50 Best Madeira Beach Condos on Holiday Lettings - Vacation rentals

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1,963 Vacation rentals

(28) Excellent 

33

Madeira Beach Vacation apartment rental

Florida / Madeira Beach

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
The condo is suitable for families, couples and groups of friends. From the private balcony there is a wonderful, wide view of the coast, from Treasure Island up to the end of Sand Key. Dolphins are often spotted in the sea in front. It receives direct sunshine from …see more

from $140 / night

$1,078 - $1,288 / week

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from $140 / night

20

Studio rental in Madeira Beach with shared pool

Florida / Madeira Beach

Studio 3 2 nights min

  • Studio
  • Sleeps 3
  • 2 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
This quaint and charming studio beach cottage sits on the famous Madeira beach, in sunny Florida! You are steps away from Madeira beach, local surf shops and stores, coffee bars, ice cream parlors, and many local restaurants. This cottage features a queen sized Murph …see more

from $65 / night

$435 - $850 / week

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from $65 / night

30

Apartment rental in Madeira Beach

Florida / Madeira Beach

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
***3 night minimum rental period, please call or email for a less than 7 night stay*** Bright and spacious 3 bedroom, 2 bath condo with direct views of the Gulf of Mexico! This condo will accommodate up to 8, has a nice sized private balcony and is right in the heart …see more

from $168 / night

$1,175 - $2,275 / week

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from $168 / night

(1) Excellent 

24

Madeira Beach Vacation apartment rental

Florida / Madeira Beach

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
You will LOVE the Madeira Beach Yacht Club! Such wonderful amenities for you to enjoy during your heated pools, billiard room, fitness rooms, hot tub, sauna. We are right across the street from the library and a grocery store and a sports complex called ROC park, where …see more

from $115 / night

$800 - $1,225 / week

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from $115 / night

(6) Very Good 

31

Condo rental in Madeira Beach

Florida / Madeira Beach

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Condo, 2 Bedrooms, 1.5 Baths, 6 Sleeps This beautiful, 4th floor, 2 bedroom, luxury condo has living room & master bedroom sliding glass door entrances to a large balcony view of the Gulf of Mexico. The Madeira Norte complex sits on the white, sugar sand beach of Madei …see more

from $118 / night

$820 - $1,380 / week

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avg. 3 hours 45 minutes

from $118 / night

(1) Very Good 

25

Vacation condo in Madeira Beach

Florida / Madeira Beach

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Nearest beach 0.1 mi
  • Swimming pool
  • Car not necessary
Enjoy the lore of the much desired Madeira Beach Yacht Club. A unique decor second floor tiled 1BR/1BA condo that has beautiful sunset and gulf views from living room. Condo offers all the comforts of home. Fully equipped kitchen. Bed linens, towels, beach towels, beac …see more

from $65 / night

$450 / week

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avg. 2 hours 7 minutes

from $65 / night

(1) Excellent 

26

Vacation apartment with shared pool in Madeira Beach

Florida / Madeira Beach

2 8 7 nights min

  • 2 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
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 …see more

from $230 / night

$1,610 - $1,995 / week

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avg. 28 minutes

from $230 / night

24

Vacation apartment with shared pool in Madeira Beach

Florida / Madeira Beach

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Begin your sun-kissed adventure to Madiera Beach at this 2-bedroom, 1.5-bathroom vacation rental condo that accommodates 6 guests. This waterfront condo is perched on the top floor of the complex with panoramic views of the Gulf of Mexico. This coastal abode boasts all …see more

from $115 / night

$805 - $1,435 / week

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avg. 24 minutes

from $115 / night

(2) Very Good 

12

Vacation condo in Madeira Beach

Florida / Madeira Beach

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
ESCAPE TO THE WHITE POWDERED SANDS OF THE GULF! Come discover the charming, quiet, and tropical atmosphere, reminiscent of the real, unspoiled Florida, at Gulf Gardens. This rental property has public beach access directly across the street. This beach cottage provides …see more

from $110 / night

$550 - $900 / week

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avg. 3 hours 6 minutes

from $110 / night

27

Madeira Beach Vacation apartment rental

Florida / Madeira Beach

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
Remember a time in your life when you were the most relaxed you’ve ever been… got that picture in your mind? Perfect- now you’re ready to imagine what it’s like whiling away the days here in this perfect spot! This beautiful condo in the quaint village of Madeira Bea …see more

