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Pine Island vacation rentals

Book unique homes, vacation rentals, and more on Airbnb

Top-rated vacation rentals in Pine Island

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

Superhost

Home in Weeki Wachee

4.86 out of 5 average rating, 129 reviews

Beach 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

ﺩ.ﺇ1,008 per night
Guest favorite

Home in Spring Hill

4.93 out of 5 average rating, 159 reviews

Weeki 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

ﺩ.ﺇ739 per night
Guest favorite

Home in Brooksville

4.98 out of 5 average rating, 131 reviews

Off 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

ﺩ.ﺇ518 per night

Popular amenities for Pine Island vacation rentals

Pine Island house rentals

Guest favorite

Home in Hernando Beach

4.85 out of 5 average rating, 128 reviews

Seascape - WHOLE HOUSE 360 water views, pool, gulf

Oct 13 – 20

ﺩ.ﺇ1,651 per night
Guest favorite

Home in Spring Hill

4.92 out of 5 average rating, 128 reviews

Newly remodeled Weeki Wachee river retreat!

Jun 12 – 19

ﺩ.ﺇ564 per night
Guest favorite

Home in Spring Hill

4.98 out of 5 average rating, 122 reviews

Landing at Weeki River Retreat -Kayaks included

Feb 8 – 15

ﺩ.ﺇ1,478 per night
Guest favorite

Home in Spring Hill

4.89 out of 5 average rating, 175 reviews

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

Aug 8 – 15

ﺩ.ﺇ617 per night
Guest favorite

Home in Spring Hill

4.95 out of 5 average rating, 117 reviews

Little Bohemia!Springs/Gulf access! Kayaks & dock!

Sep 4 – 11

ﺩ.ﺇ619 per night
Guest favorite

Home in Weeki Wachee

4.89 out of 5 average rating, 188 reviews

Angie's Acre

Apr 29 – May 6

ﺩ.ﺇ404 per night
Guest favorite

Home in Inverness

4.96 out of 5 average rating, 190 reviews

Inverness Home with a View

Aug 2 – 9

ﺩ.ﺇ376 per night
Guest favorite

Home in Spring Hill

4.91 out of 5 average rating, 244 reviews

The Chubby Mermaid (Weeki Wachee)

Mar 5 – 12

ﺩ.ﺇ990 per night
Guest favorite

Home in Hernando Beach

4.94 out of 5 average rating, 185 reviews

Sunset View | Waterfront | 4 Kayaks | Weeki Wachee

Aug 30 – Sep 6

ﺩ.ﺇ1,516 per night
Guest favorite

Home in Weeki Wachee Gardens

4.95 out of 5 average rating, 128 reviews

Bigfoot's Bungalow: Enjoy Clear Main River Waters

Oct 13 – 20

ﺩ.ﺇ1,766 per night
Guest favorite

Home in Port Richey

4.99 out of 5 average rating, 184 reviews

Heated & Screened in Pool-All Essentials Provided

Sep 20 – 27

ﺩ.ﺇ490 per night
Guest favorite

Home in Lady Lake

4.97 out of 5 average rating, 266 reviews

Cozy Lady Lake Guest House

Jul 27 – Aug 3

ﺩ.ﺇ334 per night

Pine Island condo rentals

Guest favorite

Condo in Crystal River

4.99 out of 5 average rating, 101 reviews

Waterfront Condo in Sawgrass Landing

Oct 19 – 26

ﺩ.ﺇ466 per night
Guest favorite

Condo in Crystal River

4.95 out of 5 average rating, 111 reviews

Retreat, waterfront condo/boat slip Crystal River

Feb 3 – 10

ﺩ.ﺇ546 per night
Superhost

Condo in Crystal River

4.8 out of 5 average rating, 110 reviews

Crystal River Bungalow with boat slip

Nov 1 – 8

ﺩ.ﺇ509 per night
Guest favorite

Condo in Redington Beach

4.97 out of 5 average rating, 455 reviews

AmazingBeachCondo/NoCleaningFee/AwesomeAmenities

Nov 9 – 16

ﺩ.ﺇ396 per night
Guest favorite

Condo in Redington Beach

4.91 out of 5 average rating, 107 reviews

Royal Orleans and Redington Beach ( Studio 203 )

