Waterfront vacation rentals in Madeira Beach

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Top-rated waterfront rentals in Madeira Beach

Guests agree: these waterfront rentals are highly rated for location, cleanliness, and more.

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Guest favorite

Apartment in Treasure Island

4.91 out of 5 average rating, 278 reviews

Attractive Beachfront Studio - Live Like a Local!

The true treasure of Treasure Island! Tucked right off of Gulf Blvd, on a secluded beach, this comfortable newly remodeled private studio is nestled on a lushly landscaped beachfront residential property with renters on-site. This cozy spot is all about barefoot luxury — you're just steps from the beach and biking or walking distance to laid back beach bars, live music & restaurants. Please note: There’s no guest parking available, but paid parking is nearby as well as a frequent public trolley.

Oct 16 – 23

G$31,001 GYD per night

Guest favorite

Condo in Saint Petersburg

4.99 out of 5 average rating, 245 reviews

PRICELESS VIEW Boca Ciega Bay Condo 1/1 #209

My place is close to Bay Pines VA Hospital, Madeira Beach, Tyrone Mall, Pinellas Trail, Bay Pines Park for biking and running, and restaurants. Wave runner, boat, kayak & paddle board rental available very nearby. There is a storage area for kayaks, paddle boards and bikes (please lock your items inside) . You’ll love my place because of the beautiful water view, peaceful good for the soul atmosphere and walkable to shopping, eating, and activities to suit all ages. Newly updated interior 2023.

Aug 9 – 16

G$41,984 GYD per night

Guest favorite

Cottage in Madeira Beach

4.96 out of 5 average rating, 134 reviews

BEACHFRONT FAIRWINDS Cottage Lower

Bright, tropical-themed beach house located directly on Madeira Beach 1/2 block from John's Pass Village. This cozy 2 bedroom & 1 bath downstairs getaway has a huge covered 400 sq. ft. deck & ocean views. Toes hit the sand off the deck & just past the dunes is the Gulf! 1 wk stay for holidays + holiday rates. Decorative items removed due to COVID. Pics are preCovid, but cottage is still very cute! If guest loses house key, guest responsible for expense of locksmith, new locks, and new keys.

Oct 31 – Nov 7

G$56,224 GYD per night

Guest favorite

Condo in Treasure Island

4.95 out of 5 average rating, 134 reviews

Exquisite, Modern Waterfront Condo, A Hidden Gem!

Sip coffee in the seating area, read a book by the pool, or enjoy a drink on the beach! Beautifully renovated, second-floor waterfront condo in Treasure Island, 2 blocks from the beach. A short walk to restaurants & shopping includes everything you need to enjoy your vacation. The condo offers high-speed internet, a full kitchen with all cooking needs, 65" Wi-Fi TV, Netflix, a community grill/pool washer/dryer, and free parking steps away. Close to Downtown St Petersburg, Clearwater & Tampa.

Aug 27 – Sep 3

G$37,300 GYD per night

Superhost

Condo in Indian Shores

4.87 out of 5 average rating, 150 reviews

Cozy condo at Belleview Gulf

Boats are welcome! Dock your boat right out the back door. Experience one of the most exciting beach areas in the U.S. This location attracts tourist from around the world making it an exciting, adventurous and ideal vacation resort. You can spend your time at the beach, ride bicycles, kayaking, walk along gulf, enjoy fancy dining, coffee shops, shopping, and club houses. Or just relax by sitting out back and watch as the dolphins and manatees swim by or bring your pole to channel fish.

May 13 – 20

G$23,440 GYD per night

Guest favorite

Condo in Tierra Verde

4.96 out of 5 average rating, 237 reviews

Natural Beauty on Tierra Verde, Waterfront Condo

Feels like the Florida Keys! Fully renovated & well appointed second floor, 1 bed, 1 bath condo in Holiday Island condo resort. The condo features a beautiful waterfront & pool view, tennis, bicycles, hot tub, dock with grills, gym, and more. Remodeled in 2015 the condo features a fully equipped kitchen, Keurig coffee maker, beautiful views from the living room, dining room, kitchen, balcony. Walking distance to many local restaurants & minutes away from St. Pete Beach & Fort DeSoto.

