Photo by Suzanne McCoy

Pineland holiday homes

We found 1,951 holiday rentals — enter your dates for availability
Discover a selection of 9 homes and other holiday rentals in Pineland that are perfect for your trip. Whether you're staying in a holiday rental with a group or just with your pet, you'll find the best amenities for hanging out with the people that matter most, which might include parking and a fireplace. You're sure to find a property to rent to meet everyone's needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts – Pineland

Showing deals for:18 Dec - 25 Dec

Marina
Exterior
Private kitchen
Living area
Exceptional
(22 reviews)

Available winter 25/26! Enjoy this warm, gated marina community next winter!

Punta Gorda

8% off
NZ$3,253
for 7 nights, 1 home
NZ$465 per night
includes taxes & fees
Available winter 25/26! Enjoy this warm, gated marina community next winter!
Exterior
Interior
Dining
Exterior detail
Exceptional
(38 reviews)

Luxury vacation home in 'Venice of America'

Cape Coral

16% off
NZ$4,031
for 7 nights, 1 villa
NZ$576 per night
includes taxes & fees
Luxury vacation home in 'Venice of America'
Eat downstairs or more formal upstairs.
Original 1926 cottage in historic district of Boca Grande.
Eat at counter/dining table/outdoor picnic table
Front porch, cozy for reading, napping
Exceptional
(90 reviews)

Blissfully Serene Palm Cottage In Town and 2 Blocks from Beach

Boca Grande

8% off
NZ$20,417
for 7 nights, 1 home
NZ$2,917 per night
includes taxes & fees
Blissfully Serene Palm Cottage In Town and 2 Blocks from Beach
Property grounds
Private kitchen
Pool
Interior
Exceptional
(10 reviews)

Relaxing 3-Bedroom Matlacha Cottage with Private Pool & Dock

Matlacha

8% off
NZ$5,787
for 7 nights, 1 cottage
NZ$827 per night
includes taxes & fees
Relaxing 3-Bedroom Matlacha Cottage with Private Pool & Dock
Double size lot in secluded cul de sac
Games on "Beachy" Backard
Dining
double high ceilings and barn doors in loft kids room.
Exceptional
(54 reviews)

Hidden Treasure - Near Beach-Pool- Private CuldeSac - Dock Rental - 10% Off Week

Captiva

8% off
NZ$9,529
for 7 nights, 1 home
NZ$1,361 per night
includes taxes & fees
Hidden Treasure - Near Beach-Pool- Private CuldeSac - Dock Rental - 10% Off Week
Pool
Private kitchen
Exterior
Outdoor dining
Exceptional
(6 reviews)

Spacious 4-bedroom house in charming Cape Coral with WiFi, AC and a heated pool.

Cape Coral

7% off
NZ$4,001
for 7 nights, 1 home
NZ$572 per night
includes taxes & fees
Spacious 4-bedroom house in charming Cape Coral with WiFi, AC and a heated pool.
Dining
Pool
Living area
Exterior
Exceptional
(25 reviews)

Villa Sunshine, spectacular Bayview, Luxury Pool home

Cape Coral

7% off
NZ$5,082
for 7 nights, 1 home
NZ$726 per night
includes taxes & fees
Villa Sunshine, spectacular Bayview, Luxury Pool home
Backyard patio: Beach vibes, backyard bliss.
Simplicity and warmth in every detail.
LARGE HEATED POOL! 7 feet deep in the deep end.
Cozy, clean, and made for connection.
Exceptional
(9 reviews)

Heated Pool | Game Room | 9 beds | 2 Living Rooms for Groups & Families! PETS OK!

Cape Coral

8% off
NZ$8,700
for 7 nights, 1 home
NZ$1,243 per night
includes taxes & fees
Heated Pool | Game Room | 9 beds | 2 Living Rooms for Groups & Families! PETS OK!
Room
Interior
Dining
Exterior detail
Exceptional
(61 reviews)

Private getaway on Pine Island. Full kitchen, lanai, deck. Beautiful yard.

Bokeelia

8% off
NZ$1,101
for 7 nights, 1 cottage
NZ$157 per night
includes taxes & fees
Private getaway on Pine Island. Full kitchen, lanai, deck. Beautiful yard.
Pool with enclosure
Living room and exit to the lanai
Main living room and exit to the lanai
Exterior
Exceptional
(40 reviews)

Villa Manatee is a beautiful waterfront vacation home in SW Cape Coral.

