Steps to Beach, Heated Pool, 2 Queen Beds, 2BA
Steps to Beach, Heated Pool, 2 Queen Beds, 2BA
Steps to Beach, Heated Pool, 2 Queen Beds, 2BA
Steps to Beach, Heated Pool, 2 Queen Beds, 2BA
Steps to Beach, Heated Pool, 2 Queen Beds, 2BA

Steps to Beach, Heated Pool, 2 Queen Beds, 2BA

2 bedrooms·2 baths
Madeira Beach • Florida

$1,965.82 USD total for 3 nights

Sep 30 – Oct 3, 2026

Madeira Beachside - Pool & Steps to the Sand
Madeira Beachside - Pool & Steps to the Sand
Madeira Beachside - Pool & Steps to the Sand
Madeira Beachside - Pool & Steps to the Sand
Madeira Beachside - Pool & Steps to the Sand

Madeira Beachside - Pool & Steps to the Sand

1 bedroom·1 bath
Madeira Beach • Florida

$1,594.68 USD total for 3 nights

Sep 30 – Oct 3, 2026

King Bed, Steps to Madeira Beach, Heated Pool, Private
King Bed, Steps to Madeira Beach, Heated Pool, Private
King Bed, Steps to Madeira Beach, Heated Pool, Private
King Bed, Steps to Madeira Beach, Heated Pool, Private
King Bed, Steps to Madeira Beach, Heated Pool, Private

King Bed, Steps to Madeira Beach, Heated Pool, Private

1 bedroom·1 bath
Madeira Beach • Florida

$1,755.85 USD total for 3 nights

Sep 30 – Oct 3, 2026

King Bed, Step to Madeira Beach, Heated Pool, Private
King Bed, Step to Madeira Beach, Heated Pool, Private
King Bed, Step to Madeira Beach, Heated Pool, Private
King Bed, Step to Madeira Beach, Heated Pool, Private
King Bed, Step to Madeira Beach, Heated Pool, Private

King Bed, Step to Madeira Beach, Heated Pool, Private

1 bedroom·1 bath
Madeira Beach • Florida

$1,646.89 USD total for 3 nights

Sep 30 – Oct 3, 2026

King Bed-Step to Madeira Beach-Heated Pool-Private
King Bed-Step to Madeira Beach-Heated Pool-Private
King Bed-Step to Madeira Beach-Heated Pool-Private
King Bed-Step to Madeira Beach-Heated Pool-Private
King Bed-Step to Madeira Beach-Heated Pool-Private

King Bed-Step to Madeira Beach-Heated Pool-Private

1 bedroom·1 bath
Madeira Beach • Florida

$1,646.89 USD total for 3 nights

Sep 30 – Oct 3, 2026

Front of Home
Front of Home
Dining Area
Dining Area
Dining Area

The Parkside Retreat at 78th Street

3 bedrooms·2 baths
Pinellas Park • Florida

$731.50 USD total for 3 nights

Sep 30 – Oct 3, 2026

Welcome to Emperor Rentals!
Have an amazing barbecue party while swimming with family and friends!
Comfortable bed to ensure you get the rest you deserve your entire stay
Feel cozy and refreshed on our beautiful couch and enjoy the well-lit environment. Make unforgettable memories with family and friends during you vacation!

Serenity Stay Villa

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

$935.37 USD $827.38 USD total for 3 nights

Sep 30 – Oct 3, 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

$1,347.00 USD total for 3 nights

Oct 4 – 7, 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 total for 30 nights

Sep 30 – Oct 30, 2026

Mermaid Manor. Only 2 block to the BEACH!
Mermaid Manor - Waterfront | Dolphins & Sunsets
Mermaid Manor - Waterfront | Dolphins & Sunsets
Mermaid Manor - Waterfront | Dolphins & Sunsets
Mermaid Manor - Waterfront | Dolphins & Sunsets