from $150 / night

$1,050 - $1,545 / week

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from $150 / night

(7) Very Good 

23

Cottage accommodation in Madeira Beach

Florida / Madeira Beach

4 3 nights min

  • Sleeps 4
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Our unit is part of Gulf Gardens Resort at 14141 Gulf Blvd Madeira Beach Fl. Quaint and charming studio cottage with full kitchen, one bath, and all the linens included. We are across the street from the beautiful Gulf of Mexico. Our cottage can comfortably sleep 4 peop …see more

from $75 / night

$450 - $550 / week

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avg. 1 hour 33 minutes

from $75 / night

(2) Excellent 

35

Vacation apartment in Madeira Beach

Florida / Madeira Beach

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
UNIQUE One of a Kind OCEAN LOVER'S Gulf coast Condo is especially made for those that are all about the JAW-DROPPING OCEAN VIEWS and being within footsteps to the Majestic Gulf of Mexico Ocean ! You will never forget your stay at the " Unique Turqoise Building -the 4 …see more

from $230 / night

$1,300 - $2,100 / week

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from $230 / night

45

Vacation apartment with swimming pool in Madeira Beach

Florida / Madeira Beach

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
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 eno …see more

from $245 / night

$777 - $1,820 / week

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avg. 2 hours 14 minutes

from $245 / night

47

Vacation apartment with swimming pool in Madeira Beach

Florida / Madeira Beach

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
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 clo …see more

from $100 / night

$630 - $1,568 / week

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avg. 2 hours 14 minutes

from $100 / night

(4) Excellent 

17

Vacation condo in Madeira Beach

Florida / Madeira Beach

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.5 mi
  • Swimming pool
Convenient ground floor condominium located in the highly sought-after Madeira Beach Yacht club. 2 bed/1 bath condo is well cared for featuring newly updated kitchen with granite counter tops and artic white solid wood cabinets. Brand new mattress in master bedroom wi …see more

from $65 / night

$450 - $900 / week

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from $65 / night

(1) Excellent 

24

Madeira Beach Vacation condo rental

Florida / Madeira Beach

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This beautiful, spacious 3 bedroom/3 bathroom penthouse corner unit is located on a scenic intra-coastal waterway directly across the street from the beach. It is approximately 2000 sq. Ft. with an extra 1000 sq. ft of balcony space. It occupies 1/2 of the top floor. Th …see more

from $143 / night

$1,000 - $1,500 / week

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avg. 1 hour 59 minutes

from $143 / night

47

Vacation apartment with swimming pool in Madeira Beach

Florida / Madeira Beach

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
A superb view from your private balcony in this new resort situated with easy walking distance to Johns Pass Village, and directly across from the most pristine section of beach in the area. The master bedroom is furnished with a King size bed, and the second bedroom i …see more

from $81 / night

$518 - $1,169 / week

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avg. 2 hours 14 minutes

from $81 / night

(5) Excellent 

20

Madeira Beach Vacation condo rental

Florida / Madeira Beach

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
Newly renovated top floor of the Madeira Norte complex. Located on the beautiful white sandy beaches of the Gulf of Mexico on the barrier Islands between St. Pete Beach and Clearwater Beach. We are directly across the street from John's Pass Village and Boardwalk. Made …see more

from $193 / night

$1,350 / week

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from $193 / night

18

Vacation home in Madeira Beach

Florida / Madeira Beach

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Child friendly
This condo is located on the second floor with pool and Gulf views. It condo sleeps four guests with a new king bed in the bedroom and a new double sofa sleeper in the living room. The unit has two wall mounted flat screen TVs and Free WiFi! Come and enjoy a quiet stay …see more

from $90 / night

$600 - $900 / week

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avg. 1 hour 40 minutes

from $90 / night

(1) Excellent 

34

Madeira Beach Vacation cottage rental

Florida / Madeira Beach

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Air conditioning
A fantastic destination in the heart of Madeira Beach, this comfortable, private, and secure cottage has been completely renovated from the inside-out (Fall 2013). Everything is new and updated, and the location can't be beat. The cottage is directly across the street …see more

from $77 / night

$504 - $1,197 / week

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avg. 2 hours 14 minutes

from $77 / night

(1) Excellent 

38

Madeira Beach Vacation home rental

Florida / Madeira Beach

3 10 Min stay varies

  • 3 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
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 TV …see more

