Vacation Home Rentals By Owner In Madeira Beach, FL

Top Reasons To Book John's Pass-Time Beach Cottages:brbr* Beachfront Property with Direct Beach Accessbrbr* Full Property to Yourself - Both Cottages - Great for Larger Families or Friends Traveling Togetherbrbr* Great Private Backyard Beach with Hammock, Grill and Picnic Tablebrbr* 2 Private Entrances, 2 Great Deck/Patio Spacesbrbr* Gulf Views From the Upper Level - Great Spot for Sunset Each Nightbrbr* Professionally Managed, 24/7brbrWelcome to John's Pass-Time Beach Cottages! This entire property is yours to enjoy, featuring two separate units—upper and lower levels—each with 2 bedrooms and 1 full bathroom. Step out your backdoor and follow the direct beach access path to the stunning coastline, perfect for all-day beach fun.brbrThe lower level offers two queen bedrooms and one full bathroom, a bright and spacious living area with SmartTV and deck access, and a fully stocked kitchen (no dishwasher). The covered outdoor deck includes lounge chairs and a dining set—ideal for outdoor dinners or relaxing after the beach. brbrUpstairs, enjoy even more space with an open-concept living area, SmartTV, and balcony access with views of the Gulf of Mexico, a great spot to gather after your beach day and unwind while taking in the breathtaking Florida sunsets. You will find two queen bedrooms and one full bathroom here as well. A larger indoor dining table sets the scene for group meals or game nights, and the fully equipped kitchen has everything you need. Please note - stairs are required to access the upper level. brbrThe private backyard features a sandy retreat with a hammock, charcoal grill, picnic table, and a direct path to the beach. Additional amenities include a laundry room, free WiFi, and parking for four vehicles.brbrThe Bed Set Up:brbrLower Level - Bedroom 1 and Bedroom 2 - Queen Bed in EachbrbrUpper Level - Bedroom 1 and Bedroom 2 - Queen Bed in EachbrbrLaundry Room Onsite for Usebrbr4 Parking SpacesbrbrNon-Smoking PropertybrbrThis Listing is for the Full PropertybrbrThe area surrounding John's Pass-Time Beach Cottages offers the perfect blend of relaxation and adventure. Just a half mile south, the popular John's Pass Village and Boardwalk awaits with waterfront dining, fresh catch seafood, shopping, live entertainment, water sports, rentals, and even a pirate ship cruise for the whole family. Step right outside your door to explore miles of stunning coastline, perfect for beachcombing and soaking in the Gulf views. Across the street, enjoy casual eats and cold drinks at Mad Beach Cantina. Head north along Madeira Beach to discover more local favorites like Lisa’s Café, Caddy’s of Madeira, and The Reef Bar and Grill—all within easy reach.brbrLooking to explore more of the area You're in a great spot! Just 45 minutes away, Tampa offers exciting attractions like ZooTampa, the Florida Aquarium, Busch Gardens, major sporting events, the Hard Rock Casino, and more. About 25 minutes inland, the vibrant city of St. Petersburg is home to world-class museums, the scenic St. Pete Pier, and a variety of great restaurants. For a fun and easy coastal adventure, hop on the beach trolley and head north or south to discover the nearby barrier islands—each with its own unique charm, plenty of beach access, state parks, and stunning Gulf views.brbrYour perfect beach getaway awaits you at John's Pass-Time Beach Cottages!

☀Beachfront Full Property Walk to John's Pass John's Pass-Time Beach Cottages

Madeira Beach, Florida, United States

Bed

Bath

Sleeps

$1015.91

Don't want the crowded condo experience with noisy neighbors having condo parties & dealing with lugging beach supplies & groceries up multiple flights of stairs Don't want to be subjected to a crowded condo or hotel complex Then this private, stand-alone four bedroom, two bath,1940 retro themed bungalow with a huge 16' x 32' inground pool with tons of amenities that are not offered at other properties is for you! Worried we don't have a lot of reviews on this new property yet Just look at our other property links below and check out the reviews on them!brbrThe bungalow is located literally on the white sands of Madeira Beach. So you will be waking up to the sound of waves lapping onto the shore. Be in the center of it all, but with privacy in your own home that has views of the beach & the crystal blue water of the Gulf. Not only that, you can open the slider to an amazing covered deck area leading to your private swimming pool!brbr***UNIQUENESS OF THE PROPERTY***brThere are very few single family houses on the beach for rent anymore as most were torn down for huge condos and hotels. So are you tired of the sterile condo or hotel experience Then you will appreciate this property. Much care was put into making your stay to be an experience with the 1940s retro vibe. Pictures of old Madeira Beach, pale blue kitchen cabinets, key west colorful rooms, shabby chic furniture, fun wall decor, and neon surfer and flamingo signs. The moment you step into the property, you will notice this is not a cookie cutter condo, but your own private home for you and your family to make memories that will last a lifetime!brbrWe also have the some sister properties you may enjoy.brhttps://www.vrbo.com/4879548 This is our 2 bedroom/1 bath 1951 retro blue beach bungalow in Treasure Island.brhttps://www.vrbo.com/1239914 This is our 3 bedroom/2 bath 1938 retro beach bungalow with plunge pool in Madeira Beach.brhttps://www.vrbo.com/4879549 This is our 3 bedroom/2 bath 1951 retro pink beach house in Treasure Island.brbr***BEACH ACCESS***brSimply walk out the back sliders and put your toes in the sand. There is also a natural play area off the back of the house that is secluded from the public part of the beach.brbr***4 BEDROOMS/2 FULL BATHS***brIncluded in this 1600 square foot beach house are 4 bedrooms. Bedroom #1 has a king bed. Bedroom #2 has a king bed. Bedroom #3 has a king bed. Bedroom #4 has two full sized beds which can accommodate up to 2 people in each bed. The kitchen has cool retro looking cabinets accented by mother of pearl backsplash. As you can see from the pictures, we are going to a shabby chic look.brbr***AMENITIES - PRIVATE POOL, BEACH CHAIRS, UMBRELLA, BEACH TOYS, KAYAK, WASHER/DRYER, FREE INTERNET, PLUS MUCH MORE!***brBeach access and a private pool in the sand. What more could you want The property also boasts a fully equipped kitchen, 65 smart flat screen TVs in every bedroom and the living room, Spectrum TV & free high speed internet. All linens and kitchen utensils are provided. A washer & dryer are available for your use outside the bungalow unlike the condos which you have to pay $4 per wash & dry your clothes in a dingy common area laundry room. We also include a laundry detergent saving you more money & making your stay more hassle-free! Parking for 3 to 4 cars is included based on the size of the vehicles. We do also include beach chairs, beach towels, beach umbrella, boogie boards for your enjoyment. Since we provide you items like beach chairs & umbrellas (most other rentals do not include the large umbrellas & beach chairs), you will save the $5 per day, per chair beach chair rental fee or the $15 per day umbrella rental fee charged on the beach! Condos can't offer all these extras as they don't have the storage space for all these extra items.brbr***LOCATION & LOCAL ACTIVITIES***brYou just can't beat the location for convenience either as John's Pass is walkable as it is 5 blocks to John's Pass. It is within walking distance to several fine dining opportunities. Thus, you can easily make do without a car.brbrHistoric John's Pass Village offers a host of entertainment options including; many great beach bar and grills, nightly live music, wine tasting, dolphin tours, jet ski rentals, parasailing, sunset boat tours, alligator petting exhibit, pirate ship cruise, & so much more. Dining options 5 blocks away are also plentiful such as Bubba Gump, The Friendly Fisherman, The Pirate's Den, The Rusty Anchor, Mad Beach Craft Brewing, Gators & more! Don't pass up the opportunity to take a stroll over the Madeira Beach Bridge for some great views!brbr***PLEASE READ***brWe do ask that you respect the maximum 10 people limit during your stay. If you have more people, you will be asked to vacate & there will be no refund. We mention this as we have had people rent the property that had 10 guests and then they had an extra car load or two of their friends over the entire stay sleeping on the floor, blow-up mattresses & on the outdoor lounge chairs. The house just can't take the wear & tear of more than 10 people so we appreciate if you would respect that when you consider renting.

