50 Best Madeira Beach Condos on Holiday Lettings - Vacation rentals

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2,148 Vacation rentals

(29) 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 $133 / night

$1,022 - $1,221 / week

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from $133 / night

24

Vacation apartment 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 $125 / night

$875 / week

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avg. 37 minutes

from $125 / night

(2) 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 

22

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
The big wrap-around balcony and the extra windows and doors give this condo a terrific open feeling. The view of the Gulf of Mexico, the beach and the pool is fantastic. The décor is traditional and comfortable plus the den can be used as another small bedroom. The f …see more

from $154 / night

$1,075 - $2,475 / week

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from $154 / 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

(7) Very Good 

Certificate of Excellence

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

Certificate of Excellence

from $75 / night

$450 / week

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avg. 1 hour 33 minutes

from $75 / night

(1) Excellent 

26

Vacation apartment 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 / week

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avg. 37 minutes

from $230 / 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
  • Child friendly
  • 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

4

Madeira Beach Vacation cottage rental

Florida / Madeira Beach

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Swimming pool
  • Car not necessary
  • Air conditioning
COME VISIT THE GEM OF MADEIRA BEACH, AND DISCOVER THE CHARM THAT HAS VISITORS COMING BACK FOR DECADES. Enjoy a quiet, tropical, old Florida feel that's a hard to find anywhere in Pinellas County. This property features lush landscaping and one of the largest, cleane …see more

from $75 / night

$450 - $475 / week

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from $75 / night

(1) 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
CONSTRUCTION SPECIAL RATES IN PLACE. SAVE BIG!!! Please note there are structural repairs scheduled for the building during the months of February 2018 through October 2018. The work will does involve concrete repair which can include loud jack-hammering work as well …see more

from $108 / night

$1,330 - $1,666 / week

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avg. 1 hour 2 minutes

from $108 / night

22

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 . Sunshine and a memorable experience await you. A snazzy decor ground floor tiled waterfront 1BR/1BA condo that has an outdoor patio area for al fresco dining is just the beginning . Condo offers all the comfo …see more

from $65 / night

$450 / week

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avg. 2 hours 7 minutes

from $65 / night

(2) Very Good 

12

Vacation condo in Madeira Beach

Florida / Madeira Beach

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • 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 - $800 / week

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from $110 / 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

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
  • Child friendly
  • 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

(2) 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.* Lovingly renovated in 2017, this gorgeous Madeira Beach property offers a great …see more

from $149 / night

$1,044 - $4,679 / week

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from $149 / 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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Responds fast!
avg. 1 hour 56 minutes

from $90 / night

(1) Excellent 

13

Vacation condo in Madeira Beach

Florida / Madeira Beach

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Child friendly
Welcome to Boca Ciega Oasis! "The Oasis" suite 409 has been totally remodeled in January 2018! All new furniture including balcony furniture. The 4th floor view is the best but 409 is also centered beautifully to take in the expansive Boca Ciega Bay! From the balcony …see more

from $110 / night

$770 / week

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avg. 3 hours 58 minutes

from $110 / 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

47

Vacation apartment with swimming pool in Madeira Beach

Florida / Madeira Beach

2 7 14 nights min

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

from $220 / night

$973 - $2,324 / week

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avg. 1 hour 2 minutes

from $220 / night

(1) Excellent 

21

Home rental in Madeira Beach

Florida / Madeira Beach

1 6 Min stay varies

  • 1 bedroom
  • Sleeps 6
  • Min stay varies
  • Child friendly
Make yourself right at home in this 2nd floor condo with a great view of the pool and the Gulf of Mexico in the distance. NEWLY renovated one bedroom condo with 2 double beds in the bedroom.  Just the place to have a home away from home. The perfect getaway! 10% discoun …see more

from $90 / night

$600 - $900 / week

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Responds fast!
avg. 1 hour 56 minutes

from $90 / night

(2) 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 56 minutes

from $225 / night

14

Madeira Beach Vacation home rental

Florida / Madeira Beach

3 6 90 nights min

  • 3 bedrooms
  • Sleeps 6
  • 90 nights min
  • Ask about children
3-MONTH STAYS OR LONGER..at This beautiful, clean 3bedroom/2bath Madeira Beach home is just a couple blocks walk to the white sandy shores of Madeira Beach for relaxation and our beautiful sunsets !!! The home has a private yard and only a few blocks away from Johns Pa …see more

from $100 / night

$700 / week

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from $100 / 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 $65 / night

$616 - $1,169 / week

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avg. 1 hour 2 minutes

from $65 / 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 

11

Vacation apartment in Madeira Beach

Florida / Madeira Beach

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Child friendly
  • Air conditioning
Seashells, Dolphins and Sunsets sums up the beauty of Madeira Beach! We want to welcome you to our newly renovated condo, located just 200 feet away from the sandy shores of the Gulf of Mexico. Whether you are relaxing on the beach looking to soak up the sun and sand …see more

from $100 / night

$700 / week

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from $100 / night

(5) 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

(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

48

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

$714 - $1,743 / week

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avg. 1 hour 2 minutes

from $245 / 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

(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 $80 / night

$672 - $1,197 / week

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avg. 1 hour 2 minutes

from $80 / 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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avg. 2 hours 43 minutes

from $160 / night

(9) Excellent 

25

Madeira Beach Vacation apartment rental

Florida / Madeira Beach

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
This beautiful fully equipped condo has beautiful water views of the Boca Ciega Bay and marina, located in the Skyline Resort on Madeira beach, one of the most desirable beaches in the Tampa Bay area. Perfect for up to 6 guests located on the 2nd floor, with a private …see more

from $109 / night

$700 - $950 / week

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avg. 2 hours 5 minutes

from $109 / 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. 1 hour 2 minutes

from $100 / night

(7) 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

25

Vacation apartment 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
You will feel happy when you walk into this freshly renovated north corner condo. And, the view will take your breath away. The cheerful, tropical décor is also quite comfortable. The kitchen is top-of-the line with granite counter tops, stainless steel appliances, a …see more

from $140 / night

$975 - $2,350 / week

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from $140 / 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 - $1,225 / week

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from $157 / night

(1) Excellent 

47

Apartment rental in Madeira Beach with swimming pool

Florida / Madeira Beach

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Updated Condo with Incredible Views of the Gulf of Mexico From Your Private Balcony. Chambre is one of Madeira Beach's most desirable buildings. Tucked away off the main highway, Chambre is beautifully maintained, secure, and is located just a few minutes from John's …see more

from $140 / night

$588 - $1,533 / week

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Responds fast!
avg. 1 hour 2 minutes

from $140 / 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 $65 / night

$791 - $1,148 / week

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Responds fast!
avg. 1 hour 2 minutes

from $65 / night

(2) Excellent 

44

Apartment rental in Madeira Beach with swimming pool

Florida / Madeira Beach

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Fantastic Value in this Updated Beachfront Resort Sea Breeze Condominiums is located centrally on beautiful Madeira Beach with everything you need for a perfect Florida vacation. Soft sugary sand, warm tropical breezes, and the warm and clean Gulf of Mexico at your do …see more

from $116 / night

$1,183 - $1,974 / week

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Responds fast!
avg. 1 hour 2 minutes

from $116 / night

(1) Very Good 

46

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 MBR306 or Madeira Bay Resort 306 in Madeira Beach* *January -Easter, reservation must fall within Sat-Sat window.* For fun in the sun & at night, this condo is just steps away from Madeira Beach and John's Pass Village & Boardwalk, an eclectic arr …see more

from $122 / night

$669 - $3,506 / week

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from $122 / night