Waterfront Key West–style community, Stunning water views, glowing sunsets, and a laid-back island vibe ✨
King SUITE! Calm, Spacious and inviting, this KING bedroom features a plush KING-sized bed, with new bedding , dresser and 2 nighstands offering comfort and style for a restful night’s sleep in a beautifully designed space.
Stunning waterfront views from the bright, open-concept living room, dining area, and fully equipped kitchen. The perfect space to relax, gather, and make unforgettable memories by the water.
Nothing compares to swimming in the pool while breathing in the fresh ocean breeze.
WELCOME to your own private scenic beach, offering exclusive access to pristine sands and tranquil waters. Perfect for relaxing in solitude, soaking up the sun, or enjoying peaceful oceanfront moments.

Waterfront Escape | Private Beach + 2 Pools

1 bedroom·1 bath
St. Petersburg • Florida
4.5(16 reviews)

$ 4.375,36 USD $ 4.221,00 USD totaal voor 30 nachten

16 nov – 16 dec 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 totaal voor 30 nachten

16 nov – 16 dec 2026

The Bayou Breeze Cottage
The Bayou Breeze Cottage
The Bayou Breeze Cottage
The Bayou Breeze Cottage
The Bayou Breeze Cottage

The Bayou Breeze Cottage

1 bedroom·1 bath
St. Petersburg • Florida
5(40 reviews)

$ 467,59 USD $ 390,07 USD totaal voor 3 nachten

16–19 nov 2026

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(30 reviews)

$ 733,93 USD $ 607,14 USD totaal voor 3 nachten

27–30 nov 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)

$ 435,05 USD totaal voor 3 nachten

22–25 nov 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

$ 504,00 USD totaal voor 3 nachten

16–19 nov 2026

[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

$ 642,00 USD totaal voor 3 nachten

16–19 nov 2026

Front porch with rocking chairs and seating by the turquoise front door
Large banyan tree with sprawling roots and branches in a grassy park
Bedroom with a white bed, black metal frame, nightstands, lamps, and a window with blinds
Park pond with a fountain, surrounded by trees and grass
Dining room with a wooden table, white chairs, large windows, and a sideboard

Spacious Family Stay - Pet Friendly

3 bedrooms·2 baths
St. Petersburg • Florida
4.8(205 reviews)

$ 764,19 USD totaal voor 3 nachten

16–19 nov 2026

Welcome to our bungalow, The Banyan House in the Historic Uptown neighborhood
Beautiful park steps away
Small workspace nook with a wooden desk, chair, and plant by the windows
A stroll in the park
Front porch seating with cushioned chairs and a round table set with coffee cups

2x King en-Suites walkable Downtown Pet Friendly

2 bedrooms·2 baths
St. Petersburg • Florida
4.82(170 reviews)

$ 780,18 USD totaal voor 3 nachten

16–19 nov 2026

Welcome to our historic downtown bungalow
Book a dolphin tour with us
Stacked washer and dryer in a laundry nook
Group of guests outdoors holding pink and white balloons
Bedroom with white bedding, bedside tables, and a window overlooking palm trees

Sprawling 5BR Bungalow Home Perfect for Groups

5 bedrooms·4 baths
St. Petersburg • Florida
4.86(80 reviews)

$ 1.694,30 USD totaal voor 3 nachten

16–19 nov 2026

Large 2 story bungalow home with huge front porch
Need a great place close to everything for your friends for your bachelorette party?
Bedroom with a bed in white bedding, nightstands with lamps, and a window with blinds.
Look what our guests say about our space
Living room with a beige sofa, wooden coffee table, wall-mounted TV, and bookshelves.

Entire historic micro resort for your event

9 bedrooms·6 baths
St. Petersburg • Florida
4.83(18 reviews)

$ 3.150,48 USD totaal voor 3 nachten

16–19 nov 2026

Front porch with turquoise front door
Pick up a share bike in the park and bike to the waterfront
Covered front porch with outdoor seating
A stroll in the park
Backyard lawn with deck seating and umbrellas

Spacious 3Unit Retreat great for Groups & Families

7 bedrooms·5 baths
St. Petersburg • Florida
5(2 reviews)

$ 2.247,26 USD totaal voor 3 nachten

16–19 nov 2026

A bed for your wary heads
Get out and smell the roses
May I have a table for 2? Sure
See the ugly duckling turned into a swan
Did someone say " let there be light" ???

The Twisted Tulip-a curious stay

1 bedroom·1 bath
St. Petersburg • Florida
4.86(7 reviews)

$ 361,77 USD totaal voor 3 nachten

16–19 nov 2026

Meet the Banyan Just steps from your door, this majestic banyan tree in the neighborhood park inspired the name of our cozy retreat. Rooted in history, just like your next memory.
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.
Outdoor patio at night with seating, string lights, and a table set with wine and snacks.
Your Neighborhood Oasis Just around the corner, unwind by the peaceful pond and fountain—perfect for a morning walk or a sunset stroll under the palms.
Vibrant gallery wall meets comfy sofa—this cozy corner is perfect for lounging, reading, or sharing a glass of wine in a bold, art-inspired setting.