Beach Front House Private Pool 1940 Retro 4 Bedroom 2 Bath & More Gulf-Blvd

Madeira Beach, Florida, United States

4

Bed

Bath

10

Sleeps

$1505.01

4000 sq ft/6 Bedroom/6 Full Bathrooms 4 living rooms/modern home located near a canal and the gulf just two blocks from the beach. Heated salt water pool! Golf Cart!! Ask for price! You can enjoy full view of the canal and partial views of the gulf from the balconies and the rooftop! Walking distance to beach, restaurants, volleyball. The house has two entrances and both sides are identical. Each side has 2000 sq ft/3 Bedroom/3 Full Bathrooms 2 living rooms. Close to Johns Pass, 2 mile. Sleeps 2brbrModern luxury meets contemporary coastal in this oversized home, located on the quiet, white sands of Sunset Beach. This unique property its a Townhome. brEach size is the same square foot, and they are identical the same, from inside to outside. This is two floors story untie with Beautiful Roof top to enjoy and relax. brWhen you come in the first floor is garage, then you go upstairs to the second floor where you have Dining room, kitchen, living room outside patio area to seat and have your coffee, Bedroom with queen size bed, closet, and full bath. brSecond floor you have second bedroom with king bed full bath closet, Lundry, third room is bunk bed 2 queen size bed closet, 55 in tv, second living room small kitchen and patio seating are. Third floor is Beautifull Roof top with 4 lunge chairs and separated comfy seating are with two sofas, two chairs coffee table and beautiful intercostal view. brbrbrEach Townhome has the identical same layout. brbr1. FloorbrOne Bedroom with Queen Size bed, closet, TV 55in. Full Bathroom.brOpen Concept Living room with 65in TV, kitchen, dining room, Patio with Beautiful Intercostal view. brKitchen Fully stocked. Featuring lots of countertop space, 3 Barstools, oven/stove, toaster, dishwasher, refrigerator and microwave. All general kitchenware, dining ware.brbr2. FloorbrOne bedroom with king bed, full bath, walk in closet, tv 55in. brSecond bedroom is Bunk Bed with queen size beds, 55in TV, full closet, full bath. Second Living room with 65in tv, small kitchen, Lundry and patio with Beautiful Intercostal view.brbr3. The last but the best floor is Roof TOP, Breathtaking Intercostal view. br Each Roof top floor has four lounge chairs, and separated area with two large sofas two chairs and coffee table.br br4. ON back of the building is pool, dining table for 10 people, 2 lounge chairs, and With Weber Grill. Pool size is about 350 square feet. brbr5. Each Garage is Long for two cars to park in, and driveway is long for another two cars, there is additional parking on side of the condo to park. brbrFamily Friendly: Pack-N-Play, highchair, kids` life vest, Beach Chairs, Beach Umbrella, Baby tub.brbrSTORM POLICY/ROAD CONDITIONS: No refunds will be given for storms. Beach weather can be unpredictable, if there is no sun you are not entitled to a refund. If there is a government/state issued emergency for a Hurricane a full refund is available.brbrF YOU HAVE ANY PROBLEMS, ANYTHING NOT WORKING OR INOPERABLE DURING YOUR STAY YOU MUST NOTIFY US IMMEDIATELY/ OR WHEN IT FIRST OCCURS. IF YOU WAIT UNTIL THE DAY YOU CHECK OUT OR AFTER YOU CHECK OUT THERE WILL BE NO REFUNDS.brbrDo not under any circumstance disturb residential neighbors with loud voices and music during your stay. There is a noise ordinance on the beaches, 10p.m. to 8a.m. that is strictly enforcedbrbr1. Keyless entry to the home is provided via a digital keypad. A unique code is provided for each stay.br2. Cleanliness is a high priority for our listings, please respect the house and clean up after yourself. We clean and disinfect the house before each arrival for your comfort. Our housekeeping will come at 10:00am please be on time to departure from the home, if you have super early take off please let us know.br3. Trash pick-up is on Monday and Thursday morning. Recycling pick-up is on Wednesday morning. If your stay falls on one of these days, We would greatly appreciate it if you place the bin at the curb the previous evening.br4. Please note we routinely spray the property for bugs and insects, however if you do come across any little critters, please keep in mind that Florida is a sub-tropical climate. To help prevent this, keep the doors closed.

