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  • Madeira Beach Tropic Breeze Unit 17 Second Floor
    From $127 per night (USD)

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    Madeira Beach Tropic Breeze Unit 17 Second Floor

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Summary: Come check out this beautifully redecorated Tropic Breezes condo! The unit is located on the second floor with ...

    From $127 per night (USD)

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  • Brand New Contemporary Home
    From $280 per night (USD)

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    Brand New Contemporary Home

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Contemporary modern, spacious, brand new luxury home. Located one minute walk to Madeira Beach. A 2 bedroom, 2 baths, wi ...

    From $280 per night (USD)

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  • Luxury Beach Condo
    From $350 per night (USD)

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    Luxury Beach Condo

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Welcome to our brand-new, spacious, 3BR/3BA beach condo, just steps away from the sand. Our condo has everything you ma ...

    From $350 per night (USD)

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  • Exclusive PENTHOUSE Footsteps from Madeira Beach! 3BR\/3BA with a Heated Pool!
    From $323 per night (USD)

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    Exclusive PENTHOUSE Footsteps from Madeira Beach! 3BR\/3BA with a Heated Pool!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    10

    Welcome to Bella Vita (Italian for the good life), Madeira’s most luxurious condo. Our family’s rare Penthouse boasts an ...

    From $323 per night (USD)

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    Details
  • UPDATED ONE BEDROOM, WATERFRONT CONDO IN THE FABULOUS MADEIRA BEACH YACHT CLUB
    From $100 per night (USD)

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    UPDATED ONE BEDROOM, WATERFRONT CONDO IN THE FABULOUS MADEIRA BEACH YACHT CLUB

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    UPDATED ONE BEDROOM, WATERFRONT CONDO IN THE FABULOUS MADEIRA BEACH YACHT CLUB COMMUNITY. Perfect location for your dre ...

    From $100 per night (USD)

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  • 4th Floor spacious 2 BR, 2 BA w\/ spectacular views of Boca Ciega Bay
    From $183 per night (USD)

    Expedia

    4th Floor spacious 2 BR, 2 BA w\/ spectacular views of Boca Ciega Bay

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Easiest Way to Get Away: 1.) Book & Pay online here on this website (7+ nights 5%, 28+ nights 10% discount automaticall ...

    From $183 per night (USD)

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  • La Coquina 306: Beachside Comfort - 2BD\/2BA
    From $128 per night (USD)

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    La Coquina 306: Beachside Comfort - 2BD\/2BA

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    7

    Summary: **BUILDING WILL BE UNDER CONSTRUCTION STARYING MAY to NOVEMBER 2024. BALCONIES WILL BE BOARDED UP AND POOL WILL ...

    From $128 per night (USD)

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  • Coastal Madeira Beach Condo - Walk to Gulf!
    From $158 per night (USD)

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    Coastal Madeira Beach Condo - Walk to Gulf!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Take a trip to coastal Florida for sunny days on the beach and plenty of community amenities when you stay at this Madei ...

    From $158 per night (USD)

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  • Remodeled beach house — Steps to the beach!
    From $250 per night (USD)

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    Remodeled beach house — Steps to the beach!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    All you need to bring is your bathing suits! We provide the pop up shades, coolers, beach wagon, beach chairs, beach tow ...

    From $250 per night (USD)

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  • Coastal Condo w\/ Balcony: Walk to Madeira Beach!
    From $138 per night (USD)

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    Coastal Condo w\/ Balcony: Walk to Madeira Beach!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Book your next Gulf Coast getaway at this charming Madeira Beach condo. Boasting an ocean-themed interior, a fully equip ...

    From $138 per night (USD)

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  • Madeira Bay Resort I 1504 NEW, amazing Gulf Beach view in top location!
    From $257 per night (USD)

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    Madeira Bay Resort I 1504 NEW, amazing Gulf Beach view in top location!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Top Reasons to Book: • Unobstructed view of the gulf from the private balcony • Beach access directly across the street ...

    From $257 per night (USD)

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  • **2 bedroom\/2 bath- Brand New Madeira Beach condo steps from John’s Pass
    From $349 per night (USD)

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    **2 bedroom\/2 bath- Brand New Madeira Beach condo steps from John’s Pass

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    2 bed/ 2 bath brand new condo on Madeira Beach steps from John’s Pass restaurants and entertainment. 1 king bed (Maste ...

    From $349 per night (USD)

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  • REMODELED, immaculately designed, BEACHFRONT condo with gorgeous water views
    From $375 per night (USD)

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    REMODELED, immaculately designed, BEACHFRONT condo with gorgeous water views

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Be the first to book a stay at Sea Breeze Condominium #404, a spacious 2BR, 2Bath renovated unit (August 2023) which com ...

