Location

Dates

Guests

Vacation rentals in South Pasadena, Florida, United States

Florida Beachside Home

Florida Beachside Home

Florida Beachside Home

Florida Beachside Home

Florida Beachside Home

Florida Beachside Home

2 bedrooms·2 baths

Walton County • Florida

5(12 reviews)

$739.50 USD total for 3 nights

Sep 22 – 25, 2026

Kitchen and Dining Area

The Walters

3 bedrooms·2 baths

St. Petersburg • Florida

5(21 reviews)

$774.05 USD $737.61 USD total for 3 nights

Sep 22 – 25, 2026

A serene and private fenced in Courtyard/Backyard with an outdoor grill.

Patio with Grill

Architecture details about the house

Open floor with Living Room, two Dining areas and Kitchen

Award winning ARCHITECT designed home DOWNTOWN&BAY

3 bedrooms·2½ baths

St. Petersburg • Florida

5(72 reviews)

$4,450.00 USD total for 30 nights

Sep 22 – Oct 22, 2026

The Parkside Retreat at 78th Street

3 bedrooms·2 baths

Pinellas Park • Florida

$611.95 USD total for 3 nights

Sep 22 – 25, 2026

The Downtown Dali House City of St. Petersburg image 1

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The Downtown Dali House City of St. Petersburg

3 bedrooms·2 baths

St. Petersburg • Florida

4.86(7 reviews)

$300/ night(excl. fees & taxes)

Magnolia near the beach and downtown St. Pete image 1

Magnolia near the beach and downtown St. Pete image 2

Magnolia near the beach and downtown St. Pete image 3

Magnolia near the beach and downtown St. Pete image 4

Magnolia near the beach and downtown St. Pete image 5

Magnolia near the beach and downtown St. Pete

5 bedrooms·3 baths

St. Petersburg • Florida

4.85(150 reviews)

$698.65 USD total for 3 nights

Sep 22 – 25, 2026

Entrance to Sunray

patio outside private to Sunray

The SunRay Tiny House

XLTwin bed with nested twin below

XLTwin bed with nested twin below

The SunRay Tiny House

1 bedroom·1 bath

St. Petersburg • Florida

4(6 reviews)

$241.45 USD total for 3 nights

Sep 22 – 25, 2026

Common Area: 🌳 Spacious Outdoor w/ table and chairs

Welcome to your perfect retreat—ideal for a solo traveler or couple.

St. Petersburg, Florida – a vibrant city bursting with sunshine, culture, and endless possibilities! Nestled on the Gulf Coast, St. Pete is a haven for art lovers, outdoor enthusiasts, and those seeking a laid-back coastal escape

A beautifully remodeled bathroom guests love.

Step outside to your private outdoor deck, complete with a dining table and chairs—perfect for morning coffee or alfresco meals in the fresh air.

Private Deck • Pet Friendly • Spacious Courtyard

0 bedrooms·1 bath

St. Petersburg • Florida

$88 – $3,000/ night(excl. fees & taxes)

Common Area: 🌳 Spacious Outdoor w/ table and chairs

Private Deck • Pet Friendly • Spacious Courtyard

Private Deck • Pet Friendly • Spacious Courtyard

Private Deck • Pet Friendly • Spacious Courtyard

Private Deck • Pet Friendly • Spacious Courtyard

0 bedrooms·1 bath

St. Petersburg • Florida

$82 – $3,000/ night(excl. fees & taxes)

[Entrance] Self-check in with keypad

[Exterior] Unit is located towards the back of the property

[Living area] Smart TV with Netflix

[Bathroom] Full size standing shower with plenty of warm water & great shower pressure.

[Living area] Sofa folds out into a sofa bed for additional sleeping space

Outskirt Downtown | 400ft² | bikes | kayak|netflix

1 bedroom·1 bath

St. Petersburg • Florida

$156 – $355/ night(excl. fees & taxes)

[Living area] Smart TV with Netflix & sofa bed

[Dining area] Free bikes, kayaks & beach gear are included in this rental!

[Kitchen] Fully stocked & equipped kitchen with updated appliances. Coffee maker & complimentary coffee provided.

[Living area] Smart TV with Netflix & sofa bed

Here's one of my 5-star reviews...improving every day!

