A wooden pier extending into calm water with a clear sky and distant land.

Pineland Vacation Rentals

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Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Pineland vacation rentals

A spacious patio with a dining table and chairs, a sofa, and a ceiling fan.

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.
$386 nightly
The price is $426
Nov 1 - Nov 2
Total with taxes and fees
3BR Coastal retreat in peaceful Bokeelia with pool, bikes, ping pong and fishing
A beachside area with colorful beach houses, a dock, and a sandy beach.

2. Matlacha Tiny Village

Matlacha Tiny Village
3.0 star property
Matlacha
8.8 out of 10, Excellent, (298 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
$221 nightly
The price is $238
Nov 6 - Nov 7
Total with taxes and fees
Matlacha Tiny Village
A modern living room with a flat-screen TV, a floor lamp, a dining table, and a sofa.

3. Lazy Cuckoo Inn

Lazy Cuckoo Inn
2.0 star property
Fort Myers Beach
8.8 out of 10, Excellent, (304 reviews)
"Great place!"
United States
Bruce
$81 nightly
The price is $90
Oct 27 - Oct 28
Total with taxes and fees
Lazy Cuckoo Inn
A multi-level house with a white exterior, a staircase, and a deck area.

4. 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 Island
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.
$1,166 nightly
The price is $1,283
Nov 1 - Nov 2
Total with taxes and fees
North Captiva Steps to Gulf Beaches Last Minute Offers Beach + Golf Cart + Club
A beach with a view of the ocean and a sunset.

5. Island Inn

Island Inn
3.5 star property
West End
9.4 out of 10, Exceptional, (1,165 reviews)
"Great location"
United States
Nicole
$215 nightly
The price is $240
Nov 8 - Nov 9
Total with taxes and fees
Island Inn
A spacious living room with a flat-screen TV, a sofa, a coffee table, and a balcony with a view of the beach.

6. 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)
"Highly recommend for families as this unit is located right by the pool and marina. Waterpark is within walking distance."
United States
DENISE H.
$434 nightly
The price is $479
Oct 27 - Oct 28
Total with taxes and fees
Bayside Villa 4224: Bright Corner Unit with Stunning Bay Views
A balcony with a pool, chairs, and a view of a water body and buildings.

7. 2 Queen Bed|Nsmk|Cape Coral FL

2 Queen Bed|Nsmk|Cape Coral FL
Caloosahatchee
10.0 out of 10, Exceptional, (154 reviews)
"Had a lovely time here!"
United States
Anonymous traveler
$60 nightly
The price is $67
Oct 27 - Oct 28
Total with taxes and fees
2 Queen Bed|Nsmk|Cape Coral FL
A balcony with a pool, chairs, and a view of a water body and buildings.

8. Cape Coral FL | King bed

Cape Coral FL | King bed
Caloosahatchee
10.0 out of 10, Exceptional, (199 reviews)
"Views of the lake from this hotel are wonderful. The pool was enjoyable as well."
United States
Anonymous traveler
$63 nightly
The price is $70
Oct 27 - Oct 28
Total with taxes and fees
Cape Coral FL | King bed
An aerial view of a coastal area with several small islands connected by bridges.

9. NEW!! The “WATERSIDE” COTTAGE~With dockage

NEW!! The “WATERSIDE” COTTAGE~With dockage
Bokeelia
10.0 out of 10, Exceptional, (52 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.
$423 nightly
The price is $466
Oct 28 - Oct 29
Total with taxes and fees
NEW!! The “WATERSIDE” COTTAGE~With dockage
An aerial view of a beach with clear turquoise waters, a sandy shoreline, and a small boat anchored near the shore.

10. 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, (63 reviews)
"House was very clean and looked just like advertised. Had a very comfortable stay and property is close to everything you need. Will definitely come back."
United States
Jennifer B.
$212 nightly
The price is $234
Oct 28 - Oct 29
Total with taxes and fees
Bright & Airy 2bed 2bath home near downtown/Weekly and monthly discounts!
A beach view from a balcony with a pool, palm trees, and a building with a balcony.

