Vacation Home Rentals By Owner In Madeira Beach, FL

Showing 72 Of 72 Vacation Rentals

$255.2

Dolphins and Manatees in Your Backyard!

Madeira Beach, Florida, United States

Located in John's Pass, great shopping, dining, nightlife, wildlife, and the beach are all within walking distance of this waterfront property. It has a private, deep water dock with a boat slip, and a small swimming pool to create a relaxing oasis for 'getting away from it all'. Dolphins, birds, and sometimes Manatees will pay you a visit as you relax in the privacy of your own backyard. For more information, seven two seven, seven nine eight, four four eight six.brbrThis unit is fully equipped and ready to be enjoyed. The bedroom has a queen size bed and the living room has a sofa and full size futon.. A boat slip is also available.brbrThe Beach Trolley runs from St. Pete Beach all the way to Clearwater Beach with a stop right in front of John's Pass. At Polito del Mar you can have the convenience of a great location with the privacy of a duplex instead of a multi-unit apartment. Relax, refresh, and enjoy.brbrKeywords: waterfront, oceanfront, duplex, boat dock, John's Pass, small pool

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Exceptional(1)

$290.71

/ Nightly

Private Vacation Home

Luxurious 2BR 2BA, 2 Kings Condo Madeira Beach

Madeira Beach, Florida, United States

Discover the epitome of coastal elegance in our 2-bedroom, 2-bathroom Executive Waterfront Condo, ideally located at Madellion Blvd in the heart of Maderia Beach, FL 33708. This penthouse exudes a sense of tranquility and sophistication, offering a spacious and inviting retreat for up to 6 guests.brbrThis Executive Waterfront Condo offers a sublime escape for couples, families, or friends seeking a sophisticated and comfortable retreat by the beach.brbrAs you step inside, you`ll find two generously sized bedrooms, each featuring a king-sized bed for your utmost comfort. The stylish decor and thoughtful design create a warm and welcoming atmosphere, perfect for relaxation and rejuvenation.brbrThe condo boasts a prime waterfront location, providing breathtaking views of the water, and easy access to the sun-soaked beaches of Maderia Beach. Spend your days soaking in the Florida sun, strolling along the shores, or simply unwinding on the private balcony with a refreshing drink in hand.brbrFor those who love to cook, the fully equipped kitchen offers a range of modern appliances and utensils, making meal preparation a breeze. You can savor your culinary creations at the dining area, or choose to dine al fresco on the balcony, enjoying the picturesque sunset over the water.brbrConvenience is key, and you`ll appreciate the 3 PM check-in time and 11 AM check-out time. Please note that we don`t allow pets, ensuring a serene and allergy-free environment for all our guests.brbrThis Executive Waterfront Condo offers a sublime escape for couples, families, or friends seeking a sophisticated and comfortable retreat by the beach. Book your stay now and experience the best of Maderia Beach in style and luxury.brbrConvenience is key, and you`ll appreciate the 3 PM check-in time and 11 AM check-out time. Please note that we don`t allow pets, ensuring a serene and allergy-free environment for all our guests.brPlease ensure that you take out the garbage regularly, as failure to do so will result in a $50 fine. Very important NO SMOKING inside our property. Please refrain from leaving cigarette butts on the property. We kindly request that you refrain from hosting parties.

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Exceptional(3)

$332.97

/ Nightly

Private Vacation Home

BOARDWALK BUNGALOW - JOHNS PASS & BEACH JUST STEPS AWAY

Madeira Beach, Florida, United States

LOCATION LOCATION LOCATION!! Boardwalk Bungalow is located right at the end of World Famous Johns Pass Boardwalk, just steps outside your front door. With beach access from under the Pass bridge, without having to cross Gulf Blvd. This DUPLEX UNIT features 2 bedrooms, 1.5 bathrooms with everything BRAND NEW! Kitchen has grey solid wood soft close cabinets, quartz countertops, stainless appliances. Updated bathrooms with chic tile selections & a small balcony with a peek at the Pass water views!brbrTHE SPACE:brbrThis fully renovated DUPLEX UNIT features one private bedroom with a queen bed on the first living level with an en suite bathroom. A second loft bedroom located up the spiral staircase with 2 queen beds, and a half bathroom. A spacious living room and kitchen, with a large quartz countertop peninsula. Just out your first level back door is a small patio space with a couple of chairs to enjoy your morning coffee with a peek at the Pass water view.brbrGUEST ACCESS INFO:brbrThe boardwalk stairs are just steps around the corner from your front door. This DUPLEX UNIT has many sets of stairs, and the entire bottom floor is garage and laundry space. Steps from the driveway bring you right up to your front door. You can walk, bike or drive anywhere you want. There are tons of restaurants and shops a minute walk away. The white sandy beach is a short 8-10 minute walk down the Pass boardwalk, or along the little side street under the Pass bridge.

