A waterfront with palm trees and a boat dock.

Pineland Vacation Rentals

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Our top choices for Pineland vacation rentals

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, (11 reviews)
"Property and house were beautiful, clean, quiet. Everything was top notch. Would definitely book again."
United States
Erik B.
The price is CA $224
CA $604 total
includes taxes & fees
Oct 11 - Oct 12
3BR Coastal retreat in peaceful Bokeelia with pool, bikes, ping pong and fishing

2. Matlacha Tiny Village

Matlacha Tiny Village
3.0 star property
Matlacha
9.0 out of 10, Wonderful, (297 reviews)
"So cute and clean nice dock to sit and relax or fish. Kayaks available to use free as well with life jackets paddles, etc. well equipped rental we can’t wait to go again! Great communication with hosts."
United States
Lori
The price is CA $189
CA $317 total
includes taxes & fees
Oct 13 - Oct 14
Matlacha Tiny Village

3. 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, (36 reviews)
"Amazing stay!Beds were comfortable, kitchen was well stocked. We would stay here again and again. "
United States
Tanya J.
The price is CA $146
CA $1,834 total
includes taxes & fees
Nov 1 - Nov 2
North Captiva Steps to Gulf Beaches Last Minute Offers Beach + Golf Cart + Club

4. Island Inn

Island Inn
3.5 star property
West End
9.4 out of 10, Exceptional, (1,161 reviews)
"Great location"
United States
Nicole
The price is CA $395
CA $441 total
includes taxes & fees
Oct 29 - Oct 30
Island Inn

5. Lazy Cuckoo Inn

Lazy Cuckoo Inn
2.0 star property
Fort Myers Beach
8.8 out of 10, Excellent, (301 reviews)
"Great place!"
United States
Bruce
The price is CA $76
CA $131 total
includes taxes & fees
Oct 11 - Oct 12
Lazy Cuckoo Inn

6. The Suites at Fishermen’s Village

The Suites at Fishermen’s Village
3.0 star property
Punta Gorda Isles
9.8 out of 10, Exceptional, (1,342 reviews)
"Stay here every time I visit Florida. Highly recommend"
United States
Dawn
The price is CA $244
CA $274 total
includes taxes & fees
Oct 22 - Oct 23
The Suites at Fishermen’s Village

7. 2 Queen Bed|Nsmk|Cape Coral FL

2 Queen Bed|Nsmk|Cape Coral FL
Caloosahatchee
10.0 out of 10, Exceptional, (153 reviews)
"Had a lovely time here!"
United States
Anonymous traveller
The price is CA $86
CA $95 total
includes taxes & fees
Oct 11 - Oct 12
2 Queen Bed|Nsmk|Cape Coral FL

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, (16 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
The price is CA $148
CA $658 total
includes taxes & fees
Oct 11 - Oct 12
Bayside Villa 4224: Bright Corner Unit with Stunning Bay Views

9. 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.
The price is CA $356
CA $662 total
includes taxes & fees
Oct 11 - Oct 12
NEW!! The “WATERSIDE” COTTAGE~With dockage

10. Edison Beach House

Edison Beach House
3.5 star property
Fort Myers Beach
9.4 out of 10, Exceptional, (1,934 reviews)
"Great stay."
United States
Angie
The price is CA $251
CA $336 total
includes taxes & fees
Oct 12 - Oct 13
Edison Beach House

11. 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, (42 reviews)
"Our stay was absolutely wonderful. The home was perfect, beautifully decorated, and had everything we needed. It felt comfortable, peaceful, and welcoming from the moment we arrived. Every detail was thoughtfully prepared, making it easy to relax and enjoy our vacation. There's a lot of space for your boat or jet skis, we will definitely go back."
United States
Jocelyn F.
The price is CA $236
CA $557 total
includes taxes & fees
Oct 11 - Oct 12
50’ of Dock for your boats. Hot tub, Boatlift, walk 2 restaurants Xtra parking.

