Holiday houses in Downtown St. Petersburg

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.

Family · Location · Cleanliness

Mid-century cottage on Coffee Pot Bayou in Old NE

TEXT US REGARDING SHORTER STAYS AND DISCOUNTED SEASONAL STAYS. Water views of Coffee Pot Bayou and private dock! Due to owner's severe allergies NO SERVICE ANIMALS OR GUIDE DOGS. It is a 30 minute walk to Vinoy Park. This beautiful home is located in the Old Historic Northeast neighborhood with relaxing water views of Coffee Pot Bayou. This lovely residence is perfect for anyone looking to enjoy the best of Saint Petersburg. Public kayak, small boat, or canoe launch at nearby Coffee Pot Park.

Family · Location · Decor

Contemporary Family Cottage

Your family can explore all that St. Pete has to offer when you stay at this centrally-located home. With parks, restaurants, shops, the St. Pete Pier, downtown and the Bay all an easy walk away, this location is ideal. The home is one of few in Historic Uptown with its own driveway, which also makes this location perfect to jump on the highway and be at the best beaches in 15 minutes or less! If you do not have a car, just down the block is Round Lake, with a bike and scooter rental hub.

Location · Family · Walkability

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.

Family · Value · Sleep quality

Captain's Quarters Bungalow

Come explore our beautiful city from this charming historic home in the Old Northeast neighborhood, just minutes from downtown St. Petersburg and a quick stroll to Vinoy Park. Perfect for family gatherings, holidays and long stays- everything you need is here! Thoughtfully designed with a mix of old and new, the home features pieces from local artists, makers, and favorite furniture brands. With 3 bedrooms and 2.5 bathrooms, it’s perfect for a relaxing stay with family or friends.

Family · Location · Quiet

'Ole' Florida Cottage - Historical Old NE

This is our 1921 cottage with old Florida charm -GREAT LOCATION! A block from the Bay Beach, parks, and four blocks from downtown St. Petersburg & the Vinoy. A short walk to great restaurants, cafés, bars, galleries, & museums. This clean, charming cottage includes a large enclosed porch with large wicker chairs to relax and enjoy your morning coffee or evening cocktail. Ceiling fans, full kitchen, many windows for light & charm. We think you will love it!

Family · Value · Condition

Modern Retreat w/ Patio Near Downtown

🌴 Top-floor condo near Crescent Lake + 5 min to downtown Stay in a bright, stylish 1BR 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.

Value · Location · Access

Minutes from Downtown St. Pete!

Welcome to your 2 bedroom retreat in the heart of Crescent Lake, St. Petersburg! Just minutes from Downtown St. Pete, this unique apartment features a spacious master bedroom with two closets and a cozy secondary bedroom. During your stay, you can enjoy cooking in the modern kitchen with granite countertops and stainless steel appliances, relax in the large living room with an HD smart TV, or unwind on the quaint patio and soak in the stunning Florida sunsets.

Location · Value · Biking

Renovated Bungalow

This renovated historic bungalow offers a stylish retreat blocks from downtown St. Petersburg. Perfect for shorter or long-term stays, it blends charm with modern luxury. Enjoy sleek finishes, a gourmet kitchen, and elegant bathroom. Relax on private porches with creek views or stroll to vibrant shops, museums or to lively bars & restaurants for an exciting night on the town. Experience St. Pete’s history and allure in this sophisticated gem.

Value · Location · Laundry

Sunset Oasis (5m to DT - walk to waterfront park)

Escape to Old Southeast, St. Pete! Newly built, private 1BD/1BA guesthouse featuring a king bed, full kitchen, in-unit washer/dryer & dedicated off-street parking. Blocks from Lassing Park & Tampa Bay views; 5 mins to downtown St. Pete & the Pier, 1 mi to USF, and 20 mins to top Gulf beaches. Includes camp chairs & towels! Perfect for remote workers, vacationers, or extended stays seeking a quiet local vibe with fast access to everything.

Family · Location · Check-in

Escape to the Sunshine Cottage

Escape to Sunshine Cottage, a charming 100‑year‑old Florida Cracker cottage in the heart of St. Petersburg. Perfect for couples, solo travelers, and anyone who wants a cozy historic stay with modern comforts. Walk to downtown restaurants, craft coffee spots, parks, galleries, and nightlife — all within a few blocks. This bright and cheerful hideaway blends vintage character with laid‑back Florida sunshine.

Location · Family · Pets

Retro 1/1 in the heart of Downtown St Pete.

Stay where Historic Old Northeast meets Downtown St. Pete! This charming second-floor 1BR/1BA is steps from the Vinoy Resort and just one block from Vinoy Park and the waterfront. Walk to restaurants, cafés, shopping, museums, nightlife, and everything downtown has to offer, no car needed. Inside, enjoy a retro-style bathroom, and vintage charm in one of St. Pete's most desirable neighborhoods.

Location · Cleanliness · Indoor spaces