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Vacation rentals in Madeira Beach, Florida, United States

Jacuzzi/ Pool #1

Modern 2BR | Pool, Gym + Pet-Friendly #12

2 bedrooms·2 baths

Tampa • Florida

5(2 reviews)

$ 808,51 USD $ 752,91 USD totaal voor 3 nachten

25–28 okt 2026

Welcome to Emperor Rentals!

Explore the beauty and comfort of our bedroom, where you can truly unwind and relax.

A fully fenced backyard with an amazing heated salt pool where you, family and friends can have fun and bond. Lounge chairs where you could relax.

Gorgeous entertainment area with Pool table. Have fun with family and friends while playing competitive games.

Welcome to an inviting house exterior design that effortlessly blends charm and modernity.

The Luxe Oasis

4 bedrooms·3 baths

Tampa • Florida

5(44 reviews)

$ 2.284,32 USD $ 2.193,49 USD totaal voor 6 nachten

30 nov – 6 dec 2026

Your Tampa Bay Vacation Entertainment Home image 1

Entertainment Awaits 3-Bedrooms, 2-Full Bath, Washer & Dryer, 8Ft Pool, Poker, & PingPong Table, Dart-broad, Grill, 900Sq. Ft. Lanai, with Privacy Fence. Smart TV in Every-room.
Just Bring Your Clothes & Food!

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Your Tampa Bay Vacation Entertainment Home image 5

Your Tampa Bay Vacation Entertainment Home

3 bedrooms·2 baths

Tampa • Florida

4.79(180 reviews)

$ 784,00 USD totaal voor 6 nachten

4–10 nov 2026

Waterfront 2/1 Apt in heart of Palm Harbor/Ozona image 1

Waterfront 2/1 Apt in heart of Palm Harbor/Ozona image 2

Waterfront 2/1 Apt in heart of Palm Harbor/Ozona image 3

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Waterfront 2/1 Apt in heart of Palm Harbor/Ozona image 5

Waterfront 2/1 Apt in heart of Palm Harbor/Ozona

2 bedrooms·1 bath

Palm Harbor • Florida

4.85(62 reviews)

$ 1.195,00 USD totaal voor 4 nachten

24–28 okt 2026

3 bed/2 bath Home W/ Gulf Water Access image 1

3 bed/2 bath Home W/ Gulf Water Access image 2

3 bed/2 bath Home W/ Gulf Water Access image 3

3 bed/2 bath Home W/ Gulf Water Access image 4

3 bed/2 bath Home W/ Gulf Water Access image 5

3 bed/2 bath Home W/ Gulf Water Access

3 bedrooms·2 baths

Palm Harbor • Florida

4.74(50 reviews)

$ 1.450,00 USD totaal voor 5 nachten

26–31 mrt 2027

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Tampa Event Compound, Hot Tub Bar

Tampa Event Compound, Hot Tub Bar

10 bedrooms·10 baths

Tampa • Florida

5(48 reviews)

$ 21.590,00 USD $ 18.426,50 USD totaal voor 7 nachten

24–31 okt 2026

#1 Largest Tampa Private Compound · 13BR Sleeps 40+ · Heated Pool/Spa

#1 Largest Tampa Private Compound · 13BR Sleeps 40+ · Heated Pool/Spa

#1 Largest Tampa Private Compound · 13BR Sleeps 40+ · Heated Pool/Spa

#1 Largest Tampa Private Compound · 13BR Sleeps 40+ · Heated Pool/Spa

#1 Largest Tampa Private Compound · 13BR Sleeps 40+ · Heated Pool/Spa

#1 Largest Tampa Private Compound · 13BR Sleeps 40+ · Heated Pool/Spa

13 bedrooms·7 baths

Tampa • Florida

$ 9.384,48 USD totaal voor 3 nachten

24–27 okt 2026

Waterfront 2/1 Apt. Ozona/Palm Harbor (Beachcomber image 1

Waterfront 2/1 Apt. Ozona/Palm Harbor (Beachcomber image 2

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Waterfront 2/1 Apt. Ozona/Palm Harbor (Beachcomber

2 bedrooms·1 bath

Palm Harbor • Florida

4.86(74 reviews)

$ 762,00 USD totaal voor 3 nachten

24–27 okt 2026

The open floor plan features an 8-foot island, connecting the gourmet kitchen, living, and dining areas. Surrounded by palm and oak trees, large windows offer views of nature w french doors leading to the outdoor deck and fully enclosed backyard

Bright dining area with seating for 8, surrounded by large windows and French doors overlooking the property’s tropical greenery. Perfect for family dinners, morning coffee, or gathering after a day in Tampa Bay.