    From $375 per night (USD)

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  • Beach Bum Vibes Nautical Haven Revamp Getaway Near Madeira Beach
    From $147 per night (USD)

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    Beach Bum Vibes Nautical Haven Revamp Getaway Near Madeira Beach

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    𝘽𝙀 𝘼 𝘽𝙀𝘼𝘾𝙃 𝘽𝙐𝙈! This nautically intimate studio apartment getaway is perfect for a small family, weekend trip ...

    From $147 per night (USD)

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  • Tiny Tangerine Citrus Charm: Cozy Studio near Stunning Madeira Beach
    From $134 per night (USD)

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    Tiny Tangerine Citrus Charm: Cozy Studio near Stunning Madeira Beach

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    This 𝙦𝙪𝙖𝙞𝙣𝙩 𝙖𝙣𝙙 𝙘𝙞𝙩𝙧𝙪𝙨𝙮 inspired space is an intimate 350 sq ft studio apartment - the perfect getaway f ...

    From $134 per night (USD)

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  • Cozy Oasis: Just Renovated Bungalow, Steps to Madeira Beach
    From $145 per night (USD)

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    Cozy Oasis: Just Renovated Bungalow, Steps to Madeira Beach

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    𝘾𝙤𝙯𝙮 𝙖𝙣𝙙 𝙘𝙝𝙞𝙘 𝙗𝙚𝙖𝙘𝙝 𝙝𝙖𝙫𝙚𝙣! Adorable getaway in this Beach Bungalow, perfect for a small family, wee ...

    From $145 per night (USD)

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  • Villa Madeira #605 3 Bedroom 2 Bath Unit WIFI
    From $312 per night (USD)

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    Villa Madeira #605 3 Bedroom 2 Bath Unit WIFI

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Summary: Absolutely magnificent 3 bedroom 2 bath 6th floor Madeira Beach Gulf Front condo at Villa Madeira with large sc ...

    From $312 per night (USD)

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  • Beautiful Madeira Yacht Club Beach Condo-1BR\/ 1.5BA. Sleeps 4 comfortably!
    From $138 per night (USD)

    Expedia

    Beautiful Madeira Yacht Club Beach Condo-1BR\/ 1.5BA. Sleeps 4 comfortably!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    ACCOMODATIONS: Steps away from the beach and your toes touching the sand! Enjoy leisurely afternoon strolls around the b ...

    From $138 per night (USD)

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  • Madeira Beach Condo Steps from the Gulf
    From $123 per night (USD)

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    Madeira Beach Condo Steps from the Gulf

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    ** Not impacted by Hurricane Idalia ** Madeira Beach has been a sought out destination for decades. Enjoy an amazing cu ...

    From $123 per night (USD)

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  • Top floor beachfront condo.  Incredibly Spacious.  Overlooking the best beach in Florida!
    From $392 per night (USD)

    Expedia

    Top floor beachfront condo. Incredibly Spacious. Overlooking the best beach in Florida!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    When you look for the perfect beachfront vacation spot for your family, this is the place. Setup for larger families (o ...

    From $392 per night (USD)

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  • Dog Friendly bay front condo, shared pool and hot tub right next to the beach
    From $185 per night (USD)

    VRBO

    Dog Friendly bay front condo, shared pool and hot tub right next to the beach

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    5

    Bay Front Oasis Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...

    From $185 per night (USD)

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  • The New Madeira Bay Resort I 1602 Gulf View
    From $202 per night (USD)

    Expedia

    The New Madeira Bay Resort I 1602 Gulf View

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    The brand new Madeira Bay Resort I #1602 is a two bedroom, two bathroom condo with a private balcony with views of the G ...

    From $202 per night (USD)

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  • Top floor beachfront unit at premier building
    From $329 per night (USD)

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    Top floor beachfront unit at premier building

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    This top floor condo will leave you breathless from the moment you arrive. The entire unit has been tastefully renovate ...

    From $329 per night (USD)

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  • Quaint Madeira Beach Cottage with Heated Pool
    From $157 per night (USD)

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    Quaint Madeira Beach Cottage with Heated Pool

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Enjoy a Gulf vacation in a private beach cottage located directly across the street from the beach. In less than a one m ...

