Welcome to Palm Villa
All new furnishings
Newly remodeled dreamy villa
Coastal charm

Palm Villa

2 bedrooms·2 baths
Holmes Beach • Florida

$ 1.614,27 USD totaal voor 7 nachten

15–22 nov 2026

Relax on the patio
Welcome to Orchid Villa
Beautifully designed
Coastal blue hues
Cable TV in the living room

Orchid Villa

2 bedrooms·2 baths
Holmes Beach • Florida

$ 1.614,27 USD totaal voor 7 nachten

15–22 nov 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)

$ 1.066,90 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

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

15–18 nov 2026

Sleeps 25 • Heated Pool • Indoor/Outdoor Games• Theater
Sleeps 25 • Heated Pool • Indoor/Outdoor Games• Theater
Sleeps 25 • Heated Pool • Indoor/Outdoor Games• Theater
Sleeps 25 • Heated Pool • Indoor/Outdoor Games• Theater
Sleeps 25 • Heated Pool • Indoor/Outdoor Games• Theater

Sleeps 25 • Heated Pool • Indoor/Outdoor Games• Theater

7 bedrooms·4 baths
Tampa • Florida

$ 2.760,80 USD totaal voor 3 nachten

15–18 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

Stunning private yard and pool
Huge Holmes Beach home
Birds eye view
So close to the beach
Spacious and welcoming foyer

Beachy Blue

4 bedrooms·4 baths
Holmes Beach • Florida

$ 3.712,87 USD totaal voor 7 nachten

27 nov – 4 dec 2026

Resort-style relaxation in your own backyard
Sparkling and inviting year-round
Welcome to Aquamarine Oasis
Airy and light-filled space
Coastal-inspired kitchen with wraparound counters

Aquamarine Oasis

3 bedrooms·2½ baths
Holmes Beach • Florida

$ 2.226,00 USD totaal voor 7 nachten

15–22 nov 2026

Sweet Craftsman home, free bikes, near beach & DT image 1
Sweet Craftsman home, free bikes, near beach & DT image 2
Sweet Craftsman home, free bikes, near beach & DT image 3
Sweet Craftsman home, free bikes, near beach & DT image 4
Sweet Craftsman home, free bikes, near beach & DT image 5

Adorable Private Craftsman

2 bedrooms·1 bath
Clearwater • Florida
4.86(267 reviews)

$ 562,00 USD $ 539,65 USD totaal voor 3 nachten

15–18 nov 2026

Beautiful elevated home with private yard
Welcome to Rollin' with the Waves
Only five houses to the sand
Your tropical getaway awaits

Rollin' with the Waves

3 bedrooms·2½ baths
Holmes Beach • Florida
5(2 reviews)

$ 2.650,65 USD totaal voor 7 nachten

27 nov – 4 dec 2026

Pompano Palms
Pompano Palms
Pompano Palms
Pompano Palms
Pompano Palms

Pompano Palms

3 bedrooms·3½ baths
Palmetto • Florida
$71/ nacht(excl. kosten & belastingen)
The Coastal Anchor Suite #410 at Little Harbor Inn
The Coastal Anchor Suite #410 at Little Harbor Inn
The Coastal Anchor Suite #410 at Little Harbor Inn
The Coastal Anchor Suite #410 at Little Harbor Inn
The Coastal Anchor Suite #410 at Little Harbor Inn

The Coastal Anchor Suite #410 at Little Harbor Inn

1 bedroom·1 bath
Ruskin • Florida

$ 15,00 USD totaal voor 3 nachten

15–18 nov 2026

The Coastal Anchor Suite #307 at Little Harbor Inn
The Coastal Anchor Suite #307 at Little Harbor Inn
The Coastal Anchor Suite #307 at Little Harbor Inn
The Coastal Anchor Suite #307 at Little Harbor Inn
The Coastal Anchor Suite #307 at Little Harbor Inn

The Coastal Anchor Suite #307 at Little Harbor Inn

1 bedroom·1 bath
Ruskin • Florida

$ 449,97 USD totaal voor 3 nachten

15–18 nov 2026

Float the afternoon away
Welcome to Under the Foxtails
Bright, open coastal living space
Stylish space to relax and chat
Modern beach style and comfort

Under the Foxtails

3 bedrooms·3 baths
Holmes Beach • Florida
$150 – $600/ nacht(excl. kosten & belastingen)
The Oaks at Keene Estate
The Oaks at Keene Estate
The Oaks at Keene Estate
The Oaks at Keene Estate
The Oaks at Keene Estate

The Oaks at Keene Estate

6 bedrooms·4 baths
Clearwater • Florida

$ 3.855,00 USD totaal voor 4 nachten

17–21 mrt 2027

Bring your bike or enjoy the Complimentary bikes available. Actual model may varies. Pinellas trail is about 0.3 miles away, perfect for biking and walking.
Adorable Bungalow near beach, DT. Pet & Bike. image 2
Adorable Bungalow near beach, DT. Pet & Bike. image 3
Fully equipped kitchen.
Adorable Bungalow near beach, DT. Pet & Bike. image 5

Adorable Private Bungalow

2 bedrooms·1 bath
Clearwater • Florida
4.81(264 reviews)
$109 – $179/ nacht(excl. kosten & belastingen)
Comfortable sleeper sofa for guests while immersed in the tranquil ocean vibe!
Wonderful open space living area to relax and watch your favorite game or a good movie!
Have a picnic right on the water with the breathtaking view!
Enjoy your morning coffee and breakfast at the open concept dining area.
The bay beach in the community is a day of fun and sun!

Bahia Beach Calm Ruskin Retreat

2 bedrooms·1½ baths
Ruskin • Florida

$ 694,40 USD totaal voor 3 nachten

15–18 nov 2026

Comfortable sleeper sofa for guests while immersed in the tranquil ocean vibe!
Wonderful open space living area to relax and watch your favorite game or a good movie!
Enjoy your favorite movie or watch your favorite team on this nice smart TV and relax!
Enjoy your morning coffee and breakfast at the open concept dining area.
Breathtaking views off the living area!

Bahia Beach Calm Ruskin Retreat

2 bedrooms·1½ baths
Ruskin • Florida

$ 586,25 USD totaal voor 3 nachten

15–18 nov 2026

Relax by the fire pit and enjoy sunset views in this private backyard
The Salty Palm
Let the kids play putt putt golf, bocce ball and more while you relax in the refreshing pool. Summertime paradise awaits!
The Salty Palm
The Salty Palm

The Salty Palm

3 bedrooms·2 baths
Bradenton • Florida
5(43 reviews)

$ 952,90 USD totaal voor 3 nachten

15–18 nov 2026

Welcome to AMI Villa
Light up the night!
Spectacular night lights over the pool
Amazing rooftop screened in patio
Comfortable family-style living area

AMI Villa

3 bedrooms·3 baths
Holmes Beach • Florida
5(3 reviews)

$ 3.077,75 USD totaal voor 7 nachten

30 nov – 7 dec 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

15–18 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