Modern Luxury | Fenced | Pet Friendly

The living area with seating for eight, has views of the private garden set amongst oak trees, palm trees, birds of paradise making it the perfect place to relax and unwind or connect with friends and family. The sofa features a pull out queen bed.

Guest Room Featuring a Queen bed, smart TV & dedicated workspace

Modern Luxury | Fenced | Pet Friendly

3 bedrooms·2½ baths

Tampa • Florida

5(1 review)

$ 912,39 USD totaal voor 3 nachten

29 nov – 2 dec 2026

Coastal Cottage Near Beaches w/ Golf Cart Rental! image 1

Rent our Golf Cart, "Bolt" !

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Coastal Cottage Near Beaches w/ Golf Cart Rental!

2 bedrooms·2 baths

Palm Harbor • Florida

4.99(71 reviews)

$ 759,00 USD totaal voor 3 nachten

24–27 okt 2026

Pvt Pool, Free Kayaks, Steps to Gulf, Fish, Bike Trail +

Pvt Pool, Free Kayaks, Steps to Gulf, Fish, Bike Trail +

Pvt Pool, Free Kayaks, Steps to Gulf, Fish, Bike Trail +

Pvt Pool, Free Kayaks, Steps to Gulf, Fish, Bike Trail +

Pvt Pool, Free Kayaks, Steps to Gulf, Fish, Bike Trail +

Pvt Pool, Free Kayaks, Steps to Gulf, Fish, Bike Trail +

1 bedroom·1 bath

Dunedin • Florida

5(93 reviews)

$ 480,03 USD totaal voor 3 nachten

29 okt – 1 nov 2026

Sit back and enjoy this beautiful coastal home where u can relax and enjoy what Florida can offer.

Pool home minutes from the beach. image 2

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Pool home minutes from the beach. image 4

Pool home minutes from the beach.

3 bedrooms·2 baths

Palm Harbor • Florida

5(33 reviews)

$ 950,00 USD totaal voor 3 nachten

30 okt – 2 nov 2026

Bright open dining space with seating for 6 and stylish modern lighting

Bayshore Beautiful Home | 4BR + Gym + Studio

Covered patio with comfy seating and a private, lush fenced yard

Bayshore Beautiful Home | 4BR + Gym + Studio

Bright open living area with dining space, bar seating, and large TV

Bayshore Beautiful Home | 4BR + Gym + Studio

5 bedrooms·3 baths

Tampa • Florida

$ 6.480,00 USD totaal voor 30 nachten

30 nov – 30 dec 2026

Gorgeous Beach Home with heated pool

Gorgeous Beach Home with heated pool

Gorgeous Beach Home with heated pool

Gorgeous Beach Home with heated pool

Gorgeous Beach Home with heated pool

Gorgeous Beach Home with heated pool

3 bedrooms·3 baths

Holmes Beach • Florida

5(9 reviews)

$ 14.959,60 USD totaal voor 28 nachten

24 okt – 21 nov 2026

Tampa 6BR Heated Pool HotTub,Theater,GameRoom,Gym

Tampa 6BR Heated Pool HotTub,Theater,GameRoom,Gym

Tampa 6BR Heated Pool HotTub,Theater,GameRoom,Gym

Tampa 6BR Heated Pool HotTub,Theater,GameRoom,Gym

Tampa 6BR Heated Pool HotTub,Theater,GameRoom,Gym

Tampa 6BR Heated Pool HotTub,Theater,GameRoom,Gym

6 bedrooms·3½ baths

Tampa • Florida

5(55 reviews)

$ 5.989,00 USD $ 5.546,04 USD totaal voor 3 nachten

24–27 okt 2026

#1 Rated Mansion • Heated Pool/Spa • Theater • Gym • Game Room

#1 Rated Mansion • Heated Pool/Spa • Theater • Gym • Game Room

#1 Rated Mansion • Heated Pool/Spa • Theater • Gym • Game Room

#1 Rated Mansion • Heated Pool/Spa • Theater • Gym • Game Room

#1 Rated Mansion • Heated Pool/Spa • Theater • Gym • Game Room

#1 Rated Mansion • Heated Pool/Spa • Theater • Gym • Game Room

6 bedrooms·4 baths

Tampa • Florida

$ 3.566,08 USD totaal voor 3 nachten

24–27 okt 2026

Waterfront in paradise!