Luxury Pool Home/Golf Cart

Madeira Beach, Florida, United States

Bed

Bath

Sleeps

$1178.57

Wake up to sweeping Gulf views in this rare 4BR/sleeps 10 Gulf-front home on Madeira Beach — direct sand access from your door. Spread across multiple levels of living with panoramic water views and private balconies. Designed for relaxed beach living with patio & outdoor BBQ area, perfect for sunset dining. Beach chairs, umbrella & gear included. Minutes from John`s Pass. High-speed WiFi & parking included. Private, spacious & truly Gulf-front — Madeira Beach at its finest.brbrA slice of Maderia beachfront! The home has a unique floorplan with accents for comfortable beach living. Your front yard is the Gulf, with the sand just a few feet from the outdoor patio. brThe home is intended to be used for fun family getaways or a romantic weekend for 2. Also perfect for remote working featuring a large office space with ocean views. brbrThree spacious floors are designed in a unique split level plan to sleep 10 with 4 bedrooms, (master & 3 guest suites) 4.5 baths, first floor with dining and large screen TV and a patio that steps onto the beach. brbrYou enter the home on the first floor which functions as a family room and includes a large screen TV and additional indoor dining area for BBQ`s. Bath with washer/dryer for convenience. Stairs lead to the second level of living with a chef`s kitchen, open living concept with comfortable couch seating and another TV. There is a large balcony for relaxing. This floor also has a guest suite bedroom with 2 Full size bunk beds (equal to 4 Full size beds) with ensuite full bath. A hallway guest half bath and a second laundry room off the kitchen.brbrThe third floor leads to the Master Suite with a private sitting area, panoramic windows, private balcony, 2 large walk-in closets and en-suite bathroom with shower and separate jacuzzi tub. brbrStep up a few stairs to a half level, the top floor has 2 Bedrooms set as King Guest Suites. This level also has a full bathroom with shower/bath combo. If you work remotely, there is a large private office with custom built in cabinets and desk. brbrThere are several living and lounging areas throughout with multiple patios and balconies, perfect for gathering or solitude. The home flows with an open concept, spiral custom wood staircase, comfy furniture and an unbeatable view with Madeira Beach as your front yard!!brbrWe provide all your beach essentials, beach towels, chairs, a buggy and an umbrella. There are hoses available for your convenience to wash the equipment and your feet prior to entering the home.brbrYou will have access to the entire home, front and back yards.brbrThe only items guest may Not use is the fireplace!brbrEnjoy a seamless stay with clear pricing, easy check-in, and everything you need for a relaxing getaway.brbrEntry to our space is secured with an electronic key lockbox, set with a unique code just for you.brbrI reside locally and my team and I are always on hand to help with anything you need. We are committed to our Guests` happiness and strive for glowing reviews, so you can count on us to be there whenever you require assistance.brbrMadeira Beach is a beach town full of activities and attractions, along with our nationally renowned beach. This home is directly on the beach, with easy walk to John`s Pass Boardwalk and dozens of restaurants, bars and shops. There are a ton of marinas and watersports in the area as well, you can rent jet ski`s, boats, charter fishing boats, dolphin tours or parasailing.brbrPlease note House Rules! brbrThe responsible party booking and staying at this home must be 25 years or older.brbrThe home is not designed for the hosting of parties or gatherings. Maximum 10 persons inside the home at any given time. If the home is misused and rules are broken, we will ask you to vacate the premises immediately without refund. brbrStandard private passenger vehicles only, 4 maximum and NO other vehiclesbrbrSmoking is prohibited inside the home and anywhere on the premises.brbrWe expect guests to treat the home with respect and leave everything in the condition it was found in. Any damage should be reported upon check-in.brbrWe are dog friendly (2 maximum) and there is a one time pet fee of $200. Please note: any damage caused by your pup will be charged accordingly.brbrTowels and linens are for normal use - not for dying hair, removing makeup, cleaning up spills, etc.brPlease Note House Rules! By booking this home, you are agreeing to the following rules:brbrThe primary guest booking must be 25 or older. Maximum occupancy is 10 guests within the home at any time. No Parties! No Gatherings! brbrQuiet Hours 10PM to 8PM. We ask that you respect our residential neighbors as this is a quiet family community. brbrWe`re dog-friendly! Two dogs max, with a $200 non-refundable pet fee. Just a heads up that any damage from your pup gets charged back. No aggressive breeds, No cats, No other animals are permitted. All Madeira Beach Municipal Laws must be followed (no dogs on the beach). brbrThe fireplace is not for guest use.brbrNo Smoking! Smoking is prohibited inside the home and anywhere on the premises.brbrStandard passenger vehicles only, maximum 4 cars. No RVs, trailers, boats, or other vehicles.brbrWe provide linens, bath towels, and starter supplies like toilet paper, and paper towels, you`ll need to purchase additional supplies if you run out of those. Bath towels are for bathing only, not for makeup removal, hair dye, beach use, or cleaning.brbrBefore checkout, please do the dishes and take out the trash to prevent pests and odors. Return keys to the lockbox when you leave. **lost keys cost - $50 to replace** Make sure to grab all your personal belongings, as we can`t be responsible for items left behind.

