Smoking-friendly holiday rentals in Upham Beach Park

Orange Grove Cove ~ Bay Pines ~ Madeira Beach Area

1.5 miles to the beach! Charming, clean, remodeled home. We provide 2 bicycles, beach gear, chairs, cooler, beach cart, toys, & umbrella. Pinellas trail is only 1 block away! Comfy king beds in both bedrooms. Pool table in the sunroom, charcoal grill, & jet bathtub. Memory foam couch bed. Welcome to the lovely quiet neighborhood of Bay Pines, FL. Great central location! Near Madeira Beach, Treasure Island & John’s Pass. Locally owned & operated by highly experienced superhosts. Big Dog Friendly!

Mahi on Madison:Near Beach w/Fenced Yard & Hot Tub

Escape to this stunning, private, and beautifully renovated home that has a bright and cheerful atmosphere. Enjoy the exclusive privacy of a fully fenced yard, featuring a relaxing hot tub, hammock, fire pit, and grill. With 3,200 sq ft of lush artificial turf with a fun mini putt-putt course, there’s plenty of space for activities and fun! We're just minutes away from shops, bars, restaurants and the Clearwater Basin Marina. Best of all, the beautiful Clearwater Beach is only 10 minutes away!

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.

Waterfront Oasis, Hot Tub, Sauna, Boat Lift

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

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.

SaltedHeated pool 5BDR3Bath9 min2ClBeach Sleeps 22

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 from November through May free of charge

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!

Studio Bedroom - Private Bathroom , Full Kitchen.

Enjoy your stay in Clearwater, Florida in our cozy studio suite! This sanctuary is a place for you to relax, reset and revive yourself. It is a mini-retreat especially designed for you to come alone, or with a friend or partner. This studio is centrally located near downtown and a a short drive from the beaches. Don't want to go out? Enjoy your stay in our tiki patio which includes a Hot Tub , dining area, seating area and television!

Beach Home Luxury S/POOL-Golf Cart

Brand New, 2000 sq ft/3 Bedroom/3 Full Bathrooms 2 living rooms/modern townhome located near a canal and the gulf just two blocks from the beach. Heated salt water pool! GOLF CART!!! Ask for avalability. (The cart has a small fee). You can enjoy full view of the canal and partial views of the gulf from the balconies and the rooftop! Walking distance to beach, restaurants, volleyball. Close to Johns Pass, 2 miles.