Pine Island vacation rentals

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Popular amenities for Pine Island vacation rentals

Pine Island house rentals

Superhost
Home in Winter Haven
5 out of 5 average rating, 4 reviews

Attached Beautiful 2 Bedroom/2 Bathroom Home.

AlbertRating, 5 stars1 month ago
Horace’s place was exceptional both inside and outside! Unfortunately I cannot say the same for all the similar places in this neighbor hood. But since I did not have access to the association bylaws, I cannot make a good judgement that is required of all places. Whatever the requirements, Horace exceeded them. I have stayed in many Holiday Inns in my lifetime. His attention to details and cleanliness is exceptional if compared to the HOLIDAY INN’S. If I return to Winter Haven in the future. I definitely want to stay at this place!
Guest favorite
Home in Sumter County
4.95 out of 5 average rating, 19 reviews

New 2023 3 bedroom home

MicheleneRating, 5 stars1 week ago
Great Stay – Highly Recommend! I had a wonderful stay at Karen’s place. The home was exactly as described—clean, comfortable, and well-equipped with everything I needed. The location was perfect for me sightseeing, work, relaxation, etc.], and check-in was smooth and easy. karen was very responsive and helpful throughout my stay. I would definitely book again if I’m in the area! You will not be disappointed. Great Place.
Superhost
Home in Inverness
4.88 out of 5 average rating, 16 reviews

Lakefront 1BR Tiny House w porch

LauraRating, 5 stars9 months ago
Very cute and comfortable house. We enjoyed the farmers market and long bike ride along the Withlacoochee Stste trail nearby. Great restaurants downtown.
Superhost
Home in East Tampa
4.74 out of 5 average rating, 102 reviews

Stylish Seminole Heights House

DesirRating, 5 stars3 months ago
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
Guest favorite
Home in The Villages
4.95 out of 5 average rating, 58 reviews

2 BR Home in an Amazing Location With 4-Seat Cart!

KevinRating, 5 stars5 months ago
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.
Guest favorite
Home in Lady Lake
5 out of 5 average rating, 18 reviews

2B/2B Newly Renovated Home in Silver Lake!

KatieRating, 5 stars3 weeks ago
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!
Guest favorite
Home in Spring Hill
4.85 out of 5 average rating, 20 reviews

Cozy 2-Bedroom Oasis with Pool (NOT heated)

JacobRating, 5 stars1 month ago
I will be definitely coming back! 🤩 #Travel #Adventure #Memories #Trip
Superhost
Home in The Villages
4.86 out of 5 average rating, 119 reviews

Patio Villa, 5 mins from Sumter, FREE Gas Cart!

CherylRating, 5 stars5 months ago
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 condo rentals

Guest favorite
Condo in Clearwater
4.88 out of 5 average rating, 104 reviews

Amazing main floor condo at Avalon

JesusRating, 5 stars4 months ago
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.
Guest favorite
Condo in Indian Rocks Beach
4.96 out of 5 average rating, 112 reviews

Renovated Condo! Across the Street From The Beach

DellaRating, 5 stars3 weeks ago
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.
Guest favorite
Condo in Treasure Island
4.93 out of 5 average rating, 128 reviews

Beachfront w/ Stunning Sunsets in Prime Location.

KellyRating, 5 stars8 months ago
For an older building the unit was well maintained and was right on the beach and close to many restaurants as well as a grocery store.
Superhost
Condo in Madeira Beach
4.91 out of 5 average rating, 121 reviews

Arie Dam 302, Beach Front Condo - 2Bed/2Bath

MikeRating, 5 stars3 days ago
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.
Superhost
Condo in Treasure Island
4.9 out of 5 average rating, 105 reviews

2/2 Newly remodeled Beach Front - Sunset Vistas

TinaRating, 5 stars3 weeks ago
Had a very good time. Condo was how it was described. Check in process was very easy. Just fyi kiddie pool did not seem to be heated, but overall everything worked at great!
Guest favorite
Condo in Indian Shores
4.91 out of 5 average rating, 377 reviews

