Holiday rentals in St. Petersburg

Historic Old North East Charmer

Be in the heart of it all when you stay at this 2/2 rental in downtown St. Pete.This beautiful 1920's home, completely remodeled in 2021, sits within walking distance to the finest dining, bars, shops and concert venues in downtown. Beaches to parks, galleries, and museums, this location is perfect. Relax on the front porch with views of the St. Pete skyline.Modern amenities include cozy living spaces & outdoor comforts.Very clean, new furniture.Fully equipped kitchen.20 minute drive to beaches

Kenwood Retreat - 1BR carriage house

This newly constructed carriage house was built to embrace the character and charm of the main house, a 1928 craftsman bungalow. Your 2nd floor 1 BR apartment is well appointed with a full chef's kitchen, a living room with a pull-out sofa, and washer/ dryer. Enjoy a morning cup of coffee or a glass of wine in the evening on the large porch. 2 min walk to Grand Central restaurants, coffee shops, boutiques, or grab a bike or scooter for a 5 min ride to Downtown St. Pete or 15 to the beaches.

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.

ST Urban Oasis heated pool

Located in unincorporated St. Pete, you can keep it simple at this peaceful and centrally-located oasis. Want to be near the city and beaches while having your own private backyard sanctuary? This is your place to enjoy it all. This home features two bedrooms, one bathroom, and a private heated pool. The backyard has been filled with beautiful large palms, bamboo, and other zen features to allow you and your family to enjoy a relaxing and easily accessible stay in beautiful St. Pete.

Downtown St. Pete Radiant Retreat

Modern townhome located in the heart of Downtown St. Pete two blocks to Central Ave, walkable to Beach Drive and Vinoy Park. Sleeps 8 (1 King + 3 Queens), 2.5 baths, private garage, fully fenced yard with BBQ, private balcony. Pet-friendly. Built for monthly stays: fast WiFi, workspace, full kitchen, in-unit washer/dryer, 85" HDTV with Fire TV, room-darkening shades, smart-lock entry. Central AC throughout with an added window unit AC to keep the master extra cool while you sleep.

Modern Retreat w/ Patio Near Downtown

🌴 Top-floor condo near Crescent Lake + 5 min to downtown Stay in a bright, stylish 2BR retreat just minutes from downtown St. Pete. Enjoy peaceful lake views from your private patio, with Crescent Lake Park steps away and Beach Drive, dining, and nightlife close by. ✔ King bed + high-end finishes ✔ Private patio with lake views ✔ Fast WiFi + smart TVs ✔ Free parking + pet-friendly Relax in a quiet, elevated space—close to everything, but away from the noise.

Prime Downtown St. Pete 1/1 walk to everything!

Retro coastal charm in the heart of St. Pete! This adorable 1950s apartment blends vintage character with an unbeatable location where Old Northeast meets downtown. Enjoy original terrazzo floors, funky yellow retro bathroom tile, and breezy jalousie windows perfect for catching the bay air just 2 blocks away. Steps from the Vinoy, Beach Drive, the Pier, waterfront parks, restaurants, coffee shops, and everything downtown St. Pete has to offer.

Babe Ruth’s Build Spanish Style Hacienda! 4BR/5BA!

Welcome to the Hacjenda Maryna. Pets Friendly, some restrictions apply. TRAVEL NURSES, OTHER MEDICAL PROFESSIONALS, AND BUSINESS PEOPLE ARE WELCOME TO BOOK EXTENDED STAYS! A beautifully designed Spanish inspired home in the heart of St Petersburg. Conveniently located close to the freeway and St Pete's exciting downtown with fun shops, restaurants, and museums. It's close to the beaches & Tropicana where the Rays play.

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.

The Boho | Walk to Gulfport Beach & Restaurants

Boho inspired cottage in the heart of the Gulfport Waterfront District. Steps away from Gulfport beach, restaurants, and nightlife. Enjoy strolling along Beach Boulevard where you'll find local coffee shops, ice cream parlors, Gulfport brewery, and eclectic shops. Relax in the comfort of your backyard oasis or enjoy some fun in the sun with the best Gulfport has to offer right outside your back door.

Oak Street Hideaway | Old NE, Walk to The Pier

Tucked under oak trees in Historic Old NE — one of St. Pete’s most iconic neighborhoods. Spacious open layout with a huge kitchen island, gas stove, and modern finishes perfect for hosting. Dreamy upstairs den ideal for kids or a home office. Private outdoor escape under a tree off the master. Walk to the Pier, Vinoy Park & Beach Drive restaurants. Downtown St. Pete at your doorstep.

Private guesthouse in Historic Old Northeast

This unique guesthouse is in a great location in Historic Old Northeast. Located 4 blocks from St. Petersburg's beautiful waterfront parks and a short walk to downtown St. Petersburg. The downtown area has a ton to offer including the newly renovated pier, restaurants, shopping, music and museums. Great for singles, couples and business travelers.