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Exceptional(2)

$2045.56

/ Nightly

Private Vacation Home

BEACH HOUSE GETAWAY! BEAUTIFUL WATER VIEWS & SUNSETS! PERFECT LOCATION!

Madeira Beach, Florida, United States

This 3 story waterfront luxury home features 2 large balconies & w/spectacular water views and sunsets. It's loaded with stylish & comfortable furnishing & accessories. It’s conveniently located across the street from entertainment, dining, & groceries. It is only 1 mile away from the infamous the white sands of Madeira Beach and minutes away the #1 tourist destination in the county, John's Pass Village. The property offers a heated swimming pool that gets up to hot tub temps, dock, spa tub, elevator & all the comforts of home. It is perfect for grilling out, outdoor activities, or the big game!

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Exceptional(39)

$355.24

/ Nightly

Private Vacation Home

3/2 Waterfront Home with Private Pool!

Madeira Beach, Florida, United States

This lovely, tropical three-bedroom, two-bath Physician's vacation home is available for your dream vacation. The waterfront house is on Crystal Island in Madeira Beach, on a quiet cul de sac. It is all on one level (no stairs). From the moment you enter the house, you see the view of your pool, dock, and a saltwater cove connecting the intracoastal waterway to the Gulf of Mexico. The large, high-ceilinged living room, master bedroom, kitchen, and dining room all look out onto the water. It is very light and spacious. The view is framed by coconut palms, hibiscus and mango trees providing shade in the afternoon, and beautiful sunsets! You see dolphins, Hank the Great Blue Heron, and egrets daily, and the occasional manatee! Ospreys land at the dock to eat their catch. brInside, everything is new and completely remodeled, not a typical rental home. The kitchen is stocked for the serious cook, with dinnerware for twelve, and the dining room table seats eight. Lots of books (including cookbooks), DVDs, CDs, puzzles, and games are provided. We have smart TVs with high-speed internet and extensive cable including HBO (with Netflix and Amazon Prime available).brThere are granite countertops in the kitchen and baths. The laundry room with washer and dryer is beside the kitchen, which is stocked with basic arrival items including detergent and paper products, coffee, and tea. Both a Keurig and a standard coffee maker are provided, as well as an electric kettle.brThe Master bedroom has a king-size bed with Waverly linens, a large flat-screen TV, a private bath with double sinks, a separate water closet, and a huge walk-in shower. brWith a split floor plan for privacy, a separate hall leads to the second bedroom with queen bed, third bedroom with twin beds, and the second bathroom.brAt your private pool just out the living room door, is a covered lanai with a ceiling fan, sofa and chairs, as well as a teak dining table and chairs and a cypress swing, lounge chairs, and gas grill. Bikes, pool floats, beach chairs, fishing poles, and umbrellas are in the garage, with plenty of parking space in the driveway. An extension cord from the garage can be used to charge your car.brThe home is near John's Pass Village, with many shops and restaurants, and within easy driving distance to museums, theme parks, and sports and other venues in St. Petersburg, Tampa, Clearwater, and Orlando. brThe owners, Cathy and Randy, live nearby in Tampa, so you can be confident that any problems or concerns will be quickly resolved. The house has had excellent care, and many guests return year after year. Please scroll down to see our 100% 5-star ratings from our previous guests. brPlease message us through VRBO with any questions. We look forward to having you as our guests, and enjoy meeting people from around the world!brbrbrbrKeywords: Home, pool, dock, house, waterfront, house, beachfront

