Living room with natural lighting.
Fenced backyard with patio and seating.
Seating area.
Inquire About Discounted Rental Rate
Maxwell Sands

Maxwell Sands

3 bedrooms·2 baths
Indian Rocks Beach • Florida

$ 1.116,37 USD $ 1.004,17 USD totaal voor 3 nachten

14–17 okt 2026

Peaceful Pond Paradise
Peaceful Pond Paradise
Peaceful Pond Paradise
Peaceful Pond Paradise
Front seating area

Peaceful Pond Paradise

3 bedrooms·2 baths
Largo • Florida
5(10 reviews)

$ 582,00 USD totaal voor 3 nachten

18–21 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)
$400 – $450/ nacht(excl. kosten & belastingen)
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 totaal voor 28 nachten

30 nov – 28 dec 2026

Funshine Flamingo's Nest
Funshine Flamingo's Nest
Funshine Flamingo's Nest
Funshine Flamingo's Nest
Funshine Flamingo's Nest

Funshine Flamingo's Nest

1 bedroom·1 bath
Largo • Florida

$ 765,90 USD totaal voor 4 nachten

31 jan – 4 feb 2027

Stylish retreat with heated pool, hot tub, game room, and bright modern interiors
Seen on HGTV | Heated Pool, Hot Tub• 5 Min Beach
Seen on HGTV | Heated Pool, Hot Tub• 5 Min Beach
Seen on HGTV | Heated Pool, Hot Tub• 5 Min Beach
Seen on HGTV | Heated Pool, Hot Tub• 5 Min Beach

Seen on HGTV | Heated Pool, Hot Tub• 5 Min Beach

3 bedrooms·2 baths
Largo • Florida
5(17 reviews)

$ 919,00 USD totaal voor 3 nachten

25–28 okt 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

14–17 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

$ 1.147,33 USD $ 1.061,98 USD totaal voor 3 nachten

19–22 okt 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.
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 totaal voor 3 nachten

14–17 okt 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

14 okt – 13 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

14 okt – 13 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

$ 1.439,00 USD totaal voor 3 nachten

18–21 okt 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

14–17 okt 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 totaal voor 7 nachten

14–21 okt 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)

$ 532,00 USD totaal voor 3 nachten

19–22 okt 2026

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)
$99 – $179/ 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

Oasis Paradise unit
Oasis Paradise unit
Oasis Paradise unit
Oasis Paradise unit
Oasis Paradise unit

Oasis Paradise unit

1 bedroom·1 bath
Clearwater • Florida

$ 447,00 USD totaal voor 3 nachten

14–17 okt 2026

BlueJay's Nest: Game Room, King Bed, Walk to Water image 2
BlueJay's Nest: Game Room, King Bed, Walk to Water image 1
BlueJay's Nest: Game Room, King Bed, Walk to Water image 3
BlueJay's Nest: Game Room, King Bed, Walk to Water image 4
BlueJay's Nest: Game Room, King Bed, Walk to Water image 5

BlueJay's Nest: Game Room, King Bed, Walk to Water

2 bedrooms·1 bath
Clearwater • Florida
5(30 reviews)

$ 870,10 USD totaal voor 3 nachten

14–17 okt 2026

BlueJay's Nest: private retreat w/ yard and patio image 1
BlueJay's Nest: private retreat w/ yard and patio image 2
Queen bed
BlueJay's Nest: private retreat w/ yard and patio image 4
Full bath with light-up mirror and extra supplies.

BlueJay's Nest: private retreat w/ yard and patio

2 bedrooms·1 bath
Clearwater • Florida
5(67 reviews)

$ 689,30 USD totaal voor 3 nachten

14–17 okt 2026

Margaritaville Pool Home
LR with two queen sleeper sofas with memory foam mattresses
LR with two queen sleeper sofas
LR and Dining area
LR and Ding area

Margaritaville Pool Home

3 bedrooms·2 baths
Clearwater • Florida
4.85(65 reviews)
$325 – $625/ nacht(excl. kosten & belastingen)
Stunning Gulf Views, Elevator to All Floors, Mini Golf, Heated Pool/Spa
Fun in the sun starts here - Hosted by RentAnnaMaria
Sunset Views from Shore to Please! - Hosted by RentAnnaMaria
Shore to Please - Hosted by RentAnnaMaria
Amazing Views! Main Living Space (3rd Floor) - Elevator to All Floors - Hosted by RentAnna Maria

Shore to Please

5 bedrooms·4½ baths
Anna Maria • Florida
5(13 reviews)

$ 3.165,45 USD totaal voor 4 nachten

8–12 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

$ 3.480,96 USD totaal voor 3 nachten

14–17 okt 2026

Gorgeous Beach Home with heated pool
Gorgeous Beach Home with heated pool
Gorgeous Beach Home with heated pool
Gorgeous Beach Home with heated pool
Gorgeous Beach Home with heated pool

Gorgeous Beach Home with heated pool

3 bedrooms·3 baths
Holmes Beach • Florida
5(9 reviews)

$ 14.959,60 USD totaal voor 28 nachten

14 okt – 11 nov 2026