    From $157 per night (USD)

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    Details
  • Madeira Bay Resort I 1505 NEW Complex with a Breathtaking Bayfront View!
    From $258 per night (USD)

    VRBO

    Madeira Bay Resort I 1505 NEW Complex with a Breathtaking Bayfront View!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Top Reasons to Book: • Beach access directly across the street as well as on site fishing and charter boats. • Onsite G ...

    From $258 per night (USD)

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  • PRIVACY, RELAX with the DOLPHINS at the SEASIDE,no people. LOUNGERS & UMBRELLA,
    From $154 per night (USD)

    Expedia

    PRIVACY, RELAX with the DOLPHINS at the SEASIDE,no people. LOUNGERS & UMBRELLA,

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    MADEIRA BEACH. TOTAL PRIVACY at SUNGLOW SEASIDE IS A RARE in TOWN PROPERTY FIND.. SLEEPS 4. THIS GROUND FLOOR END UNIT ...

    From $154 per night (USD)

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  • Luxury Remodeled & Beautifully Furnished  - Beach View Balcony - Crimson #104
    From $275 per night (USD)

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    Luxury Remodeled & Beautifully Furnished - Beach View Balcony - Crimson #104

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    You won't need to walk far to the beach from Crimson Condo #104! Located just steps from the beautiful gulf waters, this ...

    From $275 per night (USD)

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  • Remodeled Large Top Floor Unit - Perfect for Family Getaways! Crimson #304
    From $270 per night (USD)

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    Remodeled Large Top Floor Unit - Perfect for Family Getaways! Crimson #304

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Crimson #304 is a popular 2 bedroom, 2 bathroom vacation retreat that is close to everything: beaches, heated pool and a ...

    From $270 per night (USD)

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  • EXCELLENT Madeira Beach GULF FRONT vacation rental at SEA BREEZE    63202B
    From $279 per night (USD)

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    EXCELLENT Madeira Beach GULF FRONT vacation rental at SEA BREEZE 63202B

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Completely updated in fall of 2013- Home away from home- Home Away from Home -Sea Breeze 202 is a GOLD rated corner two- ...

    From $279 per night (USD)

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  • BEST DEALS NOW !AMAZING BEACH, PRIVACY, UNWIND. SLEEP 4, FREE CHAIRS, BBQ, PKG
    From $150 per night (USD)

    Expedia

    BEST DEALS NOW !AMAZING BEACH, PRIVACY, UNWIND. SLEEP 4, FREE CHAIRS, BBQ, PKG

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    SIMPLY AMAZING MILE OF PRIVATE RESIDENTIAL BEACHFRONT.....SUNGLOW SEASIDE, ST PETERSBURG-MADEIRA BEACH DOWNTOWN CENTRAL ...

    From $150 per night (USD)

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  • **DIRECT BEACH FRONT**GREAT LOCATION** 2 BEDROOM 2 BATH**AWESOME VIEWS**
    From $225 per night (USD)

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    **DIRECT BEACH FRONT**GREAT LOCATION** 2 BEDROOM 2 BATH**AWESOME VIEWS**

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Direct Gulf Front Condo with sweeping views of the Gulf of Mexico and the beach.. The master bedroom also faces the bea ...

    From $225 per night (USD)

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  • The New Madeira Bay Resort I 1609 Marina View
    From $204 per night (USD)

    Expedia

    The New Madeira Bay Resort I 1609 Marina View

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    The brand new Madeira Bay Resort I #1609 is a two bedroom, two bathroom condo with a private balcony. King size bed in t ...

    From $204 per night (USD)

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  • The New Madeira Bay Resort I 1401 Marina View
    From $249 per night (USD)

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    The New Madeira Bay Resort I 1401 Marina View

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    The brand new Madeira Bay Resort I #1401 is a three bedroom, two bathroom condo with a private balcony. King size bed in ...

    From $249 per night (USD)

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  • The New Madeira Bay Resort I 1707 Marina View
    From $196 per night (USD)

    Expedia

    The New Madeira Bay Resort I 1707 Marina View

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    The brand new Madeira Bay Resort I #1707 is a two bedroom, two bathroom condo with a private balcony. King size bed in t ...

    From $196 per night (USD)

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  • Superb Location on the Beaches of Madeira. Great Corner Unit Views. Beachfront Pool on the Sand!
    From $320 per night (USD)

    VRBO

    Superb Location on the Beaches of Madeira. Great Corner Unit Views. Beachfront Pool on the Sand!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    This spacious corner unit condo overlooking the sand gives the perfect setting for your Florida family vacation. Set in ...

