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 total for 30 nights

Sep 22 – Oct 22, 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)

$502.00 USD $482.65 USD total for 3 nights

Sep 22 – 25, 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
$370 – $1,256/ night(excl. fees & taxes)
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)

$443.49 USD total for 3 nights

Oct 10 – 13, 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)

$2,104.33 USD total for 3 nights

Sep 22 – 25, 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
$207 – $297/ night(excl. fees & taxes)
Relax poolside with sun loungers and an umbrella for the perfect balance of sun and shade.
Unwind under the stars by the propane fire pit with comfy Adirondack seating.
Easy arrivals with wide parking space right at the front
Relax in the living room with a smart TV, ceiling fan, and comfy seating.
Backyard fun awaits—heated pool, fire pit, and giant games for everyone.

Heated Pool Retreat with Fire Pit, Outdoor Dining & Games

3 bedrooms·2 baths
Clearwater • Florida

$1,042.71 USD total for 3 nights

Sep 22 – 25, 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

Sep 22 – Oct 22, 2026

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 for 3 nights

Sep 22 – 25, 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)

$847.50 USD total for 3 nights

Sep 22 – 25, 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)

$666.70 USD total for 3 nights

Sep 22 – 25, 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

$1,283.69 USD $1,184.71 USD total for 3 nights

Sep 22 – 25, 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)

$1,555.96 USD total for 3 nights

Oct 2 – 5, 2026

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 total for 4 nights

Mar 17 – 21, 2027

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
$75 – $130/ night(excl. fees & taxes)
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 total for 3 nights

Sep 22 – 25, 2026

Paradise on Parkview Lane
Paradise on Parkview Lane
Paradise on Parkview Lane
Paradise on Parkview Lane
Paradise on Parkview Lane

Paradise on Parkview Lane

3 bedrooms·1 bath
Largo • Florida
5(1 review)

$899.00 USD total for 3 nights

Jan 3 – 6, 2027

A fun outdoor game area for adults and kids alike, featuring putt putt golf, ladder ball, axe throwing, giant Connect 4, and cornhole. Cozy string lights create a welcoming vibe, perfect for family fun, friendly competition, and relaxing evenings.
Florida Vacation Pool Home in Largo
While kids enjoy games like cornhole, adults can relax by the cozy fire pit or gather for an outdoor movie night, creating the perfect balance of fun and relaxation for everyone.
Relax and unwind in the spacious six-person hot tub, perfect for soaking under the open sky after a long day. Designed for comfort and group enjoyment, it’s ideal for couples, families, or friends looking to enjoy a warm, private retreat during their stay.
Florida Vacation Pool Home in Largo

Florida Vacation Pool Home in Largo

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

$1,164.66 USD total for 3 nights

Oct 31 – Nov 3, 2026

Mid day snacks by the pool are always nice too.
The spacious master bath offers dual vanities to allow quick prep for the beach.
There is always a late afternoon, early evening kayak option.
Or, sea side putting practice before dinner?
The smart TV in the kitchen allows the cook to enjoy the game or movie also.

Aloha Paradise

3 bedrooms·3 baths
Indian Rocks Beach • Florida
5(20 reviews)

$1,810.26 USD total for 3 nights

Sep 30 – Oct 3, 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)

$1,047.50 USD total for 3 nights

Sep 22 – 25, 2026

🌴Beautiful Pool Home! Beach in 6 min! Sleeps 8 🌴
🌴Beautiful Pool Home! Beach in 6 min! Sleeps 8 🌴
🌴Beautiful Pool Home! Beach in 6 min! Sleeps 8 🌴
🌴Beautiful Pool Home! Beach in 6 min! Sleeps 8 🌴
🌴Beautiful Pool Home! Beach in 6 min! Sleeps 8 🌴

🌴Beautiful Pool Home! Beach in 6 min! Sleeps 8 🌴

3 bedrooms·2 baths
Largo • Florida
5(49 reviews)

$880.90 USD total for 3 nights

Sep 22 – 25, 2026

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

$1,067.94 USD $963.01 USD total for 3 nights

Sep 22 – 25, 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)
$595 – $625/ night(excl. fees & taxes)
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)

$5,378.80 USD total for 28 nights

Sep 22 – Oct 20, 2026