Walk score 82 | bikes | kayak | 214mbps | foam bed

1 bedroom·1 bath

St. Petersburg • Florida

$106 – $293/ night(excl. fees & taxes)

Beach Living & Shuffleboard

16100 2nd St - Web Quality (4)

Full-Equipped Kitchen for making family meals

16100 2nd St - Web Quality (22)

She's A Shore Thing

3 bedrooms·2 baths

Redington Beach • Florida

$1,145.96 USD total for 3 nights

Oct 3 – 6, 2026

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Azure Palms Hideaway

3 bedrooms·2 baths

St. Petersburg • Florida

$164/ night(excl. fees & taxes)

Spacious 3Unit Retreat great for Groups & Families

Spacious 3Unit Retreat great for Groups & Families

Spacious 3Unit Retreat great for Groups & Families

Spacious 3Unit Retreat great for Groups & Families

Spacious 3Unit Retreat great for Groups & Families

Spacious 3Unit Retreat great for Groups & Families

8 bedrooms·5 baths

St. Petersburg • Florida

$1,981.75 USD total for 3 nights

Sep 23 – 26, 2026

Large 2 story bungalow home with huge front porch

Entire historic micro resort for your event

Entire historic micro resort for your event

Entire historic micro resort for your event

Entire historic micro resort for your event

Entire historic micro resort for your event

10 bedrooms·6 baths

St. Petersburg • Florida

$3,198.95 USD total for 3 nights

Sep 23 – 26, 2026

Spacious Family Stay - Pet Friendly

Pick up a share bike in the park and bike to the waterfront

Spacious Family Stay - Pet Friendly

Spacious Family Stay - Pet Friendly

Spacious Family Stay - Pet Friendly

Spacious Family Stay - Pet Friendly

4 bedrooms·2 baths

St. Petersburg • Florida

$765.90 USD total for 3 nights

Sep 23 – 26, 2026

Sprawling 5BR Bungalow Home Perfect for Groups

Sprawling 5BR Bungalow Home Perfect for Groups

Sprawling 5BR Bungalow Home Perfect for Groups

Sprawling 5BR Bungalow Home Perfect for Groups

Sprawling 5BR Bungalow Home Perfect for Groups

Sprawling 5BR Bungalow Home Perfect for Groups

6 bedrooms·4 baths

St. Petersburg • Florida

$1,595.30 USD total for 3 nights

Sep 23 – 26, 2026

2x King en-Suites walkable Downtown Pet Friendly

2x King en-Suites walkable Downtown Pet Friendly

2x King en-Suites walkable Downtown Pet Friendly

2x King en-Suites walkable Downtown Pet Friendly

2x King en-Suites walkable Downtown Pet Friendly

2x King en-Suites walkable Downtown Pet Friendly

2 bedrooms·2 baths

St. Petersburg • Florida

$605.75 USD total for 3 nights

Sep 22 – 25, 2026

Lets extend a hand of frienship

A bed for your wary heads

Lets cook, eat and be happy

A space to chill and relax outdoors

The Twisted Tulip-a curious stay

1 bedroom·1 bath

St. Petersburg • Florida

4.89(36 reviews)

$200/ night(excl. fees & taxes)

A bed for your wary heads

The Twisted Tulip-a curious stay

EV charge on site for limited use. Please contact us for instructions

May I have a table for 2?

Sure

Did someone say " let there be light" ???

The Twisted Tulip-a curious stay

1 bedroom·1 bath

St. Petersburg • Florida

$305.85 USD total for 3 nights

Sep 22 – 25, 2026

Cozy meets creative in this sunny lounge! Enjoy fast Wi-Fi, Smart TV, and artistic touches throughout—ideal for relaxing with a good show or planning your next St. Pete adventure.

Cozy Couples Artsy Retreat with Local Art Walkable

Cozy Couples Artsy Retreat with Local Art Walkable

Cozy Couples Artsy Retreat with Local Art Walkable

Cozy Couples Artsy Retreat with Local Art Walkable

Cozy Couples Artsy Retreat with Local Art Walkable

2 bedrooms·1 bath

St. Petersburg • Florida

$485.00 USD total for 3 nights

Sep 22 – 25, 2026

Cozy Dali Inspired Loft for Couples & Small Groups

Cozy Dali Inspired Loft for Couples & Small Groups

Cozy Dali Inspired Loft for Couples & Small Groups

Cozy Dali Inspired Loft for Couples & Small Groups

Relax with a book or journal—your peaceful, artistic corner

Cozy Dali Inspired Loft for Couples & Small Groups

2 bedrooms·1 bath

St. Petersburg • Florida

$437.75 USD total for 3 nights

Sep 22 – 25, 2026

Pond-side ART-home with private pool. DOGS WELCOME

5 bedrooms·3 baths

Pinellas Park • Florida

5(20 reviews)

$318/ night(excl. fees & taxes)

The Coffee Pot Cottage

The Coffee Pot Cottage

The Coffee Pot Cottage

The Coffee Pot Cottage

The Coffee Pot Cottage

The Coffee Pot Cottage

2 bedrooms·1 bath

St. Petersburg • Florida

5(26 reviews)

$679.69 USD $563.75 USD total for 4 nights

Oct 17 – 21, 2026