Waterfront in paradise!

Waterfront in paradise!

Waterfront in paradise!

Waterfront in paradise!

Waterfront in paradise!

3 bedrooms·3 baths

Palm Harbor • Florida

$ 2.740,09 USD totaal voor 14 nachten

24 okt – 7 nov 2026

Beachfront Condo on Anna Maria Island, FL, USA

Beachfront Condo on Anna Maria Island, FL, USA

Beachfront Condo on Anna Maria Island, FL, USA

Beachfront Condo on Anna Maria Island, FL, USA

Beachfront Condo on Anna Maria Island, FL, USA

Beachfront Condo on Anna Maria Island, FL, USA

2 bedrooms·2 baths

Anna Maria • Florida

$ 3.870,00 USD totaal voor 14 nachten

24 okt – 7 nov 2026

The heated saltwater pool gets lovely sun and features plenty of sun loungers and cabanas.

Tampa Tropical-Heated Saltwater Pool-10 Min to TPA

The well equipped kitchen has stainless steel appliances and is outfitted with everything you need to cook a good meal at home.

Maybe boxing is your style? Knock yourself out.

The large, 2-story gym is a favorite. No need to abandon your fitness routine during your stay!

Tampa Tropical-Heated Saltwater Pool-10 Min to TPA

1 bedroom·1 bath

Tampa • Florida

5(11 reviews)

$ 749,10 USD totaal voor 3 nachten

29 okt – 1 nov 2026

Relax after a day of taking in the sight around Tampa Bay.

Modern living, dining gathering space.

Walk, roller blade, job or rent a bike with city bike share program, all steps away.

Fully stocked Keurig machine and open kitchen greet you each morning.

The place where everyone ends up gathering!

Bayshore • South Tampa Luxury: Private Bath

2 bedrooms·1 bath

Tampa • Florida

4.93(43 reviews)

$ 54.982,00 USD totaal voor 120 nachten

24 okt 2026 – 21 feb 2027

Stylish 2BR Corporate Stay | Pool + Balcony #2

Stylish 2BR Corporate Stay | Pool + Balcony #2

Stylish 2BR Corporate Stay | Pool + Balcony #2

Stylish 2BR Corporate Stay | Pool + Balcony #2

Stylish 2BR Corporate Stay | Pool + Balcony #2

Stylish 2BR Corporate Stay | Pool + Balcony #2

2 bedrooms·2 baths

Tampa • Florida

5(71 reviews)

$ 854,84 USD $ 794,61 USD totaal voor 3 nachten

27–30 okt 2026

the Seaside 21 image 1

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the Seaside 21

2 bedrooms·2 baths

Holmes Beach • Florida

4.77(22 reviews)

$ 2.169,00 USD totaal voor 7 nachten

13–20 nov 2026

South Tampa Retreat | Pool, King Bed & Jacuzzi Tub

South Tampa Retreat | Pool, King Bed & Jacuzzi Tub

South Tampa Retreat | Pool, King Bed & Jacuzzi Tub

South Tampa Retreat | Pool, King Bed & Jacuzzi Tub

2 bedrooms·1 bath

Tampa • Florida

$ 1.189,19 USD totaal voor 7 nachten

24–31 okt 2026

Furnished 2BR Corporate Apartment in South Tampa | Pool, Parking

Furnished 2BR Corporate Apartment in South Tampa | Pool, Parking

Furnished 2BR Corporate Apartment in South Tampa | Pool, Parking

Furnished 2BR Corporate Apartment in South Tampa | Pool, Parking

2 bedrooms·1 bath

Tampa • Florida

$ 1.827,53 USD totaal voor 7 nachten

1–8 nov 2026