Holiday houses in South Pasadena

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Top-rated holiday rentals in South Pasadena

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite

Guesthouse in Gulfport

4.92 out of 5 average rating, 729 reviews

graceful haven...

This boutique-sized, moon-drenched studio is more than just a place to lay your head. From the delicate metal birds swirling above your bed, to the tender light reflecting off the burnished aluminum countertop, your senses will be soothed and tickled by its quietly exuberant design & decor. Nestled in a lush tropical garden, the space is just a block away from Gulfport's Art Village with its sunset waterfront, delightful shops, and many fine restaurants. (or, see my “bohemian treat” listing)

14–21 Aug

$222 NZD per night

Guest favourite

Cottage in Gulfport

4.96 out of 5 average rating, 135 reviews

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...!

9–16 Aug

$259 NZD per night

Guest favourite

Apartment in South Pasadena

4.95 out of 5 average rating, 137 reviews

Beautiful 2/1 Eclectic Modern Apt - WeAreJoyful

Our apartment 'Joyful' 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 driving, 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. This apartment is on the second floor.

19–26 Jun

$323 NZD per night

Guest favourite

Guest suite in Saint Petersburg

4.98 out of 5 average rating, 792 reviews

Private Guest Suite 2 miles from Beach

Private, small completely renovated Guest Suite with Private parking, private separate entrance with deck. Space is best for 1-2 people: small, but thought out. 2 miles from Treasure Island beach. 2.5 miles from the St Pete beach! Beautiful quaint neighborhood. Near great fishing spot Kitchenette Full Bathroom Comfy queen size bed Cool AC unit ❗️WE HAVE GREAT REVIEWS, but please view before booking “Is this guest suite right for you” below under “things to note” to have the trip you desire

26–31 Jul

$126 NZD per night

Guest favourite

Guest suite in Gulfport

4.92 out of 5 average rating, 453 reviews

Gulfport Studio STEPS to Beach & Restaurants

Calling all beach lovers! Fall in love with this unique Gulfport Beach Cottage! Colorful, light & bright. Located on a corner lot STEPS from popular Beach Blvd & Gulfport beach, fishing pier, eclectic Gulfport shops, cafes and everything FUN! Gulfport has artsy and quirky shops, fabulous waterfront restaurants and a thriving art scene. Gulfport is a funky community all its own. Gulfport has an Art Walk on the First Friday and Third Saturday and a Tuesday market every week. Don’t miss it!

5–12 Jul

$244 NZD per night

Guest favourite

Guest suite in Saint Petersburg

4.94 out of 5 average rating, 117 reviews

St. Pete OASIS ~ reduced price for November

LGBTQ+ / 420 friendly! We live on the property; the suite is detached from the main house. Back yard/Pool area is a shared space. Pvt. fenced back yard and pool! Room features full bath, small kitchenette with microwave, hotplate, coffee maker and minifridge. Beach chairs available to use. 8 min from downtown 10 min to the beach! "Grand Central" district with great shops, galleries, bars and restaurants! Free shuttle that runs all day just a block away, to downtown and to the beach.

23–30 Aug

$171 NZD per night

Guest favourite

Guest suite in St. Petersburg

4.95 out of 5 average rating, 108 reviews

Modern Romatic Suite: 5 Min to St Pete Beach

The Modern Studio boasts trendy decor, queen size memory foam mattress, a comfortable couch and an efficiency kitchen. There is also a private fenced yard with patio set to enjoy the Florida sunshine. We are Conveniently located: ▪️5 min drive to St Petersburg Beach and Gulfport ▪️15-20 minutes to vibrant Downtown St Pete. ▪️Blocks to the Pinellas County Trail for the avid bike rider. ▪️1/2 mile walk to the new Sun Runner bus system for easy transportation from downtown to the beach

19–26 Jul

$199 NZD per night

Guest favourite

Guesthouse in St. Petersburg

4.98 out of 5 average rating, 133 reviews

Central Cozy Cottage w/ Heated Pool & Hot Tub!

Welcome to cute & cozy Turtle Cottage located right in the center of St. Pete, close to both Downtown AND several gorgeous Florida beaches. NO CLEANING FEE with competitive, seasonal pricing = a FANTASTIC DEAL for this space! A BEAUTIFUL NEW HEATED POOL & HOT TUB await in the private, fenced-in tropical backyard. Sorry, no pets/animals or babies/children/teens. Adults 21+ only and limited to 2 verified guests. 100% smoke-free property, inside & out. DEI honored here. Come & enjoy!

20–27 Aug

$231 NZD per night

Guest favourite

Guest suite in St. Petersburg

4.97 out of 5 average rating, 107 reviews

PRIVATE 1-bedroom suite || BEACH within 5 miles

Grab your suitcase and head down to St Pete for a mini-staycation! Enjoy our welcoming beaches, crystal clear gulf water, practice your golf swing, or have fun at one of the events and festivals that the area offers so generously. You'll have our beautiful suit waiting for you with everything you need for a comfortable stay: - Private entrance - Free parking for 2 cars (or your car and your jet-skis) - Smart TV - High-speed WiFi - Comfortable Queen size bed with crisp white linens

3–10 Sep

$238 NZD per night

Guest favourite

Tiny home in Gulfport

4.94 out of 5 average rating, 144 reviews

Pelican's Nest - Pet Friendly

The Pelican's Nest is a cozy tiny home that has been remodeled with you in mind. Enjoy the beachy vibes inside the home or relax outside where you can connect to nature with your private yard. Enjoy a fire or dinner on your outdoor dining table. Have your pet staying with you? No worries! They are welcome here. Located a mile 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 the St Pete pier.

20–27 Oct

$213 NZD per night

Guest favourite

Guest suite in St. Petersburg

4.96 out of 5 average rating, 112 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.

15–22 Jun

$179 NZD per night

Guest favourite

Bungalow in Saint Petersburg

4.99 out of 5 average rating, 107 reviews

Sandy Beaches Bungalow

Experience the epitome of Mid-Century Modern elegance in this stunning bungalow nestled within the prestigious waterfront enclave of Causeway Isles. Situated a mere 1.5 miles from the captivating shores of Treasure Island Beach and conveniently positioned along the picturesque Pinellas Bike Trail, this fully furnished haven beckons for 30 day+ rentals. **Snowbirds bring your pup and make this your winter home**

14–21 May

$377 NZD per night