Cottages at Madeira Beach


Properties Available 400 properties available
Stay more, SAVE more! We offer lower nightly rates on extended stays from Sept-Mar. No coupon code needed! Just enter your dates, at least 14 nights, for pricing. Top Reasons to book this Bayside Unit: • Treasure Island’s newest, boutique condo-resort offers the best of both worlds; beachfront and bayfront. • Watch stunning sunsets from the gul
Oceana 204 East
Condo Pet Friendly
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 4.9 (53 Reviews)
Stay more, SAVE more! We offer lower nightly rates on extended stays from Sept-Mar. No coupon code needed! Just enter your dates, at least 14 nights, for pricing. Top reasons to Book: • Covered parking for multiple vehicles underneath the home. • Two private gulf facing balconies as well as a private boardwalk for easy access to the beach. Para
Paradiso Al Mare Beach House
House
Bedrooms 3 bedrooms
Bathrooms 2 Full
Guests 10 guests
Rating 4.7 (34 Reviews)
Stay more, SAVE more! We offer lower nightly rates on extended stays from Sept-Mar. No coupon code needed! Just enter your dates, at least 14 nights, for pricing. ***NOTICE: ROOF WORK CURRENLTY IN PROGRESS ON BUILDING 10. ESTIMATED COMPLETION END OF JANUARY 2026, COULD VARY BASED ON WORK. PLEASE CALL FOR DETAILS. **** Top Reasons to book : •
Land's End 10-403 Beach Front - Premier
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 4 guests
Rating 4.9 (42 Reviews)
Stay more, SAVE more! We offer lower nightly rates on extended stays from Sept-Mar. No coupon code needed! Just enter your dates, at least 14 nights, for pricing. Top Reasons to book: • You’ll love the beautiful décor, and comfortable furnishings throughout this unit • As you enter, you'll be greeted by floor to ceiling sliding glass doors and
Trillium 4A - Premier
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 4.9 (97 Reviews)
Stay more, SAVE more! We offer lower nightly rates on extended stays from Sept-Mar. No coupon code needed! Just enter your dates, at least 14 nights, for pricing. Top Reasons to book : • Short proximity to the onsite heated pool. • All the fabulous amenities including two Hot Tubs, Charcoal BBQ Grills, Community Gazebos, Shuffleboard, Volleybal
Land's End 11-406 Beach Front - Premier
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 4 guests
Rating 4.9 (59 Reviews)
Stay more, SAVE more! We offer lower nightly rates on extended stays from Sept-Mar. No coupon code needed! Just enter your dates, at least 14 nights, for pricing. ***NOTICE: ROOF WORK CURRENLTY IN PROGRESS ON BUILDING 10. ESTIMATED COMPLETION END OF JANUARY 2026, COULD VARY BASED ON WORK. PLEASE CALL FOR DETAILS. **** Top Reasons to book : •
Land's End 10-402 Beach Front - Premier
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 4 guests
Rating 4.9 (69 Reviews)
Stay more, SAVE more! We offer lower nightly rates on extended stays from Sept-Mar. No coupon code needed! Just enter your dates, at least 14 nights, for pricing. Top Reasons to Book:* 173 Yards to the Gulfport Beach Recreation Area* 5 Miles to St. Pete Beach* Pet Friendly up to 20lbs. (Additional Cost Applies) * On-Site Parking and Laundry Faci
Beach Quarters #8
Condo Pet Friendly
Bedrooms 1 bedrooms
Bathrooms 1 Full
Guests 4 guests
Rating 4.9 (33 Reviews)
Stay more, SAVE more! We offer lower nightly rates on extended stays from Sept-Mar. No coupon code needed! Just enter your dates, at least 14 nights, for pricing. Top Reasons to Book Sea Club #6:* Close to Beach Access* Private Balcony* Beautifully Landscaped Grounds* Onsite Heated Pool and Shuffleboard* Fishing Dock on Intracoastal Waterway* Pr
Sea Club #6 - Footprints in the Sand
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 4 guests
Rating 5 (6 Reviews)
Top Reasons to Book this Gulf Front Condo:* Amazing Views of The Gulf of Mexico and Sunset Beach* Wrap Around Private Balcony* Gated Community and Onsite Amenities* Spacious and Luxurious * Professionally Managed; 24/7 ServicetWelcome to Mansions By the Sea, a stunning 2-bedroom, 2-bathroom beachfront condo offering luxury, space, and breathta
Mansions By The Sea 903B - Premier
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 4 guests
 New Property!
Top Reasons to book: • Short proximity to the onsite heated pool.• All the fabulous amenities including two Hot Tubs, Charcoal BBQ Grills, Community Gazebos, Shuffleboard, Volleyball, Tennis and Pickleball Courts.• Located on the peninsula, this community offers the best of both worlds- easy access to the Bay and Beach.This beautiful 2-bedroom, 2-b
Land's End 1-408 Bay Front
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 4 guests
Rating 4.9 (10 Reviews)
Top Reasons To Book This Condo:* Private Balcony Overlooking the Gulf, Beach, and Pool Deck—Perfect for Sunsets!* Easy Beach Access Just Steps From Your Front Door* Beachside Heated Pool, Hot Tub, Pool Deck with Lounge Chairs* Beautiful and Spacious Beachfront Condo at San Remo in Redington Shores* Professionally Managed, 24/7Welcome to San Re
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New Property Introductory Discount

New Property Introductory Discount 

Limited time only Promo Code NEW100

San Remo 206
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
 New Property!
Stay more, SAVE more! We offer lower nightly rates on extended stays from Sept-Mar. No coupon code needed! Just enter your dates, at least 14 nights, for pricing. ****NOTICE: Major exterior renovation project beginning December 1st, 2025 and to last approx. 10 months. Noise will be associated with the work. Access to areas on grounds/parking wil
Bayshore Yacht & Tennis 409 - Premier
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 4.8 (27 Reviews)

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