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(zzgl. Gebühren & Steuern)
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 gesamt für 3 Nächte

24.–27. 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 gesamt für 3 Nächte

25.–28. 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

1.186,13 $ USD 1.096,90 $ USD gesamt für 3 Nächte

25.–28. Okt. 2026

Bright bath w/ clean design & practical comfort.
Luxurious outdoor sauna surrounded by lush tropical greenery.
Sunset-lit pool perfect for unwinding year-round
Spa-like bath w/ stone accents for soothing moments.
Cozy guest room offering calm, sunny comfort.

Luxury Pool Home in Riverview Tampa

4 bedrooms·2½ baths
Riverview • Florida
5(25 reviews)

1.251,36 $ USD gesamt für 3 Nächte

26.–29. 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.
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

1.168,27 $ USD gesamt für 3 Nächte

25.–28. 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 gesamt für 30 Nächte

24. Okt. – 23. Nov. 2026

Welcome to Emperor Rentals!
Have an amazing barbecue party while swimming with family and friends!
Create amazing memories with family during this trip in this stunning house!
Love homecooked meals? Eat your favorite meals without going out in this beautiful dining table. Have questions about the property? Send us an inquiry now!
Comfortable bed to ensure you get the rest you deserve your entire stay

Serenity Stay Villa

4 bedrooms·2 baths
Largo • Florida
5(26 reviews)

810,66 $ USD gesamt für 3 Nächte

1.–4. Nov. 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)

1.937,90 $ USD 1.620,60 $ USD gesamt für 4 Nächte

24.–28. 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 gesamt für 3 Nächte

24.–27. Okt. 2026

Welcome to Emperor Rentals!
Prepare and make great meals in our wonderful spacious and fully equipped kitchen. If you love cooking, this property is great for you! Book it now!
Our large living area with comfortable L-Shaped modern couch will ensure a great and relaxing time for all of our guests. If you have any questions about this property, please send us an inquiry today!
Relax after a long day of activities with family and friends. Have an amazing sleep in this beautiful room that has a queen-size bed, TV, drawers, and closet.
Aerial side view of our amazing property! Worry not about kids playing in the fully fenced backyard during your stay! Inquire about this property now!

Paradise Cove House

4 bedrooms·1 bath
Pinellas Park • Florida
5(59 reviews)

807,47 $ USD 715,80 $ USD gesamt für 3 Nächte

24.–27. Okt. 2026

The Bayou Breeze Cottage
The Bayou Breeze Cottage
The Bayou Breeze Cottage
The Bayou Breeze Cottage
The Bayou Breeze Cottage

The Bayou Breeze Cottage

1 bedroom·1 bath
St. Petersburg • Florida
5(28 reviews)

519,57 $ USD 431,66 $ USD gesamt für 3 Nächte

31. Okt. – 3. Nov. 2026

The Coffee Pot Cottage
The Coffee Pot Cottage
The Coffee Pot Cottage
The Coffee Pot Cottage
The Coffee Pot Cottage

The Coffee Pot Cottage

2 bedrooms·1 bath
St. Petersburg • Florida
5(26 reviews)

598,33 $ USD 498,66 $ USD gesamt für 3 Nächte

24.–27. 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 gesamt für 3 Nächte

24.–27. Okt. 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

1.406,00 $ USD gesamt für 3 Nächte

24.–27. Okt. 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 gesamt für 4 Nächte

31. Jan. – 4. Feb. 2027

Pool
Kitchen
Patio
Patio
Patio

Pond-side ART-home with private pool. DOGS WELCOME

5 bedrooms·3 baths
Pinellas Park • Florida
5(20 reviews)
$318/ Nacht(zzgl. Gebühren & Steuern)
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)

937,08 $ USD gesamt für 3 Nächte

25.–28. Okt. 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 gesamt für 3 Nächte

24.–27. Okt. 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

484,77 $ USD gesamt für 3 Nächte

24.–27. Okt. 2026

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Largo Waterview 6BR *Heated Pool/Hot Tub *GameRoom

5 bedrooms·4 baths
Largo • Florida
5(9 reviews)

7.200,00 $ USD 6.648,00 $ USD gesamt für 3 Nächte

24.–27. Okt. 2026

Outdoor seating with Heated Pool
Heated Pool
Living room
Living room
Kitchen

Pool Home-Close to Beach/St Pete

3 bedrooms·2 baths
Largo • Florida
$213 – $391/ Nacht(zzgl. Gebühren & Steuern)
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 gesamt für 30 Nächte

24. Okt. – 23. Nov. 2026

Welcome to your home away from home.
Keycode Door Lock for easy and private entry.
Entry to your spacious getaway.
Welcome to The Pelican where memories are ready to be made.
The Pelican on a Wide Canal w a Fun Spacious Home. image 5

The Pelican | Waterfront Hernando Beach Retreat

3 bedrooms·2 baths
Hernando Beach • Florida
5(14 reviews)

1.318,85 $ USD gesamt für 3 Nächte

24.–27. Okt. 2026