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Vacation rentals in Madeira Beach, Florida, United States

Primary Bedroom

Kitchen & Living Area

Sea Club #1 - Seas the Day, Steps from the Beach

2 bedrooms·2 baths

Indian Shores • Florida

Covered waterfront Condo!

Primary Bedroom - King size bed

Primary Bedroom

Living Space with a View

Sea Club Condo #102

1 bedroom·1 bath

Indian Shores • Florida

Dolphin's Den View from Covered Balcony

Dolphin's Den Living Space

Dolphin's Den Master Bedroom

Dolphin's Den Master Bedroom

Dolphin's Den Kitchen

Sea Club Condo 14 - Dolphins Den

2 bedrooms·2 baths

Indian Shores • Florida

Sea Club Condo #44

Sea Club Condo #44

2 bedrooms·2 baths

Indian Shores • Florida

Sea Club #19 Intracoastal Condo

Sea Club #19 Intracoastal Condo

Sea Club #19 Intracoastal Condo

Sea Club #19 Intracoastal Condo

Sea Club #19 Intracoastal Condo

Sea Club #19 Intracoastal Condo

2 bedrooms·2 baths

Indian Shores • Florida

Footprints in the Sand Covered Balcony

Sea Club Community Pool

Sea Club Condo #6

Footprints in the Sand Master Bedroom

Footprints in the Sand - Two Bedroom Condo

Sea Club Condo #6

2 bedrooms·2 baths

Indian Shores • Florida

Sea Haven - 2 Bedroom Condo Intracoastal Views

Sea Haven Living Space

Sea Haven Kitchen

Good Vibes Only Sitting Area

Sea Haven Guest Bedroom

Sea Club Condo #47

2 bedrooms·2 baths

Indian Shores • Florida

Dolphin's Lookout

Dolphin's Lookout - Primary Bedroom

Dolphin's Lookout - Queen Sofa Sleeper

Dolphins Lookout Full Kitchen

Sea Club Community Swimming Pool

Sea Club Condo #32

2 bedrooms·2 baths

Indian Shores • Florida

Private tropical pool oasis with loungers, shade, and resort-style vibes

Tropical-inspired bedroom with en suite bath and stylish barn door

Private pool deck with lounge chairs, pool noodles, and floats included. Fully fenced, tropical landscaping, sleeps 10. Gulfport/South St. Pete, FL.

Private tropical pool oasis with loungers, shade, and lush palms

Open-plan living and kitchen — 65-inch smart TV, breakfast bar with 4 stools, and mustard yellow sofas. 4-bedroom vacation rental, St. Petersburg, FL.

Tropical Disco 70s Disco Lounge and Heated Pool Near St Pete Beach

4 bedrooms·2 baths

St. Petersburg • Florida

5(187 reviews)

1.229,11 $ USD gesamt für 3 Nächte

9.–12. Nov. 2026

Waterfront Home with Heated Pool 2 Mi from Beaches

Waterfront Home with Heated Pool 2 Mi from Beaches

Waterfront Home with Heated Pool 2 Mi from Beaches

Waterfront Home with Heated Pool 2 Mi from Beaches

Waterfront Home with Heated Pool 2 Mi from Beaches

Waterfront Home with Heated Pool 2 Mi from Beaches

3 bedrooms·2 baths

St. Petersburg • Florida

4.9(51 reviews)

1.497,00 $ USD gesamt für 3 Nächte

27.–30. Okt. 2026

Steps from the beach! Newly listed updated unit image 1

Cross the parking spaces and dunes... to have your toes in the sand. Famous beach bars /restaurants to the left of the peach condos on the left.

Steps from the beach! Newly listed updated unit image 3

primary bedroom

primary bedroom

Steps from the beach! Newly listed updated unit

2 bedrooms·1 bath

St. Pete Beach • Florida

4.94(16 reviews)

1.317,00 $ USD gesamt für 3 Nächte

23.–26. Okt. 2026

Sunset on Indian Shores Beach

Community Swimming Pool

The Intracoastal #205

3 bedrooms·2 baths

Indian Shores • Florida

Dining room with views of the pool.

Enjoy golden hour from the private outdoor deck and pool.

Open layout kitchen and living room.

Cozy living room.

Enjoy a game of air hockey or ping pong.

