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Pineland Vacation Rentals

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Check prices for these dates

In two weeks
Dec 26 - Dec 28
In two months
Feb 6 - Feb 8
In three months
Mar 6 - Mar 8
In four months
Apr 3 - Apr 5

Our top choices for Pineland vacation rentals

Outdoor pool
The Suites at Fishermen’s Village- 2 Bedroom Suites

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, (1043)
"Clean room, beautiful area, excellent staff"
United States
Crystal
The price is ￥28,197
￥31,580 total
includes taxes & fees
Dec 15 - Dec 16
The Suites at Fishermen’s Village- 2 Bedroom Suites
2 outdoor pools, cabanas (surcharge), pool umbrellas
Sundial Beach Resort & Spa

Sundial Beach Resort & Spa

Sundial Beach Resort & Spa
5.0 star property
Mid Island
8.6 out of 10, Excellent, (2584)
"wonderful family friendly and spotless resort"
United States
Mary Anne
The price is ￥55,926
￥70,866 total
includes taxes & fees
Dec 14 - Dec 15
Sundial Beach Resort & Spa
Dock
Matlacha Tiny Village

Matlacha Tiny Village

Matlacha Tiny Village
3.0 star property
Matlacha
8.8 out of 10, Excellent, (268)
"Very nice place with all necesary accommodations for a Pleasant stay. "
United States
isabel
The price is ￥18,207
￥32,064 total
includes taxes & fees
Dec 19 - Dec 20
Matlacha Tiny Village
Sun loungers, beach towels
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.

Modern boho 2bed 2bath home, 8 mins to downtown cape and near beach.
Pelican
9.4 out of 10, Exceptional, (38)
"Everything was as listed! My husband and I had a great stay while visiting friends. Location was perfect and the space was super cozy! Would definitely recommend!"
United States
julie l.
The price is ￥15,535
￥38,581 total
includes taxes & fees
Dec 23 - Dec 24
Modern boho 2bed 2bath home, 8 mins to downtown cape and near beach.
Smart TV
Boca Sunny Side Condo in Florida

Boca Sunny Side Condo in Florida

Boca Sunny Side Condo in Florida
2.0 star property
Rotonda West
10.0 out of 10, Exceptional, (2)
"Excellent "
United Kingdom
Peter S.
The price is ￥14,172
￥46,865 total
includes taxes & fees
Dec 19 - Dec 20
Boca Sunny Side Condo in Florida
Fridge, microwave, oven, stovetop
Water Front Boundary Vacation Home Villa close to beaches, golfing, Fishing

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, (60)
"We had a great time even the weather was bad we had an amazing time in the home play games and watch movies "
United States
Adam L.
The price is ￥14,396
￥47,645 total
includes taxes & fees
Dec 12 - Dec 13
Water Front Boundary Vacation Home Villa close to beaches, golfing, Fishing
Terrace/patio
Waterfront Condo with Pool & Boat Slip

Waterfront Condo with Pool & Boat Slip

Waterfront Condo with Pool & Boat Slip
Caloosahatchee
10.0 out of 10, Exceptional, (24)
"Great stay, would book again if in area"
United Kingdom
Tom f.
The price is ￥15,180
￥55,552 total
includes taxes & fees
Dec 14 - Dec 15
Waterfront Condo with Pool & Boat Slip
Outdoor pool, a heated pool
Hidden Secret Waterfront Retreat

Hidden Secret Waterfront Retreat

Hidden Secret Waterfront Retreat
2.0 star property
Hancock
10.0 out of 10, Exceptional, (3)
"The pool was very nice, and the seating by the canal was amazing, it was so relaxing, and the owner was quick to respond and very friendly!"
United States
bethany r.
The price is ￥49,370
￥87,341 total
includes taxes & fees
Jan 10 - Jan 11, 2026
Hidden Secret Waterfront Retreat
Grand Studio Suite, Kitchenette | Living area | 43-inch Smart TV with cable channels, Hulu, streaming services
Lazy Cuckoo Inn

Lazy Cuckoo Inn

Lazy Cuckoo Inn
2.0 star property
Fort Myers Beach
9.0 out of 10, Wonderful, (223)
"Great location and very clean, cute place"
United States
Sarah
The price is ￥8,915
￥15,011 total
includes taxes & fees
Dec 15 - Dec 16
Lazy Cuckoo Inn
TV
New Fully Renovated Condo Unit 2A

New Fully Renovated Condo Unit 2A

New Fully Renovated Condo Unit 2A
Punta Gorda Isles
10.0 out of 10, Exceptional, (14)
"The house was very clean, beautiful neighborhood, and relaxing."
United States
Anonymous traveler
The price is ￥11,605
￥41,470 total
includes taxes & fees
Dec 16 - Dec 17
New Fully Renovated Condo Unit 2A
House | 1 bedroom, Internet
Hibiscus House Bed Breakfast Citrus Room

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, (1)
"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 ￥28,713
￥32,015 total
includes taxes & fees
Dec 14 - Dec 15
Hibiscus House Bed Breakfast Citrus Room
Outdoor dining
Boho getaway - walkable to downtown Fort Myers!

Boho getaway - walkable to downtown Fort Myers!