12. 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.
The price is CA $238
CA $831 total
includes taxes & fees
Oct 11 - Oct 12
Captiva Villa 3213 | Chic Residence | Great Amenities | Walk to the Beach

13. Bayside Villa 5110 | Upscale Bayfront Residence | In-unit laundry | Walk to the Beach

Bayside Villa 5110 | Upscale Bayfront Residence | In-unit laundry | Walk to the Beach
Captiva
9.6 out of 10, Exceptional, (23 reviews)
"Well kept condo."
United States
Joseph S.
The price is CA $225
CA $865 total
includes taxes & fees
Oct 11 - Oct 12
Bayside Villa 5110 | Upscale Bayfront Residence | In-unit laundry | Walk to the Beach

14. Cape Coral FL | King bed

Cape Coral FL | King bed
Caloosahatchee
10.0 out of 10, Exceptional, (197 reviews)
"Views of the lake from this hotel are wonderful. The pool was enjoyable as well."
United States
Anonymous traveller
The price is CA $89
CA $100 total
includes taxes & fees
Oct 11 - Oct 12
Cape Coral FL | King bed

15. Bayside Villa 4208 | Stunning Harbourview Residence| Walk to the Beach

Bayside Villa 4208 | Stunning Harbourview Residence| Walk to the Beach
Captiva
9.2 out of 10, Wonderful, (31 reviews)
"Very nice condo overlooking waterway. Nice pool and easy in and out. "
United States
William B.
Bayside Villa 4208 | Stunning Harbourview Residence| Walk to the Beach

16. Bayside Villa 4116 | Newly Renovated Marina View Residence | Walk to the Beach

Bayside Villa 4116 | Newly Renovated Marina View Residence | Walk to the Beach
Captiva
8.4 out of 10, Very good, (8 reviews)
"My husband and I enjoyed our stay here. The location was perfect, with restaurants and shops being within easy walking distance. The pool was beautiful and never crowded. "
United States
Maureen J.
The price is CA $225
CA $737 total
includes taxes & fees
Oct 11 - Oct 12
Bayside Villa 4116 | Newly Renovated Marina View Residence | Walk to the Beach

17. Waterfront Condo with Pool & Boat Slip

Waterfront Condo with Pool & Boat Slip
Caloosahatchee
10.0 out of 10, Exceptional, (26 reviews)
"Great location! Great kitchen! Very comfortable beds. Pool area and pool were the best. Great dock. We had the best stay at Seatuit."
United States
Mark L.
The price is CA $116
CA $479 total
includes taxes & fees
Oct 14 - Oct 15
Waterfront Condo with Pool & Boat Slip

18. Southernmost Inn King Suite on Canal

Southernmost Inn King Suite on Canal
Saint James City
10.0 out of 10, Exceptional, (19 reviews)
"Great spot. We have stayed multiple times, love the location. Everything has been great and look forward to going back! "
United States
Tracy L.
The price is CA $168
CA $298 total
includes taxes & fees
Oct 11 - Oct 12
Southernmost Inn King Suite on Canal

19. 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, (41 reviews)
"Great stay here! Clean and spacious. Loved the amenities and the location ease of access."
United States
Brianna L.
The price is CA $115
CA $413 total
includes taxes & fees
Oct 23 - Oct 24
Modern Luxurious Condo, King Bed Suite, Waterfront + Pool, Near Downtown

20. Coastal Chic Cottage "Sandpiper" minutes to the beach! Free bikes

Coastal Chic Cottage "Sandpiper" minutes to the beach! Free bikes
West End
9.0 out of 10, Wonderful, (23 reviews)
"Loved our stay at the cottage. It was a perfect getaway for 2. Short walk to a quiet beach. Convenient to restaurants and Ding Darling.We will be back!"
United States
Catherine B.
The price is CA $200
CA $569 total
includes taxes & fees
Oct 24 - Oct 25
Coastal Chic Cottage "Sandpiper" minutes to the beach! Free bikes
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 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, 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 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 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Pineland vacation rentals we have selected for you start as low as CA $131 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 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?

Tiki Hut Paradise 4-bedroom Bokeelia House w Golf Cart Tesla Charger Island Time: This Pineland vacation home rental has air-conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

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.