Vacation rentals in Pineland

Apartment in Fort Myers Beach

A screened-in outdoor space features a sparkling pool, surrounded by paver stones and tropical plants. Two loungers are positioned nearby, providing a comfortable area to relax. Sunlight filters through, casting soft shadows across the patio.

4.99 out of 5 average rating, 69 reviews

Island Sunshine Poolside Gem

AmyRating, 5 stars6 days ago

Island Sunshine was the perfect get away for my husband and I. Great location to the beach, with easy access. The unit was clean and welcoming. Angie had all the amenities that we needed for our stay. There were plenty of chairs and beach buggies. She let us know as soon as our unit became available. She introduced herself to my husband and I as she was taking care of her properties. I would highly recommend her and Island Sunshine. I hoping to visit this location again in the near future.

Tiny home in Port Charlotte

5 out of 5 average rating, 6 reviews

Minutes to Sand, Dog Friendly, Hot Tub Luxury

EricRating, 5 stars6 months ago

We transferred over to Richard’s Airbnb location seamlessly during the last hurricane. The place was very spacious, comfortable, with high end finishings, easily accommodating myself, daughter, granddaughter, and pet. Richard was a great host especially considering the circumstances. Very responsive and openly communicative when needed or necessary. We would definitely stay at Richard’s Place again when in the area. Eric - out of state traveler

5 out of 5 average rating, 17 reviews

Home in Bonita Springs

Casa Bonita by the Sea

EmilioRating, 5 stars4 months ago

It was a wonderful stay. It’s a beautiful house with everything included for what you need to have a great stay. Agata is a great person and takes care of all details so that her guests feel at home. We would be delighted to go back soon, and it will surely be in this house. Everything in this house is amazing.

4.95 out of 5 average rating, 92 reviews

Home in Captiva

Ocean Views |Fast WiFi & Pool |5 Min Walk to Beach

AprilRating, 5 stars3 weeks ago

This home is splendid on every level! The Hosts were super responsive, very nice people, and the house is even better than in the photos! Both inside and out. From the furniture to the kitchen to the absolutely beautiful, and Very Large balconies…this special home is surrounded on 3 sides by Water!! So you get a Sunrise and Sunset view each day!! Pretty Magical! Nature is everywhere…so many different bird calls, and the Osprey Family Nest with Mama, Papa and Baby Osprey is in full view from inside of the house and on both the Upper Balcony off the Main Bedroom as well as the Lower Balcony off the kitchen and screened Patio. It provided hours of peaceful entertainment! All of this surrounded by manicured lawns, with golf course views. It’s the best of both worlds! I very much look forward to staying again!

Cottage in Fort Myers Beach

A wall-mounted sign features the words 'Welcome to the BEACH' in bold turquoise lettering, set against a white background. Above the sign, a decorative ship wheel adds a nautical touch to the entryway.

4.89 out of 5 average rating, 28 reviews

DEJA BLUE 1000 FT from Beach Great for Families

MaddyRating, 5 stars11 months ago

The place was great! Perfect size for 3 or 4 people. The beach supplies (wagon, chairs, umbrella) were SOOO handy! It was just a short walk over to the beach. The kitchen was well stocked with supplies to cook if desired. Since the hurricane, there was a limited amount of restaurants open. We didn’t mind this since we cooked but just a heads up!

4.93 out of 5 average rating, 141 reviews

A light-filled living area features a large, comfortable sectional sofa and a rustic wooden coffee table. A flat-screen TV is mounted on the wall, alongside a decorative mirror and indoor plants, creating an inviting space for relaxation.

Home in Naples Park

675 FantaSea | New Heated Resort Pool & Fire Pit

MindyRating, 5 stars2 weeks ago

I highly recommend staying at this home! The pool area was amazing, the pool was warm and so beautiful in the evening! The kitchen is equipped with everything you need to prepare meals which is so important to me! It felt like home away from home! Keith was immediately responsive with anything we needed! Keith was so accommodating in working with us due to flight times changing! Perfect trip!

4.67 out of 5 average rating, 123 reviews

A serene white sand beach stretches along the shore, meeting calm turquoise waters. Gentle waves lapping at the beach create a tranquil atmosphere, with a clear sky overhead. Distant vegetation adds a natural element to the landscape.

Home in Cape Coral

La venezia beautiful 4 bedroom pool/spa heated

JamesRating, 5 stars4 days ago

Elizabeth was a very good host responding quickly to any concerns our questions we had. Very nice home and was a great place for our family and grandkids to enjoy the pool relax and play some board games as we visited the area. Thanks so much for offering your home!

