Pet-friendly holiday rentals in South Pasadena

Centrally Located Cozy 1-bed Private Cottage!

This charming private cottage is ideally located near beautiful views, beaches, art, culture, restaurants, and a variety of family-friendly activities. Guests love the space for its peaceful ambiance, great location, and inviting outdoor areas. It’s a perfect stay for couples, solo travelers, business guests, or anyone looking for a cozy getaway. Enjoy private parking just steps from the entrance, along with a BBQ grill, a brand-new hot tub, and an outdoor gas fireplace—perfect for relaxing!!!

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...!

Heated Pool! Huge Walk In Shower! 5 min to beach!

Welcome to Coastal Paradise! This modern villa is newly remodelled and professionally furnished with a beautiful coastal theme. It has a very spacious open layout with plenty of space for the whole family. A huge master walk in shower with two shower heads and four body jets! Out back is a private heated pool with lounge chairs, grill, a hammock, corn hole and a beautiful patio set to enjoy a meal outdoors. Madeira beach is only a 5 min drive away! We also provide all your beach necessities!!

Pet Friendly Pool Oasis St Pete/Gulfport

Exceptionally private artist's home with a salt pool ( not heated) in a tropical landscaped fenced backyard and a large screened porch, surrounded by palm trees. 10 mns to St Pete beach , Treasure Island, Sunset beach or downtown St Petersburg. 5 mns to the old Florida downtown Gulfport and one block to pinellas trail. Our Eco and pet friendly ,(only green cleaning products and no pesticides) 1400 sqft home ( plus the 300 sqft porch) home is in a safe residential area, close to everything.

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.

Private Guesthouse Near Beach & Downtown

Welcome to our charming studio in the heart of St. Petersburg, Florida! Our cozy dog-friendly space is the perfect retreat for solo travelers or couples looking to experience all this vibrant city offers. Located just 10 mins from Treasure Island and less than a half mile from a Sun Runner bus stop, the location offers easy access to all of the city’s great destinations. Enjoy your own private entrance and plenty of street parking in our quiet, shaded neighborhood. We can't wait to host you!

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

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.

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

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.

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.

FLASH SALE! Lets Flamingle! <1mi to beach! Sleeps4

🚨Special Offer: We’re running a limited-time Flash Sale for select dates! Message us to unlock exclusive savings for your short term or mid term stay‼️ 🦩Let’s Flamingle in this bold, pink 1BR retreat near Upham Beach! Located in a gated complex, this tropical paradise features cozy flamingo decor, FAST Wi-Fi, smart TV, full kitchen, and lush vacation vibes. One of 4 fun themed units perfect for beachside escapes. Book now and let the good vibes roll! 🌴☀️🦩