50 Best Madeira Beach Condos on Holiday Lettings - Vacation rentals

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186 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 $110 / night

$916 - $1187 / week

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from $110 / 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 $99 / night

$680 - $950 / week

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avg. 3 hours 45 minutes

from $99 / night

44

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
We help make the most of your vacation by providing Free Admission to some of the area's top attractions each and every day! Create exciting memories, have more fun, and truly experience your destination! Sandy Shores is located on the sugary sand beaches of Madeira Bea …see more

from $87 / night

$1330 - $1589 / week

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avg. 20 minutes

from $87 / night

(5) 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 52 minutes

from $75 / 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 $130 / night

$900 - $1100 / week

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avg. 2 hours 0 minutes

from $130 / night

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 $180 / night

$1260 - $1855 / week

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avg. 50 minutes

from $180 / night

25

Home rental in Madeira Beach with swimming pool

Florida / Madeira Beach

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • 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

$2100 - $3500 / week

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from $300 / night

35

Madeira Beach Vacation cottage rental

Florida / Madeira Beach

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Air conditioning
We help make the most of your vacation by providing Free Admission to some of the area's top attractions each and every day! Create exciting memories, have more fun, and truly experience your destination! A fantastic destination in the heart of Madeira Beach, this comfo …see more

from $60 / night

$791 - $1148 / week

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avg. 20 minutes

from $60 / 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 - $2225 / week

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from $129 / 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
AVAILABILITY LEFT FOR APRIL 7-MAY 28, 2016 -ask about our DEALS!! STUNNING Ocean Views and new Bedroom Flooring as of MAY 2015!! Be the first to stay in this updated unit and take a look at our Please note a booking REQUIRES A GUEST AGREEMENT From the Owner that MUST …see more

from $158 / night

$1100 - $2300 / week

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from $158 / 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 $108 / night

$750 - $1200 / week

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from $108 / night

(1) Excellent 

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 $100 / night

$700 - $1400 / week

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from $100 / night

20

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 $80 / night

$525 - $850 / week

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avg. 1 hour 51 minutes

from $80 / night

(2) Excellent 

44

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
We help make the most of your vacation by providing Free Admission to some of the area's top attractions each and every day! Create exciting memories, have more fun, and truly experience your destination! Stay on the Beach Across from John's Pass. Fantastic Location! Th …see more

from $66 / night

$1330 - $1442 / week

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avg. 20 minutes

from $66 / night

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

$1350 - $2200 / week

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avg. 1 hour 51 minutes

from $225 / 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. Note: 1 week minimum stay, requires Saturday arrival in season.  …see more

from $80 / night

$525 - $850 / week

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avg. 1 hour 51 minutes

from $80 / night

(3) 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

$680 / week

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from $97 / night

(2) Very Good 

20

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 rig …see more

from $80 / night

$525 - $850 / week

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avg. 1 hour 51 minutes

from $80 / 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

$650 - $900 / week

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avg. 1 hour 57 minutes

from $110 / night

(7) Excellent 

25

Apartment rental in Madeira Beach

Florida / Madeira Beach

1 2 90 nights min

  • 1 bedroom
  • Sleeps 2
  • 90 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Car not necessary
This relaxing Key West style apartment is just across the road from the beach, a short walk from the shops, bars and restaurants of Johns Pass and has beautiful views of the intracoastal. The large back yard has a Florida garden, full of indigenous plants and plenty of …see more

from $104 / night

$728 / week

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from $104 / night

48

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
We help make the most of your vacation by providing Free Admission to some of the area's top attractions each and every day! Create exciting memories, have more fun, and truly experience your destination! Our condo at the beautiful and modern Las Brisas resort delivers …see more

from $72 / night

$455 - $1498 / week

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avg. 20 minutes

from $72 / night

(2) 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

(1) Very Good 

0

Vacation apartment in Madeira Beach

Florida / Madeira Beach

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Ask about children
SEABREEZE 603 of Maderia Beach is perfect for a family beach getaway! Spacious 2/2 direct gulf front condo Enjoy watching spectacular sunsets and peaceful mornings from your balcony. Gather in the spacious living room with a queeen sleeper sofa and loveseat or around …see more

from $143 / night

$1000 - $1800 / week

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from $143 / night

(8) Excellent 

25

Madeira Beach Vacation apartment rental

Florida / Madeira Beach

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night 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 26 minutes

from $109 / night

29

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
Light, bright and comfortable describes this Gulf front condo. And, it has a fantastic million dollar views of the beach and Gulf of Mexico from every room as well as the balcony. The remolded kitchen is fully equipped. This is a perfect condo for 2 couples to share …see more