    From $320 per night (USD)

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  • Surf Song 348 Gulf Front Balcony Across from John's Pass Village
    From $192 per night (USD)

    Expedia

    Surf Song 348 Gulf Front Balcony Across from John's Pass Village

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    This one bedroom, one bathroom condo features a private balcony with a direct Gulf Front view. - Kitchen: Full size app ...

    From $192 per night (USD)

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  • The New Madeira Bay Resort I 1407 Marina View
    From $204 per night (USD)

    VRBO

    The New Madeira Bay Resort I 1407 Marina View

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    The brand new Madeira Bay Resort I #1407 is a two bedroom, two bathroom condo with a private balcony. King size bed in t ...

    From $204 per night (USD)

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    Details
  • The New Madeira Bay Resort I 1701 Marina View
    From $259 per night (USD)

    Expedia

    The New Madeira Bay Resort I 1701 Marina View

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    The brand new Madeira Bay Resort I #1701 is a three bedroom, two bathroom condo with a private balcony. King size bed in ...

    From $259 per night (USD)

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    Details
  • The New Madeira Bay Resort I 1301 Marina View
    From $281 per night (USD)

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    The New Madeira Bay Resort I 1301 Marina View

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    The brand new Madeira Bay Resort I #1301 is a three bedroom, two bathroom condo with a private balcony. King size bed in ...

    From $281 per night (USD)

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    Details
  • The New Madeira Bay Resort I 1501 Marina View
    From $245 per night (USD)

    Expedia

    The New Madeira Bay Resort I 1501 Marina View

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    The brand new Madeira Bay Resort I #1501 is a three bedroom, two bathroom condo with a private balcony. King size bed in ...

    From $245 per night (USD)

    Expedia

    Details
  • The New Madeira Bay Resort I 1403 Marina View
    From $214 per night (USD)

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    The New Madeira Bay Resort I 1403 Marina View

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    The brand new Madeira Bay Resort I #1403 is a two bedroom, two bathroom condo with a private balcony. King size bed in t ...

    From $214 per night (USD)

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    Details
  • The New Madeira Bay Resort I 1305 Marina View
    From $261 per night (USD)

    Expedia

    The New Madeira Bay Resort I 1305 Marina View

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    The brand new Madeira Bay Resort I #1305 is a three bedroom, two bathroom condo with a private balcony. King size bed in ...

    From $261 per night (USD)

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    Details
  • The New Madeira Bay Resort I 1608 Gulf View
    From $230 per night (USD)

    VRBO

    The New Madeira Bay Resort I 1608 Gulf View

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    The brand new Madeira Bay Resort I #1608 is a two bedroom, two bathroom condo with a private balcony. King size bed in t ...

    From $230 per night (USD)

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    Details
  • The New Madeira Bay Resort I 1702
    From $206 per night (USD)

    Expedia

    The New Madeira Bay Resort I 1702

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    The brand new Madeira Bay Resort I #1702 is a two bedroom, two bathroom condo with a private balcony with views of the G ...

    From $206 per night (USD)

    Expedia

    Details
  • The New Madeira Bay Resort I 1601 Marina View
    From $267 per night (USD)

    VRBO

    The New Madeira Bay Resort I 1601 Marina View

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    The brand new Madeira Bay Resort I #1601 is a three bedroom, two bathroom condo with a private balcony. King size bed in ...

    From $267 per night (USD)

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    Details
  • The New Madeira Bay Resort I 1708 Gulf View
    From $222 per night (USD)

    Expedia

    The New Madeira Bay Resort I 1708 Gulf View

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    The brand new Madeira Bay Resort I #1708 is a two bedroom, two bathroom condo with a private balcony. King size bed in t ...

    From $222 per night (USD)

    Expedia

    Details
  • The New Madeira Bay Resort I 1308 Gulf View
    From $212 per night (USD)

    VRBO

    The New Madeira Bay Resort I 1308 Gulf View

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    The brand new Madeira Bay Resort I #1308 is a two bedroom, two bathroom condo with a private balcony. King size bed in t ...

    From $212 per night (USD)

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    Details
  • Madeira Beach 2 Bedroom, 1 Bath Pool, Hot Tub, Gym
    From $299 per night (USD)

    Expedia

    Madeira Beach 2 Bedroom, 1 Bath Pool, Hot Tub, Gym

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Beautiful 2-bedroom 1 bathroom in the highly sought-after Madeira Beach Yacht Club. A gated, waterfront community is loc ...