Indian Shores Gulf Front Rental

Brandon & TiffanyRating, 5 stars1 month ago
We had a fantastic stay at this beachfront condo in Indian Shores! Traveling with our two young children, we really appreciated how easy it was to get to the beach—just steps away, making it perfect for a stress-free family vacation. The condo was clean, comfortable, and had everything we needed for our stay. The hosts were extremely responsive and accommodating, especially when our flight plans changed, which made the trip even smoother. We would absolutely stay here again and highly recommend it to anyone looking for a relaxing beach getaway!
Superhost
Condo in New Tampa
4.8 out of 5 average rating, 114 reviews

Beautiful and spacious condo centrally located

MiguelRating, 5 stars3 days ago
Alexandra’s place was perfect—clean, cozy, and exactly as described. The location was great. Highly recommend staying here!
Top guest favorite
Condo in Clearwater
4.93 out of 5 average rating, 145 reviews

5 *Waterfront Condo,3 Beds,2 Baths, Pool, HOT-TUB.

RobertRating, 5 stars4 days ago
The condo was beautiful. Clean and spacious. Lots of amenities. Close to the public beach, restaurants, bars, and shops. Plus David ordered a perfect week of weather for us! Wonderful.

Pine Island cottage rentals

Guest favorite
Cottage in Eustis
4.96 out of 5 average rating, 107 reviews

Redbird cottage and farm. Equestrian lake cottage

AllenRating, 5 stars2 weeks ago
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.
Guest favorite
Cottage in Ruskin
4.91 out of 5 average rating, 113 reviews

Little Manatee River Cottage

TimRating, 5 stars2 weeks ago
Great location and wonderful place. Super responsive host. I'd love to go back
Top guest favorite
Cottage in Homosassa Springs
4.98 out of 5 average rating, 142 reviews

Tranquil Waterfront Cottage

JoJoRating, 5 stars1 week ago
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!!!
Top guest favorite
Cottage in Tampa
4.97 out of 5 average rating, 195 reviews

Bay Lake Cottage

TonyaRating, 5 stars4 weeks ago
This was our second stay at this cottage and we are already looking forward to booking again! My husband and I appreciate the attention to detail with every aspect of our stay. Kristen is a fantastic host. We didn’t have to bother her during our stay because the cottage is stocked with everything we needed. Another awesome stay.
Top guest favorite
Cottage in Weeki Wachee
4.96 out of 5 average rating, 266 reviews

The Hideaway - Quaint and Peaceful Cottage

DavidRating, 5 stars1 week ago
Very comfortable cottage. I was in Weekie Wachee to do some cave diving. The location is very close to everything I was there for. I can’t say enough good things about Jamie, she had great instructions and an electronic lock programmed to a very easy for me to remember code. The cottage was clean and nicely stocked with basic necessities. Linens and towels were clean as was the whole cottage and grounds. Jamie asked me what type of food I was looking for and recommended 2 places one I went to twice the other I went to and would go back. I’d definitely book again when I’m back in Weekie Wachee.
Guest favorite
Cottage in Homosassa
4.97 out of 5 average rating, 100 reviews

💯 Remodeled Cottage, Animal free property

KevinRating, 5 stars10 months ago
Great little place for our little vacation
Top guest favorite
Cottage in Weeki Wachee
4.95 out of 5 average rating, 194 reviews

Coastal Cottage Getaway

LauraRating, 5 stars2 weeks ago
Maria and Jeff's cottage is exactly how it looks in the pictures! Very peaceful and right on the water. It is small, but very comfortable for two people and beautifully decorated. There was a basket of goodies on the table for our arrival, which was a thoughtful touch. It was great to have the kayaks available for us to use and was a large part of why we chose this place. We took them out every day. Saw manatees twice! Also had a pair of whooping cranes grace our yard one morning! The Bayport restaurant is right down the street and had music and lots of outdoor seating. Anything you could need is close by, but you'd never know it sitting by the water and listening to the peacefulness. We would absolutely recommend Maria and Jeff's place!
Top guest favorite
Cottage in Spring Hill
4.92 out of 5 average rating, 155 reviews

Weeki Wachee Barefoot Cottage, Waterfront, Kayak’s

StefaniRating, 5 stars2 weeks ago
Second time staying here and we will be back again! Best place we have stayed!

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.

Destinations to explore

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