Lux Maderia Beachfront Home

Madeira Beach, Florida, United States

Bed

Bath

Sleeps

$716.99

Stay more, SAVE more! We offer lower nightly rates on extended stays from Sept-Mar. No coupon code needed! Just enter your dates, at least 14 nights, for pricing. br br Top Reasons to Book this Beautiful Townhome:brbr* Brand New Townhouse with Modern Design and Amenitiesbrbr* 4 Floors Featuring a Rooftop Deck with Amazing Viewsbrbr* 5 Spacious Bedrooms and 4 Full Bathrooms; Private Elevatorbrbr* Less than 1-minute Walk to the Beachbrbr* Heated Pool with Convenient Outdoor Showerbrbr* Walking Distance to Shops, Bars, and Restaurantsbrbr* Dogs Allowed (Fees and Weigh Limits Apply) brbr* Professionally ManagedbrbrWelcome to Azul Townhome A5! This brand-new townhome offers a spacious and modern retreat with 4 floors, 5 bedrooms, and 4 full bathrooms – perfect for families or groups!brbrOn the ground level, you'll find the entrance and garage access. The attached garage, stocked with beach chairs, bikes, toys, and a wagon, will fit 2 with a driveway in front for a 3rd vehicle. The property also features an elevator with access from the ground floor to the rooftop deck for ultimate convenience. The 2nd floor features a spacious living room with an oversized, comfy couch and balcony access. The private balcony has table and chairs making it an ideal place to gather. This floor also includes a bedroom with a king bed and TV, plus a full bathroom with a tub/shower. The top-of-the-line kitchen boasts stainless steel appliances and is fully stocked with dishes, utensils, and cookware for easy at-home dining. Gather around the large dining table or enjoy casual seating at the kitchen island – a great space for entertaining.brbrOn the 3rd floor, you'll find three additional bedroom and 2 full bathrooms. There is a king bedroom with a TV, a room with a Bunk Bed that is a twin-over-full size, and a queen bedroom with a twin fold-out/convertible chair, TV and attached bath. This floor also offers a washer and dryer for added convenience.brbrThe 4th floor boasts a queen bedroom with a TV and attached bath, plus access to the rooftop deck. The rooftop deck is the ultimate hangout spot, featuring a wet bar, outdoor TV, lounge chairs, a table and chairs, and breathtaking views of Madeira Beach. Enjoy outdoor dining, evening cocktails, or simply unwind while taking in the scenery.brbrThe Set Up:brbr1st Level - Entrance and Attached Garage with ping-pong table.brbr2nd Level - Living and Kitchen/Dining. Bedroom with King Bed. Full Bathroom.brbr3rd Level - 3 Bedrooms, 2 Full Bathrooms. Bedroom with King Bed. Bedroom with Bunk Bed (Twin over Full). Bedroom with Queen Bed and Foldout Convertible Chair (Twin).brbr4th Level - Bedroom with Queen Bed and Attached Full Bathroom. Roof Top Deck.brbrDogs Allowed. 2 Max. 50lbs/dog Weight Limit. $100 Non Refundable Pet Feebrbr**Please Note: This is a fully nonsmoking property ** brbrAzul Townhomes are a new build in Madeira Beach. Enjoy the onsite heated pool with an outdoor shower, perfect for relaxing after a day at the beach. Each unit features a private rooftop balcony where you can unwind and take in the views. Centrally located and just a quick 300ft walk to the beach via a nearby crosswalk for easy access. Experience beach living at its finest here!brbrMadeira Beach offers a stunning soft sand beach perfect for relaxing or beachcombing. For a fun-filled adventure, head 2 miles south to John's Pass Village and Boardwalk, packed with shops, restaurants, water activities, and even a pirate ship ride for the kids! brbrRight next door to the townhome, enjoy a round of mini-golf at Smugglers Cove. Within walking distance, you'll find a variety of local favorites like Brass Captain Saloon and BBQ, Original Pizza, Pete's Sushi and Poke, the laid-back Saltwater Hippie for cocktails and more. Plus, grab essentials at Winn Dixie Grocery Store or stop by the local surf shop for beach gear. This location is also convenient to trolly stops, adding for another fun adventure to explore other local islands in the area.brbrWhether you're relaxing poolside, exploring local dining, or soaking up the sun on this beautiful stretch of beach, Azul Townhomes offers everything you need for an unforgettable getaway.

☀NEW Townhome Azul A5 Acros from Beach Private Roof Top Deck Heated Pool

Madeira Beach, Florida, United States

5

Bed

4

Bath

11

Sleeps

Select Dates for Price

Escape the cold winters in this grand 3 bedroom, 2.5 bath Key-West Style waterfront home offering gorgeous views of Boca Ciega Bay. Lounge by the private pool in a fully enclosed large yard. Fish right off the private dock, or launch a kayak for a paddle through the intercostal. Dock your boat or watercraft right outside your back gate. Entertain guests rain or shine by the pool-side covered ground-floor patio.brbrFrench doors lead from the kitchen and additional seating area to a back balcony perfect for sipping morning coffee or an evening cocktail while you watch dolphins swimming in the Bay.brbrThis home is approximately 3 blocks from the Gulf Beaches entrance. Swim, jog, walk on the beach every morning, or, pull your beach cart filled with chairs to watch the sunset. Every day is an adventure living the beach life!brbrWalk to Candy Kitchen to grab a treat. Visit the shops, restaurants, and nightlife at John's Pass Village are 5 minutes away by car, or catch the Trolley along Gulf Blvd. 1.5 blocks away. Grocery stores, a post-office, the community park with tennis courts are less than 5 minutes away. Explore downtown St. Pete which is a short 15-minute drive.brbrDue to City requirements, this a 6-month rental only. Parking for 4 cars; garage storage available upon request.

CALLING SNOW BIRDS: Waterfront home on Boca Ciera Bay/3 blocks to Gulf/Beach.

