House holiday rentals in Upham Beach Park

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.

Waterfront/ Sunsets/ Heated Pool/ Tiki Bar/ Dock

Welcome to The Tiki Retreat, Your Waterfront Oasis on Boca Ciega Bay!
Step into a bright, coastal 3 bedroom home where relaxing waterfront living meets vibrant tropical vibes. Enjoy stunning views, a private dock, a heated salt water pool, and your private tiki bar all set against the backdrop of beautiful Boca Ciega Bay, home to dolphins, manatees, and an array of wildlife. This spot has everything you need for an unforgettable stay. Feel free to bring your family pet (with pre-approval)

Gulfside Resort: 3 bed, 2 bath /pool access

Welcome to GulfSide Resort, a family-owned gem just a block and a half from St. Pete Beach! Our comfortable vacation suites face a beautiful pool and are a short stroll away from beach bars, restaurants, and shopping. Enjoy our pool, shuffleboard, and putting green, plus complimentary beach chairs and toys. Perfect for group gatherings, we can host up to 35 guests comfortably. Experience relaxation and fun with your loved ones at GulfSide Resort—your ideal vacation spot! The house sleeps 6.

Waterfront Oasis, Hot Tub, Sauna

Welcome to our beautiful waterfront home nestled between St Pete Beach & Gulfport, FL, where you'll experience the joys of the quintessential Florida lifestyle! Relax in the large outdoor living space, fish off the dock, boat on the pristine waters of the Gulf of Mexico and take in the ocean breeze. ☑ 2 mi to St. Pete Beach, 2.5 mi to Gulfport & 5 mi to John's Pass ☑ On the Intracoastal Waterway w/boat access out to the Gulf of Mexico ☑ Hot tub, Sauna, Outdoor kitchen, bar, dock, boat lift

Hibernate in our Bear Creek Home

This 3 bedroom 2 bath home is located in beautiful Bear Creek. Don't worry, no bears! Great place to relax and enjoy the pool, in a quiet, safe neighborhood. Next to Pinellas Trail, a 40 mile paved trail. Great for walking, running and biking. You can bike downtown 6 mi or 4.6 miles to beaches. We have bikes and for those more adventuresome we have kayaks you may use. House features stable, high speed internet. Close to great restaurants, drugstores, supermarkets and coffee shops.

Turtle House Sunset Beach With King Bed

This historic, super cute, beautifully landscaped one bedroom home is located on a quiet street in Sunset Beach and is a short 200 steps to the Gulf. Walk to Caddys, restaurants, brewery, taco stand, and tiki bars. 3 room with King bed, Central air, Washer and Dryer. Driveway for one car. Paid street parking, Stainless Steel Appliances. Dishwasher. Microwave, Coffee station, Granite counter tops. , Beach Chairs and Umbrella. Come vacation at the Treasure Island Turtle House.

Beautiful Treasure Island Getaway, Heated Pool

Welcome to your dream home, located just steps away from one of the most pristine beaches on the west coast. Nestled in a family-friendly neighborhood, this exquisite three story residence is only a block away from the sandy shores of Treasure Island, and is surrounded by an array of fantastic restaurants and bars. Get ready to experience a perfect blend of convenience and the allure of a vacationer's paradise. Read on to learn more about the home!

Waterfront Condo with Boat Slip & Fishing Dock

Escape to this peaceful, 2-bedroom waterfront condo on Boca Ciega Bay. Perfect for families, this ground-floor retreat offers stunning bay views, a heated pool, and a private dock. Rent your own private boat slip or just fish right off the dock. Enjoy a bright, modern space that comfortably sleeps your group. You're just a short walk from the beach, local dining, and vibrant nightlife. Your serene coastal getaway awaits!

Luxury Beachfront Condo, Pool + Gulf Views #603

Water views in every room—wake up to sweeping Gulf vistas and unwind with unforgettable sunsets from your shared balcony. This bright 2 bed, 2 bath top-floor condo on the 6th floor offers a full kitchen, comfortable furnishings, and everything you need for a relaxing beach escape. Just steps from the sand, enjoy long walks, nearby dining, live music, and easy access to John’s Pass and local attractions.

Sunny 1BR/1BA Steps to St Pete Beach

🏖️Just a 5-min walk to the sand, this cozy 1BR/1BA offers king bed, full kitchen, Netflix, A/C, laundry, outdoor shower, beach umbrella/chairs, self check-in, parking 🏝️Located in the heart of St Pete Beach, you’re just steps from the white sand, shops, restaurants, and vibrant nightlife. Whether you’re looking to surf, soak up the sun, or explore the Gulf coast, everything is right at your doorstep.

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.

Bungalow Heated Pool Home 10 minutes to Beaches

Welcome to the Starfruit House. A completely renovated three bedroom two bathroom beach cottage with a in-ground heated pool! This home features the feel of old Key West with all new modern updates. Within a few miles of the most popular beaches in the area, minutes to downtown St. Pete, and a quick bike ride to Gulfport. Enjoy the tropical feel of the outdoors, and then come inside to relax.