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

16 nov – 16 dec 2026

Sleeps 24-Beachfront Entire Resort- Outdoor Pool 7BR
Sleeps 24-Beachfront Entire Resort- Outdoor Pool 7BR
Sleeps 24-Beachfront Entire Resort- Outdoor Pool 7BR
Sleeps 24-Beachfront Entire Resort- Outdoor Pool 7BR
Sleeps 24-Beachfront Entire Resort- Outdoor Pool 7BR

Sleeps 24-Beachfront Entire Resort- Outdoor Pool 7BR

7 bedrooms·7 baths
Madeira Beach • Florida

$ 4.709,84 USD totaal voor 3 nachten

16–19 nov 2026

Steps to Beach, Heated Pool, 2 Queen Beds, 2BA
Steps to Beach, Heated Pool, 2 Queen Beds, 2BA
Steps to Beach, Heated Pool, 2 Queen Beds, 2BA
Steps to Beach, Heated Pool, 2 Queen Beds, 2BA
Steps to Beach, Heated Pool, 2 Queen Beds, 2BA

Steps to Beach, Heated Pool, 2 Queen Beds, 2BA

2 bedrooms·2 baths
Madeira Beach • Florida

$ 1.551,55 USD totaal voor 3 nachten

16–19 nov 2026

King Bed, Steps to Madeira Beach, Heated Pool, Private
King Bed, Steps to Madeira Beach, Heated Pool, Private
King Bed, Steps to Madeira Beach, Heated Pool, Private
King Bed, Steps to Madeira Beach, Heated Pool, Private
King Bed, Steps to Madeira Beach, Heated Pool, Private

King Bed, Steps to Madeira Beach, Heated Pool, Private

1 bedroom·1 bath
Madeira Beach • Florida

$ 1.410,81 USD totaal voor 3 nachten

16–19 nov 2026

King Bed, Step to Madeira Beach, Heated Pool, Private
King Bed, Step to Madeira Beach, Heated Pool, Private
King Bed, Step to Madeira Beach, Heated Pool, Private
King Bed, Step to Madeira Beach, Heated Pool, Private
King Bed, Step to Madeira Beach, Heated Pool, Private

King Bed, Step to Madeira Beach, Heated Pool, Private

1 bedroom·1 bath
Madeira Beach • Florida

$ 1.324,55 USD totaal voor 3 nachten

16–19 nov 2026

Madeira Beachside - Pool & Steps to the Sand
Madeira Beachside - Pool & Steps to the Sand
Madeira Beachside - Pool & Steps to the Sand
Madeira Beachside - Pool & Steps to the Sand
Madeira Beachside - Pool & Steps to the Sand

Madeira Beachside - Pool & Steps to the Sand

1 bedroom·1 bath
Madeira Beach • Florida

$ 1.280,28 USD totaal voor 3 nachten

16–19 nov 2026

King Bed-Step to Madeira Beach-Heated Pool-Private
King Bed-Step to Madeira Beach-Heated Pool-Private
King Bed-Step to Madeira Beach-Heated Pool-Private
King Bed-Step to Madeira Beach-Heated Pool-Private
King Bed-Step to Madeira Beach-Heated Pool-Private

King Bed-Step to Madeira Beach-Heated Pool-Private

1 bedroom·1 bath
Madeira Beach • Florida

$ 1.324,55 USD totaal voor 3 nachten

16–19 nov 2026

Front of Home
Front of Home
Dining Area
Dining Area
Dining Area

The Parkside Retreat at 78th Street

3 bedrooms·2 baths
Pinellas Park • Florida

$ 791,29 USD totaal voor 3 nachten

16–19 nov 2026

"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

$ 1.330,00 USD totaal voor 3 nachten

16–19 nov 2026

Harborview Grande #405
Harborview Grande #405
Harborview Grande #405
Harborview Grande #405
Harborview Grande #405

Harborview Grande #405

3 bedrooms·2 baths
Clearwater • Florida
5(71 reviews)

$ 2.145,95 USD totaal voor 4 nachten

16–20 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

16 nov – 16 dec 2026

Start your morning with coffee on your private balcony overlooking the peaceful harbor.
Bright, comfortable living room with beautiful harbor views and plenty of space to relax.
KING + TWIN bedroom with a dedicated workspace—flexible sleeping for families plus room to work.
Private KING bedroom with TV, ceiling fan, charging stations and plenty of storage.
Heated waterfront pool and sundeck overlooking the harbor—perfect after a day at the beach.

