Waterfront holiday rentals in Gulfport

The Little Cottage

Are you ready to getaway? Come stay at this beautiful, quaint, beach escape in downtown Gulfport! Located within walking distance to shopping, bars, restaurants, dog park and the Gulfport pier. This artsy Little Cottage is pet friendly and has everything you need to vacation easy. The property boasts breathtaking landscaping and sits directly across from Wood Ibis Park. Less than a 10 minute drive to Treasure Island, Madeira Beach, St. Pete Beach and Downtown St. Pete. Your getaway starts now!

King Bed Studio| Clean & Private |Central Location

Welcome to a thoughtfully designed private studio—efficient and exceptionally clean. If your priority is a comfortable king bed, a well-maintained space, and easy access to both downtown St. Petersburg and the beaches (about a 20-minute drive), this is a reliable choice. This is one of two private studios within a tiny house setup, ideal for solo travelers or couples. Guests also have access to a shared outdoor gazebo with seating, hammocks, greenery, dining space, and a fully equipped kitchen.

Queen Studio | Clean & Private | Central Location

Welcome to our thoughtfully designed private studio—efficient and exceptionally clean. If your priority is a comfortable queen bed, a well-maintained space, and access to downtown St. Petersburg and the beaches (about a 20-minute drive), this is a reliable choice. One of two private studios in a tiny house setup, ideal for solo travelers or couples. The space is compact and designed for comfort. Guests have access to a shared gazebo with seating, hammocks, greenery, dining space, and a kitchen.

Private waterfront balcony, heated pool, hottub

Wake up to waterfront views! Sip morning coffee on 20-ft private balcony overlooking Boca Ciega Bay, watch dolphins, unwind in the heated pool & spa while taking in stunning sunsets. This quiet corner condo offers a serene escape minutes from Madeira Beach, St. Pete, and local attractions, perfect for couples or solo travelers. Highlights: • Direct waterfront views • Heated pool, hot tub • Nearby boat rentals, trails, & Madeira Beach • 5 mins to Gulf beaches + 15 mins to Downtown St. Pete

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.

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.

Waterfront Oasis, Hot Tub, Sauna

Welcome to our beautiful waterfront home nestled between St Pete Beach & Gulfport, FL, where you'll experience the joys of the quintessential Florida lifestyle! Relax in the large outdoor living space, fish off the dock, boat on the pristine waters of the Gulf of Mexico and take in the ocean breeze. ☑ 2 mi to St. Pete Beach, 2.5 mi to Gulfport & 5 mi to John's Pass ☑ On the Intracoastal Waterway w/boat access out to the Gulf of Mexico ☑ Hot tub, Sauna, Outdoor kitchen, bar, dock, boat lift

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.

Waterfront Condo With Pool and Multiple Views!

Enjoy the beach and the bay while staying in this upscale 3rd-floor condo unit just steps away from the beach! This beautiful unit offers 1 king bedroom plus 1 queen sleeper sofa. The 758 sq ft condo features a large waterfront pool with docks, outdoor grills, dining areas, free wifi, beach toys, and a full-size updated kitchen with everything you need for an enjoyable experience. Shops, restaurants, grocery stores, and entertainment are all nearby. Come enjoy paradise on Treasure Island!

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! 🤍

PRICELESS VIEW Boca Ciega Bay Condo 1/1 #209

My place is across the street from Target and many restaurants within walking distance. There is a PSTA Bus stop right at the entrance to the condo property.Uner and Lyft are availablThe Pinellas Trail is across the street. The VA Hospital and Bay Pines Park are biking or walking distance. The closest beach is Madeira Beach 2 miles from the condo. All Utilities, Cable/Internet are included. Parking is free and close to the elevators. Plenty of parking spaces are available also.

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.