    From $299 per night (USD)

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  • PENTHOUSE BEACHFRONT, SLEEP 4, <br>  2 MIN to TOWN. FREE LOUNGERS, BBQ, WiFi
    From $180 per night (USD)

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    PENTHOUSE BEACHFRONT, SLEEP 4, <br> 2 MIN to TOWN. FREE LOUNGERS, BBQ, WiFi

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    SUNGLOW SEASIDE. A QUAINT PROPERTY, Few PEOPLE, No elevators or congested common areas. COME RELAX by the SEASIDE AT S ...

    From $180 per night (USD)

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  • 2 Bedroom 2 Bath - Partial Beach View
    From $265 per night (USD)

    Expedia

    2 Bedroom 2 Bath - Partial Beach View

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Sandy Shores #211 - Under new ownership and freshened up with new paint, appliances, kitchen backsplash, bedding, smart ...

    From $265 per night (USD)

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    Details
  • The Penthouse at Madeira Beach 5 bedroom (sleeps 14) gorgeous Gulf views
    From $831 per night (USD)

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    The Penthouse at Madeira Beach 5 bedroom (sleeps 14) gorgeous Gulf views

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    14

    ***ATTENTION 2023 FALL GUESTS. The elevator closest to the Penthouse is currently out of service due to renovations. Ple ...

    From $831 per night (USD)

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    Details
  • Happy Home - Bright, updated beach house in Madeira Beach, top location!
    From $257 per night (USD)

    Expedia

    Happy Home - Bright, updated beach house in Madeira Beach, top location!

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    Top reasons to Book: • The location- just steps away from, many restaurants, live entertainment, and the sugary white sa ...

    From $257 per night (USD)

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  • Sand Beach lifestyle and boardwalk vacation house
    From $750 per night (USD)

    VRBO

    Sand Beach lifestyle and boardwalk vacation house

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Welcome "Madeira Beach Area" - just steps from the beautiful white-sanded Beach and famous John's Pass Boardwalk! Great ...

    From $750 per night (USD)

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  • Ocean Sands 1107: Amazing Gulf Front Retreat in
    From $228 per night (USD)

    Expedia

    Ocean Sands 1107: Amazing Gulf Front Retreat in

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Summary: Amazing 11th floor 2 bedroom 2 bath Gulf Front condo with upgrades galore and panoramic views from every window ...

    From $228 per night (USD)

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    Details
  • Stunning Top Floor Views and an Interior to Match. On the Beach. Close to Johns Pass Village.
    From $307 per night (USD)

    VRBO

    Stunning Top Floor Views and an Interior to Match. On the Beach. Close to Johns Pass Village.

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    This is the ultimate beachfront condo, complete with simply amazing views from the top floor of this immaculately mainta ...

    From $307 per night (USD)

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  • Surf Song 223 Escape to Island Life
    From $179 per night (USD)

    Expedia

    Surf Song 223 Escape to Island Life

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Surf Song Resort #223 Escape to island life in this 2 bedroom, 2 bath poolside condo on the second floor with a view of ...

    From $179 per night (USD)

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  • Surf Song 119 Coastal Retreat on Madeira Beach
    From $186 per night (USD)

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    Surf Song 119 Coastal Retreat on Madeira Beach

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    Surf Song Resort #119 You will feel like you're on vacation the moment you step into this 2 bedroom, 2 bath poolside co ...

    From $186 per night (USD)

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  • Surf Song 236 Beach Vibes
    From $154 per night (USD)

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    Surf Song 236 Beach Vibes

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    This one bedroom, one bathroom condo offers all the convenience of being beach side and even has a partial view of the G ...

    From $154 per night (USD)

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    Details
  • Surf Song 237 Florida Charm on Madeira Beach
    From $171 per night (USD)

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    Surf Song 237 Florida Charm on Madeira Beach

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Surf Song Resort #237 12960 Gulf Blvd, Madeira Beach, FL 33708 TRS office located just a block away: 13030 Gulf Blvd, Ma ...

    From $171 per night (USD)

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  • Surf Song 344 Cool Breezes Across from John's Pass Village
    From $198 per night (USD)

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    Surf Song 344 Cool Breezes Across from John's Pass Village

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    This one bedroom, one bathroom condo offers all the convenience of being beach side and even has a partial view of the G ...

    From $198 per night (USD)

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    Details
  • Madeira Beach Ground Floor One Bedroom Poolside
    From $106 per night (USD)

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    Madeira Beach Ground Floor One Bedroom Poolside

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Summary: Tropic Breeze 7 is a one-bedroom and one-bath located on the first floor with a pool view. This condo has two d ...