from $225 / night

$1,350 - $2,200 / week

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avg. 1 hour 40 minutes

from $225 / night

27

Vacation apartment with shared pool in Madeira Beach

Florida / Madeira Beach

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
When you walk into this condo you are greeted by a bright fresh décor. The newly updated kitchen with stainless steel appliances, beautiful tile and wood floors plus comfortable furniture makes this a great spot for a beach vacation. Updated master bathroom with nice w …see more

from $129 / night

$900 - $2,225 / week

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from $129 / night

(1) Excellent 

34

Madeira Beach Vacation apartment rental

Florida / Madeira Beach

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask about children
*TeemingVR presents Madeira Beach Yacht Club 329 or MBYC329B in Madeira Beach* *This condo requires Sat-Sat booking window and an application must be submitted 30 days prior to arrival. If your travel plans do not fit these criteria, please call us directly for other …see more

from $149 / night

$1,044 - $4,679 / week

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from $149 / night

23

Apartment rental in Madeira Beach with shared pool

Florida / Madeira Beach

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
This top floor condo has a large, screened in balcony facing the beach and the Gulf of Mexico. The décor is a traditional and comfortable plus the den can be used as another small bedroom with kids bunk beds in it. The kitchen is fully equipped and you are within walk …see more

from $129 / night

$900 - $2,225 / week

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from $129 / night

19

Vacation home in Madeira Beach

Florida / Madeira Beach

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Child friendly
Tropic Breezes 8 is conveniently located poolside on the first floor. This condo is updated with new living room furniture, a flat screen TV, King size bed, new paint and bedroom tile! Condo includes Free WiFi! 10% Discount for stays of 28 days or longer! This condo is …see more

from $90 / night

$600 - $900 / week

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avg. 1 hour 40 minutes

from $90 / night

(2) Very Good 

22

Vacation apartment in Madeira Beach

Florida / Madeira Beach

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Ask about children
AMAZING SUNSETS and WHITE SANDY BEACHES AWAIT YOU... IN UNIT 503 The condo offers a truly breathtaking views from the 5th floor. Open up the sliders and let in the gulf breeze or sit out on the balcony while enjoying a meal. This is the place to come and relax!! Up …see more

from $125 / night

$1,200 / week

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from $125 / night

(2) Excellent 

17

Vacation studio in Madeira Beach

Florida / Madeira Beach

Studio 2 3 nights min

  • Studio
  • Sleeps 2
  • 3 nights min
  • Air conditioning
  • Pet friendly
Studio apartment Upstairs with queen bed, 1 bath, full kitchen - Sleeps 2 Cottage by the Pass upstairs unit offers all the charm of days gone by as well as all the modern conveniences. Cottage by the Pass is located just steps from the white sand, with no streets to cr …see more

from $100 / night

$700 / week

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from $100 / night

(1) Very Good 

39

Vacation apartment with swimming pool in Madeira Beach

Florida / Madeira Beach

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
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 …see more

from $200 / night

$714 - $1,778 / week

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avg. 2 hours 14 minutes

from $200 / night

(4) Excellent 

28

Madeira Beach Vacation condo rental

Florida / Madeira Beach

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.5 mi
  • Swimming pool
The Yacht Club at Madeira Beach laps the Boca Ciega Bay and is only 150 yards from Madeira's finest white sand beach. The complex is a private, gated immaculately kept facility and boasts a club house with a small, well equipped gym, Jacuzzi, sauna, showers & billiards …see more

from $97 / night

$679 / week

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from $97 / night

(1) Good 

24

Vacation condo rental

Florida / Madeira Beach

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Vacation Beach Condo 2/2 with heated swimming pool directly across the street from the famous John's Pass in Madeira Beach Florida that offers fishing, boating, watersports, shopping, restaurants, clubs,.sports bar .... Vacation paradise at its finest !!!! No Smoking …see more

from $175 / night

$1,050 - $1,435 / week

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Responds fast!
avg. 2 hours 23 minutes

from $175 / night

(4) Very Good 

43

Vacation apartment with swimming pool in Madeira Beach

Florida / Madeira Beach

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Resort with full service Spa, marina, restaurant, and two blocks from John's Pass. Gulf facing view from your private balcony. All the amenities of home. -- Freshly updated and furnished with Bamboo flooring and the interior design will welcome you with its' charm an …see more

