Location

Dates

Guests

Vacation rentals in Madeira Beach, Florida, United States

250 steps to the Beach! image 1

250 steps to the Beach! image 3

250 steps to the Beach! image 4

250 steps to the Beach! image 5

250 steps to the Beach! image 6

250 steps to the Beach!

2 bedrooms·1 bath

Indian Rocks Beach • Florida

4.82(159 reviews)

$ 1.525,00 USD totaal voor 7 nachten

23–30 okt 2026

Private studio/pets friendly/10 mins to Downtown

Private studio/pets friendly/10 mins to Downtown

Private studio/pets friendly/10 mins to Downtown

Private studio/pets friendly/10 mins to Downtown

Private studio/pets friendly/10 mins to Downtown

Private studio/pets friendly/10 mins to Downtown

0 bedrooms·1 bath

St. Petersburg • Florida

4.32(19 reviews)

$ 316,00 USD totaal voor 3 nachten

23–26 okt 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 totaal voor 3 nachten

25–28 okt 2026

Sugar Sands Retreat #2

Sugar Sands Retreat #2

Sugar Sands Retreat #2

Sugar Sands Retreat #2

Sugar Sands Retreat #2

Sugar Sands Retreat #2

1 bedroom·1 bath

Indian Rocks Beach • Florida

$ 581,12 USD totaal voor 3 nachten

23–26 okt 2026

Sugar Sands Retreat #3

Sugar Sands Retreat #3

Spacious yard for relaxing

Sugar Sands Retreat #3

1 bedroom·1 bath

Indian Rocks Beach • Florida

$ 543,93 USD totaal voor 3 nachten

30 okt – 2 nov 2026

Vaulted ceilings with modern coastal feel

Sofa bed for extra guests

Sugar Sands Retreat #1

King bed with ensuite

Try standup paddle boarding

Sugar Sands Retreat #1

1 bedroom·1 bath

Indian Rocks Beach • Florida

$ 631,48 USD totaal voor 3 nachten

30 okt – 2 nov 2026

Blue Heron Cottage #1

Blue Heron Cottage #1

Blue Heron Cottage #1

Blue Heron Cottage #1

Blue Heron Cottage #1

Blue Heron Cottage #1

1 bedroom·1 bath

Indian Rocks Beach • Florida

Two blocks to bliss/beach

Two blocks to bliss/beach

Two blocks to bliss/beach

Two blocks to bliss/beach

Two blocks to bliss/beach

Two blocks to bliss/beach

3 bedrooms·2 baths

Indian Rocks Beach • Florida

$ 972,34 USD totaal voor 3 nachten

23–26 okt 2026

What could be more Florida than daquiries poolside?

Swimming in a heated pool at night?

Azul Paradise

5 bedrooms·4 baths

Indian Rocks Beach • Florida

5(41 reviews)

$422 – $1.900/ nacht(excl. kosten & belastingen)

🌴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)

$173 – $399/ nacht(excl. kosten & belastingen)

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

$ 476,86 USD totaal voor 3 nachten

23–26 okt 2026

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

$ 520,93 USD totaal voor 3 nachten

23–26 okt 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 totaal voor 3 nachten

3–6 jan 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)

$ 1.083,24 USD totaal voor 3 nachten

31 okt – 3 nov 2026

Sunset Paradise #6

Sunset Paradise #6

Sunset Paradise #6

Sunset Paradise #6

Sunset Paradise #6

Sunset Paradise #6

2 bedrooms·2½ baths

Indian Rocks Beach • Florida

$ 1.080,28 USD totaal voor 4 nachten

24–28 okt 2026

Sunset Paradise #5

Sunset Paradise #5

Sunset Paradise #5

Sunset Paradise #5

Sunset Paradise #5

Sunset Paradise #5

2 bedrooms·2 baths

Indian Rocks Beach • Florida

$ 1.102,88 USD totaal voor 4 nachten

24–28 okt 2026

Magnolia near the beach and downtown St. Pete image 1

Magnolia near the beach and downtown St. Pete image 2

Magnolia near the beach and downtown St. Pete image 3

Magnolia near the beach and downtown St. Pete image 4

Magnolia near the beach and downtown St. Pete image 5

Magnolia near the beach and downtown St. Pete

5 bedrooms·3 baths

St. Petersburg • Florida

4.85(150 reviews)

$ 773,23 USD totaal voor 3 nachten

26–29 okt 2026

Bermuda Bay Beach and Racquet Club Condo. 2bdrm/2b

Bermuda Bay Beach and Racquet Club Condo. 2bdrm/2b

Bermuda Bay Beach and Racquet Club Condo. 2bdrm/2b

Bermuda Bay Beach and Racquet Club Condo. 2bdrm/2b

Bermuda Bay Beach and Racquet Club Condo. 2bdrm/2b

Bermuda Bay Beach and Racquet Club Condo. 2bdrm/2b

2 bedrooms·2 baths

St. Petersburg • Florida

4.67(12 reviews)

$ 3.075,66 USD totaal voor 28 nachten

24 okt – 21 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 totaal voor 3 nachten

1–4 nov 2026

Waterfront Key West–style community, Stunning water views, glowing sunsets, and a laid-back island vibe ✨

King SUITE! Calm, Spacious and inviting, this KING bedroom features a plush KING-sized bed, with new bedding , dresser and 2 nighstands offering comfort and style for a restful night’s sleep in a beautifully designed space.

Stunning waterfront views from the bright, open-concept living room, dining area, and fully equipped kitchen. The perfect space to relax, gather, and make unforgettable memories by the water.

Nothing compares to swimming in the pool while breathing in the fresh ocean breeze.

WELCOME to your own private scenic beach, offering exclusive access to pristine sands and tranquil waters. Perfect for relaxing in solitude, soaking up the sun, or enjoying peaceful oceanfront moments.

Waterfront Escape | Private Beach + 2 Pools

1 bedroom·1 bath

St. Petersburg • Florida

4.5(16 reviews)

$ 4.379,88 USD $ 4.225,30 USD totaal voor 30 nachten

24 okt – 23 nov 2026

Living room with natural lighting.

Fenced backyard with patio and seating.

Inquire About Discounted Rental Rate

Maxwell Sands

3 bedrooms·2 baths

Indian Rocks Beach • Florida

$ 1.141,86 USD $ 1.025,83 USD totaal voor 3 nachten

23–26 okt 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)

$390 – $2.339/ nacht(excl. kosten & belastingen)

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)

$ 6.182,23 USD totaal voor 28 nachten

30 nov – 28 dec 2026

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)

$ 949,51 USD totaal voor 3 nachten

25–28 okt 2026