Location

Dates

Guests

Vacation rentals in Madeira Beach, Florida, United States

Private backyard retreat with hot tub, fire pit & outdoor dining under café lights

Relax under the courtyard pergola beside the fire table in your private outdoor lounge.

Relax in the hot tub beneath the pergola with bar seating and ambient string lights.

Spacious great room with plenty of comfortable seating for the whole group to relax together.

Primary king suite with a private office and en suite bath.

The Salted Dream House

5 bedrooms·2½ baths

Largo • Florida

$ 2.770,06 USD totaal voor 5 nachten

23–28 okt 2026

Casa Noir by Perez Benitez image 1

Casa Noir by Perez Benitez image 2

Casa Noir by Perez Benitez image 3

Casa Noir by Perez Benitez image 4

Casa Noir by Perez Benitez image 5

Casa Noir by Perez Benitez

4 bedrooms·2 baths

St. Petersburg • Florida

5(6 reviews)

$300/ nacht(excl. kosten & belastingen)

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 totaal voor 3 nachten

23–26 okt 2026

Ruhiges Zimmer mit tropischem Pool und Strandzugang

Ruhiges Zimmer mit tropischem Pool und Strandzugang

1 bedroom·1 bath

St. Petersburg • Florida

Gulf front pool

Front of the building

Hallway into condo

Sand Isle I

2 bedrooms·2 baths

Indian Rocks Beach • Florida

4.77(100 reviews)

$ 847,50 USD totaal voor 3 nachten

15–18 nov 2026

Spacious living room.

Fully equipped kitchen and plenty of seating

Open concept living room

Beach AND Pool!2/2 large condo

2 bedrooms·2 baths

Indian Rocks Beach • Florida

5(152 reviews)

$ 1.333,40 USD totaal voor 5 nachten

16–21 nov 2026

Living room with Full Size sleep sofa

Private condo steps to beach (3)

Private condo steps to beach (3)

Newly remodeled bathroom as of 1/2024

Fully equipped kitchen

Private condo steps to beach (3)

1 bedroom·1 bath

St. Pete Beach • Florida

$ 1.511,70 USD totaal voor 6 nachten

23–29 okt 2026

Waterfront 3BR 2 1/2 Bath, Amazing View-Sunrises!

3 bedrooms·2½ baths

St. Pete Beach • Florida

5(3 reviews)

$ 13.750,00 USD totaal voor 30 nachten

1–31 jan 2027

Your favorite beach getaway (4)

Your favorite beach getaway (4)

Your favorite beach getaway (4)

Shared Laundry room located on 1st flooor

Your favorite beach getaway (4)

Your favorite beach getaway (4)

1 bedroom·1 bath

St. Pete Beach • Florida

5(3 reviews)

$ 1.606,00 USD totaal voor 6 nachten

23–29 okt 2026

Holiday Family Retreat. 4BR/3BA + Private Suites

Holiday Family Retreat. 4BR/3BA + Private Suites

Holiday Family Retreat. 4BR/3BA + Private Suites

Holiday Family Retreat. 4BR/3BA + Private Suites

Holiday Family Retreat. 4BR/3BA + Private Suites

4 bedrooms·3 baths

St. Petersburg • Florida

$399/ nacht(excl. kosten & belastingen)

Modern Cozy Spot. Near Beach & DT. Yard & Parking image 1

Modern Cozy Spot. Near Beach & DT. Yard & Parking image 2

Modern Cozy Spot. Near Beach & DT. Yard & Parking image 3

Modern Cozy Spot. Near Beach & DT. Yard & Parking image 4

Modern Cozy Spot. Near Beach & DT. Yard & Parking image 5

Adorable Studio East, close to beaches & downtown

0 bedrooms·1 bath

St. Petersburg • Florida

4.88(41 reviews)

$ 2.881,44 USD $ 2.214,83 USD totaal voor 28 nachten

23 okt – 20 nov 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)

$ 984,66 USD $ 857,57 USD totaal voor 3 nachten

23–26 okt 2026

Studio w/ yard & parking, near beach & downtown. image 1

Studio w/ yard & parking, near beach & downtown. image 2

Studio w/ yard & parking, near beach & downtown. image 3

Studio w/ yard & parking, near beach & downtown. image 4

Studio w/ yard & parking, near beach & downtown. image 5

Adorable Studio West, close to beaches & downtown

0 bedrooms·1 bath

St. Petersburg • Florida

4.72(50 reviews)

$ 2.881,44 USD $ 2.348,15 USD totaal voor 28 nachten

3 nov – 1 dec 2026

Building Arial View

St Pete Beachside Condo

1 bedroom·1 bath

St. Pete Beach • Florida

5(3 reviews)

$ 1.297,68 USD totaal voor 5 nachten

23–28 okt 2026

Beautiful Waterfront Condo short walk to the beach image 1

Beautiful Waterfront Condo short walk to the beach image 2

Beautiful Waterfront Condo short walk to the beach image 3

Beautiful Waterfront Condo short walk to the beach image 4

Beautiful Waterfront Condo short walk to the beach image 5

Romantic Waterfront Getaway short walk to beach

3 bedrooms·2 baths

Indian Rocks Beach • Florida

$ 3.416,35 USD $ 2.823,88 USD totaal voor 29 nachten

23 okt – 21 nov 2026

Exterior view of Studio East & Studio West. Each studio has private entrance and private yard, connected with a gate.

