Holiday rentals with a washing machine and dryer in Upham Beach Park

Walk to beach shops food drinks “The Sweet”

Cozy, romantic, 1 king bed, super cute and super sweet! Just a short walk to beautiful Indian Rocks Beach, nature parks with trails, shopping, orange grove, and many restaurants and fun beach bars! Guests have private entrance, private full bath, kitchenette, sofa sleeper, large back yard with fire pit, bbq grill, beach chairs, wagon and cooler. Zoning permits 2 people per bed only and one on futon. All guests must be listed on the reservation. No Pets allowed. Florida State License # DWE6215889

Historic Kenwood KING walkable to Central Ave

Welcome to our newly renovated beachy 2nd floor guesthouse in Historic Kenwood. This spacious 1 bedroom (King bed), 1 bath is an easy walk, bike, or short drive to St Pete restaurants, bars, breweries, antique shops, museums, live entertainment and so much more. Grand Central District is just a 5 min walk, Edge District is 1 mile, Downtown is 2 miles, and St Pete beach is 15 minutes away. Guests have a private deck with seating for 2, Wi-Fi, and laundry accessible via shared fenced backyard.

Cozy Cottage for Lovers

Relax, reconnect and revitalize in this private, intimate cottage that has everything you need to leave the hustle and bustle behind. Surrounded by lush tropical vegetation in the shade of giant live oaks and located in the Gulfport Arts District, you're a short walk or bike ride from excellent urban parks, restaurants, live music, fashion and art boutiques, dancing at the Gulfport Casino, community theater, and a beautiful beach that looks out over sailboats moored in Boca Ciega Bay.

Beach Front Penthouse Riley's Retreat Island Inn

800 sq ft top floor condo with spectacular views of the Gulf of Mexico, Boca Ciega Bay, and the City. Located in the iconic Island Inn Beach Resort; step out of the lobby and onto the sand! Florida sunrises and sunsets are legendary, and you can enjoy both from your private top floor balcony. We offer one of the finest condo's in the building with the unique ability to enjoy North, South, East, and West vistas. This condo is unlike any other unit in the building--a must see!

Pelican's Nest - Pet Friendly

The Pelican's Nest is a cozy tiny home that has been remodeled with you in mind. Enjoy the beachy vibes inside the home or relax outside where you can connect to nature with your private yard. Enjoy a fire or dinner on your outdoor dining table. Have your pet staying with you? No worries! They are welcome here. Located a mile 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 the St Pete pier.

Avocado Casita 10 mins to Beaches

Newly built studio -- small space, smart design. An intimate studio space meant for a minimalist lifestyle complete with full amenities. Compact yet comfortable, it’s the perfect place for a restful sleep in between your daytime adventures. Pack light, live easy. 3 blocks from Stetson Law School 3-4 blocks from the Pinellas Trail ~1.5 miles to Gulfport’s Beach Blvd 3 miles to Award Winning St. Pete Beach 4 miles to Award Winning Treasure Island ~4.5 miles to Downtown St Pete

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.

FLASH SALE! Fiesta Siesta <1mi to beach |sleeps 4

🚨Special Offer: We’re running a limited-time Flash Sale for select dates! Message us to unlock exclusive savings for your short term or mid term stay 🌵Welcome to Fiesta Siesta — a vibrant cactus-themed 1BR in sunny St. Pete Beach! Located in a gated complex just a short walk or drive to Upham Beach, this colorful retreat has FAST Wi-Fi, smart TV, full kitchen, and major good vibes. One of 4 fun themed units! Book now and let the fiesta (and siesta) begin! 🌵☀️🎊

St. Pete Beach Condo • Heated Pool • Walk to Beach

Relax in this bright, first-floor beach condo just a 4-minute walk to St. Pete Beach. Enjoy a full kitchen, king bedroom, washer/dryer in unit, fast WiFi, and a comfy living area with a sleeper sofa. The gated community offers a heated pool, grilling area, and free parking. Beach chairs, beach towels, and umbrellas are included—everything you need for an easy, comfortable getaway. Walking distance to many restaurants and shops, making this the perfect location!.

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.

Dolphin Cove Waterfront St. Pete Beach w/ Pool

THIS is the Florida life! A private oasis with a stunning tropical backyard and an oversized SALTWATER pool. Enjoy 140+ ft of waterfront on Bear Creek canal, where manatees and dolphins visit daily! Kayak just 15 minutes to nearby islands. Beaches are a quick 7-minute drive, downtown is 15 minutes away, and shops/restaurants are right across the street. The home is simple and unupdated, but the backyard is a true paradise you won’t forget!

Direct Gulf View On The Beach w/ Music & Food #502

Directly on the beach. You cannot beat the views of the Gulf and you are ON the beach. Go downstairs and put your feet in the sand. 3 minute walk to live music, beach bars and restaurants. Private beach out front and short walk to all the action. It truly is the best of both worlds! We have full time staff in the building, if you need anything at all during your stay, do not hesitate to reach out!