House vacation rentals in Upham Beach Park

4.97 out of 5 average rating, 174 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.

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Superhost

4.7 out of 5 average rating, 109 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

LocationFamilyPets

4.99 out of 5 average rating, 108 reviews

A well-lit kitchen is equipped with wooden cabinets and a spacious countertop. Three white bar stools are arranged at the island, which is adorned with a vase of fresh flowers and a platter. Large windows allow natural light to brighten the room.

Home in St. Pete Beach

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.

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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 out of 5 average rating, 224 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.

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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, 181 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.

LocationFamilyCleanliness

4.97 out of 5 average rating, 236 reviews

Coastal Pool Retreat *5 Min to Madeira Beach Sand

Presented by "ST PETE VACATION HOMES"---check us out online! We have 5 nearby Airbnb homes! 🌴 Home sleeps 12 guests. OUTSIDE FEATURES: * saltwater cocktail pool (optional pool heater) * oversized chess board * huge fire pit * large tiki hut w/ lounge seating & outdoor tv * plentiful poolside furniture * 3 hole putting green LOCATION: • Madeira Beach~5 minutes • Walmart, Restaurants + Coffee ~3 minutes • John’s Pass Village & Boardwalk~8 minutes • Downtown St. Pete~25 minutes

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Superhost

Home in Clearwater

5 out of 5 average rating, 5 reviews

Providence Cove | Heated Salt Pool • Sleeps 12

Welcome to Providence Cove, your luxury retreat just minutes from Clearwater Beach! Relax in the heated saltwater pool, enjoy private mini golf, gather around the fire pit, and create unforgettable memories with family and friends. Sleeps up to 12 guests and features stylish bedrooms, a fully equipped kitchen, fast Wi-Fi, private parking, and a curated vacation guide with our favorite local beaches, restaurants, and attractions. 🌴✨🌊🫶🏻🌞

FamilyTVBackyard

4.98 out of 5 average rating, 185 reviews

Home in Pinellas Park

Insta Worthy Retreat -HTD Pool- Arcade Room- Golf

☀️ Looking for a place the whole family/group can enjoy? This centrally located modern home is full of fun and style, with everything you need—from a fully stocked kitchen 🍽️ to beach supplies ⛱️ and more. Enjoy an Insta-worthy space with 5-hole mini golf, giant outdoor games, a heated pool, arcade & board games, and cozy spaces inside and out. 📍 Just 6 miles to the beach and Downtown St. Pete—perfect for your getaway!

ValueFamilyCheck-in

5 out of 5 average rating, 20 reviews

Home in Treasure Island

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!

LocationFamilyHospitality

4.99 out of 5 average rating, 191 reviews

A charming cottage exterior is showcased with a light green facade and a welcoming front porch. Two outdoor chairs are positioned to the sides of the entrance, flanked by tropical plants. The sky features a blend of warm colors during sunset, enhancing the peaceful ambiance.

Home in Gulfport

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.

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4.97 out of 5 average rating, 167 reviews

A serene outdoor space features a heated pool surrounded by several lounge chairs and an umbrella for shade. Lush green plants and a wooden privacy fence complement the vibrant color of the cottage in the background, enhancing the inviting atmosphere.

Home in Gulfport

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.

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