Mermaid Manor - Waterfront | Dolphins & Sunsets

2 bedrooms·2 baths
Treasure Island • Florida

$856.85 USD total for 3 nights

Oct 9 – 12, 2026

Funshine Pointe Capri - Newly Renovated - Intercoastal Views
Funshine Pointe Capri - Newly Renovated - Intercoastal Views
Funshine Pointe Capri - Newly Renovated - Intercoastal Views
Funshine Pointe Capri - Newly Renovated - Intercoastal Views
Funshine Pointe Capri - Newly Renovated - Intercoastal Views

Funshine Pointe Capri - Newly Renovated - Intercoastal Views

1 bedroom·1 bath
Treasure Island • Florida
5(178 reviews)

$463.02 USD total for 3 nights

Oct 19 – 22, 2026

Park & Pool Across the Street and 9 Mins to Beach
Park & Pool Across the Street and 9 Mins to Beach
Park & Pool Across the Street and 9 Mins to Beach
Park & Pool Across the Street and 9 Mins to Beach
Park & Pool Across the Street and 9 Mins to Beach

Park & Pool Across the Street and 9 Mins to Beach

4 bedrooms·2 baths
St. Petersburg • Florida
4.95(43 reviews)

$1,293.00 USD total for 7 nights

Sep 30 – Oct 7, 2026

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

$1,157.31 USD total for 3 nights

Sep 30 – Oct 3, 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 total for 3 nights

Sep 30 – Oct 3, 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

$2,665.33 USD total for 7 nights

Sep 30 – Oct 7, 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

$1,314.25 USD $1,212.22 USD total for 3 nights

Oct 5 – 8, 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 total for 3 nights

Sep 30 – Oct 3, 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)

$1,151.76 USD total for 3 nights

Oct 16 – 19, 2026

Treasure Island Waterfront Luxury Condo image 5
Treasure Island Waterfront Luxury Condo image 1
Treasure Island Waterfront Luxury Condo image 2
Treasure Island Waterfront Luxury Condo image 3
Treasure Island Waterfront Luxury Condo image 4

Treasure Island Waterfront Luxury Condo

2 bedrooms·2 baths
Treasure Island • Florida
5(3 reviews)

$2,087.00 USD total for 6 nights

Sep 30 – Oct 6, 2026

Sun Oasis
Primary bedroom — king bed with coastal luxury bedding, wall-mounted smart TV, and direct sliding glass door access to the private screened pool.
Coastal dining room at Sun Oasis — a farmhouse-style table set for six with blue place settings and teal glassware, teal front door visible beyond, flowing into the living room.
Full living room — two plush sofas, striped armchair, coastal round ottoman, oversized Oasis on 40th turtle 70-inch TV art, guest book on the coffee table, and the game room archway beyond.
Screened private pool with string lights for relaxing evening swims

Pool, Game Room and Fire Pit Near Madeira Beach

3 bedrooms·2 baths
St. Petersburg • Florida
5(72 reviews)

$886.20 USD $815.58 USD total for 3 nights

Sep 30 – Oct 3, 2026

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/ night(excl. fees & taxes)
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 $511.15 USD total for 3 nights

Sep 30 – Oct 3, 2026

Prime location, Pool Oasis near St. Pete Beach
Prime location, Pool Oasis near St. Pete Beach
Prime location, Pool Oasis near St. Pete Beach
Prime location, Pool Oasis near St. Pete Beach
Prime location, Pool Oasis near St. Pete Beach

Prime location, Pool Oasis near St. Pete Beach

2 bedrooms·2 baths
St. Petersburg • Florida
5(39 reviews)

$1,501.25 USD total for 3 nights

Sep 30 – Oct 3, 2026

FREE NIGHT! Jeffreys Bay African retreat!
FREE NIGHT! Jeffreys Bay African retreat!
FREE NIGHT! Jeffreys Bay African retreat!
FREE NIGHT! Jeffreys Bay African retreat!
FREE NIGHT! Jeffreys Bay African retreat!

FREE NIGHT! Jeffreys Bay African retreat!

2 bedrooms·1 bath
Treasure Island • Florida

$676.10 USD total for 3 nights

Apr 22 – 25, 2027