from $140 / night

$975 - $2350 / week

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from $140 / night

(3) Excellent 

26

Vacation apartment in Madeira Beach

Florida / Madeira Beach

3 6 28 nights min

  • 3 bedrooms
  • Sleeps 6
  • 28 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
If your plans call for sitting on your balcony and watching spectacular, technicolor sunrises and sunsets, you have found your place on the beach. This panoramic corner unit has a full wrap around balcony with plenty of seating for everyone. Madeira Towers is a quite co …see more

from $87 / night

$613 - $1050 / week

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avg. 3 hours 43 minutes

from $87 / night

(1) 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 - $1338 / week

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from $103 / night

(4) Very Good 

41

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
We help make the most of your vacation by providing Free Admission to some of the area's top attractions each and every day! Create exciting memories, have more fun, and truly experience your destination! Resort with full service Spa, marina, restaurant, and two blocks …see more

from $65 / night

$420 - $1148 / week

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avg. 20 minutes

from $65 / 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
  • Child friendly
  • 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 $83 / night

$575 - $800 / week

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from $83 / night

(2) Very Good 

44

Vacation apartment with swimming pool in Madeira Beach

Florida / Madeira Beach

3 8 14 nights min

  • 3 bedrooms
  • Sleeps 8
  • 14 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
We help make the most of your vacation by providing Free Admission to some of the area's top attractions each and every day! Create exciting memories, have more fun, and truly experience your destination! Updated, spacious, and completely outfitted location for your Flo …see more

from $200 / night

$707 - $1960 / week

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avg. 20 minutes

from $200 / night

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

(3) Good 

47

Madeira Beach Vacation apartment rental

Florida / Madeira Beach

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
We help make the most of your vacation by providing Free Admission to some of the area's top attractions each and every day! Create exciting memories, have more fun, and truly experience your destination! Oversized Two Bedroom Condo in a New Resort and Spa. Private Balc …see more

from $72 / night

$455 - $1442 / week

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Responds fast!
avg. 20 minutes

from $72 / 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

$1350 / week

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from $193 / night

44

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
We help make the most of your vacation by providing Free Admission to some of the area's top attractions each and every day! Create exciting memories, have more fun, and truly experience your destination! Sandy Shores is perfectly located on the sand in Madeira Beach. J …see more

from $72 / night

$1330 - $1442 / week

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Responds fast!
avg. 20 minutes

from $72 / night

(2)  

44

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
We help make the most of your vacation by providing Free Admission to some of the area's top attractions each and every day! Create exciting memories, have more fun, and truly experience your destination! Sandy Shores is located on the sugary sand beaches of Madeira Bea …see more

from $72 / night

$1330 - $1442 / week

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Responds fast!
avg. 20 minutes

from $72 / night

6

Vacation cottage in Madeira Beach

Florida / Madeira Beach

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Air conditioning
  • Pet friendly
You will love this 'Old Florida' tropical beach cottage w/ all the amenities of today. Enjoy the privacy & charm of your own beach cottage that has just been redecorated w/ new furniture and everything that you can even think of. Clean & bright tropical colors. Fully eq …see more

from $115 / night

$805 / week

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from $115 / night

(3) Very Good 

24

Vacation apartment in Madeira Beach

Florida / Madeira Beach

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
Sugar Sands Retreat is one of 3 units in a connected building setting 'triplex'. All 3 connected units use the same parking area; however, units do have assigned parking spaces. In addition, all 3 connected units share the pool area, amenities and beach access. Sat - Sa …see more

from $130 / night

$915 - $3830 / week

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avg. 3 hours 43 minutes

from $130 / night

44

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
We help make the most of your vacation by providing Free Admission to some of the area's top attractions each and every day! Create exciting memories, have more fun, and truly experience your destination! A superb view from your private balcony in this new resort situat …see more

from $60 / night

$392 - $1120 / week

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avg. 20 minutes

from $60 / night

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 and balcony. Condo offers all the comforts of home. Fully equipped kitchen. Bed linens, towels, beach t …see more

from $65 / night

$450 / week

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Responds fast!
avg. 1 hour 13 minutes

from $65 / 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
From the moment you enter, this totally renovated north corner condo will take your breath away. Enjoy sweeping views of the beach and the Gulf of Mexico from your private balcony. Inside your condo, the contemporary décor creates the perfect atmosphere to relax and u …see more

from $140 / night

$975 - $2350 / week

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from $140 / night