View of Indian Rocks Beach from the Balcony
Indian Rocks Beach Sunset
Beautiful Sunsets! Direct Beachfront Condo w/ Pool image 3
Beautiful Sunsets! Direct Beachfront Condo w/ Pool image 4
14 x 14 Pool, 4ft deep

Beautiful Sunsets! Direct Beachfront Condo w/ Pool

2 bedrooms·2 baths
Indian Rocks Beach • Florida
4.93(43 reviews)

$2,108.85 USD total for 7 nights

Nov 30 – Dec 7, 2026

Blue Heron Cottage #1
Blue Heron Cottage #1
Blue Heron Cottage #1
Blue Heron Cottage #1
Blue Heron Cottage #1

Blue Heron Cottage #1

1 bedroom·1 bath
Indian Rocks Beach • Florida
Driftwood Sands #307
Driftwood Sands #307
Driftwood Sands #307
Driftwood Sands #307
Driftwood Sands #307

Driftwood Sands #307

3 bedrooms·2 baths
Indian Rocks Beach • Florida
5(4 reviews)

$6,182.23 USD total for 28 nights

Nov 30 – Dec 28, 2026

Spacious living room.
Heated pool.
Fully equipped kitchen and plenty of seating
Dining area
Open concept living room

Beach AND Pool!2/2 large condo

2 bedrooms·2 baths
Indian Rocks Beach • Florida
5(152 reviews)

$1,333.40 USD total for 5 nights

Nov 15 – 20, 2026

Gulf front pool
Condo!
Front of the building
Hallway into condo
Hallway

Sand Isle I

2 bedrooms·2 baths
Indian Rocks Beach • Florida
4.77(100 reviews)

$847.50 USD total for 3 nights

Nov 15 – 18, 2026

Your private backyard oasis—unwind under the stars with a fire and make some s’mores.
Soak under the stars after exploring Florida’s beautiful Gulf Coast.
Spacious fenced backyard with fire pit, lawn games, and lounge seating
Bright, cozy bedroom with warm accents, natural light, and stylish decor
Bright coastal bedroom with cozy decor, soft light, and fresh greenery

Sunshine State of Mind

3 bedrooms·2 baths
Largo • Florida
5(64 reviews)

$693.22 USD $606.17 USD total for 3 nights

Nov 15 – 18, 2026

No Crossing the Street You are Staying ON THE BEACH
Miles of Powder White Sand
Jump in the Gulf When it's Time for Water Break
Play doubles or 3x3 or 6x6
Living Room w/Recliners

Beach Paradise w/Balcony+Pool

2 bedrooms·2 baths
Indian Rocks Beach • Florida
4.6(5 reviews)

$1,985.41 USD total for 4 nights

Dec 4 – 8, 2026

Chill & Play: 4br home- Heated Pool, Lanai, Beach! image 1
Chill & Play: 4br home- Heated Pool, Lanai, Beach! image 2
Chill & Play: 4br home- Heated Pool, Lanai, Beach! image 3
We have since added a couple outdoor chairs and a table here
Chill & Play: 4br home- Heated Pool, Lanai, Beach! image 5

Chill & Play: 4br home- Heated Pool, Lanai, Beach!

4 bedrooms·2 baths
Largo • Florida
4.93(45 reviews)

$1,132.25 USD total for 3 nights

Nov 16 – 19, 2026

Beachside Paradise | Steps to Sand & Sunsets image 1
Beachside Paradise | Steps to Sand & Sunsets image 2
Beachside Paradise | Steps to Sand & Sunsets image 3
Beachside Paradise | Steps to Sand & Sunsets image 4
Beachside Paradise | Steps to Sand & Sunsets image 5

Hart's Paradise @ Barefoot Beach

1 bedroom·1 bath
Indian Shores • Florida
4.77(82 reviews)

$620.00 USD total for 3 nights

Nov 21 – 24, 2026

Master bedroom King Size Bed Sliding doors to balcony
Master Bedroom King size bed
Master Bedroom 42" Roku TV
Master bedroom Sliding doors to balcony
Master bedroom Reading chair with view of beach

Sea Gate 206 Beautiful Beach Front Condo/3 BR - 2 BTH

3 bedrooms·2 baths
Indian Shores • Florida
5(180 reviews)

