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Madeira Beach Luxury Holiday Homes

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    Travellers to Madeira Beach are booking July dates now. Secure your holiday rental today, and have the perfect trip.
    34 Matching Rentals in Madeira BeachView all 231 rentals
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    Villa Madeira #309 Madeira Beach Updated 3 bedroom Beachfront1 / 23
    (7)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Captains Townhouse1 / 43
    (4)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Yoda Beach House1 / 39
    (7)Very good
    5 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
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    Reviewed 11 October 2016
    House Pro's:Very roomyOn the beachConveniently located close to John's Pass, shopping/diningHouse Con'sBUGS, BUGS and more BUGS! Palmetto bugs are breeding in this...
    Reviewed 31 August 2016
    This was our first visit to YODA House and Madeira Beach. We booked this property for the location, proximity to a variety of restaurants, and most of all the layout of the...
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    About this property
    Fantastic Beach House. Private and comfortably furnished for the whole family. If you are searching for a spacious and private home that puts you directly on the the white, sandy beaches of Madeira, this is the place. With its unique floor plan, this house gives everyone in the group space and...
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    Madeira Beach, Florida 33708
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 14
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    Madeira Beach House | Beachfront house with private pool and amazing views1 / 25
    (1)Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Waterfront
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    • Private Outdoor Pool (Unheated)
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 March 2018
    The beach was easily accessed by a boardwalk right outside our front door, or from a path through the gate of our private pool. The house is located in between 2 hotels, but the...
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    About this property
    4 Br, 2 Ba • Sleeps 8 4 Bedroom/ 2 Bathroom Beachfront House with Pool on the Sand of Madeira Beach. Our Madeira Beach home is a quintessential beach house sitting right smack dab on the sand of one of Florida's most beautiful beaches. The large pool and deck are the perfect place for enjoying...
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    Madeira Beach, Florida 33708
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Walk into this beachfront paradise home and sail into another world. The Admirals Townhouse is a rare find on a pristine and uncrowded section of Madeira Beach. The views from the living room, master bedroom, twin balconies, and beachfront patio are simply breathtaking. A private wood-lined pathway...
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    Madeira Beach, Florida 33708
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Unheated)
    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is the ultimate beachfront condo, complete with simply amazing views from the top floor of this immaculately maintained complex located just a few blocks from Johns Pass Village in Madeira Beach. The condo has been completely outfitted for all your vacation needs, with comfort and luxury in...
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    Madeira Beach, Florida 33708
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Waterfront
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to our spectacular Madeira Norte gulf front condo at John's Pass. Relax and enjoy our sandy beaches and the breath-taking sunset view from our 2-bedroom, 2-bath, direct beach front, full-furnished condo. Walk-outs from both the master bedroom and living room to our large balcony which...
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    Madeira Beach, Florida 33708
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Terrace
    • Ocean Views
    • Waterfront
    • Central Heating
    • Hot Tub
    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Description of the Madeira Beach vacation condo rental Our DIRECT BEACH FRONT condo at the prestigious OCEAN SANDS in Madeira Beach, Florida is available for rent. It features 2 bedrooms, 2 bathrooms and a fully-equipped kitchen. We take pride in offering you a spacious, clean and well-maintained...
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    Madeira Beach, Florida 33708
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Patio
    • Waterfront
    • DVD Player
    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    • Hot Tub
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    For avail and other questions, best to call us at the number listed on contact owner vs email- phone is best as availability changes constantly. Whether You're Looking For A Round Of Great Golf... Fantastic Offshore Fishing...A Much Needed Family Get Away...Or Just A Relaxing Time At Our...
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    Location Information
    Madeira Beach, Florida 33708
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    SPECIAL NOTE FOR LAS BRISAS GUESTS BETWEEN THE DATES OF AUGUST 13 TO NOVEMBER 4, 2018: There is a building-wide balcony restoration project that is scheduled to take place between the dates of August 13 and November 4, 2018. It is very likely that the pool will be closed during this time and...
