Shores of Madeira

471 properties available

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 a panoramic view of the Gulf of Mexico. • Enjoy direct beach access as well as an outdoor heated pool! • Open floor plan with plenty of room for the entire family to

Special

Stay Longer on the Beach & Save 5%

Book your long-term Florida beach getaway now and take advantage of 5% savings on stays of 28+ nights. Use STAYLONGER5 on travel between October 1, 2026 and January 31, 2027 at select condos and homes.

*Offer is valid on new online bookings when you book by January 1, 2027, for stays of 28 nights or more with travel between October 1, 2026 and January 31, 2027. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.

🌴 Save Up to 10% on Your Florida Getaway 🌴

Save up to 10% on qualifying stays of 4 nights or more at Resort Rentals when you book by October 31, 2026. Travel now–December 31, 2026, and use code ENDOFYEAR10 at checkout.

Plan the beach getaway, family vacation, or end-of-year retreat you’ve been waiting for.

*Offer is valid on new online bookings when you book by October 31, 2026, for 4-night minimum stays from now through December 31, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.

Trillium 2C - Premier

***NOTICE - POOL CLOSURE*** The pool will be closed for maintenance beginning Monday Sept 14, 2026 for approx. 2 weeks. Timeline may vary.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 Amazing Gulf Front

Special

Stay Longer on the Beach & Save 5%

🌴 Save Up to 10% on Your Florida Getaway 🌴

Save up to 10% on qualifying stays of 4 nights or more at Resort Rentals when you book by October 31, 2026. Travel now–December 31, 2026, and use code ENDOFYEAR10 at checkout.

Plan the beach getaway, family vacation, or end-of-year retreat you’ve been waiting for.

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. About this Land's End Condo:This top floor 2 bedroom, 2 bathroom has been nicely updated and is ready for you! The kitchen has been beautifully updated and is fully equipped and ready

Special

Stay Longer on the Beach & Save 5%

🌴 Save Up to 10% on Your Florida Getaway 🌴

Save up to 10% on qualifying stays of 4 nights or more at Resort Rentals when you book by October 31, 2026. Travel now–December 31, 2026, and use code ENDOFYEAR10 at checkout.

Plan the beach getaway, family vacation, or end-of-year retreat you’ve been waiting for.

Land's End 3-404 Bay Front

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 Home:* Single Family Home all to Yourself* 2 Blocks from the Beach!* Awesome Wrap Around Deck* Dogs Welcome (2 max. Fees Apply)* Private Yard Fully Fence

Special

Stay Longer on the Beach & Save 5%

🌴 Save Up to 10% on Your Florida Getaway 🌴

Save up to 10% on qualifying stays of 4 nights or more at Resort Rentals when you book by October 31, 2026. Travel now–December 31, 2026, and use code ENDOFYEAR10 at checkout.

Plan the beach getaway, family vacation, or end-of-year retreat you’ve been waiting for.

Top Reasons To Book This Condo:* Canal-Front Condo with Peaceful Water Views* Approximate 5-minute Walk (0.2 miles) to Beach Access* Pool, Shared Laundry, and 1 Assigned Parking Space Onsite* Open-Concept Living Area with Sun Room - Bright and Spacious* Professionally Managed, 24/7Welcome to Club Capri #101! This bright and spacious 2-bedroo

Special

Stay Longer on the Beach & Save 5%

🌴 Save Up to 10% on Your Florida Getaway 🌴

Save up to 10% on qualifying stays of 4 nights or more at Resort Rentals when you book by October 31, 2026. Travel now–December 31, 2026, and use code ENDOFYEAR10 at checkout.

Plan the beach getaway, family vacation, or end-of-year retreat you’ve been waiting for.

Top Reasons To Book This Suite:* Beachfront Access – Steps from Beautiful Treasure Island Beach* Resort Amenities – Shuffleboard, Cornhole, Grills, and Recreation Room* Heated Pool – Perfect for Relaxing After a Day at the Beach* Ground Floor Suite - No Stairs Required* Professionally ManagedWelcome to Tropic Terrace Suite #9, a freshly updated gro

Special

Stay Longer on the Beach & Save 5%

🌴 Save Up to 10% on Your Florida Getaway 🌴

Save up to 10% on qualifying stays of 4 nights or more at Resort Rentals when you book by October 31, 2026. Travel now–December 31, 2026, and use code ENDOFYEAR10 at checkout.

