House vacation rentals in Upham Beach Park

Beach front cottage on Treasure Island, FL

Beautiful brand new cottage located directly on the Gulf of Mexico. Quiet and quaint, old style cottage that has miles of beach to walk and enjoy. The cottage is newly built, and includes state of the art bathroom and kitchenette. The kitchen includes fridge with ice maker, microwave, airfryer, induction cooktop, and fully equipped. The cottage is within walking distance to grocery store, trolley transit, dining, and is only 15-20 minutes to downtown St. Pete. Mainly weekly or monthly rentals.

Location · Amenities · Access

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.

Location · Value · Air conditioning

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.

Value · Location · Layout

Central location - mins to Downtown and Beaches

☀️Rest assured, you’ll wake up close to all the excitement St. Petersburg has to offer! Perfect for solo travelers, couples, or small groups of friends and family, this cozy home is centrally located between downtown and the beaches, offering the ideal balance of fun and relaxation. 🚗 Quick Drive Times: • 8 min – Downtown St. Pete & The Pier • 12 min – St. Pete Beach • 25 min – Clearwater Beach • 25 min – Tampa & Airport Experience the best of St. Petersburg—scroll down to learn more!🌊

Location · Value · TV

Beautiful Tampa Bay Pool Home Near Gulf Beaches

A beautiful Gulf Coast residence with many amenities to offer. Bright and open furnished spaces, for relaxing and entertaining up to 10 guests. A quiet, upscale neighborhood , your just 6 minutes from Madeira Beach and many other Gulf of Mexico beaches. Or, fun & sun in the private pool outback. 20 minutes from Downtown St Pete, which offers restaurants, museums, the new Pier, and excellent night life. Very close to countless restaurants, shopping, coffee shops, and grocery stores.

Location · Value · Pets

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.

Family · Location · Pets

ST Urban Oasis heated pool

Located in unincorporated St. Pete, you can keep it simple at this peaceful and centrally-located oasis. Want to be near the city and beaches while having your own private backyard sanctuary? This is your place to enjoy it all. This home features two bedrooms, one bathroom, and a private heated pool. The backyard has been filled with beautiful large palms, bamboo, and other zen features to allow you and your family to enjoy a relaxing and easily accessible stay in beautiful St. Pete.

Value · Location · Outdoor spaces

*POOL* Fenced Yard *Shuffleboard Court*

Add my listing to your wishlist by clicking the heart in upper right corner • 4 off-street parking spaces • Smart Locks + self check-in • Ring camera for security • Fully equipped kitchen + essentials • 10ft Stock Tank *POOL* • HUGE fenced-in yard • Outdoor shuffleboard court, corn hole & BBQ • Onsite washer+dryer • 2 adult bikes + 2 kids bikes --ride into Gulfport! • 8min drive to beaches • Dedicated Work space + 730Mpbs wifi • 65in smart TV + streaming apps

Location · Family · Comfort

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!

Location · Family · TV

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.

Family · Location · Wifi

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.

Value · Location · Sleep quality

Oak Tree House

Make yourself at home away from home. Bring your family to this great place and enjoy the evenings in our beautiful patio deck and relax in the Jacuzzi. Now with a brand new outdoor shower. Located Just 2 miles away from Treasure Island beach and close to bars, restaurant’s, world class sporting events, craft beer, art galleries, local shopping and so much more…

Location · Family · Kitchen