Holiday rentals in Fort De Soto

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.

Boutique Stay Near the Bay | Walk to Downtown.

Feel both transported and perfectly at home. The Barefoot House is your serene escape in the heart of Historic Old Northeast — where charm, comfort, and culture meet. Tucked away in a quiet alley, this thoughtfully designed retreat is just blocks from St. Pete’s stunning waterfront parks and a 5-minute stroll to downtown’s vibrant mix of restaurants, cafés, bars, museums, and art galleries. Guests love our blend of calming details & walkable access to everything St. Pete has to offer.

The Lady Fish by Duncan Real Estate

Nestled on the far North end of Anna Maria Island, with the beach cottage is just around the corner, The Lady Fish is a three-bedroom, two-bathroom vacation home. Guests will enjoy a full gourmet kitchen, perfect for cooking up your catch of the day! The living area is spacious, with plenty of seating for family and friends to take in a movie on the flat panel HDTV. 3 bedrooms offer comfortable sleeping for up to 6 guests. All have TVs. Step outside and enjoy a fantastic outdoor living.

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! 🤍

Lux Spa Retreat•Pool•Hot Tub•Sauna•10 min to Beach

You asked, we delivered. Inspired by our Top 1% listing and consistent 5⭐ stays at “The Tiny Oasis”, Haus De Noir is a moody, boutique 3BR/3BA retreat with Plunge Pool, Hot Tub, Sauna, Outdoor Cinema and More! Slip into the Midnight Kafana, your own after-hours Hideaway Bar with Karaoke, Lights, and Late-Night energy. Fully stocked with everything you need and then some! Family-Owned and Managed! We don’t just host we LOVE what we do! Just 10 mins to Indian Rocks & Madeira Beach🏝️.

Your Island Escape! • Discounted Summer Rates

Paradise found! Escape to your private island oasis in beautiful Tierra Verde. 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 starts here—book today!

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.

GulfPort Paradise, Bali-like Oasis with Pool

The perfect vacation spot. If you’re looking for a quiet, comfortable, boho-modern house, this is the place for you. Perfect for guests that want to experience living like a Gulfport local with chill vibes. The location couldn't be better for exploring everything that the area has to offer. Nestled in the adorable town of Gulfport, the property is just a 1 block walk from the Marina and waterfront of Boca Ciega bay.

★Right on the beach ★ Relax and Enjoy ♥ Sunsets!

An unforgettable experience awaits you at this getaway apartment right on the white sand beaches of Anna Maria Island. Wake up every morning to the best views of the turquoise waves of the gulf and spend your days enjoying the warm waters, filling your social media with dolphin pictures and dramatic sunsets.

Cozy AF Medusa the Bus-Lux

Welcome to the Cozy AF Medusa: The Bus Lux! This one-of-a-kind school bus has been transformed into a luxurious tiny house, handcrafted with custom 3D-printed designs and Medusa-inspired decor. Every corner has been thoughtfully designed to tell a story, making your stay as immersive as it is unforgettable.

Boat Dock + Kayaks + Dolphins + Beaches + Hot tub!

✨Welcome to Retro Tides! 🌊 ✨A newly renovated waterfront retreat near Anna Maria Island Gulf Beaches! Observe Dolphins from your Private Dock! Relax in the Tiki Hut + Hot Tub! Take the Kayaks for a spin! This getaway is made for boating, fishing, beaching, and relaxing in true Florida style! 🌴

10 min AMI | 15 min IMG | Heated Pool

Escape to paradise in this beautifully designed 2-bedroom, 2-bathroom bungalow, located in the heart of sunny Bradenton just 10 min to Anna Maria Island. This chic and tranquil retreat boasts modern comforts and coastal charm, offering the perfect getaway for relaxation and rejuvenation.