Dock of the Bay, #204 Walk Everywhere • Harbor Views • 2 King Suites

2 bedrooms·2 baths
Clearwater • Florida
5(210 reviews)

$ 1.059,85 USD totaal voor 3 nachten

19–22 nov 2026

Welcome to Dock Holiday! Bright waterfront living with beautiful harbor views and Clearwater Beach just a 5-minute walk away.
Relax on your private balcony overlooking the harbor—perfect for morning coffee or an evening glass of wine.
Private KING bedroom with TV, ceiling fan, charging stations and plenty of storage.
Two QUEEN beds make this spacious second suite ideal for families, friends, or groups who want comfortable sleeping arrangements and plenty of room.
Enjoy the heated bayfront swimming pool and sundeck—perfect for swimming, lounging, and relaxing with beautiful harbor views.

Dock Holiday, #205 Walk to Beach! Pool + Free Parking + Beach Gear

2 bedrooms·2 baths
Clearwater • Florida
5(198 reviews)

$ 1.095,06 USD totaal voor 3 nachten

7–10 dec 2026

Dockside Duo = TWO complete side-by-side waterfront condos—perfect for families and friends traveling together.
Beautiful harbor views from your private balconies—start the morning with coffee by the water.
Condo #1 – Dock of the Bay: Spacious waterfront living room with sleeper sofa, Roku TV and Cable.
Condo #2 – Dock Holiday: Bright waterfront living room with sleeper sofa, Roku TV and Cable.
Condo #1 – Dock of the Bay: Comfortable KING bedroom with TV, ceiling fan, charging stations and ample storage.

Dockside Duo, #204 & #205 Side-by-Side Waterfront Condos | Walk to Beach

4 bedrooms·4 baths
Clearwater • Florida
5(7 reviews)

$ 2.812,07 USD totaal voor 4 nachten

7–11 dec 2026

Mermaid Manor. Only 2 block to the BEACH!
Mermaid Manor - Waterfront | Dolphins & Sunsets
Mermaid Manor - Waterfront | Dolphins & Sunsets
Mermaid Manor - Waterfront | Dolphins & Sunsets
Mermaid Manor - Waterfront | Dolphins & Sunsets

Mermaid Manor - Waterfront | Dolphins & Sunsets

2 bedrooms·2 baths
Treasure Island • Florida

$ 693,00 USD totaal voor 3 nachten

16–19 nov 2026

Funshine Pointe Capri - Newly Renovated - Intercoastal Views
Funshine Pointe Capri - Newly Renovated - Intercoastal Views
Funshine Pointe Capri - Newly Renovated - Intercoastal Views
Funshine Pointe Capri - Newly Renovated - Intercoastal Views
Funshine Pointe Capri - Newly Renovated - Intercoastal Views

Funshine Pointe Capri - Newly Renovated - Intercoastal Views

1 bedroom·1 bath
Treasure Island • Florida
5(178 reviews)

$ 650,22 USD totaal voor 3 nachten

22–25 nov 2026

Park & Pool Across the Street and 9 Mins to Beach
Park & Pool Across the Street and 9 Mins to Beach
Park & Pool Across the Street and 9 Mins to Beach
Park & Pool Across the Street and 9 Mins to Beach
Park & Pool Across the Street and 9 Mins to Beach

Park & Pool Across the Street and 9 Mins to Beach

4 bedrooms·2 baths
St. Petersburg • Florida
4.95(43 reviews)

$ 7.870,00 USD totaal voor 30 nachten

16 nov – 16 dec 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

$ 945,06 USD totaal voor 3 nachten

16–19 nov 2026

Pelican Point Clearwater Beach view
Pelican Point Clearwater Beach view
Pelican Point Clearwater Beach view
Pelican Point Clearwater Beach view
Pelican Point Clearwater Beach view

Pelican Point Clearwater Beach view

1 bedroom·1 bath
Clearwater • Florida

$ 516,00 USD totaal voor 3 nachten

20–23 nov 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 totaal voor 3 nachten

16–19 nov 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

$ 1.314,25 USD totaal voor 3 nachten

29 nov – 2 dec 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)

$ 2.350,00 USD totaal voor 3 nachten

16–19 nov 2026

Sun Harbor Bay Haven-4 min walk to the beach, dog friendly
Sun Harbor Bay Haven-4 min walk to the beach, dog friendly
Sun Harbor Bay Haven-4 min walk to the beach, dog friendly
Sun Harbor Bay Haven-4 min walk to the beach, dog friendly
Sun Harbor Bay Haven-4 min walk to the beach, dog friendly

Sun Harbor Bay Haven-4 min walk to the beach, dog friendly

3 bedrooms·2½ baths
Clearwater • Florida
5(22 reviews)

$ 1.219,27 USD totaal voor 3 nachten

17–20 nov 2026

Water views,4m beach walk, boat dock, free parking
Water views,4m beach walk, boat dock, free parking
Water views,4m beach walk, boat dock, free parking
Water views,4m beach walk, boat dock, free parking
Water views,4m beach walk, boat dock, free parking

Water views,4m beach walk, boat dock, free parking

3 bedrooms·2½ baths
Clearwater • Florida
4.87(55 reviews)

$ 1.219,27 USD totaal voor 3 nachten

16–19 nov 2026