
Pine Island vacation rentals
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Top-rated vacation rentals in Pine Island
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Popular amenities for Pine Island vacation rentals
Pine Island house rentals

Attached Beautiful 2 Bedroom/2 Bathroom Home.
We were in town for baseball and the place was perfect for myself and my elderly Mom. Clean and close to what we needed. We had an issue with the lock on the door the first day but the owner came right away and got us in and figured out we were doing something wrong with code. Very nice folks and stayed in contact with us throughout our stay. Highly recommend the host!

Stylish Seminole Heights House
This place was very cozy and literally walking distance from everything. Place was clean and it was super easy to contact the host and they contacted us back very quickly. The only that was a little inconvenient was we really needed the pull out couch for a bed and it was so uncomfortable and warn out that we had to buy an air mattress for us to accommodate the sleeping. Also there is only 1 tv for the whole place so when my niece who was sleeping in the living room went to bed we didn’t have entertainment throughout the night for the rest of us. My family works over night so we are night owls and more tvs would have helped a lot. Outside of that the place was amazing and definitely would book again with a smaller group

2 BR Home in an Amazing Location With 4-Seat Cart!
Ryan was easy to reach and very responsive to any questions. His home was spotless and extremely well equipped. Our favorite room for relaxing was the lanai. It was well furnished and air conditioned which is unusual based on our past Air BnB rentals. The location is in close proximity to 3 pools,multiple golf courses and Sumter Landing square. Overall this was a great experience.

2B/2B Newly Renovated Home in Silver Lake!
Sarah’s house was wonderful! It was perfect for meeting up with family that lives near The Villages. Home was comfortable and convenient to everything in the Spanish Springs area. Sarah was quick to respond to messages and very helpful. I look forward to staying here next time we are down for a visit!

Home away from home entire house
Nice clean facility. Very close to many activities. Nice and quiet and peaceful neighborhood. Would stay there again.

Luxe BeachHouseA Heated Pool, 2 min walk to Beach
This property and location were exactly what I was looking for to celebrate a 40th birthday with friends. The house was exactly as described as was the property. The 28th Street beach access was back open so getting to the beach was a quick 5 minute walk. The beach chairs, wagon and assorted toys were a nice bonus since we were all travelling from out of town. Our propane tanks were nearly empty and so that hindered our ability to cook out and enjoy the firepit on the last night as we hoped. I would recommend checking those as soon as you arrive. Also, bring your own shampoo, conditioner and soap as that was not provided. Those two things aside (and only including as a head's up for future renters), this was exactly what we were looking for in terms of space and location. I would consider renting this property again if I'm in the area with a large group. Jimmy was responsive to all my questions leading up to the trip.

Cozy 2-Bedroom Oasis with Pool (NOT heated)
I will be definitely coming back! 🤩 #Travel #Adventure #Memories #Trip

Patio Villa, 5 mins from Sumter, FREE Gas Cart!
This place is great and so cute! Gary and his wife did a nice job of offering everything you need for a comfortable stay. The front porch is perfect for relaxing outside in the beautiful Florida weather. The golf cart is a Great amenity. The guidebook in the villa was great, thank you for taking the time to make recommendations on area restaurants and things to do. We will be back when we can relax, rather than work and enjoy those pool passes! :) Thank you!!
Pine Island cottage rentals

Redbird cottage and farm. Equestrian lake cottage
Beautiful venue for my intimate wedding elopement. Alisha allowing me to take photos with the horses was a magical addition to my perfect big day. Lovely place to stay as always.

Little Manatee River Cottage
Great location and wonderful place. Super responsive host. I'd love to go back

Tranquil Waterfront Cottage
AMAZING. Great hosts, great place! I stayed here by myself and it was heaven on earth. I am a nature lover and this exceeded my expectations. The house & the property are stunning. The house is a lovely mix of tasteful tropical & Victorian decor. The outside is like being in the garden of Eden. So private & peaceful. I was able to meet manatees my first evening taking the kayak out; they were as interested in me as I was in them and came all around me and the baby came up to say hi. It was one of the most amazing experiences I’ve had. It was just me and the manatees not another human in sight. The next morning I paddled out again and saw otters playing. I saw turtles, lizards, many beautiful birds, including green heron, great blue heron, and an owl. Coffee in the morning on the patio & a fire at night under the canopy of trees. Close to so much to do- springs, beach, nature parks, but by far the best was being able to paddle pretty much out the back door. I’m so glad I stayed here!!!

The Hideaway - Quaint and Peaceful Cottage
Excellent stay. We will book here again. Jamie is a Superhost, and the property is well situated. We’ve used AirBnB in multiple continents, and guests can book here with confidence. The area is safe, the property is very clean, the beds are comfortable, and it works extremely well for a family of four.

💯 Remodeled Cottage, Animal free property
Great little place for our little vacation

Cozy Cottage 5mins From Disney Parks!
We had stayed at Jonathan's place two years prior, and were so pleased, we booked it again for this past week. The location is off the main road - quiet, nice areas to walk, etc - but very close to all the Disney attractions and restaurants. Since we were last at Jonathan's home, he has done some nice updates, which made the place look fresh and new. Jonathan was also very prompt in responding to any messages I sent - always very friendly, helpful and professional. If we come down to the Orlando area again, we will definitely book this place!!

Modern Vacation Cottage near Walt Disney World
Perfect location with easy access to surrounding food and stores. Very clean and feels like home!

