Beachfront holiday rental in Gulfport

4.98 out of 5 average rating, 105 reviews

Condo in Madeira Beach

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.

An aerial view captures the waterfront community, highlighting the proximity to the beach and nearby amenities. Serene blue waters of the canal intertwine with the residential buildings, while the expansive shoreline stretches in the background, offering a picturesque setting for relaxation and exploration.

4.98 out of 5 average rating, 160 reviews

Beach, dolphin/manatee sightings, fishing, sunsets

Welcome to the newly remodeled condo in the Heart of Treasure Island. This bright and modern retreat is perfect for relaxing and avoiding the crowds. Perfect location for beach lovers and wildlife watchers alike with waterfront views of the canal from the living room, kitchen and bedroom windows and beautiful sunsets. Just 2 blocks or a 5 minute walk to the beautiful white sandy beach and a few feet from the canal and heated pool. Visit nearby restaurants, John's Pass Boardwalk and live music.

Bungalow in Indian Shores

4.96 out of 5 average rating, 193 reviews

Private Beachfront 2BR BUNGALOW*POOL*PETS ok

DIRECT BEACHFRONT BUNGALOW "MARLIN'S HIDEAWAY." Rare free standing direct beach front house! with private sandy beach backyard! NOT a condo - No crowded elevators, hallways, lobby area, NO faraway parking spaces FEATURES: Great room plan, Sleeps 6, 2 BR + sleeper sofa, all SMART TVs, high speed Wi-Fi. Kitchen is fully equipped. Bathroom is tub/shower with seat. Approx 850 sq ft. Private, fenced deck - PETS ok. BARRETT BEACH BUNGALOWS is a boutique resort ONLY 4 bungalows share heated pool

4.86 out of 5 average rating, 273 reviews

The outdoor pool area, surrounded by palm trees, features a clean, inviting pool with lounge chairs positioned around it. In the background, the beach can be seen, with soft white sand meeting the clear ocean waters.

Condo in St. Pete Beach

Gulf Strand Beach Resort

Modern, spacious condo situated directly on beautiful St Pete Beach with a balcony. Miles of white sand and warm clear water. All year round heated swimming pool and hot tub exclusively for guests. Covered patio and barbeque. Fully equipped kitchen with large fridge freezer, dishwasher, cooker and microwave. Washer and dryer in the apartment. Designated free parking space. Steps from large supermarket and many restaurants. Excellent guest services on site and simple check in and out process.

4.96 out of 5 average rating, 105 reviews

A view from the balcony showcases a sandy beach lined with palm trees and manicured green lawns. The calm blue water reflects clear skies, while a distant shoreline is visible. A bench can be seen on the grass, inviting relaxation.

Condo in Isla del Sol

Isla Sunsets

Enjoy peaceful relaxation and serene sunsets in this top floor condo on the beautiful Isla Del Sol. The large private balcony, which overlooks the private beach and community pool, has plenty of seating options for enjoyment throughout your day in paradise. Inside, a king bed, two twin beds, and a queen size sofa bed offer comfort and versatility. This condo features an updated kitchen, bathrooms, and styling throughout. Only a short walk or bike ride to the Don Cesar or several top beaches!

Condo in Pass-a-Grille Beach

Two beach chairs are placed under a large white umbrella on the pristine white sand. The tranquil blue water of the ocean is visible in the background, complemented by clear skies and palm fronds gently swaying in the breeze.

4.99 out of 5 average rating, 170 reviews

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! 🤍

Superhost

The image shows a view of the beach, with smooth, sandy shores leading to a row of modern condo buildings in the background. The condos are designed with balconies, featuring multiple stories and large windows, under a clear blue sky.

Condo in Indian Shores

4.9 out of 5 average rating, 427 reviews

Indian Shores Gulf Front Rental

Beautiful 2 bed 1 bath luxury condo on the Gulf of Mexico. We are steps from the beach. Unit has partial water view. Beautiful state of the art kitchen and luxurious furnishings. Everything you need for your perfect vacation. Totally non-smoking unit. Come and stay with us. This is a second floor walk up condo. There are 27 steps. May not be suitable for the elderly or small children. Check in 3pm. Check out 10am Our maximum occupancy is 4 people including children.

A tranquil view captures the sandy shoreline meeting the calm waters of the Gulf, with gentle waves lapping at the beach. Lush palm trees are positioned in the foreground, while a small blue trash bin is nestled among the greenery. The sky features soft clouds, hinting at the day's potential.

4.97 out of 5 average rating, 148 reviews

Beach Front Penthouse Riley's Retreat Island Inn

800 sq ft top floor condo with spectacular views of the Gulf of Mexico, Boca Ciega Bay, and the City. Located in the iconic Island Inn Beach Resort; step out of the lobby and onto the sand! Florida sunrises and sunsets are legendary, and you can enjoy both from your private top floor balcony. We offer one of the finest condo's in the building with the unique ability to enjoy North, South, East, and West vistas. This condo is unlike any other unit in the building--a must see!

The exterior of the Ocean Club building is showcased, featuring a modern design with a white façade and large balconies. Palm trees line the front, enhancing the tropical setting. A welcoming entrance is visible, set against a backdrop of a bright sky with soft clouds.

Beachfront Condo in Exclusive Resort

The most stunning views from this brand new condo directly on Treasure Island Beach. This lovely unit is on the 4th, 5th, or 6th floor and provides sweeping views of the ocean. This units has 2 bedrooms and 2 full bathrooms. The inviting open concept living area has one of the best views of the ocean, especially when the retractable sliding doors are opened. The dining table on your private balcony provides a perfect dining area, with the ocean providing a beautiful backdrop.

An open-concept living area features a light-colored, patterned sofa paired with a wooden coffee table. A large flat-screen TV is mounted on the wall, and a serene window nook offers natural light, enhancing the coastal charm of the space.

4.97 out of 5 average rating, 218 reviews

*Shore Thing* Walk to Beach | Intercoastal Views

🏖️ Shore Thing Condo 🏖️ Escape to pure coastal paradise at this chic Treasure Island condo. You are mere footsteps from sugar-sand beaches, refreshing salt air, and unmatched sunsets. Keep an eye on the water as dolphins and manatees drift right by! 🐬🌅 Indoors, unwind in elevated, modern coastal design. From cooking in the upscale kitchen to swimming in the heated pool, our signature service guarantees your peace of mind is the top priority. Book today! ✨🐚

Apartment in Treasure Island

An inviting studio interior is shown with light-coloured walls and a modern kitchenette visible in the background. A doorway leads to a bathroom featuring tropical-themed wallpaper. A small dining table and chair are positioned in front of a cozy seating area with a dark sofa.

4.99 out of 5 average rating, 146 reviews

Popular Beachside Studio w Relaxing Patio & Palms!

The true gem of Treasure Island! Tucked right off of Gulf Blvd this is one of three stylish studio units nestled in a coconut palm-fringed private courtyard with a residential cottage onsite. This cozy spot overlooking a lush tropical garden is just steps from a white sand beach & walking distance to dozens of laid back beach bars, live music & dining. Please note: There’s no guest parking on-site, but paid parking is nearby as well as a frequent public trolley.