Studio 1 (East) private porch

Studio 1 (East) private porch and outdoor

Studio 1 (East)

Studio 1 (East)

Adorable Pair - 2 private modern studios

2 bedrooms·2 baths

St. Petersburg • Florida

4.5(2 reviews)

$ 6.282,04 USD totaal voor 28 nachten

3 nov – 1 dec 2026

Adorable Private Cottage close to beach & downtown

Adorable Private Cottage close to beach & downtown

Adorable Private Cottage close to beach & downtown

Adorable Private Cottage close to beach & downtown

Adorable Private Cottage close to beach & downtown

Adorable Private Cottage close to beach & downtown

2 bedrooms·1 bath

St. Petersburg • Florida

5(268 reviews)

$139 – $1.999/ nacht(excl. kosten & belastingen)

Welcome to Emperor Rentals!

Featuring a plush blue couch that beckons you to sink in and relax.

Indulge in the ultimate comfort and luxury of our exquisite bathroom, complete with a delightful combination of a tub and shower, elegant his and her sinks, and a modern toilet.

This kitchen is more than just a functional space; it's a culinary sanctuary that inspires creativity, fosters connection, and nourishes the soul. Huge fridge, white cupboards, blue painted walls, complete appliances, and well-stocked utensils.

Tidal Retreat

2 bedrooms·2 baths

Indian Rocks Beach • Florida

5(4 reviews)

$ 752,47 USD totaal voor 3 nachten

4–7 nov 2026

Largo Heated Pool + Hot Tub, sleeps 16, gameroom

Largo Heated Pool + Hot Tub, sleeps 16, gameroom

Largo Heated Pool + Hot Tub, sleeps 16, gameroom

Largo Heated Pool + Hot Tub, sleeps 16, gameroom

Largo Heated Pool + Hot Tub, sleeps 16, gameroom

Largo Heated Pool + Hot Tub, sleeps 16, gameroom

3 bedrooms·2 baths

Largo • Florida

4.5(12 reviews)

$ 1.262,00 USD totaal voor 3 nachten

23–26 okt 2026

Clearwater Beach House • Heated Pool • Hot Tub

Clearwater Beach House • Heated Pool • Hot Tub

Clearwater Beach House • Heated Pool • Hot Tub

Clearwater Beach House • Heated Pool • Hot Tub

Clearwater Beach House • Heated Pool • Hot Tub

Clearwater Beach House • Heated Pool • Hot Tub

5 bedrooms·2 baths

Largo • Florida

$ 1.852,48 USD totaal voor 3 nachten

23–26 okt 2026

Enjoy the pool, drinks and a meal as the sun dips into the Gulf.

Grab the free paddle board and explore the waters around Indian Rocks Beach

Add a 2nd 6-seater golf cart after booking so everyone can ride

Bahia Paradise

4 bedrooms·4 baths

Indian Rocks Beach • Florida

5(1 review)

$ 2.287,02 USD totaal voor 3 nachten

1–4 nov 2026

Beautiful View Overlooking Canal, Dock, and Lift

Aerial View of Back of Property

Welcome to Villa Azure

V Azule- Evening- Canal, Lift

V Azule- Outside Dining-Patio

Villa Azule | Luxury Waterfront Retreat • Walk to Indian Rocks Beach

4 bedrooms·5 baths

Indian Rocks Beach • Florida

4.88(146 reviews)

$ 2.065,13 USD totaal voor 3 nachten

26–29 okt 2026

Your private backyard oasis—unwind under the stars with a fire and make some s’mores.

Soak under the stars after exploring Florida’s beautiful Gulf Coast.

Spacious fenced backyard with fire pit, lawn games, and lounge seating

Bright, cozy bedroom with warm accents, natural light, and stylish decor

Bright coastal bedroom with cozy decor, soft light, and fresh greenery

Sunshine State of Mind

3 bedrooms·2 baths

Largo • Florida

5(64 reviews)

$ 693,95 USD totaal voor 3 nachten

15–18 nov 2026

1 Bedroom Apartment/ Pets friendly/ 15 mins DTSP image 1

1 Bedroom Apartment/ Pets friendly/ 15 mins DTSP image 2

1 Bedroom Apartment/ Pets friendly/ 15 mins DTSP image 4

1 Bedroom Apartment/ Pets friendly/ 15 mins DTSP image 5

1 Bedroom Apartment/ Pets friendly/ 15 mins DTSP image 6

1Bedroom/ 10 mins to Downtown Saint Peterburg

1 bedroom·1 bath

St. Petersburg • Florida

4.36(25 reviews)

$85 – $95/ nacht(excl. kosten & belastingen)