Dec 14 – 21

G$27,374 GYD per night

Superhost

Condo in Madeira Beach

4.87 out of 5 average rating, 180 reviews

Beach is steps away! Paradise is waiting!

Our little slice of paradise: 1 bedroom ground floor condo in Madeira Beach Yacht Club. 2 heated pools, gym, jacuzzi, & fishing piers. Across from a Park with tennis courts, basketball, & walking trails. Grocery, CVS, restaurants and bars in walking distance. Beach toys & beach cart provided for you to enjoy the white sands of Madeira Beach, a few steps away. Our charming beach community has plenty of attractions and activities with small-town charm. Just minutes from John's Pass!

Aug 12 – 19

G$29,142 GYD per night

Guest favorite

Apartment in Saint Petersburg

4.89 out of 5 average rating, 145 reviews

The Oasis

Welcome to Boca Ciega Oasis! The "Oasis" suite 409 has been totally remodeled in January 2022. This includes a new queen sofa couch in LR, new refrigerator, stove, washer/dryer, and balcony tables and chairs. The 4th-floor view is the best but 409 is also centered beautifully to take in the expansive Boca Ciega Bay! Directly below the balcony is the swimming pool, Hot tub, and observation pier! The marina is to your left. See all while sitting in our bar height chairs and tables.

Sep 8 – 15

G$31,379 GYD per night

Guest favorite

Condo in Madeira Beach

4.93 out of 5 average rating, 122 reviews

Sunsets in Paradise from Balcony with Gulf Views

The new pool is now open, featuring a sun shelf! Stunning views of the Gulf of Mexico from this beautiful and modern 5th floor condo! This highly rated vacation or relaxation destination is perfectly situated just steps away from the beach in Madeira. You will enjoy your private balcony, a 2 bed/2bath space, community pool and proximity to everything. We offer high speed internet, beach equipment, towels and linens and everything you would need to enjoy your stay. Welcome!

Oct 10 – 17

G$36,247 GYD per night

Guest favorite

Condo in Indian Shores

4.96 out of 5 average rating, 143 reviews

1 BR direct beachfront! Now avail. 8/29-9/11.

Our condo is directly on the beach!! It is close to restaurants and dining, mini-golf, Clearwater and St. Pete's Beach. About 25 miles from Tampa, Florida for the Buccaneers NFL football and Lightning NHL hockey! We are about 37 miles from Busch Gardens. Only 95 miles to Disney World in Orlando! Mini-golf right across the street! You’ll love my place because of the neighborhood. My place is good for couples, small families, solo adventurers, and business travelers.

Dec 4 – 11

G$30,615 GYD per night

Guest favorite

Apartment in Madeira Beach

4.85 out of 5 average rating, 336 reviews

B⎈AT HOUSE OASIS⚓Steps to the water⚓Walk to Beach!

Wake up just feet from the water, and hear the Sea Gulls at the freshly renovated Boat House! Behind Johns Pass village, this stand alone apartment (NOT A BOAT) canal view, filled with boats, and frequent visits from dolphin! Shops, restaurants, nightlife and the beach, all just a short walk from you! 100 yard walk to Johns Pass, stroll the board walk, grab some ice cream and take a short walk to the beach!*Queen bed*fast wifi*Smart TV*Waterfront docks and view!

Jul 8 – 15

G$26,388 GYD per night

Guest favorite

Condo in Madeira Beach

4.99 out of 5 average rating, 150 reviews

Lux Condo w/ 2 balconies, Ocean & Marina views

This luxury condo features 2 private balconies, w/ spectacular ocean & marina views. It's stylish decor, meticulously picked quality & comfortable furnishing/accessories are sure to please. It’s conveniently located just across the street from the pristine white sands and sunsets of the Gulf of Mexico. It is adjacent to the #1 tourist destination in the county, John's Pass Village. The property offers a heated swimming pool, hot tub, fitness room & event center.

Apr 6 – 13

G$55,359 GYD per night