    From $106 per night (USD)

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  • Corner Unit Direct Beachfront  - 30 day rental
    From $157 per night (USD)

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    Corner Unit Direct Beachfront - 30 day rental

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Gorgeous views from this direct beach front 5th floor Corner 2 bedroom 2 bath 1120 square foot unit. Wrap around balcony ...

    From $157 per night (USD)

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    Details
  • Villa Madeira 202 Beautiful updates, breathtaking view, walk to John's Pass!
    From $261 per night (USD)

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    Villa Madeira 202 Beautiful updates, breathtaking view, walk to John's Pass!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Top Reasons to Book: • Spacious balcony featuring breathtaking views of the Gulf of Mexico. • Shared covered lounge ...

    From $261 per night (USD)

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  • Stunning 3 bed\/2 bath beachfront condo in Madeira Beach, FL
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    Expedia

    Stunning 3 bed\/2 bath beachfront condo in Madeira Beach, FL

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    The beachfront condo directly overlooks the glistening Gulf of Mexico and sparkling white, sandy beach of Madeira Beach, ...

    Click For Pricing

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  • Sea Breeze 707 Gulf Front Balcony with Heated Pool
    From $283 per night (USD)

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    Sea Breeze 707 Gulf Front Balcony with Heated Pool

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Sea Breeze #707 is a direct Gulf Front condo with a large private balcony overlooking the beach. Spacious two bedroom, t ...

    From $283 per night (USD)

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  • Las Brisas 407 3BR 2BA Gulf Front
    From $340 per night (USD)

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    Las Brisas 407 3BR 2BA Gulf Front

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    10

    Las Brisas #407 is a spacious 3 bedroom, 2 bathroom condo with a balcony. Stunning direct gulf front view. The master be ...

    From $340 per night (USD)

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    Details
  • Madeira Bay Resort 414 Beach Access
    From $176 per night (USD)

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    Madeira Bay Resort 414 Beach Access

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Madeira Bay Resort #414 is a two bedroom, two bathroom condo with a private balcony. The master bedroom has a king size ...

    From $176 per night (USD)

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  • Sea Breeze 505 Gulf Front Balcony with Heated Pool
    From $228 per night (USD)

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    Sea Breeze 505 Gulf Front Balcony with Heated Pool

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Sea Breeze #505 is a direct Gulf Front condo with a large private balcony overlooking the beach. Spacious 710 sq. ft. fl ...

    From $228 per night (USD)

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    Details
  • Madeira Bay Resort 313 Marina View w\/Beach Access
    From $192 per night (USD)

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    Madeira Bay Resort 313 Marina View w\/Beach Access

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Madeira Bay Resort #313 is a two bedroom, two bathroom condo with a private balcony. View of marina, sunrises, waterway ...

    From $192 per night (USD)

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    Details
  • Villa Madeira 601 Gulf Front Corner Unit Large Balcony
    From $308 per night (USD)

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    Villa Madeira 601 Gulf Front Corner Unit Large Balcony

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Villa Madeira is a Gulf Front property with large screened balconies. Expansive view of the Gulf of Mexico. So close to ...

    From $308 per night (USD)

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    Details
  • Madeira Bay Resort 506 Gulf View w\/Beach Access
    From $195 per night (USD)

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    Madeira Bay Resort 506 Gulf View w\/Beach Access

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Madeira Bay Resort #506 is a two bedroom, two bathroom condo with two private balconies. The master bedroom has a king s ...

    From $195 per night (USD)

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    Details
  • Villa Madeira 610 Gulf Front Large Balcony
    From $290 per night (USD)

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    Villa Madeira 610 Gulf Front Large Balcony

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Villa Madeira is a Gulf Front property with large screened balconies. Expansive view of the Gulf of Mexico. So close to ...

    From $290 per night (USD)

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    Details
  • Madeira Bay Resort 307 Marina View w\/Beach Access
    From $177 per night (USD)

    VRBO

    Madeira Bay Resort 307 Marina View w\/Beach Access

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Madeira Bay Resort #307 is a two bedroom, one bathroom condo with a private balcony. Views of marina, sunrises, waterway ...

    From $177 per night (USD)

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    Details
  • Gulf Lane 2BR Beach House w\/Private Path to Beach
    From $203 per night (USD)

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    Gulf Lane 2BR Beach House w\/Private Path to Beach

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    This two bedroom, one bathroom beach house is Gulf Front and offers a large deck overlooking the beach! Lots of natural ...

    From $203 per night (USD)

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    Details
  • Madeira Bay Resort 416 Beach Access
    From $162 per night (USD)

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    Madeira Bay Resort 416 Beach Access

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Madeira Bay Resort #416 is a two bedroom, two bathroom condo with a private balcony. The master bedroom has a king size ...

