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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. **ELEVATORS OUT OF SERVICE** Please note that the elevators are currently out of service and not operating. At this time, we do not have a guaranteed timeline for these repairs to be
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.

Westwinds 213
Condo
Bedrooms 1 bedrooms
Bathrooms 1 Full
Guests 4 guests
Rating 4.8 (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. Top Reasons to Book:-Less than 400 Feet to the Beach-Dog Friendly (Restrictions and additional fees apply)-Private off-street parking-Recently Updated and New Stainless Steel Appliance
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.

Beach Life 2
House Pet Friendly
Bedrooms 2 bedrooms
Bathrooms 1 Full
Guests 6 guests
Rating 4.9 (56 Reviews)
Top Reasons To Book Sunset Vistas #403S:* Awesome Onsite Amenities - Large Heated Pool, Hot Tub, Fitness Center, Snack Bar, Kiddie Pool and More! * Bright and Spacious Condo with Private Balcony and Gulf Views* Beachfront Property with Direct Beach Access Onsite* Located One Mile From John's Pass Village and Boardwalk, Loaded With Tons of Shop
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.

Sunset Vistas 403S
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 5 (11 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)
Top Reasons To Book Bungalows #4:* 400ft away from Beach Access - Just Across the Street* Dogs Allowed - 1 Dog, 50lb Max. Fees Apply* Large 2 Bedroom, Poolside Unit* Onsite Heated Pool, Outside Games and Charcoal Grills* Professionally Managed, 24/7Welcome to The Bungalows #4! This updated 2-bedroom, 1-bathroom unit is the perfect spot for your
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.

The Bungalows #4
Condo Pet Friendly
Bedrooms 2 bedrooms
Bathrooms 1 Full
Guests 6 guests
Rating 4.6 (3 Reviews)
Top Reasons To Book This Condo:* Easy Beach Access - Across the Street from Beach - Just a Quick 2-Minute Walk (about 0.1 mile)* Heated Pool, Gas Grills and Elevator for Guest Use* Beautifully Updated and Well-Maintained 2-bedroom, 2-bathroom Condo with Private Balcony* Central Location on Madeira Beach - Restaurants Nearby! * Professionally
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 Place #201
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 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 fantastic south co
Land's End 9-201 Beach Front - Premier
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 4 guests
Rating 5 (43 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
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.

Beach Quarters #2
Condo Pet Friendly
Bedrooms 1 bedrooms
Bathrooms 1 Full
Guests 4 guests
Rating 5 (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: • Direct waterfront views from your private dock! • The location- Walking distance to the sugary white sands of Madeira Beach. • Plenty of comfortable outdoor furn
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.

Coconut Paradise
House
Bedrooms 3 bedrooms
Bathrooms 1 Full
Guests 8 guests
Rating 4.9 (57 Reviews)
Top Reasons to book this Beautiful Piece of Paradise: • 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. • Access the private balcony from th
Land's End 7-203 Beach Front - Premier
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 5 guests
Rating 4.9 (27 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
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.

Land's End 3-305 Bay Front - Premier
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 4 guests
Rating 5 (20 Reviews)
****NOTICE: The building is currently undergoing a major exterior renovation project beginning December 1, 2025 and is expected to continue for approximately 10-12 months, length could vary. Construction activity typically takes place Monday–Friday from 8:00 AM to 4:30 PM, and guests may experience noise during these hours. Please note: Access to
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.

Bayshore Yacht & Tennis 409 - Premier
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 4.8 (27 Reviews)

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