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$438.44

/ Nightly

Private Vacation Home

Spacious 4-bedroom house in Beautiful Madeira Beach

Madeira Beach, Florida, United States

Welcome to our Tropical Oasis, located in Madeira Beach. Our home is perfect for families, couples, multi-generational travel, and anyone who needs the space to spend time together or enjoy some privacy for enjoyment & relaxation.brbrThe spacebrThe home has been renovated and updated with a new kitchen, new hardwood floors, new furnishings, and much more. This 4 bedroom 2 bath home has a king size pillow top bed in the master, another king size bed in 2 of the guest rooms, and custom bunk beds with 3 twin beds and a queen bed in the fourth guest room. The fourth guestroom has 3 mounted TVs as well. The kitchen area is fully equipped and seats 8 for dining. You can also dine under the stars pool side on our brick patio equipped with a gas grill.brbrPlease note: the home is a triplex so the pool and grill areas are shared with 2 one-bedroom units. The common areas are very private though and infrequently used by others.brbrGuest accessbrOur home is centrally located just steps to the white expansive sandy beach and intracoastal waters. There are several restaurants within walking distance, including the brand new Caddy's that is the only beach front restaurant in Madeira Beach. Walk the beach to the waterfront boardwalk of John's Pass Village; beach shops, numerous restaurants, cruise boats, fishing charters, dolphin watch, jet skis, and parasailing.brbrLocal dining, dancing, and entertainment are just steps away. Ride the local trolley from St Petersburg Beach to Clearwater Beach. Visit downtown St Petersburg; The Pier, Baywalk, Salvador Dali Museum, and Tropicana Field Home of The Rays. For an evening of entertainment: Mahaffey Theater, Florida Orchestra, Tampa Performing Arts Center, or Ruth Echart Hall.brbrThis Home is just 30 minutes from Tampa's Busch Gardens, Historic Ybor City, Channelside, and Hyde Park. For days out, Sunken Gardens, Sponge Docks, Orlando's Disney World, Universal Studios, and Sea World. Visit the Kennedy Space Center, Lion Country Safari, Parrot Jungle, or the Indian Reservations of the Everglades.brbrWe hope you enjoy this home as much as we do!

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$250.46

/ Nightly

Private Vacation Home

Cottage Pool Across From the Beach

Madeira Beach, Florida, United States

Relax and unwind at this charming 2-bedroom, 2-bathroom coastal bungalow in the heart of Madeira Beach. Located just steps from the Gulf, this inviting home offers the perfect blend of comfort, convenience, and classic Florida charm—ideal for couples, families, or friends looking for a laid-back beach getaway.brbrPrime Beach LocationbrSituated directly across from the beach, you’ll enjoy effortless access to the soft white sands and beautiful Gulf waters. Spend your days soaking up the sun, swimming, or catching unforgettable sunsets just a short stroll from your front door.brbrHeated Pool & Relaxing Outdoor SpacebrThis boutique-style community features a large heated pool surrounded by tropical landscaping, creating a peaceful oasis to unwind after a day at the beach. There’s also a shared BBQ area, perfect for casual outdoor meals and enjoying the Florida weather.brbrComfortable & Inviting Living SpacebrInside, the home is bright, clean, and thoughtfully furnished for a relaxing stay. The open layout provides a welcoming space to gather, while comfortable seating and cozy touches make it easy to feel right at home.brbrFully Equipped KitchenbrThe kitchen comes stocked with everything you need, including cookware, utensils, and essential appliances—perfect for preparing anything from quick breakfasts to full dinners during your stay.brbrPrivate Screened PorchbrEnjoy your morning coffee or unwind in the evening on the private screened porch, offering a quiet and comfortable spot to relax after a day of exploring.brbrComfortable BedroomsbrBoth bedrooms feature comfortable bedding and fresh linens to ensure a restful night’s sleep. With two full bathrooms, there’s plenty of space and convenience for groups and families.brbrWalkable to John’s Pass – Dining, Shopping & EntertainmentbrOne of the best parts of this location is the easy walk to John's Pass Village & Boardwalk, a vibrant waterfront destination filled with local shops, restaurants, and activities. Browse unique boutiques, enjoy fresh seafood, grab ice cream, or sip drinks at nearby bars and breweries. For those seeking adventure, you’ll find jet ski rentals, fishing charters, boat tours, and sunset cruises all just minutes away.brbrYour Madeira Beach EscapebrWith its unbeatable location, heated pool, and relaxed coastal atmosphere, this home offers everything you need for a memorable stay. Whether you’re here for beach days, local exploration, or simply to unwind, this Madeira Beach retreat is the perfect place to make lasting vacation memories.brbrThis property is managed by Azul Bay Vacation Rentals. Lic. # DWE6218386.

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Exceptional(1)

$375.34

/ Nightly

Private Vacation Home

Beach House Retreat with a Private Heated Pool!