from $77 / night

$490 - $1,197 / week

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avg. 2 hours 14 minutes

from $77 / night

33

Vacation apartment with swimming pool in Madeira Beach

Florida / Madeira Beach

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
You will love this! A one bedroom/one bath ground floor condo with a screened patio with plenty of outdoor seating. Just a few steps from the intercoastal where you can enjoy fishing from the docks or just relaxing with a good book. The Madeira Beach Yacht Club has aw …see more

from $90 / night

$625 - $850 / week

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from $90 / night

12

Condo rental in Madeira Beach

Florida / Madeira Beach

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
This gorgeous ocean front condo is beautifully decorated with all the amenities and comforts of home complete with granite kitchen and new furnishings and flooring. This nicely furnished unit comes with fully equipped kitchen for cooking and entertaining, washer and dry …see more

from $200 / night

$1,400 - $2,275 / week

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Responds fast!
avg. 46 minutes

from $200 / night

16

Madeira Beach Vacation home rental

Florida / Madeira Beach

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Pet friendly
The Jungle Oasis Studio is a ground floor unit that boasts ocean views. Upon walking into the unit to your right you will find a bathroom with toilet, sink and shower. You will also enter right into the kitchen with microwave, refrigerator, two top burner stove, toaster …see more

from $100 / night

$850 - $1,085 / week

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from $100 / night

(1) Excellent 

22

Madeira Beach Vacation home rental

Florida / Madeira Beach

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Pet friendly
Shell Island is a one bedroom one full bath ocean front condo. It is a second floor unit that boasts beautiful ocean views. The bedroom has a Queen size bed with beach/ocean views from the side windows. The living room also features ocean views and has a queen size murp …see more

from $157 / night

$1,099 / week

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from $157 / night

(19) Very Good 

17

Madeira Beach Vacation apartment rental

Florida / Madeira Beach

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
LOCATION, LOCATION, LOCATION. Lovely 2 bedroom, Jack and Jill bath condo in the beautiful Madeira Beach Yacht Club right on the Boca Ciega Bay, 150 yards from endless Gulf of Mexico Beach. This gated, lanscaped club boasts two pools, fitness center, hot tub, fishing p …see more

from $102 / night

$710 / week

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from $102 / night

23

Vacation condo with shared pool in Madeira Beach

Florida / Madeira Beach

2 6 14 nights min

  • 2 bedrooms
  • Sleeps 6
  • 14 nights min
  • Swimming pool
  • Air conditioning
This south facing corner unit overlooking the pool extends your view all the way to St. Pete's Beach. The condo has been totally renovated and equipped with all new appliances and furnishings. Included are top quality granite countertops and large porcelain flooring til …see more

from $172 / night

$1,200 / week

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from $172 / night

33

Home accommodation in Madeira Beach

Florida / Madeira Beach

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Child friendly
This one bedroom, poolside condo is decorated in a beautiful Palm Tree theme. Enjoy the new Smart TV's and Free WiFi, fresh paint, window treatments, comforters and two new couches too. This condo comfortably sleeps four guests with two double beds. 10% Discount for sta …see more

from $90 / night

$600 - $900 / week

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Responds fast!
avg. 1 hour 40 minutes

from $90 / night

17

Vacation condo in Madeira Beach

Florida / Madeira Beach

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
2BR/2 BA SURF SONG TOWNHOUSE #343 CONDO Location - Space - Privacy - Unmatched Amenities - Clean - Well Equipped - Reasonably Priced - BEST DEAL ON THE BEACH! Perfect for a memorable family beach vacation. Keyless entry on entrance doors for added security and conve …see more

from $93 / night

$645 - $800 / week

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from $93 / night

(15) Excellent 

21

Madeira Beach Vacation apartment rental

Florida / Madeira Beach

2 6 14 nights min

  • 2 bedrooms
  • Sleeps 6
  • 14 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary
A different sunset view every night! Madeira Beach 5th floor oceanfront condo with extraordinary gulf views from the living room as well as the master bedroom. Triple panel sliding glass doors in each room open to a very large balcony with storage. Excellent newly fu …see more

from $160 / night

$1,100 / week

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Responds fast!
avg. 2 hours 57 minutes

from $160 / night