Smoking friendly holiday rentals in Upham Beach Park

Modern studio, pool & sauna | 10 min to DT & BEACH

Enjoy a stylish stay at this private studio within our family home. With private entry and dedicated parking, the studio has a kitchenette, private patio, fenced in space for outdoor living, and is pet friendly. There’s a queen bed and full size pullout sofa. The studio is stocked for hosting, beaching, or just relaxing with coffee and a book. As your hosts you might see us (or our pups!) around and we love to highlight the wonderful places between downtown St. Pete, Gulfport, and the beaches.

Heated pool & hot tub | 10 min to beach & DT

Enjoy a stylish stay at the centrally-located Pineapple Palace. Nestled between St. Pete Beach & Downtown St. Petersburg, this private mid-century pool home is a dreamy Florida vacation. There are 3 beds/2 baths with a spacious outdoor living area, screened in pool, outdoor bar, hot tub, and more. This space is perfect for vacations, bachelorette weekends, staycations, and events. For events, please DM the details. We’re excited to host you & share our unique guide to all things St. Pete! ☀️

Paradise Cottage Largo Beaches 1 mile High ground

We are PARADISE COTTAGE, and the standards of super host are status quo! We're ready for you! Although only 2 miles from the Gulf, we're on high ground! We are on a Priority One Energy Grid. With over 300 huge potted plants, many trees, etc we live in a lush tropical "Paradise". Our guests' highest praises include private, quiet, serene, safe and secluded; attributes we're fortunate to claim We have no neighbors while being so close to so much. Read the next section "The Space" to learn more.

Sunshine, Beaches & Refreshing Pool/Screen Patio

Step inside, you’re greeted by an open living area, and beautifully updated kitchen and appliances. Step outside to your private paradise! The large screened-in pool lanai beckons you to relax, lounge around, take a dip, fire up the grill and unwind in the Florida sunshine. This is where unforgettable memories are made. ☑ 5 mi to beautiful Sand Key Beach park and Clearwater Beach! ☑ 10 mi to John’s Pass Boardwalk. ☑ 9 mi to CLW/St Pete Airport & 23 mi to Tampa INTL. ☑ Sun room w/ping pong tabl

Paws Paradise Studio-2 Miles to Beach-Kitchen-Yard

Dog friendly safe and secure Studio apartment with fenced yard and only minutes away from the great white sandy beaches of Treasure Island and St.Pete Beach. This updated space is great for short-term or extended stays. Outfitted with a mini kitchen and its own private entrance with covered patio and fire pit area. A 15 minute drive east is beautiful Downtown St Petersburg with its newly opened Pier. Walking distance to Walgreens and the very popular local favorite Deadbobs Bar. A 40" Roku tv.

A slice of paradise!

The guest cottage (approx. 300 sq ft) is separate from the main house, where we reside, with a beautiful saltwater pool to cool off in after your day's adventures! The property is 5 blocks from downtown Gulfport, with waterfront restaurants, bars, arts district, unique shopping, and beach. Close access to new tennis courts, bayside beach and minutes away from modern downtown St. Petersburg, and world-famous beaches. We are not set up to host pets or children and no unaccounted for guests.

Private & Cozy Tiny Home/Cottage

This is a cozy converted workshop with all the amenities of a traditional home! You'll have a comfy bed that sleeps 2 with an air mattress upon request, TV with streaming options, fun decorations, WiFi, air conditioning, W/D, closet space, cooking stuff, & bathroom. If you love tiny homes, you'll love this. Because of it being a converted workshop, it still has that feeling in some regard. It's a little rustic, but still charming. It's not a hotel, nor does it try to be. Pets are welcome.

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).

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!

Walk to Sunset Beach! 3BR/3BA Home w/New Furniture

🔥 URGENT LAST-MINUTE DEAL! Get 20% OFF Welcome to your Sunset Beach getaway! This fully renovated 3-bedroom, 3-bathroom Treasure Island home blends mid-century modern style with laid-back beachy charm. Just steps from Sunset Beach, it’s perfect for families, couples, or friends seeking a relaxing coastal escape. Enjoy private baths, outdoor dining, parking for 4, washer/dryer, and all the beach gear you’ll need for a memorable stay by the Gulf Coast. Book now and soak up the sun!

SaltedHeated pool 5BDR3Bath/9 min2ClBeach Sleep22

This is the perfect vacation home for families! 5 bedrooms 3 full bathroom home with a screened and HEATED Pool, screened covered patio with sitting area and big outside dining table for gatherings and overall enjoyment of the outdoor spaces. Strategically located 10 min from the famous Clearwater beach, less than 10 minutes to bellair beach13 minutes from Indian Rocks beach it is in a prime location with many events happening nearby. Pool heated free of charge by request

St. Pete Beach Efficiency/Bikes

Private entry, Mother in law suite. It is a small space, one room, updated, in a safe and comfortable beach community. The space is located in the Upham Beach area walking distance to the beach. One Secure off street parking. No guest parking. No second car. No street parking. No unregistered guests. Outside space is shared, but plenty of room to store boards, bikes, other recreational equipment. No parties or gatherings. Two bikes and beach equipment on sight.