Dec 8 – 15

ﺩ.ﺇ344 per night
Guest favorite

Condo in St. Pete Beach

4.92 out of 5 average rating, 200 reviews

Sunset Beach Condo in Treasure Island

Sep 13 – 20

ﺩ.ﺇ470 per night
Guest favorite

Condo in Redington Beach

4.9 out of 5 average rating, 144 reviews

2min walk to the beach/pool, BBQ/great area, RO110

Aug 26 – Sep 2

ﺩ.ﺇ422 per night
Guest favorite

Condo in Indian Shores

4.96 out of 5 average rating, 142 reviews

1 BR direct beachfront! Now available May 22-27!

Oct 30 – Nov 6

ﺩ.ﺇ576 per night
Guest favorite

Condo in Indian Rocks Beach

4.79 out of 5 average rating, 223 reviews

Waterfront Condo w/ Boat dock, 2 min walk to beach

Mar 20 – 27

ﺩ.ﺇ523 per night
Superhost

Condo in Saint Petersburg

4.86 out of 5 average rating, 400 reviews

Waterfront condo on top floor @ Boca Ciega Resort

Nov 3 – 10

ﺩ.ﺇ478 per night
Guest favorite

Condo in Largo

4.89 out of 5 average rating, 179 reviews

Modern and Cozy Condo 6 Minutes from the Beach !

Sep 19 – 26

ﺩ.ﺇ394 per night
Guest favorite

Condo in Tampa

4.96 out of 5 average rating, 129 reviews

Waterfront condo with sunset views of Tampa Bay.

Aug 25 – Sep 1

ﺩ.ﺇ559 per night

Pine Island cottage rentals

Guest favorite

Cottage in Weeki Wachee

4.92 out of 5 average rating, 313 reviews

Kayak Kottage: waterfront, kayaks, bikes, dockage

Jun 21 – 28

ﺩ.ﺇ652 per night
Guest favorite

Cottage in Crystal River

4.97 out of 5 average rating, 295 reviews

1BR~Near Water + Heart of Cr. River | Manatee-Scallop-Golf-Fish-Boat-Beach-Food-Fun

Mar 27 – Apr 3

ﺩ.ﺇ361 per night
Guest favorite

Cottage in Homosassa Springs

4.97 out of 5 average rating, 107 reviews

Tranquil Waterfront Cottage

Oct 4 – 11

ﺩ.ﺇ476 per night
Guest favorite

Cottage in Floral City

4.93 out of 5 average rating, 181 reviews

Waterfront Cottage 2BR 1B

Jul 24 – 31

ﺩ.ﺇ367 per night
Guest favorite

Cottage in Hernando

4.91 out of 5 average rating, 165 reviews

The Hernando Lake House

Dec 22 – 29

ﺩ.ﺇ336 per night
Guest favorite

Cottage in Spring Hill

4.91 out of 5 average rating, 146 reviews

The Aripeka Shack

Sep 3 – 10

ﺩ.ﺇ532 per night
Guest favorite

Cottage in Tavares

4.97 out of 5 average rating, 204 reviews

Lakeside Cottage on Lake Dora

Nov 15 – 22

ﺩ.ﺇ519 per night
Superhost

Cottage in Hudson

4.84 out of 5 average rating, 125 reviews

My Happy Place!

Jun 1 – 8

ﺩ.ﺇ319 per night
Guest favorite

Cottage in Dunnellon

4.99 out of 5 average rating, 225 reviews

JoMo Retreat on the Withlacoochee River!

Dec 9 – 16

ﺩ.ﺇ470 per night
Guest favorite

Cottage in Weeki Wachee

4.84 out of 5 average rating, 150 reviews

Relax Canalside at our Cottage, fast 200mbps wifi

Nov 16 – 23

ﺩ.ﺇ679 per night
Guest favorite

Cottage in Spring Hill

4.9 out of 5 average rating, 110 reviews

Weeki Wachee Barefoot Cottage, Waterfront, Kayak’s

Apr 18 – 25

ﺩ.ﺇ787 per night
Guest favorite

Cottage in Indian Rocks Beach

4.93 out of 5 average rating, 175 reviews

Kooky Coconut Cottage, Indian Rocks Beach

Dec 13 – 20

ﺩ.ﺇ653 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

  1. Airbnb
  2. United States
  3. Florida
  4. Hernando County
  5. Pine Island