Bermuda Bay Beach and Racquet Club Condo. 2bdrm/2b
Bermuda Bay Beach and Racquet Club Condo. 2bdrm/2b
Bermuda Bay Beach and Racquet Club Condo. 2bdrm/2b
Bermuda Bay Beach and Racquet Club Condo. 2bdrm/2b
Bermuda Bay Beach and Racquet Club Condo. 2bdrm/2b

Bermuda Bay Beach and Racquet Club Condo. 2bdrm/2b

2 bedrooms·2 baths
St. Petersburg • Florida
4.67(12 reviews)

$ 3.075,66 USD totaal voor 28 nachten

24 okt – 21 nov 2026

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)

$ 4.379,88 USD $ 4.225,30 USD totaal voor 30 nachten

24 okt – 23 nov 2026

Save Book Thanksgiving Now Special Won't Last Long
Save Book Thanksgiving Now Special Won't Last Long
Save Book Thanksgiving Now Special Won't Last Long
Save Book Thanksgiving Now Special Won't Last Long
Save Book Thanksgiving Now Special Won't Last Long

Save Book Thanksgiving Now Special Won't Last Long

4 bedrooms·3 baths
Clearwater • Florida
4.58(98 reviews)

$ 2.380,00 USD totaal voor 3 nachten

24–27 okt 2026

Urban Escape: Artificial Beach W/Volleyball Pit
Urban Escape: Artificial Beach W/Volleyball Pit
Urban Escape: Artificial Beach W/Volleyball Pit
Urban Escape: Artificial Beach W/Volleyball Pit
Urban Escape: Artificial Beach W/Volleyball Pit

Urban Escape: Artificial Beach W/Volleyball Pit

4 bedrooms·3 baths
Clearwater • Florida
4.78(9 reviews)

$ 1.804,00 USD totaal voor 3 nachten

24–27 okt 2026

Oceanview Gulf-Front 2BR/2BA | Pass-a-Grille Beach
Front of house.
Oceanview Gulf-Front 2BR/2BA | Pass-a-Grille Beach
Oceanview Gulf-Front 2BR/2BA | Pass-a-Grille Beach
Beautiful day at the beach

Oceanview Gulf-Front 2BR/2BA | Pass-a-Grille Beach

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

$ 4.292,11 USD $ 3.687,52 USD totaal voor 7 nachten

11–18 nov 2026

Pass-a-Grille Gulf Front Cottage, Ocean View
Pass-a-Grille Gulf Front Cottage, Ocean View
Pass-a-Grille Gulf Front Cottage, Ocean View
Pass-a-Grille Gulf Front Cottage, Ocean View
Beach. Steps from the cottage

Pass-a-Grille Gulf Front Cottage, Ocean View

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

$ 7.403,48 USD $ 6.330,76 USD totaal voor 28 nachten

1–29 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

24 okt – 23 nov 2026

Gulf Breeze Getaway - Sand Key image 1
Gulf Breeze Getaway - Sand Key image 2
Gulf Breeze Getaway - Sand Key image 3
Gulf Breeze Getaway - Sand Key image 4
Gulf Breeze Getaway - Sand Key image 5

Gulf Breeze Getaway - Sand Key

2 bedrooms·2 baths
Clearwater • Florida

$ 5.650,00 USD totaal voor 30 nachten

24 okt – 23 nov 2026

Your private pool, heated year-round to 80°F and ready for fall swims. Sun loungers and an umbrella line the deck, and the fully fenced backyard keeps the fun contained.
Red Adirondack chairs circle the fire pit under café lights. Fall evenings in Clearwater were made for slow talks and s'mores.
The whole backyard in one frame: heated pool, lounge chairs and cornhole on the lawn. Kids play, grown-ups relax, all inside a fenced yard.
Open-concept living made for your whole crew: a colorful mural, big sectional and dining table in one bright space, so nobody is stuck in another room while dinner comes together.
King primary suite with green and gold accents, a smart TV and ceiling fan. Your own retreat at the end of the day.

Heated pool, fire pit, games · dog friendly

3 bedrooms·2 baths
Clearwater • Florida

$ 1.168,27 USD totaal voor 3 nachten

25–28 okt 2026

Welcome to your home away from home!
This large pool and spacious patio will make it hard to decide if you want to go to the beach or stay in.
Renovated inside and out!
Double sinks, soaker tub and walk in shower!
This brand new kitchen is stocked with everything you need for your meals in!

Twin Oaks Retreat

5 bedrooms·3 baths
Clearwater • Florida

$ 1.186,13 USD $ 1.096,90 USD totaal voor 3 nachten

25–28 okt 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)

$ 246,42 USD totaal voor 3 nachten

1–4 nov 2026

Front of Home
Front door to unit
Entrance Stairs
Kitchen
Closet in Kitchen area

The Blue House in Clearwater

2 bedrooms·1 bath
Clearwater • Florida

$ 3.559,50 USD totaal voor 30 nachten

24 okt – 23 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

$ 577,00 USD totaal voor 3 nachten

1–4 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

$ 496,00 USD totaal voor 3 nachten

24–27 okt 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

$ 1.858,90 USD totaal voor 3 nachten

25–28 okt 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

$ 2.805,20 USD totaal voor 3 nachten

26–29 okt 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

$ 662,45 USD totaal voor 3 nachten

25–28 okt 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

$ 673,50 USD totaal voor 3 nachten

25–28 okt 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

$ 1.401,05 USD totaal voor 3 nachten

25–28 okt 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 totaal voor 3 nachten

24–27 okt 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

$ 341,90 USD totaal voor 3 nachten

8–11 nov 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

$ 543,80 USD totaal voor 3 nachten

25–28 okt 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

$ 517,55 USD totaal voor 3 nachten

26–29 okt 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

24–27 okt 2026