Holiday houses in South Pasadena

4.92 out of 5 average rating, 177 reviews

The spacious living area features a blue sofa with decorative pillows, a white coffee table, and a dining space with a round table and four chairs. A ceiling fan circulates air, and the kitchen is visible in the background, complemented by light-colored cabinetry.

Condo in St. Pete Beach

Updated Condo minutes from the beach - heated pool

Welcome to this fabulous and spacious newly updated condo close to the beach and many restaurants. Closest beach is 12 min walk or 2 min drive. John Pass Village is only 6 minutes drive, Downtown St Pete and newly re-opened St Pete Pier is a must visit for either night life or nice dinner. Egan Park and tennis courts are across the street. Pool is in the building- hours of operation is from dusk to down.Pool is heated to 82f during the day. Roku TV's in bedroom and 65" Smart Tv in living room

4.87 out of 5 average rating, 131 reviews

Inground Pool w/ Game Room - Fully Renovated House

Beautifully remodeled 3 bedroom 2 bath farmhouse with INGROUND POOL in the heart of Gulfport. Looking for the BEACH?(St Pete Beach, Treasure Island etc) We are 6 mins away! If you are looking for amazing restaurants and bars in the middle of St Petes we are only 10 minutes to DOWNTOWN! If your are here for some baseball we are 15 minutes away from Tropicana field and St Pete Pier! If you are looking to explore In clearwater or Downtown Tampa we are only 25 minutes away including TAMPA Airport!

4.97 out of 5 average rating, 178 reviews

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.

Home in Gulfport

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.

A sunlit sunroom features a wooden dining table surrounded by six woven chairs. A tropical-themed mural adorns the wall, depicting surfboards and palm leaves. Large windows and sliding glass doors offer views of the outdoor space, while a vibrant rug adds a pop of color to the floor.

4.9 out of 5 average rating, 107 reviews

Heated Pool~2 Miles St Pete Beach~Hot Tub~Games!

Welcome to Sandpiper House! A beautifully designed 5 bedroom/3 bath home & ONLY 2 MILES FROM ST PETE BEACH! The absolute PERFECT location between the BEST beaches & Downtown St Pete! You'll find a beautiful HEATED pool, new pool-deck pavers, HOT TUB & lots of space to sunbath. House is equipped with tons of GAMES & beach amenities to get the most out of your FL vacation! PING PONG & game room! Caldwell Park 2 blocks away--green space & jungle gym! PLEASE MESSAGE ME FOR LOWER WEEKDAY RATES!!

Guesthouse in St. Petersburg

The studio features a spacious layout with a comfortable futon couch adorned with decorative cushions. A fully equipped kitchen is visible in the background, complemented by a dining table with white chairs. Large windows provide natural light, enhancing the airy feel of the blue walls.

4.94 out of 5 average rating, 115 reviews

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!

Apartment in South Pasadena

A vibrant living area showcases a rust-colored sofa adorned with teal and navy cushions. Above, a colorful abstract painting hangs against a soft pink wall. A glass coffee table with a decorative item and a small succulent adds charm, while a leafy plant enhances the corner.

4.93 out of 5 average rating, 216 reviews

Stylish & Eclectic Modern 2/2 Apt - WeAreGrateful

2 Bedroom 2 Baths Eclectic Modern Apartment Our apartment 'GRATEFUL' is a combination of pleasing colors and a delicate attention to detail in every corner that will let you experience the magic of an eclectic space in the heart of St Petersburg. With the beautiful sand beaches under 5 minutes away, you can feel the breeze as soon as you step outside. You also can try St Petersburg’s diverse restaurant scene and visit the museums displaying art permanent collections and traveling exhibits.

The kitchen features modern white cabinetry and a large island with a light countertop. A dining table for multiple guests is set nearby, adorned with tableware. Natural light fills the space through the window blinds, highlighting the open layout connecting to the living area.

4.84 out of 5 average rating, 241 reviews

** Home Away From Home **

Why book 3 or 4 hotel rooms when you can book this beautiful and completely remodeled 4-bedroom, 2.5 bath 1788 sq. ft. home, centrally located in desirable South Pasadena Florida. Professionally decorated in a contemporary beach décor, stunning, spacious and very private! There is no lack of amazing things to do around the home, but if you want to be close to the St. Pete Beach, you are only 2.5 miles away and 6.5 miles to downtown St. Petersburg where night life entertainment abounds.

4.98 out of 5 average rating, 123 reviews

Cottage in Gulfport

Cozy Cottage for Lovers

Relax, reconnect and revitalize in this private, intimate cottage that has everything you need to leave the hustle and bustle behind. Surrounded by lush tropical vegetation in the shade of giant live oaks and located in the Gulfport Arts District, you're a short walk or bike ride from excellent urban parks, restaurants, live music, fashion and art boutiques, dancing at the Gulfport Casino, community theater, and a beautiful beach that looks out over sailboats moored in Boca Ciega Bay.

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.

4.9 out of 5 average rating, 187 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.

4.96 out of 5 average rating, 142 reviews

An inviting view into the living area is framed by a decorative arch. A vibrant green plant adds a touch of nature, while a cozy brown couch and accent chairs are arranged around a circular coffee table. Colorful artwork decorates the walls.

Guesthouse in Gulfport

Gulf Guesthouse - king bed, 3 blocks to downtown.

Be our guest! Welcome to our family compound where you will enjoy the treetop views from our second story carriage house guest apartment. You'll be surrounded by the tropical serenity of lush palms and plants, both inside and out, while being just around the corner from the excitement of downtown Gulfport. Our updated one bedroom apartment is fully furnished and stocked with all of the things you'll need for an extra comfortable, enjoyable stay. We look forward to hosting you!

Superhost

Apartment in St. Pete Beach

4.78 out of 5 average rating, 316 reviews

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! 🌴☀️🦩

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.

4.95 out of 5 average rating, 190 reviews

Charming Side Garden Suite (no cleaning fee)

This private guest suite is centrally located between the beaches of 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.

Popular amenities for South Pasadena holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in South Pasadena

5.0 out of 5 average rating, 27 reviews

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5.0 out of 5 average rating, 34 reviews

Waterfront Oasis w/ Private Dock + Sunroom

5.0 out of 5 average rating, 24 reviews

Mangrove Haven | Pool + Hot Tub + Waterfront Dock

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ABC Pet Friendly Pool & Hot Tub| 5' St. Pete Beach

Superhost

Home in Gulfport

4.93 out of 5 average rating, 30 reviews

Waterfront Paradise• Pool, Hot Tub, Dock & Games

5.0 out of 5 average rating, 35 reviews

Paradise Palms - Private Pool Oasis - St. Pete

Holiday home in South Pasadena

4.91 out of 5 average rating, 47 reviews

Heated Pool 4BD 3BA| Near St. Pete Beaches +Dining

An outdoor patio is showcased with four adirondack chairs positioned around a circular fire pit. The setting features a grassy area leading to a dock on the water. Decorative lights hang above, and the view includes a pastel sunset and boats moored nearby.