Pet-friendly holiday rentals in Upham Beach Park

4.97 out of 5 average rating, 178 reviews

A spacious backyard is featured, bordered by a wooden fence for privacy and lined with tropical plants and trees. A concrete patio area is included, which features a grill covered for protection. The lawn is open and well-maintained, providing a serene outdoor space.

Cottage in Gulfport

The Pelicans Roost / Gulfport

The Pelicans Roost is a remodeled home, with a new fully stocked kitchen with all your cooking and entertaining needs. All new furnishings, a screened in back porch and a patio with an outside table and grill. The yard is completely fenced and lined with tropical plants and trees for your privacy. This spacious and comfortable home is clean and in a quiet neighborhood just 5 blocks from all that downtown Gulfport has to offer- the Marina,Beach,Restaurants, Shops, Fishing, Galleries and more...!

4.97 out of 5 average rating, 183 reviews

The living area showcases a blue accent wall and a plush velvet sofa, complemented by wooden chairs and a light fixture. A flat-screen TV is mounted on the wall, while the open kitchen features stainless steel appliances and a bar with stools for casual dining.

Home in Gulfport

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.

Apartment in Sunset Beach

A bright bedroom features a spacious bed adorned with light blue and white striped linens. Natural light floods the room through sliding glass doors that lead to a private balcony with an ocean view. Two decorative lamps and a textured area rug enhance the serene atmosphere.

4.89 out of 5 average rating, 160 reviews

2 Story Penthouse | Pool | Balcony | Gulf View 602

This luxury penthouse suite has been freshly remodeled and includes a direct, panoramic ocean view! The direct Gulf views are STUNNING, best on the island guaranteed. You will have direct pool and beach access. This two story condo has a townhouse layout with a private balcony on the second floor. Walking distance to local restaurants and bars. You are a short drive to St. Johns Pass, Clearwater, Fort Desoto State park and downtown St. Pete! 6 guest limit and no smoking strictly enforced.

4.7 out of 5 average rating, 115 reviews

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

A private backyard features a custom-made pool surrounded by a wooden deck. Lounge chairs and a sun umbrella are positioned nearby, while palm trees and lush greenery offer a tropical ambiance. A white privacy fence encloses the space, enhancing the serenity.

5.0 out of 5 average rating, 228 reviews

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.

A welcoming living area features light-colored seating with orange and gray accents. A wooden coffee table is centered on a decorative rug. Natural light filters through the vertical blinds, illuminating the room's neutral tones, complemented by a potted plant and wall-mounted lighting.

4.9 out of 5 average rating, 189 reviews

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.

A private heated pool is surrounded by wooden decking, offering lounge chairs for relaxation. An oversized umbrella provides shade, while tropical plants enhance the outdoor space. The rear of the house is visible, along with a patio door leading into the home.

4.98 out of 5 average rating, 120 reviews

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.

Superhost

The exterior of the Ocean Club building is showcased, featuring a modern design with a white façade and large balconies. Palm trees line the front, enhancing the tropical setting. A welcoming entrance is visible, set against a backdrop of a bright sky with soft clouds.

Apartment in Treasure Island

4.86 out of 5 average rating, 671 reviews

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.

4.93 out of 5 average rating, 136 reviews

An outdoor patio area features a tiled surface surrounded by greenery and a wooden fence. A round table with chairs is positioned next to a gas grill, while a large tree provides shade. Potted plants add a touch of nature to the space.

Tiny home in Gulfport

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

4.99 out of 5 average rating, 289 reviews

Cottage in Gulfport

Gulfport Art District - One Block From Beach!

Welcome to Uncle Finley's! Situated in the heart of Gulfport's Art and Waterfront District, This cottage listing is for unit A of the duplex. Step outside and walk to Gulfport Beach only one short block away, experience the highly-rated restaurants and shops, or browse local arts and crafts during the weekly Tuesday Morning Market during your stay. Want to experience more of Tampa Bay? Downtown St. Pete, St. Pete Beach, and I-275 access are only ten minutes away.

Flat in Historic Old Northeast

4.9 out of 5 average rating, 111 reviews

Modern Retreat w/ Patio Near Downtown

🌴 Top-floor condo near Crescent Lake + 5 min to downtown Stay in a bright, stylish 1BR retreat just minutes from downtown St. Pete. Enjoy peaceful lake views from your private patio, with Crescent Lake Park steps away and Beach Drive, dining, and nightlife close by. ✔ King bed + high-end finishes ✔ Private patio with lake views ✔ Fast WiFi + smart TVs ✔ Free parking + pet-friendly Relax in a quiet, elevated space—close to everything, but away from the noise.