Shores of Madeira

473 properties available

Top Reasons To Book This Beachfront Condo:* Private Balcony with Amazing Beach and Gulf of Mexico Views* Beachfront, Heated Pool On Grounds with Pool Deck and Lounge Chairs* Direct Beach Access Outside the Pool Gate* Bright, Open Living Space Filled with Natural Sunlight* Professionally Managed, 24/7Escape to this beautifully updated 2-bedroom

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.

Emerald Isle 304 - 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: • All the Amenities! Large Heated Pool, Kiddie Pool, Hot Tub, Fitness Center, Bicycles, Beach Tiki Bar and Café all in one location!• Living room and main bedroom

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. Top Reasons to Book! • First floor unit with easy pool access! • Short and convenient walk to the sand! • Relaxing pool with sun loungers!Introducing The Royal Orleans, a charming one-

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 Beautiful Home: * Single Family Home All To Yourself - 3 Story Home - 2 Large, Partial Wrap Around Balconies* Quick Walk to Sunset Beach Access - Less than 400ft!* Garage Converted into Game Room with Ping Pong, Corn Hole, Large Screen Smart TV, Mini Fridge, Games and More!* Gorgeous Updates and Top of the Line Finishes

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: • Walking distance to a wide variety of local restaurants and entertainment. • Located just a block from the easy beach access. • Includes access to a shared dock on the intercoastal as well as a waterfront pool! Stay more, SAVE more! We offer lower nightly rates on extended stays from Sept-Mar. No coupon code needed! Just ent

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. 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 2B - 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 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

Top Reasons To Book This Beachfront Condo:* Direct Beachfront Condo with Stunning, Unobstructed Views from the 6th Floor* Spacious Pool Deck with Lounge Chairs, Heated Pool, and Hot Tub* Other Onsite Amenities Including Direct Beach Access, Gas Grills, Shuffleboard, and Elevator* Stylish, Fully Updated Condo with Modern Finishes* Professionall

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.

*** POOL UPDATE: The pool is temporarily closed while necessary repairs are being completed. A reopening date has not yet been confirmed, and this notice will be updated as soon as the pool becomes available again. Thank you for your understanding. ***Top Reasons To Book This Condo:* Prime Location Directly across from John’s Pass Village and Boar

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.

Madeira Norte 406 - Premier

*** POOL UPDATE: The pool is temporarily closed while necessary repairs are being completed. A reopening date has not yet been confirmed, and this notice will be updated as soon as the pool becomes available again. Thank you for your understanding. ***Top Reasons To Book This Condo:* Beachfront Condo - Great Beach and Gulf Views from 4th Floor - S

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: * Quick, Easy Drive to the Beach - Treasure Island to the North and St Pete Beach to the South* Heated Community Pool* Dedicated Workspace for Remote Worker* Lush, Landscaped Courtyard with Shared Grills and Table Areas* Professionally ManagedWelcome to Boca Shores #123, a bright, comfortable, and nicely updated

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. Open and airy with lots of beach front charm. This large south corner condo has everything you need for a perfect vacation. It is completely remodeled.... Rows of windows open the space t

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 8-201 Beach Front - Premier

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