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Pineland Holiday Rentals

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Holiday Rentals in Pineland

The Suites at Fishermen’s Village- 2 Bedroom Suites

3.0 star property
Punta Gorda Isles
9.8 out of 10, Exceptional, (1027)
"We loved our stay and plan on returning. Loved the sunset cruise from the marina "
United States
Paul
The price is NZ$413
includes taxes & fees
16 Nov - 17 Nov
The Suites at Fishermen’s Village- 2 Bedroom Suites

Edison Beach House

3.5 star property
Fort Myers Beach
9.4 out of 10, Exceptional, (1552)
"All around great place to stay"
United States
David
The price is NZ$358
includes taxes & fees
19 Nov - 20 Nov
Edison Beach House

Sundial Beach Resort & Spa

5.0 star property
Mid Island
8.6 out of 10, Excellent, (2581)
"wonderful family friendly and spotless resort"
United States
Mary Anne
The price is NZ$751
includes taxes & fees
16 Nov - 17 Nov
Sundial Beach Resort & Spa

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

North Captiva
9.6 out of 10, Exceptional, (100)
"Everything was perfect."
United States
Tom C.
North Captiva Point House - Boat/Water Taxi Only **NEWLY RENOVATED **

Island Inn

3.5 star property
West End
9.4 out of 10, Exceptional, (1116)
"Really nice, updated, and clean room with a screened waterfront balcony in a perfect place on the island (far enough away from the big resorts to be in a quieter area, but close enough to the center area of the island to be convenient). "
United States
Chris
The price is NZ$471
includes taxes & fees
18 Nov - 19 Nov
Island Inn

4 Bedroom Beach Home on a Private Island with a Private Pool

North Captiva
9.8 out of 10, Exceptional, (26)
"My family and I (8 adults) stayed at Sandy Feet during the week of New Years, and had a great time. The home is absolutely gorgeous, and accurately described in the listing. We all had fun using the pool and foosball tables, laying out on the deck(s), of course walking the beach. This home has everything you could possibly want to make your vacation on North Captiva a success. Yamirka (owner) and Tortuga Properties were both very communicative and responsive to whatever questions we had. ...
United States
Daniel W.
4 Bedroom Beach Home on a Private Island with a Private Pool

Lazy Cuckoo Inn

2.0 star property
Fort Myers Beach
9.0 out of 10, Wonderful, (220)
"Great location and very clean, cute place"
United States
Sarah
The price is NZ$164
includes taxes & fees
16 Nov - 17 Nov
Lazy Cuckoo Inn

Landing Apartments near North Fort Myers

4.0 star property
Hancock
9.4 out of 10, Exceptional, (44)
"It was a good deal for the price"
United States
Lucretia
Landing Apartments near North Fort Myers

Resort Harbour Properties

3.5 star property
Punta Rassa
9.6 out of 10, Exceptional, (361)
"Pool was beautiful. Beach was disappointing."
United States
Linda
Resort Harbour Properties

Matlacha Tiny Village

3.0 star property
Matlacha
8.8 out of 10, Excellent, (265)
"Amazing spot. Love it. Quiet, and very suitable for us. The hosts are amazing; they will do anything in their power to accommodate your needs. Highly recommend it."
United States
Isabel
The price is NZ$361
includes taxes & fees
16 Nov - 17 Nov
Matlacha Tiny Village

Sanibel Siesta on the Beach

2.5 star property
Mid Island
10.0 out of 10, Exceptional, (2)
"Long weekend get away from the cold! Right on the beach!"
United States
Lisa
Sanibel Siesta on the Beach

2 Private Cabanas with kitchen and a Private Pool.

Pelican
9.4 out of 10, Exceptional, (26)
"Property manager was great. Really enjoyed our stay. Would highly recommend others to stay here. "
United States
David H.
2 Private Cabanas with kitchen and a Private Pool.

Luxurious Waterfront Villa with 4 Bedrooms, Private Heated Pool and Hot Tub!

Pelican
9.8 out of 10, Exceptional, (122)
"Great place to spent your holiday. We really enjoyed the house, the pool and the neighborhood. A full recommendation and a five star rating. Thank you Damien"
Germany
Björn H.
Luxurious Waterfront Villa with 4 Bedrooms, Private Heated Pool and Hot Tub!

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

Trafalgar
10.0 out of 10, Exceptional, (42)
"Very beautiful home with a great pool. We throughly enjoyed our stay and the management was very accommodating during our stay. The bikes, beach toys and coolers were great to have during our stay."
United States
Lesley B.
PALM BREEZE - SWIM UP TO THE BAR! Integrated spa, Outdoor grill, Fire pit!

BEAUTIFUL NEW CONDO 2025 SANIBEL ISLAND!!! SANDY BEACH LAGOON POOL PICKLEBL🏝️🌅 🏖️

4.0 star property
Mid Island
9.8 out of 10, Exceptional, (51)
"AMAZING!!! AMAZING Couple getaway!!! Everything you need for a memorable vacation!!!"
United States
Ken S.
BEAUTIFUL NEW CONDO 2025 SANIBEL ISLAND!!! SANDY BEACH LAGOON POOL PICKLEBL🏝️🌅 🏖️

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

North Captiva
9.2 out of 10, Wonderful, (19)
"The property and entire process was great. The owner and hosts had great communication from booking to check out. The house was well stocked with everything needed from kitchen supplies to games to play. Great having the pool area to cook dinner while my daughters were playing. We would definitely book here again."
United States
Kevin S.
Fully renovated Luxury House pool! HUGE 5 BD 5 BA 9 bed! Sleeps 16! 2 golf carts

Luxury family friendly WATERFRONT home with a POOL, PLAYGROUND, FIREPIT & BEACH

Fort Myers
9.6 out of 10, Exceptional, (23)
"We had a very relaxing stay and Andy was very helpful and communicative even though his wife had just given birth to a baby! 10/10 would recommend :) "
United States
Mussia K.
The price is NZ$721
includes taxes & fees
17 Nov - 18 Nov
Luxury family friendly WATERFRONT home with a POOL, PLAYGROUND, FIREPIT & BEACH

Paradise Vacation Pool Home Last minute $155

Pelican
10.0 out of 10, Exceptional, (6)
"We really enjoyed the stay. Barbara was wonderful, very responsive, location was amazing and condo was perfect as described. Plan on coming back "
United States
Chasity E.
Paradise Vacation Pool Home Last minute $155

NEW EVERYTHING!! 4-bed 3 bath South Facing spill over spa pool. 2 king suites

3.0 star property
Pelican
10.0 out of 10, Exceptional, (21)
"This home was a great property. Plenty of kitchen tools. The pool and patio right on the canal were special. From the bikes, kayaks and outdoor bbq, to the 2 master suites, this place had everything. There was a park a mile away with basketball, pickleball, tennis as well. Would definitely stay here again!"
United States
Lance H.
NEW EVERYTHING!! 4-bed 3 bath South Facing spill over spa pool. 2 king suites

An incredible spot to unwind and enjoy quality time with family and friends

Caloosahatchee
9.4 out of 10, Exceptional, (51)
"Awesome back yard. Wish we would have had a little more sunshine to enjoy it but the property is great and right on the canal."
United States
Dave J.
An incredible spot to unwind and enjoy quality time with family and friends
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 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 NZ$164 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 16 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.