Plan the beach getaway, family vacation, or end-of-year retreat you’ve been waiting for.

Tropic Terrace Suite 9

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

Special

Stay Longer on the Beach & Save 5%

🌴 Save Up to 10% on Your Florida Getaway 🌴

Save up to 10% on qualifying stays of 4 nights or more at Resort Rentals when you book by October 31, 2026. Travel now–December 31, 2026, and use code ENDOFYEAR10 at checkout.

Plan the beach getaway, family vacation, or end-of-year retreat you’ve been waiting for.

Trillium 4C - Premier

Top Reasons To Book This Beachfront Condo:* Direct Gulf-Front Location with Stunning Beach and Water Views * Private Balcony with Outdoor Dining and Unforgettable Sunsets* Large Pool Deck with Lounge Chairs and Heated Beachside Pool Onsite* Spacious 2-Bedroom, 2-Bath 5th Floor Condo with Nearly 1,200 sq. ft. of Living Space* Professionally Mana

Special

Stay Longer on the Beach & Save 5%

🌴 Save Up to 10% on Your Florida Getaway 🌴

Save up to 10% on qualifying stays of 4 nights or more at Resort Rentals when you book by October 31, 2026. Travel now–December 31, 2026, and use code ENDOFYEAR10 at checkout.

Plan the beach getaway, family vacation, or end-of-year retreat you’ve been waiting for.

Top Reasons To Book This Suite:* Beachfront Access – Steps from Beautiful Treasure Island Beach* Resort Amenities – Shuffleboard, Cornhole, Grills, and Recreation Room* Heated Pool – Perfect for Relaxing After a Day at the Beach* Great Location - 1 Mile to John's Pass Village and Boardwalk* Professionally ManagedWelcome to Tropic Terrace Suite

Special

Stay Longer on the Beach & Save 5%

🌴 Save Up to 10% on Your Florida Getaway 🌴

Save up to 10% on qualifying stays of 4 nights or more at Resort Rentals when you book by October 31, 2026. Travel now–December 31, 2026, and use code ENDOFYEAR10 at checkout.

Plan the beach getaway, family vacation, or end-of-year retreat you’ve been waiting for.

Tropic Terrace Suite 22

Top Reasons To Book This Suite:* Steps to the Beach – Easy Onsite Access to Treasure Island's Sandy Shores* Resort Amenities – Shuffleboard, Cornhole, Grills, and Recreation Room* Heated Pool – Perfect for Relaxing After a Day at the Beach* Comfortable King Bed – Freshly Updated Studio Retreat* Professionally ManagedWelcome to Tropic Terrace Suite

Special

Stay Longer on the Beach & Save 5%

🌴 Save Up to 10% on Your Florida Getaway 🌴

Save up to 10% on qualifying stays of 4 nights or more at Resort Rentals when you book by October 31, 2026. Travel now–December 31, 2026, and use code ENDOFYEAR10 at checkout.

Plan the beach getaway, family vacation, or end-of-year retreat you’ve been waiting for.

Tropic Terrace Suite 37

****NOTICE OF ROOF WORK - BUILDING 7. ROOF WORK WILL BEGIN JUNE 1ST 2026 FOR APPROX 6 WEEKS. *** 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 fabul

Special

Stay Longer on the Beach & Save 5%

🌴 Save Up to 10% on Your Florida Getaway 🌴

Save up to 10% on qualifying stays of 4 nights or more at Resort Rentals when you book by October 31, 2026. Travel now–December 31, 2026, and use code ENDOFYEAR10 at checkout.

Plan the beach getaway, family vacation, or end-of-year retreat you’ve been waiting for.

Land's End 7-401 Beach Front - Premier

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

Special

Stay Longer on the Beach & Save 5%

🌴 Save Up to 10% on Your Florida Getaway 🌴

Save up to 10% on qualifying stays of 4 nights or more at Resort Rentals when you book by October 31, 2026. Travel now–December 31, 2026, and use code ENDOFYEAR10 at checkout.

Plan the beach getaway, family vacation, or end-of-year retreat you’ve been waiting for.

Land's End 6-205 Beach Front - Premier

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