Cape Coral

7% off
NZ$4,237
for 7 nights, 1 home
NZ$605 per night
includes taxes & fees
Villa Manatee is a beautiful waterfront vacation home in SW Cape Coral.
Dining
Living area
Private kitchen
Room
Exceptional
(20 reviews)

Cape Coral Nature Retreat with Adjacent Boating, Fishing & Trails

Cape Coral

8% off
NZ$3,069
for 7 nights, 1 home
NZ$438 per night
includes taxes & fees
Cape Coral Nature Retreat with Adjacent Boating, Fishing & Trails
Private kitchen
Outdoor dining
Exterior
Dining
Exceptional
(7 reviews)

Turtle House - Waterfront with Dock - Unbelievable Sunset View

Matlacha

16% off
NZ$3,361
for 7 nights, 1 home
NZ$480 per night
includes taxes & fees
Turtle House - Waterfront with Dock - Unbelievable Sunset View
Living area
Interior
Private kitchen
Living area
Exceptional
(15 reviews)

New! Hidden- Speakeasy-penny floor. 3bd 3bath Boat dock & Walk 2 town FABULOUS

Matlacha

6% off
NZ$5,813
for 7 nights, 1 home
NZ$830 per night
includes taxes & fees
New! Hidden- Speakeasy-penny floor. 3bd 3bath Boat dock & Walk 2 town FABULOUS
Pool
So close to our beautiful beach.
Living area
Interior
Exceptional
(48 reviews)

Upgraded beach house located just steps away from the beach. Pool and Hot tub.

Captiva

9% off
NZ$7,990
for 7 nights, 1 home
NZ$1,141 per night
includes taxes & fees
Upgraded beach house located just steps away from the beach. Pool and Hot tub.
Dining
Exterior
Private kitchen
Pool
Exceptional
(5 reviews)

Two minute walk to a soft sandy beach with some of the best shelling in the US.

Captiva

8% off
NZ$8,687
for 7 nights, 1 home
NZ$1,241 per night
includes taxes & fees
Two minute walk to a soft sandy beach with some of the best shelling in the US.
Curb view
Pool and lanai
Kitchen
Living area
Exceptional
(44 reviews)

Beautiful modern pool home; Furnished lanai, gas grill; Free Wifi; Nearby park

Cape Coral

8% off
NZ$3,887
for 7 nights, 1 home
NZ$555 per night
includes taxes & fees
Beautiful modern pool home; Furnished lanai, gas grill; Free Wifi; Nearby park
Interior
Outdoor dining
Dining
Room
Exceptional
(27 reviews)

Are you looking for old Florida.? Lower heart rate? No high rises/ traffic?

Bokeelia

15% off
NZ$1,955
for 7 nights, 1 home
NZ$279 per night
includes taxes & fees
Are you looking for old Florida.? Lower heart rate? No high rises/ traffic?
Living area
Private kitchen
Interior
Games room
Very good
(6 reviews)

Modern, cozy and brand new oasis

Cape Coral

7% off
NZ$2,105
for 7 nights, 1 home
NZ$301 per night
includes taxes & fees
Modern, cozy and brand new oasis
Living area
Marina
Pool
Room
Exceptional
(8 reviews)

3-bedroom waterfront pool house in Manatee Bay. BYOB: Bring your own boat

Saint James City

7% off
NZ$5,343
for 7 nights, 1 home
NZ$763 per night
includes taxes & fees
3-bedroom waterfront pool house in Manatee Bay. BYOB: Bring your own boat
Outdoor dining
Living area
Pool
Marina
Exceptional
(11 reviews)

The Perfect Day in Matlacha! Direct Gulf Access!

Cape Coral

6% off
NZ$4,683
for 7 nights, 1 home
NZ$669 per night
includes taxes & fees
The Perfect Day in Matlacha! Direct Gulf Access!
Exterior
Living area
Private kitchen
Living area
Excellent
(24 reviews)

Spacious "Crab Cakes" Cottage on N. Captiva with GolfCart, Starlink and new AC

Captiva

8% off
NZ$5,781
for 7 nights, 1 cottage
NZ$826 per night
includes taxes & fees
Spacious "Crab Cakes" Cottage on N. Captiva with GolfCart, Starlink and new AC
Interior
Living area
Room
Living area
Exceptional
(17 reviews)

Waterfront Oasis with Boat Lift & Hot Tub in Bokeelia

Bokeelia

8% off
NZ$3,947
for 7 nights, 1 home
NZ$564 per night
includes taxes & fees
Waterfront Oasis with Boat Lift & Hot Tub in Bokeelia
  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Choose a holiday rental for your Pineland getaway

Learn about the unique charm of Pineland with a stay in a holiday home rental. This city has something for everyone. With a holiday rental, you get a home away from home – many rentals offer full kitchens and outdoor grills for some home cooking.