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    Madeira Beach, Florida 33708
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    302 - Chambre1 / 43
    (4)Average
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Air Conditioning
    • Patio
    • DVD Player
    • Private Outdoor Pool (Unheated)
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    • Hot Tub
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 July 2017
    We stayed at 302 Chambre for a week in mid-July. The booking process through iTrip was super easy. Their communication was great and the arrival/entry process went just as...
    Reviewed 3 June 2016
    My wife and I stayed here with friends for a week in May. Our last visit to the are was 20 years ago. We loved this condo!They have everything you need to make it your home...
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    About this property
    Incredible View from your Huge Private Balcony --Over 200 sq. ft. of balcony with plenty of room for lounging in the sun, dining, and watching the most incredible views of the sunset that you can find. Just a few steps past the elevator your feet will be in the white, sugary sands of Madeira...
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    Madeira Beach, Florida 33708
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Terrace
    • Balcony
    • Private Outdoor Pool (Heated)
    • DVD Player
    • Parking
    • Hot Tub
    • Internet Access
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    **TeemingVR presents SB208 or Sea Breeze 208** *Reservation must fall within Sat-Sat booking window* Located in the heart of famous Madeira Beach, Sea Breeze 208 has all the best that Teeming VR has to offer- fantastic poolside amenities, a cheerful modern décor and views to die for. Whether...
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    Location Information
    Madeira Beach, Florida 33708
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Air Conditioning
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    • Private Outdoor Pool (Unheated)
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    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Great view from this 4th floor unit in secluded Chambre Condominiums. Enjoy the very best that Madeira Beach has to offer. After your first stay here, you'll understand why this building has so many repeat visitors. Situated directly on the beach, and setback far enough from the main road to...
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    Location Information
    Madeira Beach, Florida 33708
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    503 - Las Brisas1 / 46
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Unheated)
    • Grill
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    • Washer
    • DVD Player
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    SPECIAL NOTE FOR LAS BRISAS GUESTS BETWEEN THE DATES OF AUGUST 13 TO NOVEMBER 4, 2018: There is a building-wide balcony restoration project that is scheduled to take place between the dates of August 13 and November 4, 2018. It is very likely that the pool will be closed during this time and...
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    Location Information
    Madeira Beach, Florida 33708
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Sea Breeze 6081 / 40
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Private Outdoor Pool (Heated)
    • Internet Access
    • DVD Player
    • Terrace
    • Balcony
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    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ** When you call, reference this unit code SB608 or Sea Breeze 608 ** *Reservation must fall within Sat-Sat booking window* You will not want to miss out on this delightful vacation spot. Unit 608 at the Sea Breeze Condominium has it all. It is situated directly on the powdery sands on the Gulf...
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    Location Information
    Madeira Beach, Florida 33708
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Washer
    • Parking
    • Terrace
    • Internet Access
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Savor Gorgeous Gulf Views and Stunning Sunsets From this Corner Condo in Renowned Madeira Beach! Situated in highly acclaimed Madeira Beach, this updated and roomy condo is the quintessential beach get-away. We invite you to gather with friends on the generous balcony to dine al fresco or to...
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    Location Information
    Madeira Beach, Florida 33708
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • DVD Player
    • Hot Tub
    • Parking
    • Private Outdoor Pool (Heated)
    • Internet Access
    • Terrace
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ** When you call, reference this unit code SB702 or Sea Breeze 702 ** *Reservation must fall within Sat-Sat booking window* Unit 702 at the Sea Breeze Condominium in Madeira Beach depicts the true essence of getting away from it all. This luxurious condo has all the comforts of home but includes...
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    Location Information
    Madeira Beach, Florida 33708
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2BR Madeira Beach Condo Steps from the Beach!1 / 26
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 August 2017
    I'm so glad that I chose this condo instead of a more expensive one. The condo is just like the pictures. It was fairly clean and had all the necessary items except rubbermaid...