Cozy Couples Artsy Retreat with Local Art Walkable

2 bedrooms·1 bath
St. Petersburg • Florida
4.76(270 reviews)

$ 545,26 USD totaal voor 3 nachten

16–19 nov 2026

Open living room with colorful rug, green sofa, and kitchen in the background
Park views
Relax with a book or journal—your peaceful, artistic corner
Enjoy the tranquility of our park
Park path beside a pond with a bench, trees, and green lawn

Cozy Dali Inspired Loft for Couples & Small Groups

2 bedrooms·1 bath
St. Petersburg • Florida
4.8(249 reviews)

$ 509,67 USD totaal voor 3 nachten

16–19 nov 2026

Beachfront Pass-a-Grille 2BR, Gulf Views
Front of house.
Beachfront Pass-a-Grille 2BR, Gulf Views
Beachfront Pass-a-Grille 2BR, Gulf Views
Beautiful day at the beach

Beachfront Pass-a-Grille 2BR, Gulf Views

2 bedrooms·2 baths
St. Pete Beach • Florida
4.99(71 reviews)

$ 3.368,95 USD $ 3.058,21 USD totaal voor 7 nachten

10–17 dec 2026

Beachfront Cottage for 2: Pass-a-Grille
Beachfront Cottage for 2: Pass-a-Grille
Beachfront Cottage for 2: Pass-a-Grille
Beachfront Cottage for 2: Pass-a-Grille
Beach. Steps from the cottage

Beachfront Cottage for 2: Pass-a-Grille

1 bedroom·1 bath
St. Pete Beach • Florida
4.85(27 reviews)

$ 7.086,07 USD totaal voor 28 nachten

1–29 dec 2026

Property grounds
the walkway to Casa Tropicana's private entrance
street view of the property
Property grounds
Both, the bedroom and living room have a TV

Beachy private suite & bathroom w/ patio close to beach & Downtown

1 bedroom·1 bath
St. Petersburg • Florida

$ 367,00 USD totaal voor 3 nachten

16–19 nov 2026

The Downtown Dali House City of St. Petersburg image 1
The Downtown Dali House City of St. Petersburg image 2
The Downtown Dali House City of St. Petersburg image 3
The Downtown Dali House City of St. Petersburg image 4
The Downtown Dali House City of St. Petersburg image 5

The Downtown Dali House City of St. Petersburg

3 bedrooms·2 baths
St. Petersburg • Florida
4.86(7 reviews)

$ 1.190,00 USD totaal voor 3 nachten

16–19 nov 2026

Azure Palms Hideaway image 1
Azure Palms Hideaway image 2
Azure Palms Hideaway image 3
Azure Palms Hideaway image 4
Azure Palms Hideaway image 5

Azure Palms Hideaway

3 bedrooms·2 baths
St. Petersburg • Florida

$ 5.170,00 USD totaal voor 30 nachten

16 nov – 16 dec 2026

FREE heated swimming Pool. SPA does not have a jet pump.
Large Heated Pool
4 bikes are provided with Helmets. 2 adults and 2 kids bike.
Garage game room. w/foosball table, pingpong, easel for kids
beach umbrellas, beach chairs and coolers are provided.

FREE Pool Heating! Pet-Friendly!!!SPECIAL PRICING 04/13-04/30 ONLY!!!

3 bedrooms·0 baths
Palm Harbor • Florida

$ 642,00 USD totaal voor 3 nachten

16–19 nov 2026

Waterfront 2/1 Apt in heart of Palm Harbor/Ozona image 1
Waterfront 2/1 Apt in heart of Palm Harbor/Ozona image 2
Waterfront 2/1 Apt in heart of Palm Harbor/Ozona image 3
Waterfront 2/1 Apt in heart of Palm Harbor/Ozona image 4
Waterfront 2/1 Apt in heart of Palm Harbor/Ozona image 5

Waterfront 2/1 Apt in heart of Palm Harbor/Ozona

2 bedrooms·1 bath
Palm Harbor • Florida
4.85(62 reviews)

$ 1.195,00 USD totaal voor 4 nachten

16–20 nov 2026

3 bed/2 bath Home W/ Gulf Water Access image 1
3 bed/2 bath Home W/ Gulf Water Access image 2
3 bed/2 bath Home W/ Gulf Water Access image 3
3 bed/2 bath Home W/ Gulf Water Access image 4
3 bed/2 bath Home W/ Gulf Water Access image 5

3 bed/2 bath Home W/ Gulf Water Access

3 bedrooms·2 baths
Palm Harbor • Florida
4.74(50 reviews)

$ 1.450,00 USD totaal voor 5 nachten

26–31 mrt 2027

Waterfront 2/1 Apt. Ozona/Palm Harbor (Beachcomber image 1
Waterfront 2/1 Apt. Ozona/Palm Harbor (Beachcomber image 2
Waterfront 2/1 Apt. Ozona/Palm Harbor (Beachcomber image 3
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Waterfront 2/1 Apt. Ozona/Palm Harbor (Beachcomber image 5

Waterfront 2/1 Apt. Ozona/Palm Harbor (Beachcomber

2 bedrooms·1 bath
Palm Harbor • Florida
4.86(74 reviews)

$ 762,00 USD totaal voor 3 nachten

16–19 nov 2026