrated spa, Outdoor grill, Fire pit!
Outdoor pool, a heated pool

PALM BREEZE - SWIM UP TO THE BAR! Integrated spa, Outdoor grill, Fire pit!

10.0 out of 10, Exceptional, (41)
"We had a wonderful time!"
PALM BREEZE - SWIM UP TO THE BAR! Integrated spa, Outdoor grill, Fire pit!
BEAUTIFUL SANIBEL ISLAND CONDO!!! - NEW EVERYTHING -NEW AMENITIES!!!
Outdoor dining

BEAUTIFUL SANIBEL ISLAND CONDO!!! - NEW EVERYTHING -NEW AMENITIES!!!

4.0 star property
9.8 out of 10, Exceptional, (47)
"Property was well maintained. Close to beach. Lovely area."
BEAUTIFUL SANIBEL ISLAND CONDO!!! - NEW EVERYTHING -NEW AMENITIES!!!
Top Location w/direct gulf access. Newly renovated kitchen and bathrooms
Terrace/patio

Top Location w/direct gulf access. Newly renovated kitchen and bathrooms

9.8 out of 10, Exceptional, (63)
"This is a great property. Quiet neighborhood which we wanted and yet close enough to everything we needed. Owner is available and helpful and on top of any problem immediately! Well stocked with everything needed. Comfortable beds. Plenty of storage areas for your things!! We were blessed with great weather to enjoy the beautiful lanai! We hope to be back next year to enjoy again!"
Top Location w/direct gulf access. Newly renovated kitchen and bathrooms
Fully renovated Luxury House pool! HUGE 5 BD 5 BA 9 bed! Sleeps 16! 2 golf carts
Interior

Fully renovated Luxury House pool! HUGE 5 BD 5 BA 9 bed! Sleeps 16! 2 golf carts

9.0 out of 10, Wonderful, (18)
"We took our multigenerational family for a few days of quiet & sunshine. They loved the place so mush that they want to go back next year!We had a few problems with the house but the management team made it right.Lovely place to spend a few days - or more!"
Fully renovated Luxury House pool! HUGE 5 BD 5 BA 9 bed! Sleeps 16! 2 golf carts
South Seas Bayside Villa 5130: Your Perfect Island Retreat
A heated pool

South Seas Bayside Villa 5130: Your Perfect Island Retreat

8.8 out of 10, Excellent, (16)
"Beautiful apartment "
South Seas Bayside Villa 5130: Your Perfect Island Retreat
Steps to BEACH/POOL/Times square
Beach nearby

Steps to BEACH/POOL/Times square

9.8 out of 10, Exceptional, (11)
"We really enjoy staying at this property. It was very clean, comfortable, and with everything you need to enjoy your stay, complete kitchen, bathroom with shampoo and conditioner, beach towels. Very well located, walking distance to beach and downtown/restaurants. I would stay here again."
Steps to BEACH/POOL/Times square
Resort Harbour Properties
Outdoor pool, a heated pool, sun loungers

Resort Harbour Properties

3.5 star property
9.6 out of 10, Exceptional, (357)
"10/10 would stay there again"
Resort Harbour Properties
102 Beachfront Condo: Views, Heated Pool, Walk to Dwtn
On the beach

102 Beachfront Condo: Views, Heated Pool, Walk to Dwtn

10.0 out of 10, Exceptional, (19)
"Great location "
102 Beachfront Condo: Views, Heated Pool, Walk to Dwtn
Stunning 3-bedroom condo with high ceilings, beach access and pool!
Smart TV, printers

Stunning 3-bedroom condo with high ceilings, beach access and pool!

9.4 out of 10, Exceptional, (3)
"Great property, very well maintained. So many extras that will amaze future guests!"
Stunning 3-bedroom condo with high ceilings, beach access and pool!
Beach View + 1-2 Min walk to Beach + Huge TVs & Fully Remodeled
Smart TV

Beach View + 1-2 Min walk to Beach + Huge TVs & Fully Remodeled

10.0 out of 10, Exceptional, (7)
Beach View + 1-2 Min walk to Beach + Huge TVs & Fully Remodeled
Stunning Gulf views! Pointe Santo Updated - 2BD 2BATH
Outdoor pool, a heated pool

Stunning Gulf views! Pointe Santo Updated - 2BD 2BATH

10.0 out of 10, Exceptional, (7)
Stunning Gulf views! Pointe Santo Updated - 2BD 2BATH
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

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 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?

South Seas Bayside Villa 5130: Your Perfect Island Retreat: This vacation home rental outside of Pineland is located on the waterfront and has a balcony, a hot tub, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

How many vacation rentals are there in Pineland?

Expedia has 14 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.