FREE NIGHT! Jeffreys Bay African retreat!
FREE NIGHT! Jeffreys Bay African retreat!
FREE NIGHT! Jeffreys Bay African retreat!
FREE NIGHT! Jeffreys Bay African retreat!
FREE NIGHT! Jeffreys Bay African retreat!

FREE NIGHT! Jeffreys Bay African retreat!

2 bedrooms·1 bath
Treasure Island • Florida
$165/ night(excl. fees & taxes)
FREE NIGHT! Aloha! Hawaiian surf inspired retreat
FREE NIGHT! Aloha! Hawaiian surf inspired retreat
FREE NIGHT! Aloha! Hawaiian surf inspired retreat
FREE NIGHT! Aloha! Hawaiian surf inspired retreat
FREE NIGHT! Aloha! Hawaiian surf inspired retreat

FREE NIGHT! Aloha! Hawaiian surf inspired retreat

1 bedroom·2 baths
Treasure Island • Florida
$146/ night(excl. fees & taxes)
Tropical retreat with private pool, stylish interiors, and playful island vibes
Tropical retreat with private pool, bold interiors, and stylish bedrooms
Private pool deck with lounge chairs, pool noodles, and floats included. Fully fenced, tropical landscaping, sleeps 10. Gulfport/South St. Pete, FL.
Open-plan living and kitchen — 65-inch smart TV, breakfast bar with 4 stools, and mustard yellow sofas. 4-bedroom vacation rental, St. Petersburg, FL.
Primary king suite — palm-leaf mural, neon accent, woven pendant lights, and barn door entry to private spa ensuite. St. Petersburg, FL vacation rental.

Tropical Disco | Pool & Fire Pit | St Pete Beach

4 bedrooms·2 baths
St. Petersburg • Florida
5(187 reviews)
$179 – $786/ night(excl. fees & taxes)
Funshine Sunset Beach - Steps from the beach!!
Funshine Sunset Beach - Steps from the beach!!
Funshine Sunset Beach - Steps from the beach!!
Funshine Sunset Beach - Steps from the beach!!
Funshine Sunset Beach - Steps from the beach!!

Funshine Sunset Beach - Steps from the beach!!

1 bedroom·1 bath
Treasure Island • Florida
5(142 reviews)

$538.86 USD total for 3 nights

Oct 3 – 6, 2026

Seasonal Waterfront Vacation Condo
Seasonal Waterfront Vacation Condo
Seasonal Waterfront Vacation Condo
Seasonal Waterfront Vacation Condo
Seasonal Waterfront Vacation Condo

Seasonal Waterfront Vacation Condo

1 bedroom·1 bath
South Pasadena • Florida
$100/ night(excl. fees & taxes)
Paddle boarding just off the dock around mangroves.
Waterfront yard with dock for fishing and launching paddle boards and kayaks and turf for chilling
Mangrove Haven
Mangrove Haven
Mangrove Haven

Mangrove Haven

3 bedrooms·3 baths
St. Petersburg • Florida
$378 – $1,619/ night(excl. fees & taxes)
Waterfront Home with Heated Pool 2 Mi from Beaches
Waterfront Home with Heated Pool 2 Mi from Beaches
Waterfront Home with Heated Pool 2 Mi from Beaches
Waterfront Home with Heated Pool 2 Mi from Beaches
Waterfront Home with Heated Pool 2 Mi from Beaches

Waterfront Home with Heated Pool 2 Mi from Beaches

3 bedrooms·2 baths
St. Petersburg • Florida
4.9(51 reviews)

$1,297.00 USD total for 3 nights

Sep 23 – 26, 2026

Angel's Waterfront Home Fishing Dock Heated Pool image 1
Angel's Waterfront Home Fishing Dock Heated Pool image 2
Angel's Waterfront Home Fishing Dock Heated Pool image 3
Angel's Waterfront Home Fishing Dock Heated Pool image 4
Angel's Waterfront Home Fishing Dock Heated Pool image 5

Angel's Waterfront Home Fishing Dock Heated Pool

3 bedrooms·2 baths
Holiday • Florida
5(11 reviews)
$270/ night(excl. fees & taxes)
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 27 – 30, 2026

Living Room
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 23 – Oct 23, 2026

House
Bedroom
Ruhiges Zimmer mit tropischem Pool und Strandzugang
Pool Outdoor
Inside other

Ruhiges Zimmer mit tropischem Pool und Strandzugang

1 bedroom·1 bath
St. Petersburg • Florida
[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

$577.00 USD total for 3 nights

Nov 1 – 4, 2026

[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

$487.00 USD total for 3 nights

Sep 23 – 26, 2026

We have it all - beautiful beach and comfortable accommodation
Living room with queen sofa bed and upgraded mattress. Comfortable rocking chairs. Smart TV - guests can use their Netflix, Amazon movie's, Hulu, etc. Basic cable is available in the living room TV as well.
Heated community pool for residents and guests only. Hours of operations: 9am-10pm.
The condo and the beach - very short walk across beach parking lot. St. Pete Beach - votes #1 beach in US by TripAdvisor in 2021.
Living room, kitchen and the coffee station

Condo in Beachfront Resort with Heated Pool

1 bedroom·1 bath
St. Pete Beach • Florida
5(29 reviews)

$607.94 USD total for 3 nights

Sep 26 – 29, 2026

Steps from the beach! Newly listed updated unit image 1
Cross the parking spaces and dunes... to have your toes in the sand. Famous beach bars /restaurants to the left of the peach condos on the left.
Steps from the beach! Newly listed updated unit image 3
primary bedroom
primary bedroom

Steps from the beach! Newly listed updated unit

2 bedrooms·1 bath
St. Pete Beach • Florida
4.94(16 reviews)

$1,317.00 USD total for 3 nights

Sep 23 – 26, 2026

Hello Traveler
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)

$680.00 USD total for 3 nights

Sep 23 – 26, 2026

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 28 – Oct 1, 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

$764.85 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

$1,606.85 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

$648.80 USD total for 3 nights

Sep 23 – 26, 2026

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

$1,938.70 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

$3,247.25 USD total for 3 nights

Sep 23 – 26, 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

$487.10 USD total for 3 nights

Sep 23 – 26, 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

$452.45 USD total for 3 nights

Sep 23 – 26, 2026