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 78 properties available
Top Reasons To Book John's Pass-Time #1:* Beachfront Property with Direct Beach Access* Ground Level Cottage, No Stairs Required* Large Private, Covered Deck with Table and Chairs* Shared Beachfront Area with Picnic Table, Hammock and Charcoal Grill* Professionally Managed, 24/7Welcome to John's Pass-Time Beach Cottage #1, a charming and cozy
Specials Tag Special
Sun, Sand & 10% Off Summer Stays


Soak up more summer and save on your next beach escape with our SUMMERSTAY2026 offer!


Enjoy 10% off 5+ night getaways between May 7 and August 30, 2026 when you book by May 31, 2026 using code SUMMERSTAY2026 at checkout. It’s the perfect opportunity to slow down, stay longer, and make the most of sunny days, warm nights, and time by the water.


**Offer is valid on new online bookings when you book by May 31, 2026, to receive 10% off for 5+ night stays from May 7, 2026 to August 30, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.

John's Pass-Time Beach Cottage #1
House
Bedrooms 2 bedrooms
Bathrooms 1 Full
Guests 4 guests
Rating 4.8 (5 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
Specials Tag Special
Sun, Sand & 10% Off Summer Stays


Soak up more summer and save on your next beach escape with our SUMMERSTAY2026 offer!


Enjoy 10% off 5+ night getaways between May 7 and August 30, 2026 when you book by May 31, 2026 using code SUMMERSTAY2026 at checkout. It’s the perfect opportunity to slow down, stay longer, and make the most of sunny days, warm nights, and time by the water.


**Offer is valid on new online bookings when you book by May 31, 2026, to receive 10% off for 5+ night stays from May 7, 2026 to August 30, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.

Trillium 2B - Premier
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 5 (86 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: * Beach access directly across the street as well as on site fishing and charter boats. * Gym Available (Building II) * Short stroll away from many shops and resta
Specials Tag Special
Sun, Sand & 10% Off Summer Stays


Soak up more summer and save on your next beach escape with our SUMMERSTAY2026 offer!


Enjoy 10% off 5+ night getaways between May 7 and August 30, 2026 when you book by May 31, 2026 using code SUMMERSTAY2026 at checkout. It’s the perfect opportunity to slow down, stay longer, and make the most of sunny days, warm nights, and time by the water.


**Offer is valid on new online bookings when you book by May 31, 2026, to receive 10% off for 5+ night stays from May 7, 2026 to August 30, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.

Madeira Bay Resort I 1502
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 4.9 (48 Reviews)
Top Reasons to Book Trillium 3A: * Beachfront Condo with Amazing Views of Madeira Beach* Beautifully Updated Throughout - Stunning Condo!* Heated Pool and Pool Deck with Lounge Chairs* Smaller, Quaint Beachfront Building with Only 15 Units Total* Perfectly Situated on Madeira Beach - Close to John's Pass Village and Boardwalk* Professionally
Trillium 3A - Premier
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 5 (57 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
Specials Tag Special
Sun, Sand & 10% Off Summer Stays


Soak up more summer and save on your next beach escape with our SUMMERSTAY2026 offer!


Enjoy 10% off 5+ night getaways between May 7 and August 30, 2026 when you book by May 31, 2026 using code SUMMERSTAY2026 at checkout. It’s the perfect opportunity to slow down, stay longer, and make the most of sunny days, warm nights, and time by the water.


**Offer is valid on new online bookings when you book by May 31, 2026, to receive 10% off for 5+ night stays from May 7, 2026 to August 30, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.

Trillium 5C - Premier
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 4.9 (73 Reviews)
Top Reasons To Book John's Pass-Time Beach Cottages:* Beachfront Property with Direct Beach Access* Full Property to Yourself - Both Cottages - Great for Larger Families or Friends Traveling Together* Great Private Backyard Beach with Hammock, Grill and Picnic Table* 2 Private Entrances, 2 Great Deck/Patio Spaces* Gulf Views From the Upper Lev
Specials Tag Special
Sun, Sand & 10% Off Summer Stays


Soak up more summer and save on your next beach escape with our SUMMERSTAY2026 offer!


Enjoy 10% off 5+ night getaways between May 7 and August 30, 2026 when you book by May 31, 2026 using code SUMMERSTAY2026 at checkout. It’s the perfect opportunity to slow down, stay longer, and make the most of sunny days, warm nights, and time by the water.


**Offer is valid on new online bookings when you book by May 31, 2026, to receive 10% off for 5+ night stays from May 7, 2026 to August 30, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.

