Vacation Rentals

Featured Properties

All Properties

29 found. Sort By: Title Bedrooms Bathrooms order

Anglers Cove

3 bed/3 full baths with gorgeous water views. Completely remodeled and very tastefully decorated. Large wrap around balcony. Lots of parking. Walking distance to restaurants and convenience store.

Arie Dam

Spectacular sunsets in this quaint beach front, 15 unit complex. Heated pool, Jacuzzi, Balcony, Wi-Fi, Fully Equipped Kitchen, Assigned parking, Washer/Dryer, Security Building and direct gulf view from all units.

Available at Arie Dam:
Unit 301
Unit 303

Beach Cottage I

Wake up to the surf in this well appointed beach front condo. Heated pool, Jacuzzi, Balcony, Wi-Fi, Washer/Dryer, Security Building, Bar-b-que area, Gas Grill, Covered parking, Fully Equipped Kitchen and direct gulf view.

Beach Place

Beach front building direct across from World Famous Johns Pass Village. Heated pool, Gas Grill, Covered Parking, Wi-Fi Washer/Dryer, Security Building, Remodeled, Fully Equipped Kitchen and Southwest beach views.

Boca Vista

Breathtaking sunrises, intracoastal views and a short two block walk to Madeira Beach can be had at this lovely mid rise condo. Heated Pool, Jacuzzi, Tennis Courts, Wi-Fi, Washer/Dryer, Security Building, Two assigned parking spots and a view of intracoastal from all units.

Boca Ciega Point

Beautiful gated waterfront community located just 1/2 mile from our lovely gulf beaches. Units in the three story condo building have open balconies overlooking Boca Ceiga Bay. Enjoy a relaxing, active lifestyle here with amenities including Heated pool, saunas, tennis courts, bocce, shuffleboard, horse shoe courts, fitness center, library, clubhouses and putting green.

Breakers 307

Quiet tropical paradise for your perfect beachfront vacation. Located on prestigious Redington Beach this complex offers a Gulf front swimming pool with large deck and BBQ grills. Close to public transportation, restaurants and shopping. This well equipped condo has everything needed for your beachfront vacation.

Charming Beach Home

CHARMING BEACH HOME Well cared for 2bd/1bath beach cottage. Small pets welcome. One block walk to Florida's white sandy beaches. Relax in the large enclosed screened porch and enjoy the beautiful outdoors rain or shine. Home has beautiful hardwood floors, updated and well equipped kitchen and Wi Fi.

Coconut Cottage

Watch the dolphins play from your backyard at this private waterfront home. Gas Grill, Washer/Dryer, Fully Equipped Kitchen, Fireplace, Private Dock and just one block walk to the beach.


Fabulous beach views from balcony, living room and master suites in these beautifully remodeled units. Heated Pool, Wi-Fi, Washer/Dryer, Fully Equipped Kitchen, Security Building, direct gulf view from all units.

Landmark Towers

Enjoy the powdery white beaches at this Sand Key beach front beauty. Heated Pool, Jacuzzi, Tennis Courts, Washer/Dryer, Balcony, Water Softener, Gated Security and just across the street from great dining and shopping.

Madeira Bay

Welcome to Madeira Bay Resort Marina and Spa overlooking the scenic intracoastal. Features include Heated Pool, Wi Fi, Washer/Dryer, Fully Equipped Kitchen, Balcony, On site Restaurant, and just a block walk to Famous Johns Pass Village.

Madeira Cove

Tropical landscaping in this newer luxury building overlooking the intracoastal and just a short walk to our sandy beaches. Heated Pool, Hot Tub, Very well equipped kitchen, Balcony, grills, fitness center, washer/dryer in unit, WI Fi and intracoastal view.

Madeira Towers

Spacious Beach Front 3 bedroom corner luxury unit with 180 degree view of gulf and bay, Heated Pool, Washer/Dryer, Fully Equipped Kitchen, Gas Grill, Security Building, Direct Gulf views.

Ocean Sands

These blue beach front beautifully maintained twin towers greet you when you enter Madeira Beach over the Tom Stewart Causeway. This tropically manicured complex boasts, Heated Pool, Hot Tub, Bar-b-que, Washer/Dryer, Wi Fi, Large balcony, Security Building and a Direct Gulf view from all units.

