Holiday rentals in Shell Key

Private Island Old FL Waterfront Heaven on Earth

Discover the hidden secret of "Terra Ceia Island" (Heaven on Earth.) This 3 bed / 2 bath completely remodeled and charming A frame home offers breath taking sunrises from the bayfront private dock. Imagine enjoying your coffee in adirondack chairs while the sun rises over the Tilette Bayou. Enjoy bike rides through the old Florida country side (Bikes included). And rent a boat and cruise the pristine waterways around the keys. This home has everything you need for relaxation, peace, and fun.

The Jungalow SOHO - Pool/Hot Tub

The Jungalow is the ultimate urban oasis. Enjoy the luxuries of the home or venture out to local attractions like the iconic Bayshore Boulevard, Historic Hyde Park, SOHO, Downtown and more. This home was designed with comfort and convenience in mind. Fully equipped with a smart tv, high-speed WIFI, pool and hot tub - this place is paradise. Central to the action - walk to unique rooftop bars, restaurants and shops or Uber to local attractions like Water Street, Amalie Arena, and the Riverwalk.

INCREDIBLE SUNSET BEACH OCEANFRONT TOP FLOOR CONDO

"This is by far the best Airbnb I have stayed at, and I have stayed at quite a few! This place matches the listing and feels just like home. Extremely impressed!" This direct-facing oceanfront condo has a million-dollar view with a panoramic view of the ocean. The secluded private balcony faces oceanfront, revealing the beach and the Gulf of Mexico, also the intercoastal waterway. Breathtaking views from all vantage points for watching the incredible sunsets and dolphins playing in the water.

Pass-a-Grille Historic Cottage Unit 2

PASS-A-GRILLE HISTORIC COTTAGE UNIT 2 A fully renovated historic beach cottage located in beautiful Pass a Grille, Florida. Steps from the Gulf of Mexico and Boca Ciega Bay. This is a duplex; Unit 2 - 2 bedroom/1 bath. Household linens, towels, cookware & dishes provided. Appliances include; dishwasher, washer/dryer, flat screen TVs and wi-fi. Vintage-style tiled bathroom and shower. High end window shades on all windows. Front and back patio area w/ BBQ grill. Private parking for 2 vehicles.

Charming 2BR Condo Near Ft. De Soto

Come enjoy your next vacation, holiday, or winter escape in Tierra Verde, Florida! Watch the sun rise over Boca Ciega bay from the balcony of this beautiful, updated first floor condo. This 2 bedroom/2 full bath unit has been thoughtfully designed and furnished with everything you need to enjoy an stress-free get-a-way that feels like home. This rental has an official Certificate of Use through Pinellas County as a Short Term Rental as well as a rental license through the state of Florida.

Beachfront in Pass-A-Grille w/ 2 bikes

Enjoy an intimate and relaxing stay on the best stretch of the St. Pete Beach of Pass-a-Grille. Walk out your door to the white sand towards the famous Don Cesar or dine on your deck facing the water. Free parking, 2 bikes, SUP board, towels, umbrella, beach chairs, & cooler! We are allowed 3 rentals under 28 yearly. Please inquire to see if you are one of the lucky guests to come. We love long term guests but understand not everyone can do this and simply need a little escape! 🤍

Tropical Island Oasis • Heated Pool • Top Beach

Escape to this newly renovated luxury 4-bedroom, 3-bath home with a private heated pool on exclusive Tierra Verde, minutes from St. Pete Beach, Pass-a-Grille Beach, Fort De Soto Park, and downtown St. Petersburg. Perfect for families, boating, fishing, kayaking, biking, and beach vacations. Relax by the pool, BBQ, dine outdoors, or gather around the fire pit after exploring award-winning Gulf beaches, waterfront restaurants, marinas, shopping, museums, and vibrant nightlife.

Waterfront Condo w/ heated pool- near Fort Desoto

100+ raving reviews! This waterfront condo features a private balcony nestled next to the mangroves and shoreline with breathtaking water views. There is a full kitchen, king bed, a queen memory foam pullout sofa all waiting for you to enjoy. The resort like complex is located in the well desired Tierra Verde and features a waterfront heated pool and hot tub, observation pier, boat dock, and more! Only a short drive from Fort Desoto, Pass-A-Grille, and St. Pete Beach.

Private place in waterfront home

Take it easy at this unique and tranquil getaway fully equipped with everything you would need! With brand new marble flooring, granite countertops and fresh paint, you will never want to leave. Your getaway is attached to a multimillion dollar waterfront home in one of the most beautiful neighborhoods in the area. Enjoy a peaceful walk in the neighborhood, a kayak ride or a leisurely bike ride while visiting this gem! Only a few steps from the beaches of Fort Desoto.

Island Escape • Pool • Beach • Now Booking Winter!

Your island escape in Tierra Verde awaits! This spacious 1BR/1BA condo with a sleeper sofa comfortably sleeps up to 4—ideal for couples, small families, or friends. Enjoy resort-style amenities, water views, and a relaxing coastal vibe. Just minutes from Fort De Soto and St. Pete Beach (both ranked Top 5 Beaches by TripAdvisor) and only 15 minutes from the energy and culture of downtown St. Pete. Your perfect getaway with an world-class Host starts here—book today!

Waterfront Stylish condo stunning Tampa Bay views

Stunning Bayfront 2/2 Condo Step into a beautifully remodeled, modern 2/2 condo with bayfront views. Enjoy a beautifully remodeled, open-concept space with a fully equipped kitchen, in-unit laundry, modern bathrooms, and a private balcony perfect for morning coffee or sunsets. Community amenities includes: heated pool fitness center tennis & pickleball courts kayak launch BBQ grills. Note: One flight of stairs required. No Elevators.

Luxury Paradise in Pass-a-Grille

Nestled just one block from the powdery white sands of prestigious Pass-a-Grille Beach and 6 blocks from historic 8th Ave, this coastal retreat captures the charm of old Florida with the comfort of modern design. Vaulted wood ceilings, airy open living spaces, and coastal décor create a relaxed yet refined ambiance. Enjoy Wi-Fi, parking, and all your beach essentials for the perfect Gulf Coast escape.