Vacation rentals with outdoor seating in Upham Beach Park

4.99 out of 5 average rating, 187 reviews

An aerial view captures a multi-story condominium overlooking a beach. Lush palm trees surround a heated pool area, with docks lining the waterfront. The expansive coastline is visible in the background, highlighting the scenic proximity of beach and bay.

Condo in Treasure Island

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.

A private entrance is visible, highlighted by a bright blue door adorned with a sun-shaped decor. Lush greenery and vibrant flowers frame the pathway, leading to a serene courtyard featuring lounge chairs, enhancing the inviting and tropical ambiance.

4.91 out of 5 average rating, 161 reviews

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.

A comfortable living area is highlighted by a tan sofa with decorative pillows, accompanied by two wicker chairs. A wooden coffee table with items displayed sits on a patterned rug. The word 'BEACH' is prominently featured on the wall, enhancing the coastal theme.

4.76 out of 5 average rating, 111 reviews

Gorgeous Beach view balcony with heated pool

Walk about 30 seconds from your door to the beautiful white sand in the Gulf of Mexico. 2nd story condo has a full kitchen, private bedroom with queen bed, central air, wi-fi and cable, year-round heated pool, free-parking pass, and on-site coin laundry. Family room has a sleeper sofa, flat screen smart TV’s in bedroom and family room. We're within walking distance from tons of restaurants, bars and shops. Well maintained quiet community. Come relax at the beach and breathe the fresh air!!!!

Guesthouse in St. Petersburg

A private backyard features a heated pool surrounded by lush tropical plants and trees. The pool has a gentle curve and is accompanied by stone steps leading into the water. A small seating area is partially visible in the background, set amongst vibrant greenery.

4.98 out of 5 average rating, 196 reviews

Central Cozy Cottage w/ Heated Pool & Hot Tub!

Welcome to cute & cozy Turtle Cottage located right in the center of St. Pete, close to both Downtown AND several gorgeous Florida beaches. NO CLEANING FEE with competitive, seasonal pricing = a FANTASTIC DEAL for this space! A BEAUTIFUL NEW HEATED POOL & HOT TUB await in the private, fenced-in tropical backyard. Sorry, no pets/animals or babies/children/teens. Adults 21+ only and limited to 2 verified guests. 100% smoke-free property, inside & out. EVERYONE is welcome here. Come & enjoy!

Apartment in St. Pete Beach

A cheerful entrance features a bright yellow door and a small outdoor seating area. Two yellow chairs and a table are positioned on the cobblestone patio, while a swing hangs from the overhang. Lush green plants adorn the space, adding a vibrant touch.

4.78 out of 5 average rating, 271 reviews

Lemon Retreat | Walk to Beach <1mi | 4plex

🍋 Squeeze the Day – Your Bright Beach Escape! 🌞 Soak up the sunshine and good vibes at Squeeze the Day, a vibrant 1-bedroom, 1-bathroom retreat bursting with cheerful, citrus-inspired charm. Located in a gated complex just steps from Upham Beach, this fun and colorful getaway is perfect for making every moment count. Whether you’re lounging at the beach or unwinding in your cozy, lively space, this is the ultimate spot for relaxation and adventure. Book now and let’s squeeze the day! 🍋🌴

Guesthouse in St. Petersburg

A well-designed fire pit area is surrounded by vibrant landscaping, featuring five blue adirondack chairs positioned around a stone circle. Lush palm trees provide a tropical ambiance, and a gravel path leads to the space, inviting relaxation in the private backyard.

4.84 out of 5 average rating, 329 reviews

NEW Luxury Casita w/Hot Tub, Fire Pit, Backyard🏝☀️🏖

Welcome to Casita Citron, a beautiful new tropical paradise in the heart of St. Pete! Tranquil & centrally-located: close to nature trails, shopping, downtown St. Petersburg, & Tampa. Minutes to St. Pete Beach, ranked #1 in USA! Washer & dryer on site. Private fully fenced in backyard with fire pit. Luxurious hot tub spa with speakers, water shooters, & LED lights. Heated outdoor shower. Memory foam mattress. SmartTV. Second queen size bed available upon request (AeroBed with foam topper).

4.96 out of 5 average rating, 107 reviews

A heated stock tank pool is surrounded by a lush tropical landscape featuring a variety of green plants. An oversized umbrella provides shade, and a colorful bungalow is visible in the background, creating a serene outdoor retreat.

Tiny home in Gulfport

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!

Guesthouse in St. Petersburg

The exterior of the cottage is highlighted, featuring a white facade with blue shutters. Two windows frame the entrance, and a welcoming door is centered below them. Four black, woven outdoor chairs are arranged on the green grass, surrounded by tropical plants and sunlight.

4.99 out of 5 average rating, 147 reviews

Centrally Located Cozy 1-bed Private Cottage!

This adorable cottage is close to great views, art, culture, restaurants, dining, the beach, and family-friendly activities! You’ll love this private cottage because of the location, the ambiance, and the outdoor space. This cozy cottage is good for couples, solo adventurers, business travelers, and anyone needing a cozy place to stay! Parking is just steps away from the cottage with a private entrance. BBQ is available, new hot tub, and an outdoor gas fireplace for a relaxing evening!

Guest favorite

A modern kitchen area is highlighted with wooden countertops and white cabinetry. A stove, microwave, and tea kettle are visible, alongside open shelving displaying glassware and decorative items. Natural light enters through a window, illuminating the space, which leads to a cozy sleeping area.

Tiny home in Gulfport

4.93 out of 5 average rating, 213 reviews

Pelican's Nest - Pet Friendly

The Pelican's Nest is a cozy tiny home that has been remodeled with you in mind. Enjoy the beachy vibes inside the home or relax outside where you can connect to nature with your private yard. Enjoy a fire or dinner on your outdoor dining table. Have your pet staying with you? No worries! They are welcome here. Located a mile 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 the St Pete pier.

The spacious studio features a king bed with a light blue and white quilt, accompanied by decorative pillows. A sleek black couch is positioned beside a wooden dresser. Two windows offer views of palm trees and natural light, while a wall-mounted television adds modern convenience.

4.87 out of 5 average rating, 149 reviews

Upham Beach #1 Location Heated Pool Stylish Studio

We are grateful to share that this beautiful condo is Guest Ready! The location is amazing, only steps from the beach. A fully stocked kitchen provides everything you need for cooking and dining and the living space is ample for relaxation. The Pool is open and heated! Most restaurants and stores are also open. For added convenience we provide beach chairs, umbrella and a buggy. Please note that some lower units are still in various phases of completion after hurricanes.

A bright living area features a comfortable gray sofa adorned with striped pillows. Natural light highlights a wooden coffee table, positioned between two woven ottomans. A serene wall art piece and a lamp provide ambient lighting, while a decorated entrance door is visible in the background.

4.84 out of 5 average rating, 177 reviews

Sunset Condo: Steps to the Beach with Pool Access

Relax in this updated condo just steps from the beach in St. Pete Beach! This family friendly second floor unit has one bedroom with two full beds, a bright living area, an updated bathroom, and a full kitchen. Catch views of the Gulf of Mexico from the private balcony! Location is everything and Sunset Condo is steps from the beach and its amazing sunsets, and within walking distance to waterfront restaurants with live music, coffee shops, & shopping on Corey Avenue.