Resort Rentals

We invite you to take a tour of our properties to find the perfect Florida vacation rental for your Florida beach vacation. You can check our rates and policies conveniently online. Our dedicated team of professionals is just a click away to assist you in planning your Florida family beach vacation and to provide the support you need to enjoy our tropical islands in one of our comfortable vacation rentals.


Please note that during certain months such as: February, March, June, July, and August, availability may be limited to Saturday-Saturday stays. For the best search results, please select "Flex Dates" in your search to see all possible options for your stay


Properties Available 401 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 Awesome Coastal Cottage: * The Beach is Across the Street - Short, Convenient Walk* Spacious Layout, Luxurious Furnishings, Plenty of Room for All* Additional
Blue Beach Cottage
House
Bedrooms 3 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. Top Reasons to Book: • Spacious screened balcony featuring breathtaking views of the Gulf of Mexico. • Shared covered lounge chairs and access to the heated swimming pool during your vis
Villa Madeira 202
Condo
Bedrooms 3 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 4.9 (115 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 this Bayside Unit:• Dogs Allowed! (Fees and Restrictions apply)• Treasure Island’s newest, boutique condo-resort offers the best of both worlds; beachfront and bay
Oceana 305 East
Condo Pet Friendly
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 4.9 (44 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:• Quick access to the heated pool• Newly updated in January 2024• Top floor unit with wide Intracoastal views• 2 Private balconies to enjoyWelcome to your perfect g
Land's End 1-406 Bay Front - Premier
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 4.9 (12 Reviews)
****** NEW UPDATES UNDERWAY!!! *********As of January 17, 2026, the home will be temporarily unavailable while extensive interior and exterior renovations are done.We’re excited to bring this beautiful beachfront home to the next level so every guest can enjoy the experience they deserve. We’ve heard feedback about maintenance and are taking
Hidden Treasure Beach House
House
Bedrooms 5 bedrooms
Bathrooms 4 Full, 1 Half
Guests 12 guests
Rating 4.8 (56 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: THE POOL IS CURRENTLY CLOSED. Work is still ongoing and hopeful to be complete by March 2026 - Dates could vary. ***Top Reasons to Book: • Take in unforgettable panoramic
Emerald Isle 204
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 4 guests
Rating 4.9 (73 Reviews)
Top Reasons To Book This Beachfront Condo:* Beautiful and Spacious Condo Directly on Madeira Beach* 3 Balconies - Main Balcony Overlooking the Beach and Gulf of Mexico* Onsite Heated Beachside Pool with Lounge Chairs * Direct Beach Access—Step Off the Pool Deck onto the Sand* Professionally Managed, 24/7Welcome to Trillium 2A, a beautiful and s
Trillium 2A - Premier
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 4.9 (85 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: • 4 total units for this building, the perfect getaway for the entire family! • TWO balconies per condo, one facing West overlooking the Gulf and one facing East.
Sunset Villas 4
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 5 guests
Rating 4.9 (81 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:* Beachfront Condo with Private Balcony* Amazing Sunset Views * Beautiful Updates Throughout* Gated Community with Lots of Onsite Amenities* Professionally ManagedW
Land's End 11-306 Beach Front - Premier
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 5 (9 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: SUNSET VISTAS WILL BE DOING A WALKWAY RESURFACING PROJECT THROUGH EACH BUILDING AND ON EACH FLOOR NOVEMBER 2025 - ESTIMATED END OF JANUARY 2026. SOME NOISE AND FLOOR CLOSURES
Sunset Vistas 407S
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 4.9 (66 Reviews)
Top Reasons to Book Gulfside Retreat: * Gorgeous 3-Story Single Family Home with Private Elevator* Easy Walk to the Beach - About 350 Yards* 2 Spacious, Private Balconies with Seating* Quiet Neighborhood Location* Bright, Beautiful and Modern Home* Professionally ManagedWelcome to Gulfside Retreat! This stunning 3-story single-family home bo
Gulfside Retreat
House
Bedrooms 4 bedrooms
Bathrooms 3 Full
Guests 9 guests
Rating 5 (10 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: SUNSET VISTAS WILL BE DOING A WALKWAY RESURFACING PROJECT THROUGH EACH BUILDING AND ON EACH FLOOR NOVEMBER 2025 - ESTIMATED END OF JANUARY 2026. SOME NOISE AND FLOOR CLOSURES
Sunset Vistas 206S
Condo
Bedrooms 2 bedrooms
Bathrooms 1 Full, 1 Half
Guests 6 guests
Rating 4.9 (72 Reviews)

Tell us what you're looking for and someone will contact you with available options.

I agree