Condo holiday rentals in Pine Island

Beach Front at “The Shore”

Welcome to The Shore —a beautifully renovated beachfront retreat in the heart of Madeira Beach. This second-floor 2-bedroom, 2-bath condo offers completely unobstructed Gulf views and the rare feeling of being almost directly on the water. Relax with your morning coffee in the signature blue chairs, watch breathtaking sunsets from the living room, and enjoy easy access to John’s Pass, waterfront dining, shopping, and the best of Gulf Coast beach living, where the shoreline feels just feet away.

Family · Location · Indoor spaces

Spectacular beach to bay views from this resort.

Our condo has spectacular water views from the Bay to the Beach. We have a large one of a kind kitchen that is unique to our resort, with granite counter tops, hardwood cabinets, and all stainless steel appliances. Everything you need to prepare a meal is provided along with basic spices and condiments, Coffee, creamer, and sugar. The master bedroom has a new king size bed and walk in closet with all beach gear also available for your use. We have 2 - 50" flat screen TV's with cable as well.

Value · Location · Pool

Waterfront Condo in Sawgrass Landing

A unique setting surrounded by palm trees and water with a boardwalk to your front door. This quiet location is canal front with views to the Salt River. The Gulf of Mexico is accessible via Crystal River located just across the Salt River from the condo. Wonderful seafood restaurants and activities, such as kayaking, snorkeling, swimming with the manatees, scalloping, biking, golfing, saltwater and freshwater fishing are all available nearby. A public beach is located 4 miles from the condo.

Location · Value · Heating

The Boho in Crystal River with boat slip/pool

Birds, boardwalks and boat slip, included in our unique bohemian inspired condo. Come and relax for a weekend or longer in this exclusive Crystal River complex. Enjoy floor to ceiling views of palm trees and fresh water tides off the deck of this cozy unit. A loft with king bed and private bathroom overlook your deck with electric grill. A boat slip is included (up to 23ft ). Enjoy the pool and lounging area. Ideal for two but allows up to four. Ask about multi unit rentals for large families.

Location · Value · Decor

Amazing views on beachfront

This spacious upper-floor, 3-bedroom condo hotel suite offers views of the Gulf of Mexico from your private balconies. While preparing your morning coffee on the spacious kitchen island, you can see the water of the Gulf of Mexico. Each suite can accommodate 10 people, with 3 bedrooms, 2 of them with a King bed in each bedroom and the third with 2 Queen beds, each of them with their own ensuite bathroom, in total 3 1/2 bathrooms, also a comfortable full-sized sofa bed in the living room.

Value · Location · Comfort

Modern, Luxurious Beach Condo -Steps To The Beach!

Come enjoy your piece of paradise on this luxurious, newly renovated beach condo, just 40 steps from the beach! The condo has two bedrooms with two private baths, and a living space with an extra half bathroom. The recently updated kitchen has new stainless steel appliances, granite countertops, and a spacious breakfast bar. The living room has a 51 inch TV and 2 leather pull-out couches. Free private parking for two cars. Beach chairs, umbrellas, towels and 2 bicycles are included!

Value · Family · Bathroom

Relax in a Newly Renovated Beach Front Paradise

Immerse yourself in the stunning beauty of the Gulf Coast at this hidden gem, perfectly nestled in the charming Indian Shores. This property exudes a coastal ambiance, providing a tranquil sanctuary to bask in the sugar-white sands and sparkling turquoise waters. Beach chairs & towels are thoughtfully provided. All you need to bring is a swimsuit & toothbrush. Exciting updates include new furniture & bedding added in '25 as well as a beautifully renovated walk-in shower in '24.

Location · Family · Check-in

Florida Breeze

If you are looking to stay in a quite and safe place here in the Sunshine estate, this may be the right place for you. This a gated condo with beautiful sunset offer lot of amenities . Kick back relax enjoy a nice cold beverage while watching the sunset and you might see a some dolphins. This location is 28 miles from honeymoon island ,36 miles from clearwater beach and 15 miles from weeki wachee spring. There is also great restaurants nearby and trail walks.

Family · Location · View

Madeira Beach Retreat. Views, Pool, Location!

Welcome to your coastal escape in one of Madeira Beach’s most prestigious beachfront buildings. This luxurious first-floor corner unit is the ideal blend of comfort, style, and location—perfectly positioned to catch the Gulf’s golden sunsets from the privacy of your expansive balcony. Whether you're here for a romantic retreat, a family getaway, or a relaxing escape with friends, every detail of this condo has been designed with your comfort in mind.

Location · Indoor spaces · Pool

2BR | Oceanfront, Backyard Beach, Fully Equipped

Experience luxury coastal living at Indian Shores in this beautifully appointed beachfront retreat at Sunplace. Featuring 2 spacious bedrooms with a king and queen bed, plus a full-size roll-out bed and Pack ’n Play, this fully equipped condo is perfect for families and groups. Enjoy direct beach access, stunning Gulf surroundings, resort-style amenities, and easy access to local dining, shops, and nearby Clearwater Beach.

Location · Nearby · Layout

Private Ocean View Beach Retreat with Balcony

Only steps from the beach, this newly updated and perfectly located beach condo is your luxury getaway. The large bedroom, lofty living area and modern open kitchen, as well as the generous balcony with direct view of the Gulf will make you never want to leave again. This condo is better equipped than your average vacation rental and comes with your private daily sunset spectacle. Continue to read for more...

Location · Family · Hospitality

Breathtaking Waterview & Pool View Condo

Waterfront condo with pool view. The view of the intercoastal is fantastic. Especially beautiful sunsets! Pinellas trail across the street to ride your bike or hike, a beautiful 38 mile trail. Plenty of restaurants nearby and grocery stores. Only 8 min drive to beach. 15 min from downtown St. Pete. Enjoy pool and hot tub overlooking intercoastal or stay indoors and enjoy puzzles and games.

Value · Location · Barbecue