Pine Island vacation rentals
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Top-rated vacation rentals in Pine Island
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Home in Weeki Wachee
4.86 out of 5 average rating, 129 reviewsBeach front House Pine Island, Tampa, Orlando
Private beach house with breathtaking beach & ocean views (+tons of space indoor & out to relax!) You'll have the privacy of the entire home, screened in patio & yard in this updated stilt house. Enjoy memory foam mattresses, stainless steel appliances, luxury linens, beach gear, WiFi, Smart TV's - everything guests need to make your stay on this quaint island a cherished memory. Breathtaking Gulf views from nearly every window of the house! A short walk up the road carries you to the beach.
Feb 12 – 19
Home in Spring Hill
4.93 out of 5 average rating, 159 reviewsWeeki Wachee, Florida Entire House- 2 bed 2 bath
Come and relax in our newly remodeled waterfront cottage. This spacious two bedroom two full bath home sits nestled between beautiful tropical trees on the crystal clear river that leads out to the gulf of mexico. The 20 x 20 master suite consist of a king bed, custom two person rain shower and walk out private balcony. First level has an open floor plan with a fully stocked kitchen ready to entertain family and friends. The garage has 6 kayaks, life jackets, fishing gear, washer and dryer.
Aug 21 – 28
Home in Brooksville
4.98 out of 5 average rating, 131 reviewsOff the Beaten Path
Our home is located on 5 acres in the middle of farms yet we are 10 minutes from shopping and a large variety of restaurants. Tampa International Airport is 50 minutes away so we have the best of both worlds. We enjoy the quiet beauty of the countryside but can be in Tampa for theatre in minutes. Hernando county boasts of some of the best golf courses in the area. We have a walking/biking trail 2 minutes from the house. Two State parks are 10 miles away and are a great way to spend the day.
Feb 24 – Mar 3
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Pine Island vacation rentals
Pine Island house rentals
Home in Hernando Beach
4.85 out of 5 average rating, 128 reviewsSeascape - WHOLE HOUSE 360 water views, pool, gulf
Oct 13 – 20
Home in Spring Hill
4.92 out of 5 average rating, 128 reviewsNewly remodeled Weeki Wachee river retreat!
Jun 12 – 19
Home in Spring Hill
4.98 out of 5 average rating, 122 reviewsLanding at Weeki River Retreat -Kayaks included
Feb 8 – 15
Home in Spring Hill
4.89 out of 5 average rating, 175 reviews"Ruf'n It" On The River w/kayaks
Aug 8 – 15
Home in Spring Hill
4.95 out of 5 average rating, 117 reviewsLittle Bohemia!Springs/Gulf access! Kayaks & dock!
Sep 4 – 11
Home in Weeki Wachee
4.89 out of 5 average rating, 188 reviewsAngie's Acre
Apr 29 – May 6
Home in Inverness
4.96 out of 5 average rating, 190 reviewsInverness Home with a View
Aug 2 – 9
Home in Spring Hill
4.91 out of 5 average rating, 244 reviewsThe Chubby Mermaid (Weeki Wachee)
Mar 5 – 12
Home in Hernando Beach
4.94 out of 5 average rating, 185 reviewsSunset View | Waterfront | 4 Kayaks | Weeki Wachee
Aug 30 – Sep 6
Home in Weeki Wachee Gardens
4.95 out of 5 average rating, 128 reviewsBigfoot's Bungalow: Enjoy Clear Main River Waters
Oct 13 – 20
Home in Port Richey
4.99 out of 5 average rating, 184 reviewsHeated & Screened in Pool-All Essentials Provided
Sep 20 – 27
Home in Lady Lake
4.97 out of 5 average rating, 266 reviewsCozy Lady Lake Guest House
Jul 27 – Aug 3
Pine Island condo rentals
Condo in Crystal River
4.99 out of 5 average rating, 101 reviewsWaterfront Condo in Sawgrass Landing
Oct 19 – 26
Condo in Crystal River
4.95 out of 5 average rating, 111 reviewsRetreat, waterfront condo/boat slip Crystal River
Feb 3 – 10
Condo in Crystal River
4.8 out of 5 average rating, 110 reviewsCrystal River Bungalow with boat slip
Nov 1 – 8
Condo in Redington Beach
4.97 out of 5 average rating, 455 reviewsAmazingBeachCondo/NoCleaningFee/AwesomeAmenities
Nov 9 – 16
Condo in Redington Beach
4.91 out of 5 average rating, 107 reviewsRoyal Orleans and Redington Beach ( Studio 203 )
Dec 8 – 15
Condo in St. Pete Beach
4.92 out of 5 average rating, 200 reviewsSunset Beach Condo in Treasure Island
Sep 13 – 20
Condo in Redington Beach
4.9 out of 5 average rating, 144 reviews2min walk to the beach/pool, BBQ/great area, RO110
Aug 26 – Sep 2
Condo in Indian Shores
4.96 out of 5 average rating, 142 reviews1 BR direct beachfront! Now available May 22-27!
Oct 30 – Nov 6
Condo in Indian Rocks Beach
4.79 out of 5 average rating, 223 reviewsWaterfront Condo w/ Boat dock, 2 min walk to beach
Mar 20 – 27
Condo in Saint Petersburg
4.86 out of 5 average rating, 400 reviewsWaterfront condo on top floor @ Boca Ciega Resort
Nov 3 – 10
Condo in Largo
4.89 out of 5 average rating, 179 reviewsModern and Cozy Condo 6 Minutes from the Beach !
Sep 19 – 26
Condo in Tampa
4.96 out of 5 average rating, 129 reviewsWaterfront condo with sunset views of Tampa Bay.
Aug 25 – Sep 1
Pine Island cottage rentals
Cottage in Weeki Wachee
4.92 out of 5 average rating, 313 reviewsKayak Kottage: waterfront, kayaks, bikes, dockage
Jun 21 – 28
Cottage in Crystal River
4.97 out of 5 average rating, 295 reviews1BR~Near Water + Heart of Cr. River | Manatee-Scallop-Golf-Fish-Boat-Beach-Food-Fun
Mar 27 – Apr 3
Cottage in Homosassa Springs
4.97 out of 5 average rating, 107 reviewsTranquil Waterfront Cottage
Oct 4 – 11
Cottage in Floral City
4.93 out of 5 average rating, 181 reviewsWaterfront Cottage 2BR 1B
Jul 24 – 31
Cottage in Hernando
4.91 out of 5 average rating, 165 reviewsThe Hernando Lake House
Dec 22 – 29
Cottage in Spring Hill
4.91 out of 5 average rating, 146 reviewsThe Aripeka Shack
Sep 3 – 10
Cottage in Tavares
4.97 out of 5 average rating, 204 reviewsLakeside Cottage on Lake Dora
Nov 15 – 22
Cottage in Hudson
4.84 out of 5 average rating, 125 reviewsMy Happy Place!
Jun 1 – 8
Cottage in Dunnellon
4.99 out of 5 average rating, 225 reviewsJoMo Retreat on the Withlacoochee River!
Dec 9 – 16
Cottage in Weeki Wachee
4.84 out of 5 average rating, 150 reviewsRelax Canalside at our Cottage, fast 200mbps wifi
Nov 16 – 23
Cottage in Spring Hill
4.9 out of 5 average rating, 110 reviewsWeeki Wachee Barefoot Cottage, Waterfront, Kayak’s
Apr 18 – 25
Cottage in Indian Rocks Beach
4.93 out of 5 average rating, 175 reviewsKooky Coconut Cottage, Indian Rocks Beach
Dec 13 – 20
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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