50 Best Madeira Beach Condos on Holiday Lettings - Vacation rentals

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1,997 Vacation rentals

(28) Excellent 

24

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 $127 / night

$1,016 - $1,298 / week

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from $127 / night

(5) Very Good 

26

Vacation condo in Madeira Beach

Florida / Madeira Beach

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Swimming pool
Perfect for up to 6 guests located on the 2nd floor, with a private balcony overlooking the marina and the heated swimming pool. The master bedroom has a king size bed, private bath and a flat screen TV. Second bedroom with two twin size beds. The living room is equi …see more

from $109 / night

$700 - $950 / week

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avg. 2 hours 27 minutes

from $109 / night

(5) Excellent 

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 $103 / night

$721 - $1,775 / week

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from $103 / 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 38 minutes

from $160 / 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 1 minutes

from $65 / 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
Our condo at the beautiful and modern Las Brisas resort delivers the perfect blend of home and vacation that you've been looking for. This is a corner unit on the second floor with privacy and space to enjoy your Florida beach vacation. The corner units at the building …see more

from $100 / night

$630 - $1,365 / week

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avg. 37 minutes

from $100 / night

35

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 Bay Resort 306 or MBR306 in Madeira Beach* *January 28-Easter, reservation must fall within Sat-Sat window. Please call us directly for other options before booking on line.* **New owners. It's their mission to share their 2 Bedroom/2 Bath …see more

from $87 / night

$605 - $2,508 / week

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Responds fast!
avg. 3 hours 24 minutes

from $87 / night

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

(2) Excellent 

35

Vacation apartment in Madeira Beach

Florida / Madeira Beach

3 7 14 nights min

  • 3 bedrooms
  • Sleeps 7
  • 14 nights min
  • 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 $186 / night

$1,300 - $2,300 / week

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from $186 / night

(5) Excellent 

24

Madeira Beach Vacation apartment rental

Florida / Madeira Beach

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
This light, bright and inviting condo has recently been re-decorated with beautiful tile throughout and comfortable furniture for relaxing. The kitchen has been updated with granite counter tops and sleek black appliances. Plus, you can enjoy the balmy weather on your …see more

from $100 / night

$700 - $1,700 / week

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from $100 / night

(1) Excellent 

25

Madeira Beach Vacation apartment rental

Florida / Madeira Beach

1 2 14 nights min

  • 1 bedroom
  • Sleeps 2
  • 14 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
Ocean Sands 504 is a beautiful, newly renovated studio right on the white sands of Madeira Beach. Enjoy our fabulous sunsets on your private fifth floor balcony. The recent updates include all stainless steel appliances in the kitchen along with beautiful white granite …see more

from $46 / night

$325 - $939 / week

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avg. 2 hours 13 minutes

from $46 / 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

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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from $110 / 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. 2 hours 8 minutes

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 - $2,375 / week

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from $168 / night

(1) Excellent 

14

Vacation condo in Madeira Beach

Florida / Madeira Beach

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 0 mi
  • Swimming pool
  • Child friendly
This beautiful beachfront condo was redecorated and updated in December 2017. You will be directly on the white sands of Florida's Gulf Coast watching the sun set off the balcony. In less than a minute, you can leave the condo and have your feet on the warm sand. Our tw …see more

from $189 / night

$1,090 - $1,890 / week

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avg. 1 hour 20 minutes

from $189 / night

(3) Excellent 

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
Please note there are structural repairs scheduled for the building during the months of February 2018 through August 2018. The work will include concrete repair work in the garage underneath the building, balcony flooring repair work, and painting the outside of the bu …see more

from $111 / night

$1,316 - $1,330 / week

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avg. 37 minutes

from $111 / night

(1) 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

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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avg. 3 hours 33 minutes

from $90 / 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. 3 hours 33 minutes

from $90 / 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 38 minutes

from $75 / 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 - $800 / week

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from $65 / night

(8) Excellent 

25

Madeira Beach Vacation apartment rental

Florida / Madeira Beach

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • 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 / week