Available at Ocean Sands:
1 Bed / 1.5 Bath
2 Bed / 2 Bath

Royal Orleans

Heated pool, nicely equipped mini-kitchens, A/C, free wireless internet, washer/dryer on premises, beach right across the street, close to dining and shopping. ***Nightly and weekend rates available***

Available at Royal Orleans:
1 Bedroom 2 Bath


Truly Unique beach front one bedroom, loft and 2 full bath rental in a small five unit building on beautiful Indian Shores. Enter the pool area from your spiral staircase off the balcony and enjoy the Heated Pool, Hot Tub, Gas Grill. Inside has been remodeled, Skylights allow lots of natural sunlight in and has Internet, Well Equipped , Completely Remodeled, Internet, Washer/Dryer and balcony.

Sea Towers

Desirable waterfront gated adult complex. Wide sweeping views of the intracoastal and Gulf from most any of the communities 8 buildings. This lovely complex is a short 5 minutes from beautiful Madeira Beach and close to grocery, shopping, golf, restaurants and just 30 minutes to Tampa. Studios, One Bedrooms and Two bedrooms are available here. 24/7 gated security, private beach, fishing piers, two heated pools, club house, tennis courts, many activities in this very active complex and a full time social director.

Sea Gate

Breathtaking views await you at this premium top floor,beach front rental in beautiful Indian Shores. Remodeled condo that will have you coming back year after year boast a Heated Pool, Tiki Hut and Grills, Undercover Parking, Wi Fi, Washer/Dryer, Balcony with direct beach views and beautifully updated and equipped condo.

Seminole Pool House

Stay awhile in this large, nicely appointed three bedroom pool home just one mile from the white sands of Madeira Beach. Washer/Dryer, Solar Heated Pool, Internet, DVD, 2 Car Garage and Circular Drive.

Snug Harbor

Prime condos in this waterfront complex with lush tropical landscaping overlooking Boca Ciega Bay. Units have Gourmet Kitchens, Spacious open floor plans and Volume Ceilings, Heated Pool, Jacuzzi, Sun Deck, Clubhouse, Washer/Dryer, Security Building, Balcony, View of intracoastal from all units.

Available at Snug Harbor:
2 Bed / 2 Bath
3 Bed / 2 Bath

Starfish Cottages

Preserving the quaint image of this Madeira Beach Property with old Florida Charm here. Two Private Beach bungalows for rent, Two bedroom is directly on beach and the one bedroom is right behind it, Enjoy the beautiful beach setting that Madeira Beach offers in these pet friendly cottages equipped with Wi Fi, Grill and beautifully landscaped grounds.

Available at Starfish Cottages:
1 BR / 1 BA
2 BR/1 BA

Sunshine Unit 3A

Listen to the surf and watch the dolphins play from your balcony in this two bedroom corner unit on peaceful Indian Shores. Small and cozy building with breathtaking views. Heated Pool, Washer/Dryer, Internet, Fully Equipped Kitchen, Undercover Parking, Security Building, Direct Gulf view from all units.

Surfside Towers

Beach Front, 10 story complex located on Madeira Beach. Panoramic views from this well appointed condo.Beachfront Heated Pool, Spa, Sundeck, Recreation Room, Fitness Center, Barbecue/Picnic area, Pool Table, Ping Pong, Game Tables, Washer/Dryer, Fully equipped kitchen and Balcony.

The Rose

Wide sandy beaches await you at the Rose condo on Indian Shores. Panoramic views from this fifth floor corner unit appointed with Wi Fi, Fully Equipped Kitchen, Remodeled Guest Bath, Heated Pool, Washer/Dryer in unit, Security Building, Direct Gulf view from all units

Atoll Tropical Hideaway

Nestled in the tropical landscapes of St Pete just five minutes to all sunny Madeira Beach has to offer. Located minutes to the Pinellas Bike Trail. Three properties here include a 1bed/1,5bath townhome attached to a 2bd/2bath home and a separate 2bd/2bath single family home. All have Fully Equipped Kitchens, Wi Fi, Cable TV, Washer/Dryer, Patio and are very nicely furnished. Plenty of shopping,restaurants and a brand new Wal Mart just minutes away.

Tropical Palm Duplex

This inviting, completely remodeled two bedroom one bath is just a one block walk to the beach. Minutes to an abundance of shopping and restaurants. This property features are: Washer/Dryer, Stainless Steel Appliances, Granite Counter Tops, Flat Screen TV, newly remodeled inside & fresh paint on outside along with tropical landscaping.


Premium Madeira Beach, beach front condos offer you spectacular beach views and beautiful sunsets 365 days a year. Heated pool, Fully e Equipped Kitchen, Washer/Dryer, WiFi and Large Balcony.

Paradise Towers

Heated pool, spa, outdoor dining, gas grills, upper sundeck, lighted fishing piers, boat slips and a luxury lounge

Rates are subject to change without notice.
All prices are plus cleaning fees and 13% sales tax.
Spring Break and Holidays will be subject to increased rates.