Vacation rentals for every style

Get the amount of space that is right for you

Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Homes

Comfortable places with all the essentials

Popular amenities for Pineland vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Pineland's top sights

Tarpon Lodge26 locals recommend

Island Girl Charters25 locals recommend

Tarpon Lodge Restaurant18 locals recommend

Randell Research Center16 locals recommend

Alden Pines Country Club15 locals recommend

Safe Harbor Pineland13 locals recommend

Other great vacation rentals in Pineland

5 out of 5 average rating, 8 reviews

A wooden dock extends over calm waters, with boats moored alongside. Lush greenery borders the scene, and distant homes can be seen on the horizon. The sky is clear, contributing to the serene atmosphere of the waterfront setting.

Home in Placida

Bay view and possible two family rental!

ArleneRating, 5 stars3 weeks ago

we had a wonderful time at Robert's place. Everything was as described. the island is a perfect getaway for anyone that wants to go on an adventure and get away from the hustle and bustle. The kitchen had everything you would need to cook, it was perfect! Everything was well thought of in this home. On a side note, golf carts need to be booked months in advance and are pretty pricey and we hoped to walk around the island but we're told upon checkin that was not allowed. we could only go to the beach and back to the property. You could walk along the beach though.

4.97 out of 5 average rating, 35 reviews

A serene outdoor space is highlighted by several blue adirondack chairs placed on a spacious paved patio. Lush palm trees and tropical plants surround the area, leading to a boat dock visible along the calm waterway, reflecting the clear blue sky.

Home in Fort Myers

Rivers Edge Oasis, Our Secluded Paradise-Sleep 21+

MatthewRating, 5 stars1 month ago

Teresa was an amazing host for a wonderful property! She was responsive to all of our needs and even provided us with local recommendations late the evening we arrived. The house comes stocked with lots of needed essential items for your stay (shampoo, laundry detergent, etc.) and was perfect for our large group. We can't wait to come back in the future!

4.82 out of 5 average rating, 22 reviews

A serene waterfront view showcases a grassy area with several lounge chairs positioned under palm trees. The sunlight reflects off the water, enhancing the natural setting. The property features a private dock along the rocky shoreline, providing access to Lemon Bay.

Home in Englewood

Cottage By the Sea A

JohnRating, 5 stars3 weeks ago

What a cute, little space. Perfect for the two of us. VERY close to the beach and it was an easy walk to the restaurants and bars. We loved how quiet and serene the location is. Highly recommend!!

4.91 out of 5 average rating, 112 reviews

Home in Fort Myers

SWFL: Lake McGregor Home - Entire Home!

ChantelRating, 5 stars1 month ago

Juan was very accommodating and we thoroughly enjoyed our stay

5 out of 5 average rating, 3 reviews

A modern kitchen showcases white cabinetry paired with stainless steel appliances, including a large refrigerator and an oven. A quartz countertop island offers seating with four gray stools, while natural light fills the space through a nearby window.

Home in Cape Coral

Modern Comfort: Spacious Home, Garden View

DeanRating, 5 stars14 months ago

The host was amazing always easy to get a hold of. They even called to check on me and my accommodations. Beautiful home and great neighborhood quite and relaxing . would recommend this stay to anyone wanting to feel welcomed.

4.88 out of 5 average rating, 26 reviews

An enclosed pool area is illuminated with colorful lights reflecting off the calm water. Steps lead into the inviting pool, surrounded by a decorative stone border. A potted plant adds a touch of greenery to the serene environment.

Home in Fort Myers

Luxury Oasis with Private Pool!

AmyRating, 5 stars1 month ago

This was our 2nd stay at this property. It is very convenient to Fort Myers Beach, Sanibel Island and grocery shopping. We love the private pool area (very nice and clean). Very comfortable spot for a family vacation. We would definitely return again in the future.

4.97 out of 5 average rating, 36 reviews

A spacious bathroom features a walk-in shower with a pebble stone floor and glass enclosure. A dual-sink vanity with a granite countertop is positioned against textured wall tiles. Natural light streams through a window adorned with plantation shutters.

Home in Naples

Beautiful Home w/ Pool & Spa, Pet Friendly!

PaulRating, 5 stars3 weeks ago

This place is great, with lots of spacious, clean rooms. We’ve done AirBnB’s in Naples yearly for a while and Dara’s place was the best for our needs. The pool faces south giving a lots of sunshine while still offering a large shaded space. In addition to the 3 bedrooms is a large den with a big flat screen TV, so I could sneak off when the wife and adult kids (yes, they still vacation with us 😉) are on a Vampire watching binge. Dara was very attentive and helpful. We’ll likely be back!