Madeira Beach, Florida, United States

Bed

Bath

Sleeps

$363.64

Welcome to your slice of paradise! This beautifully updated 2-bedroom, 1.5-bath condo is located directly on the beach and features stylish upscale coastal dcor throughout. With stunning views of the Gulf and the lively charm of John's Pass Village just across the street, you'll have the best of both worldssun, sand, and endless entertainmentall at your fingertips.br br No car No problem. Enjoy walking access to beach shops, waterfront restaurants, boat rentals, and more.br Inside, the condo comfortably accommodates up to 6 guests with an open-concept living and dining area that's perfect for relaxing and spending time together. The kitchen is fully updated with granite counters, shaker-style cabinets, and stainless steel appliancesideal for cooking up vacation meals.br br Step out onto your private balcony and take in the views of the beach and Gulf of Mexico. Whether you're sipping morning coffee or watching the sunset, the view never disappoints.br br This family-friendly getaway also offers on-site grills, a heated beachfront pool, and everything you need for a stress-free stay, including linens, towels, a fully stocked kitchen, and in-unit washer and dryer.br br Whether you're planning a week-long vacation or a month-long escape, this coastal gem is ready to welcome you.br br Important Information:br br Must be 25 or older to reserve, and the person booking must be present for the entire stay.br br Please note, this property is self-catering. We provide a starter supply of soaps, toilet paper, and paper towels, but these will not be replenished during your stay.

Madeira Norte - The Perfect Beachfront Escape

Madeira Beach, Florida, United States

Bed

Bath

Sleeps

$513.53

Summary:brbrSol Mate Beach CottagebrbrbrbrThe Space:brbrCompletely renovated and updated 1930's beach house ready to host your beach adventures! Enjoy residing in a quiet neighborhood within a few steps away from the beach. Relax with a beverage around the firepit on the furnished patio, or head inside to relax in the central air conditioning. You'll be able to cook up a delicious dinner in the full kitchen, which is painted in cheerful beach colors just like the rest of the home. Amenities like a private washer/dryer and a desk workspace on the third floor (perfect for remote work or school assignments) make this home a family-friendly retreat perfect for all ages.brbrbrbrWhat's nearby:brbrWhen you're not relaxing at the beach, there's plenty to enjoy in the area! Guests are less a quarter mile from the historical John's Pass & Boardwalk at this home, where it's easy to enjoy local restaurants and shopping. Guests can even rent jet skis and hop on a fishing charter! For local food, guests can enjoy The Boardwalk Grill and Mad Beach Craft Brewing within a mile of the home. Don't forget to walk over to the Candy Kitchen for a frozen banana! For a fun local adventure, walk one-third-of-a-mile over to the Alligator and Wildlife Discovery Center and enjoy getting up close and personal with some of Florida's most famous animals.brbrbrbrThings to know:brbrFree high-speed WiFibrbrSnowbird-friendlybrbrOne dog weighing up to 20 pounds is welcome with a feebrbrThere is enough room for three cars to park at this homebrbrBeach towels, beach umbrellas, beach chairs, boogie boards, inflatable boat w/paddles, pop up tent, skim board, blow up raft and more beach toys are available for guest usebrbrbrbr*Please note that this home has an active Ring security camera at the front door

Dog Friendly Home with High Speed WiFi and Central AC Snowbird Friendly

Madeira Beach, Florida, United States

Bed

Bath

Sleeps

$467.82

Searching for a space large enough for the whole group in the best location along the Gulf Beaches This is the spot. Combining all three one bedroom units into a single rental of our triplex building, this unique property offers a larger family, or multiple groups the opportunity to all stay together! brbr brbrEnjoy our premium cottages of Gulf Mist, Sandy Shores, and Tropic Sun as your own for your perfect Florida vacation. brbr brbrPLEASE NOTE: This is a triplex made up of three separate living units. Meaning, each has a separate locked entry, kitchen, bathroom, living room, and bedroom. The units do not connect internally. Perfect for some groups, but maybe not a great fit if you have young children. brbr brbrIsland Paradise Cottages, centrally located in Madeira Beach inside a quiet and secure neighborhood, and just off the main road. The cottages are just a 5 minute walk over to the very best beaches that the Gulf of Mexico has to offer, and you are in very easy walking distance of Johns Pass Village, with many excellent restaurants, activities, and attractions. Access to the bay for paddle boarding and kayaking is just a short walk away through the neighborhood, and you can catch the beach trolley nearby if you need to get a little further away. brbr brbrOur little piece of paradise is perfectly setup for vacationing and relaxing with lush landscaping, an extra large island style tiki hut for socializing and BBQ grilling, a beautiful heated pool, as well as a full inventory of bikes, kayaks, paddle-boards and games exclusively for our Guests' use. brbr brbrWe've combined three connected fully updated one bedroom, one bath units into a single rental unit. Each is fully setup and equipped for a perfect vacation stay, with complete privacy for each, along with private adjoining outdoor patio areas for socializing. brbr brbr-- Large Private Balcony/Patio Area for Relaxing Outdoors brbr brbr-- Three Master Bedrooms with Queen Size Bed and en-suite Full Bathroom with Walk-In Shower brbr brbr-- Three Separate Living rooms and dining areas all with a Premium Queen Sleep Sofa brbr brbr-- Three Fully equipped kitchens for just about any type of meal preparation brbr brbr-- Free High-Speed WI-FI, Free Cable TV, Free Assigned Parking for up to 3 vehicles brbr brbr-- Year round heated pool with beautiful patio area, shared with the other cottages in the courtyard brbr brbr-- Thatched Tiki Style picnic area with propane BBQ Grills and plenty of seating brbr brbr-- On-site Coin operated Washers and Dryers for laundry brbr brbr-- Free use of our kayaks, paddle-boards, bikes, and games brbr brbr-- All linens and towels (both Beach and Bath) are provided. 24 hour guest services hotline for any issues or questions. brbr brbr-- Gas Firepit in the Courtyard for Evening Relaxation.brbr-- Gas Firepit in the Courtyard for Evening Relaxation. brbr brbrWe help make the most of your vacation by providing Free Admission to some of the area's top activities & attractions each and every day, including Busch Gardens, The Clearwater Aquarium, The Dali Museum, The Tampa Zoo, evening cruises, bike rentals and more! Create exciting memories, have more fun, and truly experience your destination. (One Free Ticket Per Day, Per Activity. Free Fun Program not eligible for stays over 28 days)brbrA Professionally Managed Vacation Rental Property Following CDC Recommended Guidelines, and Providing 24hr Guest Support. brbr brbrAll our properties include free parking, a complete linen set, beach and bath towels, a starter set of paper goods, hand soap, dishwashing soap and trash bags, free WiFi access, and a 24hr Guest hotline for any issues. Need a Pack n' Play for your stay We've got you covered - no charge!

