Holiday rentals in St. Petersburg

Stunning bungalow retreat in St. Pete!

Your home away from home in St. Pete! Our bungalow is located in a highly desirable neighborhood just a mile from vibrant downtown. Fully renovated; the 1930's charm remains but with a modern fully-equipped kitchen, stylish bathroom, furniture/décor, and private deck. Refinished hardwood floors, too Features include: Driveway for 1 car King bedroom Queen sleeper sofa 2 Smart TVs: live & streaming apps Front porch with rocking chairs Deck with outdoor dining Washer & dryer Experienced hosts :)

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!

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.

Our Modern Downtown Oasis

The apartment is a lower unit with personal touches. The unit is in a central location but in a quiet residential neighborhood. Bedroom has a sound-proofed ceiling and with black out blinds you can sleep as long as you want. Perfect for a couple for a getaway or a remote work location. Fully equipped kitchen and in-unit laundry. The unit has Gigabit 🛜 As packing is such a hassle, we include most of the "essentials". We think we’ve thought of everything. THIS IS A NO SMOKING PROPERTY

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!

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! 🤍

King Bed Studio | Outdoor Kitchen | Free Parking

Welcome to our thoughtfully designed studio—small but full of comfort, efficiency, and charm. If your priority is a cozy bed , a truly clean space and location, look no further. Loved by hundreds of wonderful guests, this is one of two private studios in a tiny house, ideal for solo travelers or couples. You’ll have everything you need, plus access to a beautiful shared gazebo with seating, dining areas, and lush greenery. We have a team of four Superhosts, available to help. 🌴☀️🏖️

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.

Coastal Retreat Near Madeira Beach With Game Room

This 2-bedroom unit with a bonus Game Room and Sunroom is the perfect getaway for up to 6 people looking to enjoy the beautiful beaches of this area. Located in a quiet neighborhood on a private cul-de-sac, it is the perfect place to rest and recharge between trips to the most beautiful beaches in the world. This location is just a quick 5-minute drive (2 miles) to the Madeira Beach access and a 10-minute drive (3.7 miles) to the famous John's Pass Village and Boardwalk.

Charming apartment in Historic Kenwood

Cute, spacious apartment located in Historic Kenwood, which was named 2020 “Neighborhood of the year” by NUSA. Our apartment is above our large garage. Lots of charm and just enough space to spread out a little for some privacy. Located close to downtown, walking distance to lots of restaurants, breweries and bars but still a short drive to our beautiful beaches. You access the apartment through our side gate and up an exterior stairway.

The Boho - 2BR Gulfport Waterfront District House

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.