Pet-friendly holiday rentals in South Pasadena

4.96 out of 5 average rating, 167 reviews

A spacious backyard is featured, bordered by a wooden fence for privacy and lined with tropical plants and trees. A concrete patio area is included, which features a grill covered for protection. The lawn is open and well-maintained, providing a serene outdoor space.

Cottage in Gulfport

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...!

Townhouse in St. Petersburg

Two coconut-shaped cups sit on a woven placemat atop a glass table, each garnished with a colorful paper umbrella and a lime wedge. The setting is serene and invites relaxing outdoor enjoyment.

4.97 out of 5 average rating, 239 reviews

Gulfport+St Pete 2BD King Oasis, close to it all!

Looking for a stylish and centrally located place to stay while visiting St Pete and Gulfport? Here it is! This 2 bed, 1 bath has king & queen memory foam mattresses, 55-inch TV, fast WIFI, washer/dryer, tankless water heater, and a fully fenced-in yard. Minutes to world famous beaches, downtown St Pete, and Beach Blvd all while being tucked away in a peaceful neighborhood oasis. Plus, only a short drive to local hot spots like Tropicana Field, Dali Museum, Sunken Gardens, & Stetson University.

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.

4.97 out of 5 average rating, 124 reviews

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.

The exterior of a cozy converted workshop features a gray wood-paneled facade with a vibrant yellow front door. Two chairs are positioned on the porch, beside a barrel and trash bins. A privacy fence can be seen in the background, surrounded by greenery.

4.84 out of 5 average rating, 877 reviews

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.

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.

4.88 out of 5 average rating, 147 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.

Tiny home in St. Petersburg

A cozy sleeping area is presented with a spacious bed, dressed in neutral linens. A light wood frame complements the soft color palette. Wall-mounted light fixtures provide gentle illumination, while a shelf adorned with plants adds a touch of greenery. A small stool is positioned beside the bed.

4.88 out of 5 average rating, 144 reviews

Charming Studio | Outdoor Kitchen | Free Parking

Welcome to our thoughtfully designed studio—small but full of comfort, efficiency, and charm. If your priority is a cozy bed , a truly clean space and location, look no further. Loved by hundreds of wonderful guests, this is one of two private studios in a tiny house, ideal for solo travelers or couples. You’ll have everything you need, plus access to a beautiful shared gazebo with seating, dining areas, and lush greenery. We have a team of four Superhosts, available to help. 🌴☀️🏖️

Tiny home in St. Petersburg

A light-filled studio space features a comfortable bed along with a simple wooden table and chairs. A mounted TV is present on the wall, and a plant adds a touch of greenery. The flooring consists of neutral tiles, enhancing the spacious feel of the room.

4.91 out of 5 average rating, 165 reviews

King Bed Studio | Outdoor Kitchen | Free Parking

Tiny home in St. Petersburg

A cozy sleeping area features a wooden bed with a light-colored comforter. Soft lighting is provided by pendant fixtures on either side. A shelf above the bed displays various plants, adding a touch of greenery to the earthy tones of the room.

4.87 out of 5 average rating, 123 reviews

Charming Studio | Outdoor Kitchen | Free Parking

Welcome to our tiny but thoughtfully designed studio—small in size yet big on comfort, care, and cleanliness. Each space is lovingly maintained by my mother, ensuring an extra spotless stay. Perfect for solo travelers or couples, you’ll enjoy a cozy bed, efficient design, and unbeatable value. Step outside to our lush shared gazebo with seating, dining areas, BBQ, and outdoor kitchen appliances—a favorite gathering spot for guests. Superhost team of four always here to help. 🌴☀️🏖️

4.93 out of 5 average rating, 105 reviews

An outdoor patio area features a tiled surface surrounded by greenery and a wooden fence. A round table with chairs is positioned next to a gas grill, while a large tree provides shade. Potted plants add a touch of nature to the space.

Tiny home in Gulfport

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

4.77 out of 5 average rating, 297 reviews

Flat in St. Pete Beach

FLASH SALE! Micro Resort| Sleeps 4| <1mi to beach!

🚨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! 🌴☀️🦩

Guest suite in St. Petersburg

A private garden space is presented, featuring a small wooden table with two folding chairs positioned on a red pathway. Lush greenery, including a palm tree and flowering plants, surrounds the area, creating a serene outdoor setting.