Walk to Beach & Johns Pass Village! Heated Pool ~ Private Patios ~ Free Parking & Amenities

Madeira Beach, Florida, United States

Bed

Bath

Sleeps

$222.97

You won’t forget the great memories in this 1 BR private, standalone bungalow right across the street from the beach as well as many other restaurants and within waking distance to John’s Pass Village. It offers privacy as it is a stand alone bungalow yet is part of an 18 unit cozy condo association that is centrally located to many great attractions. There is a heated pool, onsite coin laundry facilities, grilling area and parking only steps away from your door! Per the HOA, pets are NOT ALLOWED on the property. Smoking is also prohibited.

Private, standalone-No Shared Walls!Right across the street from Madeira Beach

Madeira Beach, Florida, United States

1

Bed

1

Bath

4

Sleeps

$324.91

Welcome to Isla Breeze, a private coastal cottage just a 2 minute walk from the sugar-soft sands of Madeira Beach. Quietly tucked off Gulf Boulevard, yet an easy walk to local restaurants and shops. brbrEnjoy morning coffee on the patio, sunset walks along the beach, and relaxing evenings around the firepit. This thoughtfully renovated 1940s cottage offers a bright, stocked kitchen, blackout curtains, beach gear, high speed WiFi, and only two easy steps to enter. Calm, private, and designed for effortless beach living.brbrThis fully renovated two-bedroom, one-bath cottage offers comfortable living space, privacy, and thoughtfully designed for relaxation after a day at the beach.brbrBedrooms:br•Primary bedroom with king bed, blackout curtains, Smart TV, and ceiling fanbr•Second bedroom with queen bed and twin trundle, blackout curtains, Smart TV, and ceiling fanbr•All linens and bedding provided for a restful staybrbrLiving & kitchenbr•Bright living area with Smart TVbr•Fully stocked kitchen with quartz countertops & stainless appliancesbr•Starter supplies provided, including coffee, tea, paper towels, and toilet paperbr•Full-size washer & dryerbr•Central air conditioning & high-speed Wi-FibrbrThe home has only two easy steps to enter.brbrOutdoor spacebr•Private patio with comfortable seatingbr•Fire pit for relaxed evenings. br•Gas grillbr•Cornhole and outdoor gamesbrbrBeach gear included:br•Beach wagonbr•Chairs & umbrellasbr•Coolerbr•Towels & beach toysbrbrLocation highlights:br•Beach access: ~150 steps / 2-minute walkbr•Walkable to restaurants & shopsbr•R.O.C. Park: ~0.7 milesbr•John's Pass Village: ~1.2 milesbr•Clearwater Beach: ~6.5 milesbr•St.Pete Beach: ~14 milesbrbrA digital guidebook will be sent out close to checkin.brbrFinal note:brThis home is thoughtfully cared for and designed with the same attention we value when traveling ourselves. If anything comes up during your stay, please reach out as we're always happy to help.brbrGuess access:brGuests will have exclusive use of the entire home and outdoor spaces during their stay.brbrFor convenience, one closet in the second bedroom and a small backyard shed are reserved for owner storage and will remain locked. all other areas of the home and patio are yours to enjoy.brbrOther things to note:brAs with many coastal neighborhoods, the area continues to improve. There may be intermittent weekday daytime construction nearby. Evenings, nights, and weekends are typically quiet, and the home remains fully private and comfortable.