$1,339.05 USD total for 3 nights

Nov 30 – Dec 3, 2026

Open-concept living with stylish dining area and stunning ocean-view balcony
Spacious Beachfront Condo with stunning Gulf views
Spacious Beachfront Condo with stunning Gulf views
Spacious Beachfront Condo with stunning Gulf views
Bright beachfront bedroom with private balcony and ocean views

Spacious Beachfront Condo with stunning Gulf views

3 bedrooms·2 baths
Indian Rocks Beach • Florida
4.64(11 reviews)

$1,178.52 USD total for 3 nights

Dec 10 – 13, 2026

Family Resort | Pool • Mini Golf • Near Beach image 1
Family Resort | Pool • Mini Golf • Near Beach image 2
Family Resort | Pool • Mini Golf • Near Beach image 3
Family Resort | Pool • Mini Golf • Near Beach image 4
Family Resort | Pool • Mini Golf • Near Beach image 5

Family Resort | Pool • Mini Golf • Near Beach

4 bedrooms·2 baths
Seminole • Florida
5(2 reviews)

$1,337.00 USD total for 3 nights

Nov 17 – 20, 2026

Screened tropical pool retreat with cozy lighting and resort-style vibes
Twilight backyard retreat with private putting green and screened patio
Coastal-inspired game room with pool table for fun indoor hangouts
Private backyard movie nights under the string lights
Cozy fire pit, outdoor movie nights, and a resort-style screened pool

Sunny Daze Getaway

4 bedrooms·2 baths
Seminole • Florida

$925.00 USD total for 3 nights

Nov 15 – 18, 2026

HOLIDAY VILLAS III- 605
HOLIDAY VILLAS III- 605
HOLIDAY VILLAS III- 605
HOLIDAY VILLAS III- 605
HOLIDAY VILLAS III- 605

HOLIDAY VILLAS III- 605

2 bedrooms·2 baths
Indian Shores • Florida
5(26 reviews)

$4,948.63 USD total for 7 nights

Nov 15 – 22, 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

Nov 15 – Dec 15, 2026

Beautiful details that set this home apart. Oceanfront Luxury home.
Ocean Front with 180 degree views inside the home of the ocean
The most epic sunsets you have ever seen!
Master #1 - King Bed ( There are two of these rooms mirrored on each side of the house)
Dinning Room

OceanfrontVilla/Pool/HotTub/8bedroom

8 bedrooms·6 baths
Redington Shores • Florida
5(4 reviews)

$5,447.60 USD total for 3 nights

Nov 15 – 18, 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 total for 3 nights

Nov 15 – 18, 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 total for 3 nights

Nov 19 – 22, 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 total for 3 nights

Dec 7 – 10, 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 total for 4 nights

Dec 7 – 11, 2026

Beautiful 1BR Condo only steps to the water & fun! image 8
Beautiful 1BR Condo only steps to the water & fun! image 5
Beautiful 1BR Condo only steps to the water & fun! image 55
Beautiful 1BR Condo only steps to the water & fun! image 3
Welcome to beautiful North Redington Beach, FL.

No Cleaning Fee, 0min to Beach, 1BR w/ parking

1 bedroom·1 bath
North Redington Beach • Florida
5(46 reviews)

$720.60 USD total for 4 nights

Nov 15 – 19, 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 total for 3 nights

Nov 15 – 18, 2026

Property grounds
Outdoor dining
Interior
Private kitchen
Room

Beachfront Condo at La Contessa!, 3BD/3BA, Poolside Cabana, Private Fishing Pier

3 bedrooms·3 baths
Redington Beach • Florida
5(12 reviews)

$11,215.25 USD total for 30 nights

Nov 15 – Dec 15, 2026

Dive into vacation mode with a sunny pool and playful float.
Resort-style St. Pete retreat with pool, game room & outdoor dining
Gather around the waterfront fire-pit seating area.
Tiki-style backyard bar with TV, ambient lighting, and private patio seating
Make game night a highlight of your stay with the foosball table.

2 Homes - 4 MN to Madiera BCH - Hottub - HTD Pool

7 bedrooms·6 baths
St. Petersburg • Florida

$2,265.00 USD total for 3 nights

Nov 15 – 18, 2026