Holiday rentals with outdoor seating in Upham Beach Park

Pass-a-Grille Historic Cottage Unit 1

PASS-A-GRILLE HISTORIC COTTAGE UNIT 1 A fully renovated historic beach cottage located in beautiful Pass a Grille, Florida. Steps from the Gulf of Mexico and Boca Ciega Bay. This is a duplex; Unit 1 - 1 bedroom/1 bath. Household linens, towels, cookware & dishes provided. Appliances include; dishwasher, washer/dryer, flat screen TVs and wi-fi. Vintage-style tiled bathroom and shower. High end window shades on all windows. Front patio area w/ BBQ grill. Private parking for 1vehicle on premises.

Escape Winter to Sala Suite #3! 2 Blocks to Beach!

Welcome to The Sala! A cozy coastal escape for two, nestled in vibrant St. Pete Beach, steps to the soft sand of Upham Beach and local hot spots! This is not your average beach stay. The Sala is your home base for sun-chasing, seafood sampling, hammock lounging & sunset strolling. Whether you’re here for fun or rest, you’ll find what you need to unwind, recharge, and enjoy every salty second. 🌴 Walk to Upham Beach ☕ Kitchen 🐾 Pet Friendly 🏖️ Beach Gear Included 🌅 Hammock 🚗 Free Parking

Spectacular beach to bay views from this resort.

Our condo has spectacular water views from the Bay to the Beach. We have a large one of a kind kitchen that is unique to our resort, with granite counter tops, hardwood cabinets, and all stainless steel appliances. Everything you need to prepare a meal is provided along with basic spices and condiments, Coffee, creamer, and sugar. The master bedroom has a new king size bed and walk in closet with all beach gear also available for your use. We have 2 - 50" flat screen TV's with cable as well.

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.

Tropical Courtyard Paradise on St. Pete Beach

Charming, cozy, well-appointed/fully stocked ground floor 1 Bedroom Unit with its own Private Entrance, Courtyard & spacious heated Pool. A short 1 minute walk to either St. Pete's Gulf side Upham Beach or all the abundant Nightlife & Restaurants on Gulf Blvd. Free WiFi(Spectrum) & 2 separate 32" HD TV's (Living Room sofa bed & Bedroom Queen bed), have all Premium movie, news, & sports channels. This Unit is affordably priced for the Budget Conscious desiring that Premium Beach Location.

Beach Front Madeira Beach

PLEASE NOTE: SEVERAL UNITS UNDER CONSTRUCTION in the building. Expected completion by May 31. Amazing beachfront condo, newly remodeled on the second floor. Vinyl plank flooring throughout, No CARPET. 2 Bedroom, 2 Bath. Completely unobstructed views of the beach. It is centrally located less than 1 mile from World Famous Johns Pass. Enjoy breathtaking sunsets from your living room with the water just feet away. The condo is walking distance to shopping, banking and many restaurants and bars.

Shipwreck Bungalow

Shipwreck Bungalow, your own private paradise! Nestled in a quaint Gulfport neighborhood. Just 10 minutes from St. Pete beach, 10 minutes from lively downtown St. Pete and a few short minutes from funky downtown Gulfport. The Bungalow is surrounded by palms, tropical plants and flowers, beautiful outdoor shower, Tiki bar, heated stock tank pool, fire pit, outdoor games, grill and spacious outdoor seating area. Enjoy lounging by the pool or exploring all this sunny area has to offer!

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.

🏝 St Pete Beach Condo🏝

Walk right out to the white powdery sand and crystal blue water of the Gulf of Mexico from this ground-floor luxury unit. Spacious 1BR/1BA condo, fully furnished, beautifully decorated, and equipped for vacation rentals. Tropical courtyard with heated pool, grill & lounge. Step through the gate—you're on St. Pete Beach. Breathtaking sunsets included. No pets. No smoking. Book your stay now and experience the magic of beachfront living—paradise awaits you every single day.

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

🚨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! 🌵☀️🎊

*Shore Thing* Walk to Beach | Intercoastal Views

🏖️ Shore Thing Condo 🏖️ Experience the ultimate blend of Sunset Bliss at this stylish Treasure Island retreat. Just steps from powdery sands, ocean breezes and breathtaking sunsets. Keep an eye out for local wildlife as dolphins and manatees glide by. Inside, enjoy coastal vibes featuring modern beachy interiors. Whether you are preparing a meal in the luxury kitchen or diving into the intercoastal heated pool, my service ensures your comfort always comes first.

Private Ocean View Beach Retreat with Balcony

Only steps from the beach, this newly updated and perfectly located beach condo is your luxury getaway. The large bedroom, lofty living area and modern open kitchen, as well as the generous balcony with direct view of the Gulf will make you never want to leave again. This condo is better equipped than your average vacation rental and comes with your private daily sunset spectacle. Continue to read for more...