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.

Be an AMI

This stylish and light home offers single-level private accommodations. The recently updated interior and private backyard oasis with plunge pool offers the perfect space for a truly relaxing and enjoyable vacation. Inside, the stylish and comfy space has room for everyone to spread out and relax while enjoying the two flat screen TVs. No expense was spared in designing and furnishing this home. The sleeper sofa pulls out to a memory foam queen bed, meaning the cottage can comfortably sleep 4.

Tampa Luxe Waterfront Private Pool, Hot Tub & More

Welcome to the first and only Airbnb Luxe property in Tampa and St. Pete—where every detail is curated for your comfort. This professionally designed waterfront home with direct Tampa Bay access features a private pool, hot tub, dock, chef’s kitchen, fast Wi-Fi, electric scooters, Weber Grill, fishing & beach gear for your adventures & more. Perfect for families or groups seeking relaxation and adventure. Ask us about private chef services and curated local experiences to elevate your stay.

Waterfront/ Sunsets/ Heated Pool/ Tiki Bar/ Dock

Welcome to The Tiki Retreat, Your Waterfront Oasis on Boca Ciega Bay!
Step into a bright, coastal 3 bedroom home where relaxing waterfront living meets vibrant tropical vibes. Enjoy stunning views, a private dock, a heated salt water pool, and your private tiki bar all set against the backdrop of beautiful Boca Ciega Bay, home to dolphins, manatees, and an array of wildlife. This spot has everything you need for an unforgettable stay. Feel free to bring your family pet (with pre-approval)

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! 🤍

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!

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.

Tiny Tulum | Tropical Oasis in Tampa’s Heart!

Welcome to Our Romantic Tulum-Inspired Retreat! Escape to a tropical paradise at our enchanting Tulum-inspired oasis, designed with romance and relaxation in mind. Nestled in a serene neighborhood, our beautifully decorated retreat offers the perfect blend of luxury, comfort, and bohemian charm, creating an idyllic getaway for couples seeking a memorable experience. Why book a generic Airbnb when you can book a hand crafted Tropical Paradise?

Oceanfront Condo | Rooftop Terrace | Arcades |

Picture this: you step onto the rooftop as the Gulf stretches out in front of you — golden hour, warm breeze, a putting green underfoot and nowhere else you'd rather be. Back inside, the kids are deep into NBA Jam while the waves crash just beyond the balcony. Hello Sunshine is a direct oceanfront condo in the heart of Indian Shores, designed like a magazine spread and stocked for the kind of trip people talk about long after they've unpacked.

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.

Black Pearl! NEW! Block and half to Beach!

Black Pearl is a brand-new luxury 4-bedroom, 4-bath home just a block and a half from the beaches of Holmes Beach. This modern coastal retreat features a rooftop deck with gorgeous views, a private pool and spa, BBQ grill, ping pong table, and corn hole. Each bedroom offers a queen bed and ensuite bath, making it perfect for families or friends seeking upscale comfort and walkable beach access on Anna Maria Island. 🏖️✨

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.