John's Pass-Time Beach Cottage #1 and #2
House
Bedrooms 4 bedrooms
Bathrooms 2 Full
Guests 8 guests
Rating 5 (1 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 Condo: * Beachfront Condo with direct views of the Gulf of Mexico* Heated Pool and Hot Tub on Grounds* Private Balcony Facing the Beach* Spacious and Upda
Specials Tag Special
Sun, Sand & 10% Off Summer Stays


Soak up more summer and save on your next beach escape with our SUMMERSTAY2026 offer!


Enjoy 10% off 5+ night getaways between May 7 and August 30, 2026 when you book by May 31, 2026 using code SUMMERSTAY2026 at checkout. It’s the perfect opportunity to slow down, stay longer, and make the most of sunny days, warm nights, and time by the water.


**Offer is valid on new online bookings when you book by May 31, 2026, to receive 10% off for 5+ night stays from May 7, 2026 to August 30, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.

Sea Breeze 503
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 4.9 (15 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: • 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
Specials Tag Special
Sun, Sand & 10% Off Summer Stays


Soak up more summer and save on your next beach escape with our SUMMERSTAY2026 offer!


Enjoy 10% off 5+ night getaways between May 7 and August 30, 2026 when you book by May 31, 2026 using code SUMMERSTAY2026 at checkout. It’s the perfect opportunity to slow down, stay longer, and make the most of sunny days, warm nights, and time by the water.


**Offer is valid on new online bookings when you book by May 31, 2026, to receive 10% off for 5+ night stays from May 7, 2026 to August 30, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.

Villa Madeira 203 - Premier
Condo
Bedrooms 3 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 5 (76 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 Beautiful Townhome:* Brand New Townhouse with Modern Design and Amenities* 4 Floors Featuring a Rooftop Deck with Amazing Views* 5 Spacious Bedrooms and 4 F
Specials Tag Special
Sun, Sand & 10% Off Summer Stays


Soak up more summer and save on your next beach escape with our SUMMERSTAY2026 offer!


Enjoy 10% off 5+ night getaways between May 7 and August 30, 2026 when you book by May 31, 2026 using code SUMMERSTAY2026 at checkout. It’s the perfect opportunity to slow down, stay longer, and make the most of sunny days, warm nights, and time by the water.


**Offer is valid on new online bookings when you book by May 31, 2026, to receive 10% off for 5+ night stays from May 7, 2026 to August 30, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.

Azul Townhomes A5
Madeira Beach Pet Friendly
Bedrooms 5 bedrooms
Bathrooms 4 Full
Guests 11 guests
Rating 5 (14 Reviews)
2 mins to beach – beach and intercoastal views – sleeps 14– 5 bed / 4 bath – elevator Top Reasons to Book this Beautiful Townhome: * Newly Built in 2025 with Private Elevator* Rooftop Balcony with Views of Gulf and Intracoastal Waterway* Prime Location Just a Quick Walk to the Beach, About 300 Feet!* Spacious Layout with Plenty of Room for
Specials Tag Special
Sun, Sand & 10% Off Summer Stays


Soak up more summer and save on your next beach escape with our SUMMERSTAY2026 offer!


Enjoy 10% off 5+ night getaways between May 7 and August 30, 2026 when you book by May 31, 2026 using code SUMMERSTAY2026 at checkout. It’s the perfect opportunity to slow down, stay longer, and make the most of sunny days, warm nights, and time by the water.


**Offer is valid on new online bookings when you book by May 31, 2026, to receive 10% off for 5+ night stays from May 7, 2026 to August 30, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.

Azul Townhomes A1
Madeira Beach Pet Friendly
Bedrooms 5 bedrooms
Bathrooms 4 Full
Guests 14 guests
Rating 5 (14 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
Specials Tag Special
Sun, Sand & 10% Off Summer Stays


Soak up more summer and save on your next beach escape with our SUMMERSTAY2026 offer!


Enjoy 10% off 5+ night getaways between May 7 and August 30, 2026 when you book by May 31, 2026 using code SUMMERSTAY2026 at checkout. It’s the perfect opportunity to slow down, stay longer, and make the most of sunny days, warm nights, and time by the water.


**Offer is valid on new online bookings when you book by May 31, 2026, to receive 10% off for 5+ night stays from May 7, 2026 to August 30, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.

Trillium 1B - Premier
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 5 (72 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 the Sunrise and Sunset Townhomes: * 2 Townhomes Side by Side* Each Townhome is 4 Stories with a Private Roof Top Deck* Approx. 300ft to the Beach - Easy Walk!*
Azul Townhomes A3 and A4 - Sunrise/Sunset
Madeira Beach
Bedrooms 10 bedrooms
Bathrooms 8 Full
Guests 24 guests
Rating 5 (1 Reviews)

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