11. Edison Beach House

Edison Beach House
3.5 star property
Fort Myers Beach
9.4 out of 10, Exceptional, (1,956 reviews)
"Great stay."
United States
Angie
$209 nightly
The price is $233
Oct 27 - Oct 28
Total with taxes and fees
Edison Beach House
A beach with a thatched-roof structure, palm trees, and a view of the sea.

12. 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, (1,351 reviews)
"Amazing place to stay when visiting Punta Gorda. Very convenient and loved having shops and restaurants so close by. Spacious unit - so much better than just a hotel room."
United States
Michelle
$192 nightly
The price is $215
Oct 27 - Oct 28
Total with taxes and fees
The Suites at Fishermen’s Village
Beach

13. 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
8.6 out of 10, Excellent, (9 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.
$468 nightly
The price is $516
Oct 27 - Oct 28
Total with taxes and fees
Bayside Villa 4116 | Newly Renovated Marina View Residence | Walk to the Beach
An aerial view of a beach with rows of blue umbrellas and beach chairs, a sandy shoreline, and a path leading through the beach area.

14. 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.
$549 nightly
The price is $604
Oct 27 - Oct 28
Total with taxes and fees
Bayside Villa 5110 | Upscale Bayfront Residence | In-unit laundry | Walk to the Beach
A coastal resort with a long sandy beach, multiple white buildings, and lush greenery.

15. 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.
$528 nightly
The price is $582
Oct 27 - Oct 28
Total with taxes and fees
Captiva Villa 3213 | Chic Residence | Great Amenities | Walk to the Beach
A beach with a single seashell in the foreground and two people in the background.

16. 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, (24 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.
$383 nightly
The price is $400
Oct 27 - Oct 28
Total with taxes and fees
Coastal Chic Cottage "Sandpiper" minutes to the beach! Free bikes
A balcony with a pool, chairs, and a view of a water body and buildings.

17. Premium 2 Queen Bed|Nsmk

Premium 2 Queen Bed|Nsmk
Caloosahatchee
10.0 out of 10, Exceptional, (183 reviews)
"Great value for a lakeside hotel."
United States
Anonymous traveler
$63 nightly
The price is $70
Oct 27 - Oct 28
Total with taxes and fees
Premium 2 Queen Bed|Nsmk
A modern kitchen with a central island, stainless steel appliances, and a decorative backsplash.

18. 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)
"We absolutely loved the location and the property. Already looking forward to coming back next year. Condo was clean, lots of space and enjoyed the screened in porch. Host is very attentive and alway quick to reply. Thanks for such a special vacation!"
United States
Buffey H.
$261 nightly
The price is $288
Oct 27 - Oct 28
Total with taxes and fees
Modern Luxurious Condo, King Bed Suite, Waterfront + Pool, Near Downtown
An aerial view of a beach with rows of blue umbrellas and beach chairs, a sandy shoreline, and a path leading through the beach area.

19. Beach Villa 2426 | Stunning Beachfront Residence on Captiva Island

Beach Villa 2426 | Stunning Beachfront Residence on Captiva Island
Captiva
9.6 out of 10, Exceptional, (26 reviews)
"There were a few minor issues, but for the most part, our stay was enjoyable. "
United States
Ronald
$704 nightly
The price is $775
Oct 27 - Oct 28
Total with taxes and fees
Beach Villa 2426 | Stunning Beachfront Residence on Captiva Island
A wooden deck with a table and chairs overlooking a body of water, palm trees, and a house in the background.

20. 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.
$190 nightly
The price is $209
Oct 29 - Oct 30
Total with taxes and fees
Southernmost Inn King Suite on Canal
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

Baymont by Wyndham Fort Myers Central

Baymont by Wyndham Fort Myers Central

10/10 Excellent
"Had a great stay here. The room was clean, comfortable, and well maintained. The staff was friendly, check-in was quick, and everything went smoothly. A great place to stay, and we'd definitely book here again. 😊"
Jose Manuel 1-night trip
Posted 1 hour ago
Baymont by Wyndham Fort Myers Central

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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Pineland in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $90 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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.