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avg. 1 hour 56 minutes

from $109 / 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 $205 / night

$1,435 - $1,855 / week

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avg. 53 minutes

from $205 / night

7

Madeira Beach Vacation home rental

Florida / Madeira Beach

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Child friendly
  • Air conditioning
Great 1 bedroom 1 bath recently updated turnkey unit but still maintains the feel of a charming beach bungalow featuring newly painted ship lap ceilings and walls. Fully equipped kitchen. This unit is 2 short blocks to the beach, has its own separate parking and entranc …see more

from $100 / night

$700 / week

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Responds fast!
avg. 2 hours 24 minutes

from $100 / 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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Responds fast!
avg. 26 minutes

from $115 / night

(1) Excellent 

34

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
*TeemingVR presents Madeira Beach Yacht Club 329 or MBYC329B in Madeira Beach* Lovingly renovated in 2017, this gorgeous Madeira Beach property offers a great location, abundant amenities and great value! Teeming Vacation Rentals understands that your much anticipated …see more

from $199 / night

$597 - $2,600 / week

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avg. 3 hours 24 minutes

from $199 / night

14

Vacation apartment in Madeira Beach

Florida / Madeira Beach

2 8 Min stay varies

  • 2 bedrooms
  • Sleeps 8
  • Min stay varies
  • Ask about children
SEABREEZE 604 of Maderia Beach is perfect for a family beach getaway! Spacious direct gulf front condo with private balcony to enjoy the beach views. Comfortable furnishing with 3 queen beds, and a sleeper sofa, sleeps 6-8. Lounge by the pool, take a dip in the Jacuzzi, …see more

from $142 / night

$1,000 - $1,800 / week

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from $142 / 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, b …see more

from $220 / night

$1,134 - $2,016 / week

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avg. 37 minutes

from $220 / night

43

Vacation apartment with swimming pool in Madeira Beach

Florida / Madeira Beach

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Please note there are structural repairs scheduled for the building during the months of February 2018 through August 2018. The work will include concrete repair work in the garage underneath the building, balcony flooring repair work, and painting the outside of the bu …see more

from $121 / night

$1,316 - $1,330 / week

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avg. 37 minutes

from $121 / 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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avg. 3 hours 33 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 - $990 / week

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from $93 / night

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

25

Home rental in Madeira Beach with swimming pool

Florida / Madeira Beach

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
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 pe …see more

from $300 / night

$2,100 - $3,500 / week

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from $300 / 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. 3 hours 33 minutes

from $225 / night

25

Vacation apartment in Madeira Beach

Florida / Madeira Beach

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Ask about children
** When you call, reference this unit code MBR603 or Madeira Bay Resort 603** *January 28-Easter, reservation must fall within Sat-Sat window. Please call us directly for other options before booking on line.* Comfortable, Classy and Convenient, this hidden treasure i …see more

from $199 / night

$659 - $2,733 / week

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avg. 3 hours 24 minutes

from $199 / 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 f …see more

from $101 / night

$693 - $1,050 / week

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avg. 37 minutes

from $101 / night

33

Home rental in Madeira Beach

Florida / Madeira Beach

1 5 Min stay varies

  • 1 bedroom
  • Sleeps 5
  • Min stay varies
  • Child friendly
Nice and Nautical! One bedroom with new bedroom carpeting and 2 new double beds located on the first floor, poolside. Beautiful new tile shower in the bath. All the comforts to make your vacation complete. 10% Discount for stays of 28 days or longer! This condo is righ …see more

from $90 / night

$600 - $900 / week

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Responds fast!
avg. 3 hours 33 minutes

from $90 / 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

(2) Very Good 

21

Madeira Beach Vacation home rental

Florida / Madeira Beach

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Child friendly
This Tropic Breezes one bedroom condo has beautiful new decor and a king size bed and is on the first floor. Unit sleeps 4 with a king size bed and double sleeper sofa in the living room, includes Free WiFi! 10% Discount for stays of 28 days or longer! This condo is ri …see more

from $90 / night

$600 - $900 / week

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Responds fast!
avg. 3 hours 33 minutes

from $90 / night