Cottages at Madeira Beach

473 properties available

**Please note that due to damage from the recent hurricanes, this property temporarily has no access to the onsite amenities; Pools, hot tub/spa, jacuzzi, cabanas, lounge tables, tiki hut, private pier, or BBQ facilities. Elevators are working but may experience intermittent outages. There may be some noise onsite while restoration work is ongoing.

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.

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 Intercoastal #205:*Intercoastal water views*Upgraded appliances*Beautifully decorated* Private, Screened in Balcony* Professionally Managed, 24/7Escape to The I

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.

The Intercoastal #205 - Beachy Chic

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

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

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: • Take in unforgettable panoramic beachfront views and warm sunshine from your private balcony. • Short drive to St Petersburg- loaded with great museums, shops and restaurants. • Shared outdoor pool on site (heated seasonally). Inside this stunning 4th floor condo, you’ll find the open floorplan, coastal décor, and comfortable

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.

Emerald Isle 403 - Premier

*** NOTICE OF ROOF WORK - BUILDING 4. ESTIMATED COMPLETION TIME IS CURRENTLY END OF SEPTEMBER, 2026 - NOT EXACT AND DATES 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 : • Completely remodeled 2

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 4-204 Bay Front - Premier

Top reasons to book this Townhouse: • Direct Beach Access Path • Just a short stroll to relax on the beautiful white sands of Treasure Island! • Low density complex, still close to all the action and entertainment! • EV-Electric Vehicle Charger available for our guests! The Sand Dunes Townhome has many interior upgrades with every possible amen

Sand Dunes Townhome C2

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 Townhome:- Directly on the Beach- Dog Friendly (Additional Costs Apply) - Two Balconies- Wine Fridge, Large TVs throughout- Close to Restaurants- 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.

Top Reasons To Book This Beachfront Condo:* Beachfront Condo with Breathtaking Gulf Views from the Private Balcony * Resort-Style Amenities – Enjoy a Beachside Heated Pool, Relaxing Hot Tub, Shared BBQ Area, and a Spacious Pool Deck — All Just Steps from your Door!* Perfect Location – Close to Family-Friendly Activities, Top-Rated Restaurants, 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.

Sand Castle II #2602 - 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: • Outdoor pool (heated seasonally), Free Spectrum WiFi and Cable, In unit washer and dryer, fishing pier, easy beach access directly across the street.• Unit inclu

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:* Pool Views – Overlook the Heated Pool from Your Suite* Resort Amenities – Shuffleboard, Cornhole, Grills, and Recreation Room* Onsite Beach Access – A Short Path to Treasure Island's Shoreline* Extra Sleeping Space – Queen Bed Plus 1-Person Sleeper Sofa* Professionally ManagedWelcome to Tropic Terrace Suite #56, a f

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 56

**NOTICE: Guests may experience some extended wait times for the elevator. One of the two elevators is currently operational and that they are actively working on getting the second elevator back in service. Thank you for your patience during this period. **Top Reasons To Book This Condo:* Direct Beachfront Location – Step Right onto the Sand!*

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.

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