4.94 out of 5 average rating, 168 reviews

Charming Side Garden Suite (no cleaning fee)

This private guest suite is centrally located between the beaches on Treasure Island and the nightlife, shopping, and dining of the Grand Central and Pier districts, along the Sun Runner public transportation route. The suite includes one bedroom, bathroom, and kitchenette, separated from the main house, with a private entrance through the side garden. Come enjoy your morning coffee in the garden, and all that St. Petersburg has to offer.

Guest suite in St. Petersburg

A spacious sleeping area features a large bed with white linens and a textured blue throw. Natural light filters through two windows adorned with light curtains. Decorative elements, including a small vase, add a subtle touch to the room's design.

4.82 out of 5 average rating, 376 reviews

Cozy St Pete Suite near beaches

Enjoy a nice comfortable in law suite, fully furnished with full kitchen and grand master bathroom. Toiletries included for your convenience. Quick commute to Tyrone Mall for shopping and dining. Beautiful sandy beaches of Madeira, Redington and St Pete Beach are minutes away. Enjoy a night out on St Pete Downtown also within short distances. Feel right at home with a clean fresh and cool Florida Suite.

Popular amenities for South Pasadena pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

4.86 out of 5 average rating, 159 reviews

A spacious living area features a mix of comfortable seating, including a dark leather sectional and various armchairs. A decorative area rug adds warmth over the hardwood floor. Natural light streams in through large windows, and a decorative fireplace stands as a central element.

Home in Historic Kenwood

Casa Kenwood

A modern living room features a stone accent wall with a large flat-screen TV mounted above a contemporary electric fireplace. Comfortably arranged seating includes a gray sofa and an accent chair. Natural light filters through the window, illuminating the space.

4.85 out of 5 average rating, 184 reviews

Tropical escape house with hot tub

5 out of 5 average rating, 4 reviews

Coastal 2 Bedroom / Walk to Downtown!

4.88 out of 5 average rating, 261 reviews

A modern kitchen features sleek white cabinetry and dark countertops. Open shelving holds decorative items and kitchen essentials. A stainless steel stove with an overhead exhaust and a matching refrigerator is visible, contributing to a clean and functional cooking space.

Home in Largo

Modern/8min by car to beach/queen bed/Free parking

An open living area features a spacious yellow sofa and a comfortable gray couch, complemented by a coffee table. Bright wall art enhances the atmosphere, and a large flat-screen TV is mounted on the wall. The kitchen is visible in the background, showcasing modern cabinetry.

4.97 out of 5 average rating, 32 reviews

Writer’s modern retreat

4.88 out of 5 average rating, 195 reviews

A cozy living area features a comfortable green sofa and a wooden coffee table, centered on a dark area rug. Walls are painted in soft blue tones and a ceiling fan offers ventilation. A welcoming sign is displayed, and natural light filters through two windows.

Home in Magnolia Heights

Baby Bungalow | Near Downtown St. Pete | Cozy Home

4.95 out of 5 average rating, 106 reviews

The image displays a collage of the Splash House. Upper left shows a cozy seating area with modern furnishings in light colors. Upper right features a bright bedroom with a spacious bed and decorative accents. Lower left highlights a tranquil pool area surrounded by a patio. Lower right showcases a bathroom with modern fixtures and a stylish double sink.

Home in Seminole

Splash House - Relaxation Haven/Private Pool

A screened-in pool area features a uniquely shaped pool with clear blue water, inviting relaxation. Sunlight filters through the mesh covering, illuminating the surrounding patio. Lush greenery lines the background, enhancing the outdoor ambiance.

4.98 out of 5 average rating, 167 reviews

The Blue Fin, 3 Bed/ Heated Pool/ XBOX

Pet-friendly home rentals with a pool

4.95 out of 5 average rating, 132 reviews

An outdoor patio area features a dining table adjacent to a heated pool. Lounge chairs are positioned nearby, under a screen enclosure. The pool is framed by a laid stone surface, with a view of lush greenery beyond the surrounding fence.

Villa in St. Petersburg

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

4.88 out of 5 average rating, 147 reviews

The marina features a variety of boats docked in calm waters, with a warehouse structure visible in the background. The scene includes several sailboats and a large yacht, complemented by industrial surroundings, reflecting a serene nautical atmosphere.