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    About this property
    Escape to paradise in Madeira Beach at this 2-bedroom, 2-bathroom vacation rental condo that comfortably sleeps 8. The private balcony, soaring palm trees, and tranquil environment will make this rental one you'll never forget. If chartering a fishing boat or jet skiing around Florida's sparkling...
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    Location Information
    Madeira Beach, Florida 33708
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
    • Ocean Views
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • DVD Player
    • Waterfront
    • Air Conditioning
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The condo is on the Gulf with direct beach access. The 25 unit complex has a 3-6ft deep graduated pool and a Hot Tub. On site management is very helpful and accommodating. Beautiful 3 bedroom condo on the beach. Recently repainted and decorated with other rehab projects underway. 'Beachy' Master...
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    Location Information
    Madeira Beach, Florida 33708
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    About this property
    New 2006 Madeira Bay Resort Condo! Overlooking Boca Ciega bay and just steps away from powder sand Madeira beach. Luxury condo resort style living at it finest. Famous Johns Pass village with shops, restaurants, and scenic views await you and your beautiful family to relax and enjoy. The unit is...
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    Location Information
    Madeira Beach, Florida 33708
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    BEACH LOVERS AND WATER ENTHUSIASTS!!! DIRECT BEACH FRONT Fabulous Gulf views from large balcony that is accessed from both the living room and master bedroom. Tastefully decorated with a beach theme. Full size washer and dryer for your convenience. Come experience the coastal lifestyle in this...
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    Location Information
    Madeira Beach, Florida 33708
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Las Brisas 402 Gulf front 4th floor condo in Madeira Beach! This three bedroom, two bath condo sleeps ten guests with a king size bed and a trundle bed in the master bedroom, two queen size beds in the second bedroom and two twin beds in the third bedroom. Both bathrooms in the unit were updated...
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    Location Information
    Madeira Beach, Florida 33708
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    Las Brisas 4031 / 38
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Reviewed 4 weeks ago
    Everything was great. I had great communication with sandy beach rentals and everything was smooth from arrival to checkout! Condo was beautiful and had lots of room for all 7...
    Reviewed 17 August 2017
    This place is right on the beach, which is exactly where we wanted to be. The layout of the condo is very open. We had 8 guests total and didn't feel cramped at all. Washer...
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    About this property
    Spacious and beautiful 4th floor, Gulf front 3 bedroom and 2 bath condo at Las Brisas in Madeira Beach with extensive upgrades: new sofa bed, new tile throughout, new kitchen and baths with granite counter tops, new ceilings, paint and mill work. Now with flat screen TVs, expanded cable service,...
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    Madeira Beach, Florida 33708
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Patio
    • Washer
    • Wi-Fi
    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Cable/satellite TV
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Ocean Sands, the premier condo building in Madeira Beach is located on an absolutely perfect section of white, soft, sandy beach and offers the most picturesque views of the beach and Gulf of Mexico. This lower floor condo is unique with its extra large, very private, beachfront terrace. The...
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    Location Information
    Madeira Beach, Florida 33708
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 7
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Hot Tub
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This beachfront, 11th floor unit at the Ocean Sands complex in Madeira Beach, boasts some of the most incredible views in the entire area. With its large, private, beach facing balcony and comfortable outdoor furniture, you'll find relaxing with a cool drink or an evening meal an absolute pleasure...
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    Location Information
    Madeira Beach, Florida 33708
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2-1208 - Ocean Sands1 / 47
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Washer
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    • Patio
    • Private Outdoor Pool (Unheated)
    • Hot Tub
    • Air Conditioning
    • Cable/satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 31 August 2017
    Excellent location. The unit was exactly as it was portrayed within listing. Would definitely stay here again.
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    About this property
    The Best on the Beach! The Ocean Sands complex is located conveniently at the North end of Madeira Beach, with easy access to Johns Pass Village as well as to the surrounding beach communities. This top floor (12th floor) corner unit on the North end of the complex gives an absolutely...