Private Madeira Beach Cottage. 2 Min Walk to Beach. Patio & Firepit

Madeira Beach, Florida, United States

Bed

Bath

Sleeps

$320.97

Gorgeous and spacious single family one level cottage perfect for a group or a quiet getaway. Featuring 3 bedrooms and 2 full baths, our home is a quick 3 minute walk down the street (one block!) to the quiet residential beach access with public beach access close by for food and entertainment. Fully stocked kitchen at your disposal with all you need to cook meals, Smart TV's with streaming apps, a patio outdoor seating. Dog friendly with pre approval- ask for more details (fees apply)!brbr** Fresh and comfy furnishings! **brbr Welcome to your new favorite vacation spot in beautiful Madeira Beach! No expense has been spared with this tastefully designed and spacious home for up to 9 guests. With all new furniture, linens and all amenities. Convenient access to everything you would need for a perfect vacation. Within walking distance of the beach, restaurants and activities, this is truly the best location for any trip! brbr- Easy walk to the beach- right down the street! (3 minute walk!) We provide beach towels and gear for you to use!brbr- Fully stocked kitchen and full use of washer/ dryer & Wi-Fi.brbr-Within walking distance of restaurants, entertainment to include live music daily and the grocery store, plus putt-putt golf where you can feed alligators!!!brbr-All linens are provided for you!brbrEnjoy self-check-in for your convenience with the electronic door lock. This single-level beach home comfortably accommodates a group with 2 living rooms and separate spaces for enjoying each other's company.brbrThe whole home is all yours! Situated on a quiet palm tree lined street with parking available for 2 cars on the driveway + street parking. In the back is a private patio area with outdoor seating to soak in the sunshine. With provided beach gear, high speed WIFI, and a great outdoor space this will become your new go-to spot!brbrWe are dog friendly! Well behaved and potty-trained dogs over 1 year old are allowed with preapproval and pet fee. Dogs must be crated when left unattended. Please ask for more details.brbrCOVID-19 update: We have implemented strict cleaning measures for disinfecting the house between guests. In addition to our regular high standards, we are disinfecting all light switches, remotes, doorknobs, keypads, all surfaces, and any additional heavily touched surfaces around the space. We want you to have peace of mind and consider us a retreat today and always. Please consider purchasing third party travel insurance as coronavirus restrictions and cases are changing to protect your trip. Our cancellation policy is firm.brbrHOUSE RULES:br*No smoking allowed (weed or cigarettes) - evidence will incur a $500 minimum fine. Please smoke away from the home away from windows or doors and dispose of cigarette butts properly.brbr*Any visitors must also be listed in the guest count. Minimum fine of $50 per person per night will apply for any undisclosed guests. The city is strict about maximum occupancy including visitors and we cannot allow more than the maximum guest count at any one time. brbr*Please observe a 9 p.m.- 8 a.m. quiet hour for our neighbors. They are our utmost priority to continue to operate short term rentals for years to come. Noise violations are taken seriously and will have one courtesy warning before removal without repayment for nights unspent.brbr*Our place is not for parties. $500 minimum fine for parties. A party is defined by any more than 9 occupants in the home at any one time. No refund will be given for nights unspent if we are forced to terminate the reservation due to a party. We want you to have a great time with up to 9 guests in the house maximum, including any visitors. This is a residential area and our neighbors rely on us not to disrupt the community. We want to continue to do short term rentals for a long time so please help us respect our neighbors.brbr*Please note while the home is cleaned very thoroughly between stays and air filters changed regularly, we do allow dogs at the home. Those with severe allergies will need to consider our home’s suitability for their unique needs.brbr*No refunds will be given for COVID-19 or weather related cancellations including hurricanes. Please consider purchasing trip insurance that covers any unforeseen circumstances. Please note during hurricane season our area is prone to inclement weather. brbr*$75 per hour charge for not checking out on time. Please communicate if you need more time, if we can accommodate we will not charge a fee.brbr*If our property has a grill, please clean after use to avoid an extra $75 grill cleaning charge.brbr*Ice makers are an extra amenity and no refunds will be given if they are not functioning properly. brbr*To maintain a fair and comfortable environment for all guests, we ask that utilities (electricity, water, gas, etc.) be used responsibly. If there is evidence of excessive utility consumption beyond normal use for the duration of your stay, we reserve the right to charge additional fees for the excess usage. These charges will be calculated based on actual costs incurred and will be billed to the guest. brbr*No paper towels or wipes (including flushable wipes) are allowed down the drains. If a plumber needs to fix an issue caused by the aforementioned items and reasons, the cost will be billed back to the guest.brbr*Guest agrees to complete a third party encrypted ID verification independent of the platform booked on for security purposes. If the guest does not complete the verification or the host is not comfortable with the screening results, host may cancel the reservation with full refund to the guest.brbr*Any cleaning or maintenance issues must be addressed to the host. We must be able to attempt to fix the issue before offering refunds. If an issue is not addressed during the stay, no refunds will be provided.brbrbr*An application, screening, signed lease and deposit is required for 90+ day rentals-please inquire for more details. Bookings over 90 days are brokered by Sojourn Realty.brbrPlease note lawn care and trash service may come on the premises during your stay. Days and times vary, please inquire if you need more specifics on when to expect these services to take place during your stay.brbrPlease note that we do not do shoveling or snow removal. Use caution in case of these situations, as we are not to be held liable.

3 Minute Walk to Beach! Sleeps up to 9- Gorgeous Beach Home

Madeira Beach, Florida, United States

Bed

Bath

Sleeps

$291.01

2025 HURRICANE NOTE: Our unit has been fully restored and ready to accept guests a/o January 20, 2025. We can provide first-hand knowedge of the area upon requests. brAmazing sunsets of the Gulf of Mexico from Madeira Beach condo located on the second floor. Updated beach modern condo with plenty of space, beds, and a large balcony on beach front property with a heated pool. brThe guest features a king bed, 2 queens & a single bed (new mattresses), tastefully decorated bathrooms, full kitchen with quartz countertops Sept'24, renovated guest bath Sept'24, updated couches in Oct'23 and of course, walking distance from famous John's Pass. Each room has been updated with smart TVs. Beach gear included for use.br brAs of May 2023 - NOW including Beach Towels for each guest stay after working with onsite management per guest feedback.

Updated Beachfront Condo, steps to John's Pass with heated pool, updated kitchen

Madeira Beach, Florida, United States

Bed

Bath

Sleeps

$317.2

This house is the perfect slice of paradise location location location the home is located on Boca ciega Bay Intercoastal Waterway only 100 steps from 137th Avenue beach access in Madeira Beach Florida with beautiful sand and beautiful beach the house has an open floor plan the living room looks out into the Intracoastal Waterway the back bedroom has a large king size bed the front bedroom has a queen size bed there are two large couches in the living room the very large TV and regular size couch the backyard has beautiful AstroTurf going out to the Seawall there is a Jacuzzi hot tub gas grill beautiful pink red and white roses the backyard is a huge garden with many trees and plants and has a tremendous amount of privacy in shade sails to protect from the Sun the pictures don't do this place justice you have to see it to appreciate it there are also boat slips in back of the house with two pontoon boats and two large boats.brI have a 35 ft yacht on a lift in the backyard that is available for rent and Captain services that sleeps six four comfortably, and a 35-ft class a diesel motorhome in the front driveway that sleeps six four comfortably these other properties are listed on VRBO also.brI have multiple rentals at this location that is why I need 24 hour approval and check in so I don't overbookbr call Tom for additional information 727-290-7457

Waterfront Home Gulf view 100 steps to Beach very private Close to everything.