Madeira Beach, Florida, United States

Beach House Retreat with a Private Pool - Your Perfect Getaway!brbrDescription:brEscape to this beach house that boasts a modern interior with sleek design elements and contemporary furnishings, along with a private pool and backyard oasis, all just steps from the pristine beach! Nestled amidst the cozy community of Madeira Beach, this unique retreat offers everything you need for an unforgettable stay. Whether you`re seeking a peaceful retreat or a vibrant hub forbrsocializing, this home provides the perfect combination of luxury, comfort, and convenience.brKey Features:br• Location: The home is ideally situated in a quiet, friendly beachside community, providing a serene escape from the hustle and bustle of city life. Restaurants and shops are a short stroll away, or drive to Clearwater Beach, St. Petes or Tampa for a change of pace!br• Accommodation: This spacious and fully renovated retreat comfortably accommodates 6 guests. The living spaces are thoughtfully appointed, providing both comfort and style. With ample natural light streaming in through large windows, the atmosphere is bright and inviting throughout the home. It`s perfect for couples, families, or a group of friends looking for a beachside getaway.br• Outdoor Oasis: Enjoy your morning coffee or evening cocktails in the backyard oasis, use the poolside BBQ and enjoy an outdoor dinner before cooling off with a late-night swim in your private pool. br• Beach Access: A short stroll down the street brings you to the sandy shores of the beach, where you can swim, sunbathe, or build sandcastles to your heart`s content.br• Fully Equipped Kitchen: Prepare delicious meals in the new fully equipped and tastefully styled kitchen with modern appliances and utensils and create effortless memories in the welcoming dining area.br• Comfortable Bedrooms: Three spacious and well-appointed bedrooms with comfortable bedding ensure a good night`s sleep after a day of adventure.br• Entertainment: Stay connected with high-speed Wi-Fi, cable and pre-loaded streaming services, while enjoying your favorite shows and movies on the large flat-screen TV in the living room - or retreat to your room as there are flat screen TVs in every bedroom!br• Local Attractions: Explore the nearby attractions such as the Pinellas Trail, charming coastal John’s Pass, and local seafood restaurants. Adventure and relaxation are at your doorstep.brAdditional Information:br• Pet-friendly (prior approval required).br• Free parking for two cars.br• Beach towels, beach chairs and umbrella provided.br• Linens and towels provided.br• In-home washer and dryer for your convenience.brbrAvailability:br• Book your dates now and secure your spot in this coastal paradise. Contact us for alternative availability and reservation times.br• Don`t miss out on the chance to experience the serenity and beauty of this beach house. Create lasting memories with loved ones and enjoy the ultimate beachside escape and poolside retreat. Book your stay today!brbrPool HeatbrbrPlease note that this rental uses an electric pool heat pump system. What this means is that heat pumps draw warmth from the surrounding air and simply transfers it to the pool. They are 100% dependent on the outside weather conditions (temperature and winds) on how they heat. We set the heat pump thermostat at 82 degrees F from November 1 - March 31 every year but we can’t guarantee that the pool temperature will be at this desired temperature on any day. For example, if the heat pump is set to 82 degrees F, and the outside ambient temperature is at 63 degrees F with windy conditions, the pool heat might not be able to meet the 82 degrees the thermostat is calling for under these adverse weather conditions.

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Exceptional(32)

$682.91

/ Nightly

Private Vacation Home

Sun-drenched Townhome on beautiful Madeira Beach!

Madeira Beach, Florida, United States

Enjoy stunning Gulf views over the dunes in the heart of Madeira Beach, known for its relaxed, family-friendly atmosphere. This spacious, modern home offers everything you need, including beach chairs, towels, umbrellas, and toys. Restaurants are nearby, and John’s Pass is just a few blocks away. The home features an open living area with beach access, a fully equipped kitchen, multiple bedrooms, and a private balcony overlooking the beach.

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Exceptional(5)

Select Dates for Price

Private Vacation Home

Charming beach bungalow for perfect beach getaway

Madeira Beach, Florida, United States

Welcome to the Delano beach bungalow. 2 bed 1bathroom. private backyard with hot tub. Home includes everything you’ll need for your beach getaway. Beach chairs, umbrellas, beach wagon, beach cruisers and so much more. Washer/dryer. Fully stocked kitchen.The back yard is fence in and small grass area for pets. Driveway is long enough to bring your boat. (Small pets are welcome) 3 minute walk to the beach and 10 minute walk to Johns pass and many other shops and restaurants. Military discount with valid military ID. Message me if you would like to break up payments for bookings. Discount give for monthly stays message me for more details

