50 Best Madeira Beach Condos on Holiday Lettings - Vacation rentals

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185 Vacation rentals

(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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from $109 / night

(24) 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 $111 / night

$923 - $1196 / week

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from $111 / night

45

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! Click on the Image for a 3D Tour of the Property! Sandy Shores is …see more

from $140 / night

$1666 / week

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from $140 / night

45

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 $116 / night

$1505 / week

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from $116 / night

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 $129 / night

$900 - $1400 / week

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from $129 / night

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

$722 - $1339 / week

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from $103 / night

(1) 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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from $110 / night

(1) Good 

45

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 $116 / night

$1505 / week

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from $116 / night

45

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 $96 / night

$616 - $1169 / week

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from $96 / night

(6) Very Good 

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 pr …see more

from $70 / night

$490 / week

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from $70 / night

(1) Excellent 

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 $198 / night

$1344 - $3318 / week

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from $198 / 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

(12) 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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from $130 / night

34

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 $84 / night

$550 - $850 / week

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from $84 / 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

36

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 $96 / night

$693 - $1197 / week

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from $96 / 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 $165 / night

$1150 - $2100 / week

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from $165 / night

(2) Excellent 

12

Vacation bungalow in Madeira Beach

Florida / Madeira Beach

1 3 2 nights min

  • 1 bedroom
  • Sleeps 3
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Car not necessary
We are located in historic John's Pass Village of Maderia Beach, Florida. This is the perfect destination for travelers looking for relaxation and comfort or for travelers looking for fun and adventure! The Sea Turtle is just a few short steps from some of John's Pass …see more

from $150 / night

$850 - $920 / week

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from $150 / 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 - $2350 / week

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from $140 / 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 Maderia Beach Yacht Club has aw …see more

from $79 / night

$550 - $800 / week

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from $79 / 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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from $180 / 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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from $225 / night

(2) 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

31

Madeira Beach Vacation home rental

Florida / Madeira Beach

2 4 30 nights min

  • 2 bedrooms
  • Sleeps 4
  • 30 nights min
  • Child friendly
Located in Madeira Beach Boca Vista 213 has a pool, spa, and tennis courts. It is a charming and spacious two bedroom two bath condominium. The views from Boca Vista 213 look at the pool and spa area. This condo has recently been updated with new carpet, laminate floors …see more

from $60 / night

$420 / week

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from $60 / night

(1) Excellent 

24

Apartment rental in Madeira Beach with swimming pool

Florida / Madeira Beach

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
Beautiful, renovated, north corner Gulf front condo. This 3rd floor condo has a million dollar view of the beach and the Gulf of Mexico. It has lots of windows plus a screened in balcony so you can take it all in! The kitchen has been renovated with stylish black app …see more

from $133 / night

$925 - $2175 / week

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from $133 / night

23

Cottage rental in Madeira Beach

Florida / Madeira Beach

2 4 4 nights min

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min
  • Child friendly
  • Air conditioning
  • Ask about pets
John's Pass-Time Beach Front Cottage 2 Bedroom/ 1 Bath Huge Deck & Outside Lounging Area Gorgeous White Sand Gulf Beach Steps to John's Pass (with countless Restaurants and Shops) Amazingly Beautiful Sunsets! Weekly rental required for holidays …see more

from $120 / night

$826 / week

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from $120 / night

(2) Excellent 

45

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 $106 / night

$1505 / week

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from $106 / night

(4) 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

49

Apartment rental in Madeira Beach with swimming pool

Florida / Madeira Beach

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • 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! The Las Brisas Resort Condominiums are located alongside the suga …see more

from $250 / night

$1813 - $3598 / week

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from $250 / night

28

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 $140 / night

$975 - $1545 / week

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from $140 / night

28

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
This large south corner condo has been tastefully renovated. The living room, dining area and kitchen have a bright, open floor plan with beautiful tile floors. The view of the beach and the Gulf of Mexico from the living room, dining area, the kitchen and the balcony …see more

from $140 / night

$975 - $2350 / week

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from $140 / night

(1) Very Good 

20

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 - $1600 / week

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from $143 / night

(3) Very Good 

45

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 $99 / night

$630 - $1197 / week

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from $99 / night

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
This premier condo has a large, screened in balcony facing the beach and the Gulf of Mexico. There will be great memories from the spectacular sunset views. The décor is a traditional and comfortable plus the den can be used as another small bedroom. The kitchen is fu …see more

from $140 / night

$975 - $2375 / week

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from $140 / night

49

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 $116 / night

$728 - $1568 / week

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from $116 / night

(1) Excellent 

24

Vacation apartment in Madeira Beach

Florida / Madeira Beach

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask about children
Stunning Oceanfront Condo in Desirable Madeira Beach with Abundant Amenities! ** During peak seasons, there is a Saturday to Saturday Rental Window. ** An extraordinary Gulf front experience awaits in this exquisite Oceanside retreat on the silver sands of Madeira Be …see more

from $161 / night

$1040 - $3730 / week

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from $161 / night

(1) Excellent 

39

Apartment rental in Madeira Beach with swimming pool

Florida / Madeira Beach

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 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 Condo with Incredible Views of the Gulf of Mexico From Yo …see more

from $114 / night

$798 - $1534 / week

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from $114 / night

(2) Very Good 

45

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 $165 / night

$1155 - $2051 / week

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from $165 / night

42

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! Location, Location! On The Beach and Across from John's Pass. Bea …see more

from $105 / night

$750 - $1316 / week

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from $105 / night

1