Paradise Passage

4 bedrooms·3 baths

Seminole • Florida

1.397,62 $ USD 1.302,33 $ USD gesamt für 3 Nächte

24.–27. Okt. 2026

Lovely fire after a day at the beach and a tasty BBQ!

Large private backyard!

Living room w/Roku TV, Games, DVD player w/DVDs, Books & Local Info! Sofa Bed is a Queen size MEMORY FOAM that is so comfortable!

No Wake Queen Bedroom with Roku TV, a bookshelf, 2 nightstands, a dresser and two closet areas.

Hannah House Vacation Rentals

5 bedrooms·2 baths

Largo • Florida

1.119,82 $ USD 1.081,24 $ USD gesamt für 3 Nächte

23.–26. Okt. 2026

St Pete Beach Condo (1)

St Pete Beach Condo (1)

St Pete Beach Condo (1)

St Pete Beach Condo (1)

St Pete Beach Condo (1)

St Pete Beach Condo (1)

1 bedroom·1½ baths

St. Pete Beach • Florida

19.504,80 $ USD gesamt für 90 Nächte

2. Nov. 2026 – 31. Jan. 2027

St Pete Beach Condo (2)

St Pete Beach Condo (2)

St Pete Beach Condo (2)

St Pete Beach Condo (2)

St Pete Beach Condo (2)

St Pete Beach Condo (2)

1 bedroom·1½ baths

St. Pete Beach • Florida

18.060,00 $ USD 16.269,00 $ USD gesamt für 90 Nächte

23. Okt. 2026 – 21. Jan. 2027

Coastal-style living room with fireplace, TV, and bright open seating

Coastal-chic living room with fireplace, built-ins, and inviting seating

Bright coastal living space with fireplace and large dining table

Screened pool patio with tiki bar, grill, and tropical lounge seating

Private tree-lined home with screened pool in a peaceful neighborhood

Twin Oaks Luxury Heated Pool and Caribbean Tiki Bar Near Indian Rocks Beach

4 bedrooms·3 baths

Largo • Florida

5(51 reviews)

944,16 $ USD gesamt für 3 Nächte

25.–28. Okt. 2026

private pool in backyard

new refrigerator

view from front door

bright and spacious living room

private lap pool and patio furniture

Captain's Cove with pool in Sunny Largo, FL

2 bedrooms·1 bath

Largo • Florida

554,21 $ USD gesamt für 3 Nächte

24.–27. Okt. 2026

air conditioned sun room

beach living room

Paradise Place, Pets/Ms. Pac Man

Paradise Place, Pets/Ms. Pac Man

2 bedrooms·2 baths

Largo • Florida

1.716,26 $ USD gesamt für 4 Nächte

1.–5. Apr. 2027

air conditioned sun room

beach living room

Paradise Place, Pets/Ms. Pac Man

Paradise Place, Pets/Ms. Pac Man

2 bedrooms·2 baths

Largo • Florida

1.716,26 $ USD gesamt für 4 Nächte

1.–5. Apr. 2027

Toes in the water...

Kitchen / eating area

Catch sunsets like this just a 2 min walk from your front door.

St Pete Beach Condo - Steps to the Sand! Pool, Pickleball, Dual Gulf & Bay Views

2 bedrooms·2 baths

St. Pete Beach • Florida

1.130,00 $ USD gesamt für 3 Nächte

23.–26. Okt. 2026

9BR Heated Pool • Hot Tub • Golf Simulator

9BR Heated Pool • Hot Tub • Golf Simulator

9BR Heated Pool • Hot Tub • Golf Simulator

9BR Heated Pool • Hot Tub • Golf Simulator

9BR Heated Pool • Hot Tub • Golf Simulator

9BR Heated Pool • Hot Tub • Golf Simulator

9 bedrooms·4 baths

Largo • Florida

5.544,91 $ USD gesamt für 3 Nächte

23.–26. Okt. 2026

Outdoor seating with Heated Pool

Pool Home-Close to Beach/St Pete

3 bedrooms·2 baths

Largo • Florida

$213 – $391/ Nacht(zzgl. Gebühren & Steuern)

Pond-side ART-home with private pool. DOGS WELCOME

5 bedrooms·3 baths

Pinellas Park • Florida

5(20 reviews)

$318/ Nacht(zzgl. Gebühren & Steuern)