Exterior view of Studio East & Studio West. Each studio has private entrance and private yard, connected with a gate.
Studio 1 (East) private porch
Studio 1 (East) private porch and outdoor
Studio 1 (East)
Studio 1 (East)

Adorable Pair - 2 private modern studios

2 bedrooms·2 baths
St. Petersburg • Florida
4.5(2 reviews)

$6,282.04 USD total for 28 nights

Nov 3 – Dec 1, 2026

Your favorite beach getaway (4)
Your favorite beach getaway (4)
Your favorite beach getaway (4)
Shared Laundry room located on 1st flooor
Your favorite beach getaway (4)

Your favorite beach getaway (4)

1 bedroom·1 bath
St. Pete Beach • Florida
5(3 reviews)

$1,606.00 USD total for 6 nights

Oct 14 – 20, 2026

Adorable Private Cottage close to beach & downtown
Adorable Private Cottage close to beach & downtown
Adorable Private Cottage close to beach & downtown
Adorable Private Cottage close to beach & downtown
Adorable Private Cottage close to beach & downtown

Adorable Private Cottage close to beach & downtown

2 bedrooms·1 bath
St. Petersburg • Florida
5(268 reviews)

$5,731.24 USD $5,552.34 USD total for 28 nights

Nov 29 – Dec 27, 2026

Miscellaneous
Beach
Miscellaneous
Miscellaneous
Terrace/patio

Waterfront 3BR 2 1/2 Bath, Amazing View-Sunrises!

3 bedrooms·2½ baths
St. Pete Beach • Florida
5(3 reviews)

$13,750.00 USD total for 30 nights

Jan 1 – 31, 2027

Bathroom
Kitchen
Beach
Building Arial View
St Pete Beach

St Pete Beachside Condo

1 bedroom·1 bath
St. Pete Beach • Florida
5(3 reviews)

$1,297.68 USD total for 5 nights

Oct 14 – 19, 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

$452.00 USD total for 3 nights

Oct 14 – 17, 2026

Common Area
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

$485.90 USD total for 3 nights

Oct 14 – 17, 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 total for 3 nights

Oct 14 – 17, 2026

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)

$772.10 USD total for 3 nights

Oct 14 – 17, 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 total for 30 nights

Oct 14 – Nov 13, 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)
$400 – $450/ night(excl. fees & taxes)
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.
Shuffleboard right in the living room for friendly rivalries after the pool. Loser does the dishes.
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.

Heated pool, fire pit, games · dog friendly

3 bedrooms·2 baths
Clearwater • Florida

$1,058.50 USD total for 3 nights

Oct 14 – 17, 2026

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)

$2,812.03 USD total for 28 nights

Oct 14 – Nov 11, 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

$1,147.33 USD $1,061.98 USD total for 3 nights

Oct 19 – 22, 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)

$4,377.62 USD $4,223.15 USD total for 30 nights

Oct 14 – Nov 13, 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 total for 30 nights

Oct 14 – Nov 13, 2026

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

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

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

$3,368.95 USD total for 7 nights

Oct 14 – 21, 2026

Pass-a-Grille Gulf Front Cottage, Ocean View
Pass-a-Grille Gulf Front Cottage, Ocean View
Beach. Steps from the cottage
Cozy Kitchen. Small but lots of space to cook
Pass-a-Grille Gulf Front Cottage, Ocean View

Pass-a-Grille Gulf Front Cottage, Ocean View

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

$11,546.81 USD total for 28 nights

Mar 31 – Apr 28, 2027

"If your in Clearwater don't think twice this place it is great!! Jack and Shelly really out did them self. My new home every time we come. Don't miss out!" - Cortney
Waterfront Condo | Steps to Clearwater Beach 2King
" My favorite place to be was the large patio, soaking in the sights and sounds of the bay. I definitely would love to go back!" - Kristine
"The place was gorgeous and well worth the price." - Rob
"My family very much enjoyed our stay in Clearwater beach and waking up to the gorgeous views of Clearwater Bay. The unit was large and very clean with a lot of helpful items (many kitchen utensils and products, beach towels and chairs, games, etc). We were sad to leave!" - Sierra

Waterfront Condo | Steps to Clearwater Beach 2King

3 bedrooms·2 baths
Clearwater • Florida

$1,439.00 USD total for 3 nights

Oct 18 – 21, 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

Oct 14 – Nov 13, 2026

Kitchen
A little piece of Beach House Heaven!
Waterfront Beach House Steps Away from #1 Beach!
Master Bedroom Balcony!
2nd floor (main living space) with gourmet kitchen and waterfront balcony attached!

Waterfront Beach House Steps Away from #1 Beach!

3 bedrooms·2 baths
Pinellas County • Florida
5(60 reviews)

$2,094.16 USD total for 3 nights

Oct 14 – 17, 2026

Brightwater Unit #3
Brightwater Unit #3
Brightwater Unit #3
Brightwater Unit #3
Brightwater Unit #3

Brightwater Unit #3

3 bedrooms·3 baths
Clearwater • Florida

$2,714.21 USD total for 7 nights

Oct 14 – 21, 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)

$281.22 USD total for 3 nights

Oct 18 – 21, 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 total for 3 nights

Nov 1 – 4, 2026