Madeira Beach, Florida, United States

Bed

Bath

Sleeps

$204.81

Live like a local this winter in our fully updated 4-bedroom beach retreat—just a 5-minute stroll to the sand and 2 blocks from iconic John’s Pass!brThe Home:brThis bright and breezy 4-bed, 2-bath coastal cottage sleeps up to 8 and features:br • 1 king bedroom, smart TVs & blackout shadesbr • Spacious living room w/ oversized sectional & 65” TVbr • Sleek kitchen w/ quartz counters, wine fridge, and 8-seat dining tablebr • Modern bathrooms w/ double vanity & walk-in pebble-floor showerbr • Washer & dryer in-unitbrOutdoor Living:br • Fully fenced tropical backyard with towering palmsbr • Outdoor dining area + grill setupbr • Private hot & cold outdoor shower – perfect after beach daysbr • Room to store bikes, beach gear, and morebrLocation Highlights:brWalk to coffee shops, restaurants, the boardwalk, and boat rentals in John’s Pass. The beach access is just a few blocks away, making every sunset walk a breeze.br Perfect for Snowbirds & Extended Getaways:br • Available for monthly or 3–6 month winter rentalsbr • Utilities + WiFi includedbr • Flexible arrival dates Enjoy all that Madeira Beach has to offer when you stay at our place.

4-bedroom house in brilliant Madeira Beach steps to Gulf and John's Pass Village

Madeira Beach, Florida, United States

Bed

Bath

Sleeps

$630.58

This is a 2 bedroom house with an attached cottage that sleeps 9 with 3 bedrooms, 3 baths and 2 kitchens. The lower unit is cozy beach cottage with 1 bedroom that sleeps 4 with a pull out couch and flat screen TV in living room, full kitchen with quartz countertops and stainless steel appliances. The upper unit has 2 bedrooms and 2 baths that sleeps 5 or 6 with a master suite with king bed, 2 beds in 2nd bedroom, sofa bed and flat screen TV in the master and living room. It also has a full kitchen with stainless steel appliances and granite countertops.

Beach house with atached apartment 30 Steps to Beach and 1 block to Johns Pass

Madeira Beach, Florida, United States

Bed

Bath

Sleeps

$1457.24

Decorated for Christmas! Indulge in the ultimate beachfront getaway on Madeira Beach, Florida! Our lively and inviting 4-bedroom Beachhouse is your ticket to sun-soaked days, sandy toes, and endless fun. Located DIRECTLY across the street from the sparkling shores, this is the beachside escape you've been dreaming of.

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

Madeira Beach, Florida, United States

Bed

Bath

Sleeps

$369.14

Welcome to your serene beachfront escape! This 2-bedroom, 2-bath corner unit is perched on the top floor of a quiet, private complex on beautiful Madeira Beach. Enjoy sweeping, unobstructed views of the Gulf of Mexico from the best seat in the buildingyour own private balcony.br br Inside, the bright and open layout offers a comfortable and relaxing stay. The spacious primary suite features a king-size bed and en-suite bathroom, while the second bedroom offers two twin beds and is just steps from the hallway bathperfect for families or guests. For added convenience, the unit includes a washer and dryer and a dedicated covered parking space.br br The complex features everything you need for a laid-back beach getaway, including a heated pool, hot tub, and a gas grill area for cookouts after a day in the sun.br br And when you're ready to explore, you're just a short walk to John's Pass Villagehome to local shops, waterfront dining, live entertainment, and unforgettable adventures on the water.br br Peaceful, private, and perfectly locatedthis is Madeira Beach at its best.br br Important Information:br br Must be 25 or older to reserve, and the person booking must be present for the entire stay.br br Please note, this property is self-catering. We provide a starter supply of soaps, toilet paper, and paper towels, but these will not be replenished during your stay.

Top-Floor Corner Unit with Stunning Beach Views Madeira Beach

Madeira Beach, Florida, United States

Bed

Bath

Sleeps

$356.66

Welcome to your perfect Gulf Coast escape — a spacious, fully loaded 3-bedroom, 3-bath beach house just steps from the sugar sand of Madeira Beach. Walk straight out the back gate and you're on the beach. No roads to cross. No parking lots to navigate. Just pure, effortless beach access.brbrInside, you'll find bright, open living spaces with coastal décor, marble floors, and everything you need to unpack, relax, and never leave. The fully equipped kitchen has stainless steel appliances and plenty of counter space for cooking in. 3BR/3BA sleeps 6 — king + 2 queens, 2 indoor baths + private 3rd full bath on the side + freestanding outdoor rinse shower. The in-unit washer and dryer keeps extended stays easy.brbrOutside is where the magic happens. Unwind at the private tiki bar with drinks and lounge on the deck. The property is fully enclosed by a privacy fence — your own private sanctuary from the world.brbrEverything for the beach is already here and waiting for you:br- Beach chairs, umbrellas & beach towelsbr- Rolling beach wagonbr- Coolerbr- Kids' sand toysbr- Outdoor showerbrbrJust pack your swimsuit and sunscreen — we've handled the rest.brbrThe location:brYou're nestled on Gulf Boulevard in the heart of Madeira Beach — one of Florida's most beloved beach communities. Step off the property and you're a short stroll from world-famous John's Pass Village & Boardwalk, with waterfront dining, live music, boutique shops, fishing charters, dolphin tours, jet ski rentals, and sunset cruises. Caddy's, Cafe Corner, and Fishbusterz are all walkable. Everything you'd want from a Florida beach vacation is right outside your door.brbrGuest access:brYou have full, private access to the entire home — all three bedrooms, three baths, the full kitchen, the deck, and the tiki bar. Private parking for up to 3 vehicles directly in front of the property. Keypad self check-in means arrival on your schedule, no coordination needed.brbrA note about the location:brThe property sits on Gulf Blvd, Madeira Beach's main coastal road. While you may hear some passing traffic from outdoors, the solid block construction and privacy fence create a noticeably quiet, peaceful interior — guests consistently remark how tranquil it feels once you're inside. The trade-off is unbeatable: walk out the back gate and you're on the beach in under 60 seconds.

Gulf-Side Beach House - Tiki Bar · Direct Beach Access · No Roads to Cross

Madeira Beach, Florida, United States

3

Bed

3

Bath