Coastal Cottage Getaway
Maria’s place was a peaceful 5 day getaway. I was able to use her kayaks right on site. Cottage was pristine clean, very comfortable, lovely decorated and amply supplied with little extras. Lots of outdoor activities in surrounding area and terrific restaurants.
Pine Island condo rentals

*Waterfront *2 Bedroom Condo *Amazing Sunsets*Pool
Our family had a wonderful time at this condo! We enjoyed waking to see the ocean every day and also had enough space to relax on our vacation. Helena provides a beach bag with towels and sand toys that were a very nice touch for our beach day. The staff at the bar/restaurant were great and we also felt safe with the 24 hour security guards on duty. This place really made our trip extra special!

Amazing main floor condo at Avalon
The condo is very beautiful and clean! it had all the amenities you would need. The pool was fantastic. It's only around 10 minutes to drive to the beach. Checking in and out was a breeze. Catinca is a friendly and amazing host. Highly recommend!! Would definitely come back.

Renovated Condo! Across the Street From The Beach
Great unit across the street from the beach. The photos matched the amenities. We felt right at home. Everything was fresh and clean. The neighbors were friendly. Beach chairs, umbrella, wagon, towels, and cooler were provided. Nice restaurants and market were within a 10-15 minute walk. We enjoyed our stay here.

Condo Minutes from Disney - No Hidden Fees
El apartamento es muy cómodo, tiene todo lo necesario para una buena estadía con la familia y está ubicado en una zona tranquila y de fácil acceso a todo. Está cerca de los parques de Disney y cerca de toda clase de tiendas, supermercados y restaurantes. Gary es muy diligente, ofrece instrucciones claras y estuvo pendiente a que no tuviéramos problemas a la llegada.

FUN 3 BDRM CONDO right on the BEACH!
Our family of 5 had a great time at Melody’s place. There was plenty of room for all of us. The beach was beautiful and not crowded at all. If you want a more secluded area away from the hustle and bustle this is a great place.

Arie Dam 302, Beach Front Condo - 2Bed/2Bath
Our family of 6 had the best time! Our condo was so nice, clean, and comfortable. It was great to have beach towels and chairs to use as well!! The beach and view was amazing. We had no idea it would be so beautiful. The pool wasn’t quite ready but that didn’t matter (repairs due to the hurricane) the ocean was enough. Our son rented a fishing pole from Hubbards Marina and had the best time fishing off the shore while our other kids swam. We would go back and stay at the same place again. The beach was not crazy busy. Early mornings and late evenings were so peaceful.

Beautiful and spacious condo centrally located
Alexandra’s place was perfect—clean, cozy, and exactly as described. The location was great. Highly recommend staying here!

Marvelous apartment near Disney first floor
My family of 4 really enjoyed our stay at this condo. It was very clean, quiet and beautiful surroundings. The property is well maintained and very secure, allowing my family to rest comfortably. Anderson provided great communication before I arrived, he was welcoming upon arrival and promptly responsive throughout the entire trip. I would highly recommend this place.
Your guide to Pine Island
All About Pine Island
Despite being the largest island off Florida’s Southwestern Gulf Coast, Pine Island has an Old Florida feel, with small villages and miles of farmland, mangroves, palm trees, and tropical fruit groves. Its secluded, small-town atmosphere is unlike the high-rise buildings and commercial businesses in the region’s more popular tourist destinations. You can spend a day or two exploring the 17-mile island’s boutiques and small waterfront restaurants, many of which feature clam and crab chowders and freshly caught seafood.
Although lacking beaches, Pine Island provides some of the best fishing in Florida. On the Matlacha Pass Bridge, which connects the island to the mainland, you’ll often see visitors reeling in redfish, snook, grouper, or mackerel. Kayaking and canoeing are popular ways to experience the waters, and nature trails scattered around the island allow visitors to explore the land and local wildlife.
The best time to stay in a vacation rental in Pine Island
The island’s subtropical climate provides mild, dry winters and hot, wet summers. Visitors seeking rentals in Pine Island, Florida often find that October through May may offer the best weather for fishing. These months generally see clear skies, comfortable temperatures, and minimal rainfall. That half of the year is when many of the region’s major events occur. A festival held in nearby Cape Coral every January is one of the most significant art shows in Southwest Florida, with over 300 artists and numerous culinary options. In March, a food festival features delicacies from more than 20 Cape Coral restaurants.
The island experiences the most rainfall June through September, but it doesn’t stop singer-songwriters from all over from flocking to Fort Meyers and Captiva Island for a major music extravaganza every September.
Top things to do in Pine Island
Randell Research Center
The Randell Research Center teaches visitors about Southwest Florida’s ecology, archaeology, and history through its museum, heritage trail, and 100-acre shellmound site. The Calusa Heritage Trail, well marked with interpretive signs, winds through nearly one mile of the mounds and canals of the Pineland archaeological site.
Museum of the Islands
This small museum features a look into the island’s rich history, with an extensive collection of vintage household artifacts, tools, generations of dolls, and newspaper articles. In addition to more than 1,700 shells, the nature collection features exhibits of the island’s plants and animals.
Cayo Costa State Park
While Pine Island is not known for its luxurious beaches, the barrier island of Cayo Costa, which is only accessible via boat, features nine miles of beautiful white-sand beaches and six miles of hiking and biking trails. During the 50-minute boat ride from Pine Island, you may even spot manatees and dolphins. Once you arrive, you can fish, snorkel, or watch for snowy plovers, tricolored herons, and other coastal birdlife.
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- Dunedin Beach
- Weeki Wachee Springs
- Sunset Beach
- Busch Gardens Tampa Bay
- Amalie Arena
- Raymond James Stadium
- Howard Park Beach
- Clearwater Beach
- Rainbow Springs State Park
- Tampa Theatre
- Curtis Hixon Waterfront Park
- ZooTampa at Lowry Park
- Plantation Inn and Golf Resort
- Splash Harbour Water Park
- Adventure Island
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- Tampa Palms Golf & Country Club
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