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Private Vacation Home

Madeira Beach House, Pets Welcome! One Block from the Sand! ️

Madeira Beach, Florida, United States

Charming 2BR Beach Cottage – Steps from the Sand! ️brbrWelcome to your home away from home —a cozy 2-bedroom, 1-bath beach cottage just one block from the beach! Pet-friendly and packed with charm, this sunny Madeira Beach escape is perfect for snowbirds or anyone dreaming of a long, relaxing getaway ( 90-day minimum stay).brbr✨ What you’ll love:br ️ Sleeps 5 comfortablybr High-speed Wi-Fi + ACbr Full kitchen with all the essentialsbr Fun little extras your family will adorebr Private fenced backyard with a patio oasisbr Driveway with room for up to 5 vehiclesbr Pets welcome!brbr Enjoy peaceful evenings watching the sunset from the spacious backyard while making memories with your family. You’re just steps away from the beach, local cuisine, fun restaurants, and vibrant nightlife—yet far enough to relax in peace and quiet. ‍♀️ brbr Custom rental packages available—PM us for details!brbr Perfect for extended stays, work-from-anywhere life, or your next seasonal escape.brBook your slice of paradise today!

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Exceptional(61)

$310.3

/ Nightly

Private Vacation Home

KEY WEST STYLED BEACH HOUSE! STEPS TO BEACH AND WALK TO JOHN'S PASS!

Madeira Beach, Florida, United States

*****ALL HURRICANE RELATED DAMAGES ARE COMPLETED. DAMAGE WAS ONLY TO THE GARAGE AREA..*****brbrThis beautiful newer Key West style beach home is located in the heart of Madeira Beach within walking distance to the Famous John's Pass. Open concept with 3 lovely bedroom and 2 baths. Lots of activities and just steps across the street to the beautiful white sandy beach and the warm blue green waters of the Gulf of Mexico. This home is perfect for families or couples. Beautifully decor and furnishings! Walk to many beach area restaurants and John's Pass which offers just about anything you may want to do from deep sea fishing, cruise ship, jet skiing, shopping, parasailing and so much more!!! . Owner has A/C set not to go below 72 degrees.

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Condo

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Most popular vacation rentals in Madeira Beach

Exceptional(61)

$1178.57

/ Nightly

Private vacation home

Lux Maderia Beachfront Home

Madeira Beach, Florida, United States

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Exceptional(61)

$1457.24

/ Nightly

Private vacation home

Sunsets Madeira Beach/ 4BR Ocean View House w/Balcony & Elevator

Madeira Beach, Florida, United States

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Exceptional(61)

$1474.65

/ Nightly

Private vacation home

Ultimate Beachfront Escape for Families & Groups. Beach& Swim Spa. Tickets to Top Attractions Daily.

Madeira Beach, Florida, United States

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Exceptional(61)

$1727.01

/ Nightly

Villa

John’s Pass|Sleeps 23|Heated Pool+Hot Tub|360° Water Views|Across Beach

Madeira Beach, Florida, United States

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Exceptional(61)

$2045.56

/ Nightly

Private vacation home

BEACH HOUSE GETAWAY! BEAUTIFUL WATER VIEWS & SUNSETS! PERFECT LOCATION!

Madeira Beach, Florida, United States

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Exceptional(61)

$3038.44

/ Nightly

Cottage

Entire Island Paradise Cottages – Heated Pool, Tiki Hut, Walk to Beach, 8 Units, Sleeps 30

Madeira Beach, Florida, United States

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Exceptional(61)

$284.12

/ Nightly

Condo

BeachFront Condo - Madeira Beach - John's Pass - Heated Pool - Remodeled

Madeira Beach, Florida, United States

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Exceptional(61)

$276.85

/ Nightly

Condo

Livin the dream beach condo 3 blocks from beach 5 minute walk! Built in ‘22

Madeira Beach, Florida, United States

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Exceptional(61)

$277.10

/ Nightly

Condo

?Beach Across the Street?Heated Pool/Hot Tub/Workout Room☀ Madeira Bay II #314

Madeira Beach, Florida, United States

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Exceptional(61)

$278.62

/ Nightly

Condo

BEST VALUE ON THE BEACH - AMAZING TOP FLOOR GULF FRONT UNIT WITH PANORAMIC VIEW

Madeira Beach, Florida, United States

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Vacation Home Rentals By Owner In Madeira Beach, FL

$255.2

$290.71

$332.97

$2045.56

$355.24

$438.44

$250.46

$375.34

$682.91

$310.3

Rent a place that suits your needs

Most popular vacation rentals in Madeira Beach

$1178.57

$1457.24

$1474.65

$1727.01

$2045.56

$3038.44

$284.12

$276.85

$277.10

$278.62

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