Apartment in Maximo

"The Merry Yacht" excellent location

Apartment in Treasure Island

An outdoor seating area is shown with a glass-top table surrounded by four blue chairs. Two charcoal grills are positioned nearby under palm trees, with a view of the water in the background. The screened cabana features a thatched roof, providing a relaxing atmosphere.

4.9 out of 5 average rating, 172 reviews

Waterside Studio in the heart of TI, walk to beach

Bungalow in Indian Shores

A serene beachfront scene showcases soft sand and gentle waves under a clear sky. Lounge chairs are arranged in the foreground, while umbrellas and beach tents are visible further along the shoreline. The bungalow's outdoor seating area is seen, surrounded by lush greenery.

4.96 out of 5 average rating, 175 reviews

Private Beachfront 2BR BUNGALOW*POOL*PETS ok

A contemporary home is presented with a light-colored exterior and a stylish wooden garage door. Lush greenery and palm trees enhance the landscape. A spacious driveway leads to the entrance, framed by well-maintained flower beds and tropical plants under a clear blue sky.

5 out of 5 average rating, 12 reviews

Paradise Palms - Private Pool Oasis - St. Pete

A charming yellow cottage is framed by lush palm trees and tropical plants, featuring a welcoming front door at the end of a paved walkway. Sunlight filters through the greenery, creating a bright and inviting atmosphere near the entrance.

4.9 out of 5 average rating, 147 reviews

St Pete Casita Studio with Salt Water Pool & Yard

A serene backyard features a rectangular pool surrounded by a spacious patio, dotted with palm trees. Two lounge chairs are positioned near the pool, complemented by a colorful umbrella. A screened-in lanai is visible in the background, enhancing outdoor relaxation.

4.97 out of 5 average rating, 102 reviews

Pool Home with 2 King Beds | Relaxing Getaways

An outdoor shuffleboard court is featured in the spacious fenced-in yard, lined with gravel and surrounded by lush greenery. A picnic table and black chairs are positioned nearby under a shaded area, creating a welcoming space for relaxation and games.

4.95 out of 5 average rating, 44 reviews

*POOL* Fenced Yard *Shuffleboard Court*

Private, pet-friendly home rentals

5 out of 5 average rating, 29 reviews

A vibrant exterior view of a cottage surrounded by lush greenery showcases a bright green facade adorned with floral artwork. Large trees provide shade, while a white picket fence and colorful plants, including pink and white flowers, enhance the welcoming atmosphere of the property.

Guest house in Gulfport

The Little Cottage

5 out of 5 average rating, 16 reviews

A line of tiny sea turtles makes its way across a sandy beach towards the water. The soft waves lap gently at the shore, reflecting warm hues of sunset in the distance. The sand shows distinct tracks left by the turtles as they journey forward.

Flat in St. Petersburg

Sweet Studio Apartment for 2 plus your pets!

An outdoor area features a fire pit surrounded by six colorful chairs on a gravel surface. A concrete space for activities is visible in the background, bordered by wooden fencing and trees, creating a private and spacious environment.

5 out of 5 average rating, 25 reviews

Pickleball, Basketball, Firepit 6 min to the BEACH

4.93 out of 5 average rating, 74 reviews

A spacious bedroom is highlighted by a large bed dressed in white linens, set against a backdrop of natural light from multiple windows adorned with black curtains. A modern ceiling fan is positioned above, while a patterned area rug complements the decor.

Flat in St. Petersburg

Stylish Apt Centrally located to Beach & Downtown

4.84 out of 5 average rating, 49 reviews

A vibrant blue wall displays a circular sign that reads 'Welcome to the Gulfport Get Away' in yellow lettering. The address number '5134' is clearly visible above the sign, contributing to the inviting exterior of the property.

Guest house in Gulfport

Your Gulfport Getaway

5 out of 5 average rating, 24 reviews

Pets OK | Peacocks! | Close to Beaches & Downtown

A modern kitchen is presented with sleek, white cabinetry and a patterned backsplash. A center table is set for four, featuring plates and glasses. Stainless steel appliances, including a microwave and refrigerator, are visible, alongside a ceiling fan that adds functionality.

5 out of 5 average rating, 29 reviews

Lora's House