Boho getaway - walkable to downtown Fort Myers!
Fort Myers River District
9.4 out of 10, Exceptional, (29)
"Comfortable place, convenient area"
United States
Don H.
The price is ￥15,682
￥43,891 total
includes taxes & fees
Dec 12 - Dec 13
Boho getaway - walkable to downtown Fort Myers!
Pool
Lakeside Retreat with Heated Pool

Lakeside Retreat with Heated Pool

Lakeside Retreat with Heated Pool
Hancock
7.8 out of 10, Good, (30)
"Nice home. Plenty of room for our whole family. The pool and canal view were a big hit."
United States
JR & Lana H.
The price is ￥13,643
￥66,363 total
includes taxes & fees
Dec 15 - Dec 16
Lakeside Retreat with Heated Pool
Private kitchen
2 Person Studio with Patio - Turtle Cove - Welcome to our stunning, newly renovated studio condo!

2 Person Studio with Patio - Turtle Cove - Welcome to our stunning, newly renovated studio condo!

2 Person Studio with Patio - Turtle Cove - Welcome to our stunning, newly renovated studio condo!
Matlacha
9.8 out of 10, Exceptional, (8)
"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 ￥7,008
￥21,349 total
includes taxes & fees
Dec 14 - Dec 15
2 Person Studio with Patio - Turtle Cove - Welcome to our stunning, newly renovated studio condo!
Fridge, microwave, oven, stovetop
Lakeside Haven with Heated Pool

Lakeside Haven with Heated Pool

Lakeside Haven with Heated Pool
Hancock
9.2 out of 10, Wonderful, (44)
"Everything was perfect!!!! Loved the privacy felt right at home during our stay ..... Pool was clean and just the right temperature..... Check in was fast and easy no issues whatsoever ..... Would definitely book again !!!!"
United States
Lisa M.
The price is ￥13,957
￥67,505 total
includes taxes & fees
Dec 16 - Dec 17
Lakeside Haven with Heated Pool
Sun loungers, beach towels
SUNSHINE GETAWAY VACATION RENTALS

SUNSHINE GETAWAY VACATION RENTALS

SUNSHINE GETAWAY VACATION RENTALS
Fort Myers
8.4 out of 10, Very Good, (137)
"Easy location to get where we needed. Clean and spacious."
United States
Chris N.
The price is ￥10,350
￥41,689 total
includes taxes & fees
Dec 21 - Dec 22
SUNSHINE GETAWAY VACATION RENTALS
Property grounds
The Lovebird-sleeps 3! Great value on Sanibel-walk to dining, shops and Historic East End Lighthouse

The Lovebird-sleeps 3! Great value on Sanibel-walk to dining, shops and Historic East End Lighthouse

The Lovebird-sleeps 3! Great value on Sanibel-walk to dining, shops and Historic East End Lighthouse
East End
9.2 out of 10, Wonderful, (50)
"Fantastic little cottage. Just the right amount of space for a quick get away for two. Complimentary bikes and beach chairs were great amenities. Highly recommend. Would absolutely stay here again. "
United States
Teresa C.
The price is ￥24,763
￥57,649 total
includes taxes & fees
Dec 16 - Dec 17
The Lovebird-sleeps 3! Great value on Sanibel-walk to dining, shops and Historic East End Lighthouse
Pool
Bright & Airy 2bed 2bath home near downtown/Weekly and monthly discounts!

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, (54)
"Every time excellent in every way!!!"
United States
Kim G.
The price is ￥16,466
￥40,080 total
includes taxes & fees
Dec 14 - Dec 15
Bright & Airy 2bed 2bath home near downtown/Weekly and monthly discounts!
Fridge, microwave, oven, stovetop
NEW! Waterfront Heated Pool, Kayaks, Fishing Pier.

NEW! Waterfront Heated Pool, Kayaks, Fishing Pier.

NEW! Waterfront Heated Pool, Kayaks, Fishing Pier.
Hancock
10.0 out of 10, Exceptional, (12)
"The house was very spacious lots of room for the whole family the pool was excellent great location for restaurants and shopping excellent place to relax we would definitely stay there again when we come to town would highly recommend it "
United States
Robert H.
The price is ￥19,464
￥62,831 total
includes taxes & fees
Dec 15 - Dec 16
NEW! Waterfront Heated Pool, Kayaks, Fishing Pier.
Beach nearby
WaterView 176B Sunny Vacation home 3 bdr, 2 ba Close to Gulf, Beaches

WaterView 176B Sunny Vacation home 3 bdr, 2 ba Close to Gulf, Beaches

WaterView 176B Sunny Vacation home 3 bdr, 2 ba Close to Gulf, Beaches
Oakland Hills
9.8 out of 10, Exceptional, (15)
"It was beautiful especially Boca Grande, went on a charter fish trip which was amazing. The property was also amazing nice dock and canoed the first day it was fun but then we saw a lot of gators but overall would come again! "
United States
Caleb R.
The price is ￥17,521
￥51,396 total
includes taxes & fees
Dec 13 - Dec 14
WaterView 176B Sunny Vacation home 3 bdr, 2 ba Close to Gulf, Beaches
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

Sanibel Island Beach Resort

Sanibel Island Beach Resort

10/10 Excellent
"Courteous staff, easy parking, close beach"
Jenna 1-night trip
Posted 1 day ago
Sanibel Island Beach Resort

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?

Luxury family friendly WATERFRONT home with a POOL, PLAYGROUND, FIREPIT & BEACH : This vacation home rental outside of Pineland is equipped with a barbecue grill, air-conditioning, and laundry facilities to help you feel comfortable during your stay. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

How many vacation rentals are there in Pineland?

Expedia has 8 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.