    From $162 per night (USD)

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  • Madeira Bay Resort 410
    From $156 per night (USD)

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    Madeira Bay Resort 410

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Madeira Bay Resort #410 is a two bedroom, one bathroom condo with a private balcony. Views of marina, sunrises, waterway ...

    From $156 per night (USD)

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    Details
  • Sea Breeze 508 Gulf Front Balcony with Heated Pool
    From $283 per night (USD)

    VRBO

    Sea Breeze 508 Gulf Front Balcony with Heated Pool

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Sea Breeze #508 is a direct Gulf Front condo with a large private balcony overlooking the beach. This corner unit also h ...

    From $283 per night (USD)

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    Details
  • Sea Breeze 301 Gulf Front Balcony with Heated Pool
    From $283 per night (USD)

    Expedia

    Sea Breeze 301 Gulf Front Balcony with Heated Pool

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Sea Breeze #301 is a direct Gulf Front condo with a large private balcony overlooking the beach. This corner unit also h ...

    From $283 per night (USD)

    Expedia

    Details
  • Madeira Bay Resort 205 Beach Access
    From $137 per night (USD)

    VRBO

    Madeira Bay Resort 205 Beach Access

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Madeira Bay Resort #205 is a two bedroom, two bathroom condo with a private balcony. The master bedroom has a queen size ...

    From $137 per night (USD)

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    Details
  • Madeira Bay Resort 413 Marina View w\/Beach Access
    From $284 per night (USD)

    Expedia

    Madeira Bay Resort 413 Marina View w\/Beach Access

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Madeira Bay Resort #413 is a two bedroom, two bathroom condo with two private balconies. Views of marina, sunrises, wate ...

    From $284 per night (USD)

    Expedia

    Details
  • Sea Breeze 703 Gulf Front Balcony with Heated Pool
    From $283 per night (USD)

    VRBO

    Sea Breeze 703 Gulf Front Balcony with Heated Pool

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Sea Breeze #703 is a direct Gulf Front condo with a large private balcony overlooking the beach. Spacious two bedroom, t ...

    From $283 per night (USD)

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    Details
  • Madeira Bay Resort 301 Marina View w\/Beach Access
    From $154 per night (USD)

    Expedia

    Madeira Bay Resort 301 Marina View w\/Beach Access

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Madeira Bay Resort #301 is a one bedroom, one bathroom condo with a private balcony. Views of marina, sunrises, waterway ...

    From $154 per night (USD)

    Expedia

    Details
  • Madeira Bay Resort 207 Marina View w\/Beach Access
    From $179 per night (USD)

    VRBO

    Madeira Bay Resort 207 Marina View w\/Beach Access

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Madeira Bay Resort #207 is a two bedroom, one bathroom condo with a private balcony. View of marina, sunrises, waterway ...

    From $179 per night (USD)

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    Details
  • Madeira Bay Resort 610 Gulf View w\/Beach Access
    From $234 per night (USD)

    Expedia

    Madeira Bay Resort 610 Gulf View w\/Beach Access

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Madeira Bay Resort #610 is a two bedroom, two bathroom condo with a private balcony. The master bedroom has a king size ...

    From $234 per night (USD)

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    Details
  • Sea Breeze 402 Gulf Front Balcony with Heated Pool
    From $242 per night (USD)

    VRBO

    Sea Breeze 402 Gulf Front Balcony with Heated Pool

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Sea Breeze #402 is a direct Gulf Front condo with a large private balcony overlooking the beach. Spacious two bedroom, t ...

    From $242 per night (USD)

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    Details
  • Sea Breeze 406 Gulf Front Balcony with Heated Pool
    From $283 per night (USD)

    Expedia

    Sea Breeze 406 Gulf Front Balcony with Heated Pool

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Sea Breeze #406 is a direct Gulf Front condo with a large private balcony overlooking the beach. Spacious two bedroom, t ...

    From $283 per night (USD)

    Expedia

    Details
  • Las Brisas 207 Gulf Front Large Balcony Sleeps 9
    From $335 per night (USD)

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    Las Brisas 207 Gulf Front Large Balcony Sleeps 9

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    9

    Las Brisas #207 is a beautiful Gulf front corner unit condo with large balcony. With 3 bedrooms and 2 bathroom, this is ...

    From $335 per night (USD)

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  • Sea Breeze 203 Gulf Front Balcony with Heated Pool
    From $242 per night (USD)

    Expedia

    Sea Breeze 203 Gulf Front Balcony with Heated Pool

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Sea Breeze #203 is a direct Gulf Front condo with a large private balcony overlooking the beach. Spacious two bedroom, t ...

