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Pine Island vacation rentals

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Popular amenities for Pine Island vacation rentals

Other great vacation rentals in Pine Island

Guest favorite

Home in Brooksville

4.98 out of 5 average rating, 134 reviews

Off the Beaten Path

Nov 28 – Dec 5

G$29,393 GYD per night
Guest favorite

Home in Spring Hill

4.89 out of 5 average rating, 179 reviews

"Ruf'n It" On The River w/kayaks

Nov 29 – Dec 6

G$32,809 GYD per night
Guest favorite

Home in Weeki Wachee

4.89 out of 5 average rating, 190 reviews

Angie's Acre

Dec 11 – 18

G$22,868 GYD per night
Guest favorite

Home in Spring Hill

4.92 out of 5 average rating, 132 reviews

Newly remodeled Weeki Wachee river retreat!

Aug 5 – 12

G$30,409 GYD per night
Guest favorite

Home in Inglis

4.93 out of 5 average rating, 222 reviews

Yellow bird

Sep 19 – 26

G$12,999 GYD per night
Guest favorite

Home in Hernando Beach

4.94 out of 5 average rating, 190 reviews

Sunset View | Waterfront | 4 Kayaks | Weeki Wachee

Oct 31 – Nov 7

G$55,585 GYD per night
Guest favorite

Home in Weeki Wachee Gardens

4.95 out of 5 average rating, 130 reviews

Bigfoot's Bungalow: Enjoy Clear Main River Waters

Apr 19 – 26

G$131,762 GYD per night
Guest favorite

Home in Weeki Wachee

4.97 out of 5 average rating, 118 reviews

Wasted Time on the Weeki Wachee - Kayak & Manatees

Sep 12 – 19

G$40,197 GYD per night

Pine Island cottage rentals

Guest favorite

Cottage in Brooksville

4.94 out of 5 average rating, 419 reviews

The Shebeen on Irish Acres, A Country get away ...

Jun 25 – Jul 2

G$20,279 GYD per night
Guest favorite

Cottage in Homosassa Springs

4.97 out of 5 average rating, 108 reviews

Tranquil Waterfront Cottage

Mar 5 – 12

G$27,048 GYD per night
Superhost

Cottage in Hudson

4.84 out of 5 average rating, 125 reviews

My Happy Place!

Aug 31 – Sep 7

G$18,103 GYD per night
Guest favorite

Cottage in Dunnellon

4.94 out of 5 average rating, 163 reviews

The Lakeside River House

Aug 8 – 15

G$25,907 GYD per night
Guest favorite

Cottage in Spring Hill

5.0 out of 5 average rating, 98 reviews

Summer Getaway: Waterfront, Clear Kayak, Fire Pit

Oct 16 – 23

G$58,258 GYD per night
Guest favorite

Cottage in Spring Hill

4.91 out of 5 average rating, 150 reviews

The Aripeka Shack

Oct 6 – 13

G$30,534 GYD per night
Guest favorite

Cottage in Weeki Wachee

4.92 out of 5 average rating, 316 reviews

Kayak Kottage: waterfront, kayaks, bikes, dockage

Jan 8 – 15

G$39,278 GYD per night
Guest favorite

Cottage in Dunnellon

4.96 out of 5 average rating, 162 reviews

Cozy Cottage. Surrounded by nature, not neighbors.

Jun 21 – 28

G$26,525 GYD per night

Pine Island condo rentals

Guest favorite

Condo in Crystal River

4.95 out of 5 average rating, 116 reviews

Retreat, waterfront condo/boat slip Crystal River

Jan 21 – 28

G$31,023 GYD per night
Superhost

Condo in Crystal River

4.81 out of 5 average rating, 118 reviews

Crystal River Bungalow with boat slip

Nov 10 – 17

G$28,297 GYD per night
Guest favorite

Condo in Redington Beach

4.86 out of 5 average rating, 313 reviews

Royal Orleans and Redington Beach ( Studio )

Apr 1 – 8

G$19,534 GYD per night
Guest favorite

Condo in Tierra Verde

4.96 out of 5 average rating, 236 reviews

Natural Beauty on Tierra Verde, Waterfront Condo

Jan 27 – Feb 3

G$28,511 GYD per night
Guest favorite

Condo in Redington Beach

4.94 out of 5 average rating, 356 reviews

Beach Condo, Heated Pool, 2 Minute Walk to Ocean

Aug 1 – 8

G$19,729 GYD per night
Guest favorite

Condo in Tampa

4.94 out of 5 average rating, 145 reviews

Lovely Waterview Condo/ heated pool

Oct 31 – Nov 7

G$33,304 GYD per night
Guest favorite

Condo in Redington Beach

4.97 out of 5 average rating, 457 reviews

AmazingBeachCondo/NoCleaningFee/AwesomeAmenities

Apr 23 – 30

G$29,512 GYD per night
Guest favorite

Condo in St. Petersburg

4.97 out of 5 average rating, 143 reviews

Sea La Vie- Studio by the bay!

Jan 6 – 13

G$27,563 GYD per night

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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