Holiday rentals in St. Petersburg

Cozy Guesthouse Near Downtown (Non-Toxic)

Come relax in this calm, newly renovated guest suite. Clean, natural, & chemical free - diffusers and oils available on site. Amenities like central a/c, laundry, private patio, full kitchen, Netflix & Hulu. A short 5 minute drive from downtown - near tons of local restaurants, entertainment, and beaches. St. Pete loves the local vibe, be sure to check out our visitors guide for suggestions on spots to see while you’re here. It doesn’t get any better than St Pete! Book your stay with us today!

Apartment in St. Petersburg

Upstairs apt. Great location less than 10 min to busy downtown St. Petersburg, Spa Beach and the St. Petersburg Pier. Walk to major restaurants, Starbucks, & Sunken Gardens. Less than 30 min. to the white sand island beaches & Tampa Airport. Large patio with gas grill. Separate kitchen. Encl. sitting porch. Queen bed, washer and dryer on premises. Beach chairs and towels. Lots of linens & kitchen supplies for long or short-term stay. Clean and comfortable. Owner on premises. No Smoking No pets.

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.

The Driftwood - Pet Friendly

Welcome to The Driftwood's nautical retreat. This cozy 2-bedroom home is a haven of maritime-inspired style, offering a unique and refreshing escape for your stay. Unwind in your private yard with a fire or dinner at the outdoor dining area. Have your pet staying with you? They are welcome here! This beautiful diverse neighborhood is one mile away from Gulfport's beach blvd. where you can shop, dine, or stroll the beach. 6 miles away will take you to the famous St Pete Beach or St Pete Pier.

2x King w/en-Suites walkable Downtown Pet Friendly

Welcome to The Banyan Micro Resort. Experience historic St. Pete. This spacious 2-bed, 2-bath downstairs apartment in the Banyan House. Perfect for couples, families, or business travelers, this stylish retreat features two oversized king suites and a fully equipped kitchen. Located in the vibrant Uptown neighborhood, you're just minutes from the Vinoy waterfront, Dalí Museum, and trendy dining. Enjoy modern comforts in a charming, historic setting, comfortably accommodating up to 4 guests.

Stylish & Eclectic Modern 2/2 Apt - WeAreGrateful

2 Bedroom 2 Baths Eclectic Modern Apartment Our apartment 'GRATEFUL' is a combination of pleasing colors and a delicate attention to detail in every corner that will let you experience the magic of an eclectic space in the heart of St Petersburg. With the beautiful sand beaches under 5 minutes away, you can feel the breeze as soon as you step outside. You also can try St Petersburg’s diverse restaurant scene and visit the museums displaying art permanent collections and traveling exhibits.

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.

Centrally Located Cozy 1-bed Private Cottage!

This adorable cottage is close to great views, art, culture, restaurants, dining, the beach, and family-friendly activities! You’ll love this private cottage because of the location, the ambiance, and the outdoor space. This cozy cottage is good for couples, solo adventurers, business travelers, and anyone needing a cozy place to stay! Parking is just steps away from the cottage with a private entrance. BBQ is available, new hot tub, and an outdoor gas fireplace for a relaxing evening!

The Flamingo House

Find your balance at the Flamingo House. Fully renovated (2022) house located in a safe and quiet neighborhood just minutes to beaches, Pinellas Trail (75 mile paved walk and bike path), shopping, restaurants. The house has 2 bedrooms and 2 bathrooms (master has a shower spa and other has a clawfoot tub), a fully equipped kitchen, large living room with HD TV, Wi-Fi , front porch, and back yard to relax and enjoy. Open dates book quickly. Don’t miss out!

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.

Waterfront, Pool & Dock | Bayfront Oasis

Wake up to Tampa Bay views at this private waterfront escape. This home features a sparkling pool, private dock with boat lift, and postcard views of downtown St. Pete in the distance. Perfect for sunrise coffee, sunset swims, and laid-back coastal living—just minutes from downtown St. Petersburg’s dining, nightlife, and beaches. Guest must be 25 years or older to stay/book.

Oak Tree House

Make yourself at home away from home. Bring your family to this great place and enjoy the evenings in our beautiful patio deck and relax in the Jacuzzi. Now with a brand new outdoor shower. Located Just 2 miles away from Treasure Island beach and close to bars, restaurant’s, world class sporting events, craft beer, art galleries, local shopping and so much more…