    From $242 per night (USD)

    Expedia

    Details
  • Madeira Bay Resort 510 Gulf View w\/Beach Access
    From $190 per night (USD)

    VRBO

    Madeira Bay Resort 510 Gulf View w\/Beach Access

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Madeira Bay Resort #510 is a two bedroom, two bathroom condo with a private balcony. The master and second bedroom both ...

    From $190 per night (USD)

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    Details
  • Madeira Bay Resort 206 Marina View w\/Beach Access
    From $173 per night (USD)

    Expedia

    Madeira Bay Resort 206 Marina View w\/Beach Access

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Madeira Bay Resort #206 is a two bedroom, one bathroom condo with private balcony. The master bedroom has a king size be ...

    From $173 per night (USD)

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    Details
  • Villa Madeira 606 Gulf Front Large Balcony
    From $267 per night (USD)

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    Villa Madeira 606 Gulf Front Large Balcony

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    5

    Villa Madeira is a Gulf Front property with large screened balconies. Expansive view of the Gulf of Mexico. So close to ...

    From $267 per night (USD)

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    Details
  • Madeira Bay Resort 611 ~ TOP FLOOR GREAT VIEWS OF THE BEACH AND CITY, CORNER UNIT FOR GREAT PRIVACY
    From $188 per night (USD)

    Expedia

    Madeira Bay Resort 611 ~ TOP FLOOR GREAT VIEWS OF THE BEACH AND CITY, CORNER UNIT FOR GREAT PRIVACY

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Madeira Bay Resort #611 is a top floor-great views beach and city corner-unit with great views of the beach and city and ...

    From $188 per night (USD)

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    Details
  • Madeira Bay Resort 210 Marina View w\/Beach Access
    From $189 per night (USD)

    VRBO

    Madeira Bay Resort 210 Marina View w\/Beach Access

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Madeira Bay Resort #210 is a two bedroom, two bathroom condo with a private balcony. Corner balcony with access from liv ...

    From $189 per night (USD)

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    Details
  • Madeira Bay Resort 602 Gulf View w\/Beach Access
    From $189 per night (USD)

    Expedia

    Madeira Bay Resort 602 Gulf View w\/Beach Access

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Madeira Bay Resort #602 is a two bedroom, two bathroom condo with two private balconies. The master bedroom has a king s ...

    From $189 per night (USD)

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    Details
  • Madeira Bay Resort 402 Beach Access
    From $164 per night (USD)

    VRBO

    Madeira Bay Resort 402 Beach Access

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Madeira Bay Resort #402 is a one bedroom, one bathroom condo with a private balcony. This spacious floorplan is handicap ...

    From $164 per night (USD)

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    Details
  • Madeira Bay Resort 412 Marina View w\/Beach Access
    From $167 per night (USD)

    Expedia

    Madeira Bay Resort 412 Marina View w\/Beach Access

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Madeira Bay Resort #412 is a two bedroom, one bathroom condo with a private balcony. Views of marina, sunrises, waterway ...

    From $167 per night (USD)

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    Details
  • Madeira Bay Resort 208 Beach Access
    From $159 per night (USD)

    VRBO

    Madeira Bay Resort 208 Beach Access

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Madeira Bay Resort #208 is a two bedroom, two bathroom condo and private balcony. The master bedroom has a queen size be ...

    From $159 per night (USD)

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    Details
  • Sea Breeze 305 Gulf Front Balcony with Heated Pool
    From $213 per night (USD)

    Expedia

    Sea Breeze 305 Gulf Front Balcony with Heated Pool

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Sea Breeze #305 is a direct Gulf Front condo with a large private balcony overlooking the beach. Spacious 710 sq. ft. fl ...

    From $213 per night (USD)

    Expedia

    Details
  • Madeira Bay Resort 504 Marina View w\/Beach Access
    From $257 per night (USD)

    VRBO

    Madeira Bay Resort 504 Marina View w\/Beach Access

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Madeira Bay Resort #504 is a three bedroom, two bathroom condo with two private balconies. Views of marina, sunrises, wa ...

    From $257 per night (USD)

    VRBO

    Details
  • Madeira Bay Resort 404 Beach Access
    From $189 per night (USD)

    Expedia

    Madeira Bay Resort 404 Beach Access

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Enjoy our updated Madeira Beach condo with a great location to beach and John's Pass! Madeira Bay Resort #404 is a two b ...

    From $189 per night (USD)

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    Details