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

1168,27 $ USD total por 3 noches

25–28 oct 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

5650,00 $ USD total por 30 noches

24 oct – 23 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

3559,50 $ USD total por 30 noches

24 oct – 23 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

1406,00 $ USD total por 3 noches

24–27 oct 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)

2094,16 $ USD total por 3 noches

24–27 oct 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 total por 3 noches

25–28 oct 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)
$109 – $179/ noche(sin comisiones ni impuestos)
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

3855,00 $ USD total por 4 noches

17–21 mar 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 total por 3 noches

24–27 oct 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)

892,70 $ USD total por 3 noches

24–27 oct 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)

711,90 $ USD total por 3 noches

24–27 oct 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)

1937,90 $ USD 1620,60 $ USD total por 4 noches

24–28 oct 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

3493,28 $ USD total por 3 noches

24–27 oct 2026

Tampa Bay 1BR Suite with Pool & Beach Access image 1
Tampa Bay 1BR Suite with Pool & Beach Access image 2
Tampa Bay 1BR Suite with Pool & Beach Access image 3
Tampa Bay 1BR Suite with Pool & Beach Access image 4
Tampa Bay 1BR Suite with Pool & Beach Access image 5

Tampa Bay 1BR Suite with Pool & Beach Access

1 bedroom·1 bath
Tampa • Florida

574,97 $ USD total por 3 noches

24–27 oct 2026

Tampa Bay Double Queen w/Pool & Beach Access image 1
Tampa Bay Double Queen w/Pool & Beach Access image 2
Tampa Bay Double Queen w/Pool & Beach Access image 3
Tampa Bay Double Queen w/Pool & Beach Access image 4
Tampa Bay Double Queen w/Pool & Beach Access image 5

Tampa Bay Double Queen w/Pool & Beach Access

1 bedroom·1 bath
Tampa • Florida

622,64 $ USD total por 3 noches

24–27 oct 2026

Elegant dinning room overlooking Lanai into the pool deck.
Putt Putt
Kayaks, putting green, heated pool, fire pit, enclosed lanai with extended seating underneath the gazebo.
Waterfront Access, Heated Pool, Mini Golf & Kayaks
Waterfront Access, Heated Pool, Mini Golf & Kayaks

Waterfront Access, Heated Pool, Mini Golf & Kayaks

5 bedrooms·3 baths
Tampa • Florida
4.77(43 reviews)

2774,92 $ USD total por 3 noches

24–27 oct 2026

Tampa Waterfront 3BR Heated Pool &Dock Dander-Free
Tampa Waterfront 3BR Heated Pool &Dock Dander-Free
Tampa Waterfront 3BR Heated Pool &Dock Dander-Free
Tampa Waterfront 3BR Heated Pool &Dock Dander-Free
Tampa Waterfront 3BR Heated Pool &Dock Dander-Free

Tampa Waterfront 3BR Heated Pool &Dock Dander-Free

3 bedrooms·3 baths
Tampa • Florida

1128,96 $ USD total por 3 noches

24–27 oct 2026

FREE heated swimming Pool. SPA does not have a jet pump.
Large Heated Pool
4 bikes are provided with Helmets. 2 adults and 2 kids bike.
Garage game room. w/foosball table, pingpong, easel for kids
beach umbrellas, beach chairs and coolers are provided.

FREE Pool Heating! Pet-Friendly!!!SPECIAL PRICING 04/13-04/30 ONLY!!!

3 bedrooms·0 baths
Palm Harbor • Florida

673,00 $ USD total por 3 noches

24–27 oct 2026

Have an amazing experience with family and friends in this magnificent property! Make memories while enjoying the beautiful nature and having a dip in this immaculate pool. Inquire now!
Unwind after a day of exploring in the spacious family room with plush sectional seating.
Spacious waterfront bedroom featuring a king bed and beautiful lake views.
Ultimate game room with air hockey, arcade games, lounge seating, and bunk beds.
Open-concept kitchen with island seating and plenty of prep space for your group.

Imperial Oasis

4 bedrooms·3 baths
Tampa • Florida
5(28 reviews)

2279,65 $ USD 2187,60 $ USD total por 6 noches

25–31 oct 2026

The Corner Cottage image 1
The Corner Cottage image 2
The Corner Cottage image 3
The Corner Cottage image 4
The Corner Cottage image 5

The Corner Cottage

2 bedrooms·1 bath
Palm Harbor • Florida
4.94(18 reviews)

620,00 $ USD 595,25 $ USD total por 3 noches

26–29 oct 2026

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)

3059,78 $ USD total por 4 noches

8–12 nov 2026

Living room
Master Bedroom
Jacuzzi/ Pool #1
Gym
Guest Bedroom

Vibrant 2BR/2BA w/ King Bed | Pool, Gym #11

2 bedrooms·2 baths
Tampa • Florida
5(10 reviews)

796,08 $ USD 741,73 $ USD total por 3 noches

26–29 oct 2026

Huge 8BR Stay | Heated Pool, Game Room, Near Beach
Huge 8BR Stay | Heated Pool, Game Room, Near Beach
Huge 8BR Stay | Heated Pool, Game Room, Near Beach
Huge 8BR Stay | Heated Pool, Game Room, Near Beach
Bedroom 7. Kids Nerf Bedroom - 2 Single Beds. No EnSuite Bathroom. 2nd Floor

Huge 8BR Stay | Heated Pool, Game Room, Near Beach

8 bedrooms·7 baths
Palm Harbor • Florida

1567,00 $ USD total por 3 noches

29 oct – 1 nov 2026

Welcome to Flamingo Bay, your peaceful Floridian escape in the heart of Tampa Bay.
The sparkling pool is the centerpiece of this tropical oasis.
The open floor plan leaves plenty of space for the whole family to spread out and relax.
This is where family and friends gather for a delicious meal. Ask about our local catering options!
Flamingo Bay offers the fastest WiFi available so you shouldn't have any problem doing Zoom calls or watching your favorite Netflix series.

Flamingo Bay

3 bedrooms·2 baths
Tampa • Florida
5(2 reviews)