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    Location Information
    Madeira Beach, Florida 33708
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2-1207 - Ocean Sands1 / 44
    (1)Average
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Hot Tub
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    • Private Outdoor Pool (Unheated)
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 June 2015
    First the pros this is a beautifully decorated condo the colors are great and the decoration very nice. The pool and property are clean and very well kept, has parking...
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    About this property
    Beachfront Luxury Situated on the 12th Floor of the Prestigious Ocean Sands Resort Stay at one of the finest and most up-to-date condominium complexes on the beach. Ocean Sands is the perfect combination of location and amenities, and this condo has been completely renovated throughout. The view...
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    Location Information
    Madeira Beach, Florida 33708
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    1-306 - Ocean Sands1 / 47
    (4)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
    • Patio
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    • Cable/satellite TV
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    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 April 2016
    Spent February-March here without one good night of sleep. Mattresses were terrible and sheets were one grade below hospital grade. This was addressed by a previous renter and...
    Reviewed 23 November 2015
    This condo was VERY large, we were 4 people, 2 adults and 2 teens, we stayed for 2 weeks and we found it to be super comfy and had space to spare. Pros:Beachfront...
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    About this property
    Enormous Private Beachfront Patio. Totally Renovated Inside. Beautifully Furnished. Now available after being completely renovated, this incredible third floor Ocean Sands condo is open for your vacation plans. You'll stay at not only one of the freshest and most elegantly furnished condos in the...
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    Location Information
    Madeira Beach, Florida 33708
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
    • Parking
    • Grill
    • Internet Access
    • Private Outdoor Pool (Heated)
    • Terrace
    • DVD Player
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ** When you call, reference this unit code SB306 or Sea Breeze 306 ** *Reservation must fall within Sat-Sat booking window* The Sea Breeze Condominium is one of the most desirable complexes in Madeira Beach. Each unit sports a roomy balcony overlooking the powdery white sand and emerald turquoise...
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    Location Information
    Madeira Beach, Florida 33708
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spectacular sunset and beach views from almost every room in this beautifully maintained, clean and comfortable condo. Enjoy morning coffee or sipping a drink from the spacious covered balcony. Fully stocked updated kitchen with granite countertops and steel appliances makes it enjoyable when...
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    Location Information
    Madeira Beach, Florida 33708
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Waterfront
    • Terrace
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Washer
    • Grill
    • Cable/satellite TV
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    3 Bedroom/2 Bath 4 Queen beds Gulf front Balcony FREE Netflix Three TVs… 55', 48' and 39' Non Smoking, No Pets Las Brisas 105 is direct gulf front with a panoramic views and sunsets you will not soon forget. Free Wi-Fi! Free Calling to US and Canada Spacious 1440 square feet...
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    Location Information
    Madeira Beach, Florida 33708
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • DVD Player
    • Cable/satellite TV
    • Waterfront
    • Washer
    • Wi-Fi
    • Air Conditioning
    • Ocean Views
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Condo, 3 Bedrooms, 2 Baths, (Sleeps 2-8) After staying in our unit you will want to return year after year. Our building Las Brisas has only 40 units and 5 floors high. Our unit has been totally redone top to bottom, 1500 square ft. top floor and is a pleasure to stay in. Three bedrooms, two...
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    Location Information
    Madeira Beach, Florida 33708
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    205 - Chambre1 / 40
    (1)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Grill
    • Wi-Fi
    • DVD Player
    • Washer
    • Hot Tub
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 April 2017
    This condo is very spacious and comfortable. The kitchen is smaller, but we didn't cook very much, since we preferred the outdoor grill beside the swimming pool and hot tub...
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    About this property
    Corner unit on the second floor, with outstanding view of the beach and Sunset! Master bedroom has a Queen size bed and private en suite bath with tub/shower. Second bedroom is furnished with two Twin size beds. TV's in both bedrooms. The large living room gives and full West and North view of...
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    Location Information
    Madeira Beach, Florida 33708
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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