Sightseeing in and around Pineland

Are you looking for attractions to visit while you're in the area? Venture out of your cosy holiday rental and experience everything that makes Pineland a fun spot to go on holiday. Here are some of the top attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Sun Splash Water Park (10.9 mi / 17.6 km)
  • Dunes Golf and Tennis Club (15.8 mi / 25.4 km)
  • Coral Oaks Golf Course (7.8 mi / 12.5 km)
  • Cape Royal Golf Club (7.9 mi / 12.7 km)
  • Palmetto-Pine Country Club (10.3 mi / 16.5 km)
  • Mike Greenwell's Bat-A-Ball & Family Fun Park (11.3 mi / 18.2 km)

Exploring the natural features in Pineland

Whether you're looking for exciting outdoor activities or just want to appreciate the scenery, you'll be sure to find the perfect setting for your holiday in Pineland. Here are a few of the area's most eye-catching sights, all within 30 miles (48.2 km) of the city centre:

  • Useppa Island (3.7 mi / 5.9 km)
  • Cabbage Key (4.5 mi / 7.2 km)
  • Cayo Costa Beaches (5.1 mi / 8.2 km)
  • North Captiva Island Beach (6.7 mi / 10.7 km)
  • Boca Grande Beaches (7.9 mi / 12.7 km)
  • Gasparilla Island State Park (8.3 mi / 13.4 km)

Transport to and around Pineland

The nearest airport is in Punta Gorda Airport (PGD), located 20.1 mi (32.3 km) from the city centre. If you can't find a flight that works for your travel itinerary, you might consider flying into Fort Myers, FL (RSW-Southwest Florida Intl.), which is 26.3 mi (42.3 km) away.

Frequently asked questions

What is the best area to stay in Pineland when booking a holiday rental?
When considering a holiday rental in Pineland, Florida, the nearby area of Bokeelia is a fantastic choice. This charming community is known for its serene atmosphere and scenic views, making it a great retreat for those looking to unwind. Bokeelia offers a selection of properties, from quaint cottages to more spacious homes, suiting a variety of preferences and group sizes.One of the top attractions in Bokeelia is the stunning Pine Island National Wildlife Refuge, where visitors can take part in the natural beauty of the region, enjoying opportunities for bird watching, hiking, and exploring the diverse ecosystems. Additionally, the Bokeelia Fishing Pier is a popular spot for both experienced anglers and those looking to enjoy the tranquil waters.Another delightful aspect of Bokeelia is its proximity to local eateries and shops, allowing visitors to experience the unique flavours of the area.
When is the best time to visit Pineland for a holiday rental?
April is the most popular month to visit Pineland, Florida, as it falls within the peak season from March to May. This period attracts a vibrant mix of travellers seeking both adventure and relaxation in the beautiful sunshine. With temperatures typically ranging from 20 to 30 degrees Celsius, visitors can enjoy outdoor activities such as kayaking through the scenic waterways or exploring the nearby wildlife reserves in comfortable warmth.March to May is ideal for those who appreciate the stunning natural beauty of the region. During these months, the landscape comes alive with flora and fauna, making it superb for nature walks and birdwatching. Whether you're lounging on the beach or embarking on a fishing trip, the pleasant climate and the array of local attractions make for a fulfilling holiday experience.If you're looking for a more budget-friendly option, consider visiting in December. During this time, this month offers a unique charm with fewer crowds and the opportunity to explore the area at a leisurely pace. You can enjoy the serenity of Pineland while still engaging in outdoor activities like biking or hiking in mild temperatures.Ultimately, the best time to visit Pineland for a holiday rental depends on your preferences for lively interactions and bustling activities or a more tranquil retreat amid nature's beauty.
What are the top attractions in Pineland?
In Pineland, Florida, visitors can enjoy a range of attractions that highlight the area's natural beauty and outdoor activities. The nearby J.N. Ding Darling National Wildlife Refuge is a must-visit, offering opportunities for bird watching, kayaking, and hiking along its scenic trails. This refuge is renowned for its diverse ecosystems and wildlife, making it a great spot for nature enthusiasts.Additionally, the area boasts the stunning beaches of Captiva Island and Sanibel Island, which are just a short drive away. These beaches are famous for their shell collecting and picturesque sunsets, providing a tranquil escape for holidaymakers.For those interested in local culture, the small community of Pineland features charming shops and restaurants that reflect the laid-back atmosphere of Southwest Florida. Visitors can also explore the historic use of the region through the Calusa Heritage Trail, which offers insights into the area's indigenous history.
Are all fees included in the Pineland holiday homes prices shown on Bookabach?
Bookabach provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Pineland holiday homes with parking?
Bookabach offers a wide selection of holiday homes in Pineland with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Pineland holiday homes?
You can find great discounts on holiday homes in Pineland on Bookabach, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Pineland holiday home booking on Bookabach?
To find Pineland holiday rentals with free cancellation, just use Bookabach's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Bookabach makes it easy to book with confidence.
Can I find long-stay holiday homes in Pineland?
A long-stay holiday home in Pineland is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Bookabach?
Bookabach's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Pineland holiday home?
Book your Pineland holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Bookabach booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Pineland?
Prices for holiday homes in Pineland vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Bookabach offers something for every taste and budget, from affordable homes in Pineland to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Bookabach as a host?
Joining Bookabach as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Bookabach makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Bookabach handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.