Shores of Madeira


Properties Available 397 properties available
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
NEW YEAR 2026

Get 10% OFF select  properties when you stay 7-14 nights between 1/2/26-4/3/26! Book by January 17, 2026.


Use code: "NEWYEAR2026" at checkout.


Offer is valid on new online bookings only when you book by January 17, 2026 for 7-14 night stays from January 2, 2026 - April 3, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.  

Land's End 1-401 Gulf View
Condo
Bedrooms 1 bedrooms
Bathrooms 1 Full
Guests 2 guests
Rating 4.8 (47 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
NEW YEAR 2026

Get 10% OFF select  properties when you stay 7-14 nights between 1/2/26-4/3/26! Book by January 17, 2026.


Use code: "NEWYEAR2026" at checkout.


Offer is valid on new online bookings only when you book by January 17, 2026 for 7-14 night stays from January 2, 2026 - April 3, 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 (71 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. ****NOTICE: Major exterior renovation project beginning December 1st, 2025 and to last approx. 10 months. Noise will be associated with the work. Access to areas on grounds/parking wil
Specials Tag Special
NEW YEAR 2026

Get 10% OFF select  properties when you stay 7-14 nights between 1/2/26-4/3/26! Book by January 17, 2026.


Use code: "NEWYEAR2026" at checkout.


Offer is valid on new online bookings only when you book by January 17, 2026 for 7-14 night stays from January 2, 2026 - April 3, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.  

Bayshore Yacht & Tennis 216
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 4.8 (36 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
NEW YEAR 2026

Get 10% OFF select  properties when you stay 7-14 nights between 1/2/26-4/3/26! Book by January 17, 2026.


Use code: "NEWYEAR2026" at checkout.


Offer is valid on new online bookings only when you book by January 17, 2026 for 7-14 night stays from January 2, 2026 - April 3, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.  

Land's End 1-307 Gulf View
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 5 (37 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 Land's End Condo: * Private Balconies Facing Channel - Watch the Boats and Dolphins Coming and Going* Alexa-Enabled Throughout Entire Condo* Close Proximity
Specials Tag Special
NEW YEAR 2026

Get 10% OFF select  properties when you stay 7-14 nights between 1/2/26-4/3/26! Book by January 17, 2026.


Use code: "NEWYEAR2026" at checkout.


Offer is valid on new online bookings only when you book by January 17, 2026 for 7-14 night stays from January 2, 2026 - April 3, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.  

Land's End 1-206 Bay Front-Premier
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 5 guests
Rating 4.7 (4 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. **CONSTRUCTION NOTICE: Please note that restoration work is underway. Parking is limited onsite. Noise may be experienced while work is ongoing. Beach Access and Pool are OPEN! ***
Specials Tag Special
NEW YEAR 2026

Get 10% OFF select  properties when you stay 7-14 nights between 1/2/26-4/3/26! Book by January 17, 2026.


Use code: "NEWYEAR2026" at checkout.


Offer is valid on new online bookings only when you book by January 17, 2026 for 7-14 night stays from January 2, 2026 - April 3, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.  

Villa Madeira 406
Condo
Bedrooms 3 bedrooms
Bathrooms 2 Full
Guests 5 guests
Rating 4.8 (42 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. This stunning Bay front condo has been completely renovated including new windows, sliding doors and new flooring. Fully equipped new kitchen with custom cabinets, granite counter top
Specials Tag Special
NEW YEAR 2026

Get 10% OFF select  properties when you stay 7-14 nights between 1/2/26-4/3/26! Book by January 17, 2026.


Use code: "NEWYEAR2026" at checkout.


Offer is valid on new online bookings only when you book by January 17, 2026 for 7-14 night stays from January 2, 2026 - April 3, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.  

Land's End 4-303 Bay Front - Premier
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 4.6 (21 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 Sea Club #10:* Close to Beach Access* Private Balcony* Beautifully Landscaped Grounds* Onsite Heated Pool and Shuffleboard* Fishing Dock on Intracoastal Waterway* P
Specials Tag Special
NEW YEAR 2026

Get 10% OFF select  properties when you stay 7-14 nights between 1/2/26-4/3/26! Book by January 17, 2026.


Use code: "NEWYEAR2026" at checkout.


Offer is valid on new online bookings only when you book by January 17, 2026 for 7-14 night stays from January 2, 2026 - April 3, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.  

Sea Club #10 - Seascape
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 4 guests
Rating 5 (12 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 800 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
NEW YEAR 2026

Get 10% OFF select  properties when you stay 7-14 nights between 1/2/26-4/3/26! Book by January 17, 2026.


Use code: "NEWYEAR2026" at checkout.


Offer is valid on new online bookings only when you book by January 17, 2026 for 7-14 night stays from January 2, 2026 - April 3, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.  

Beach Life 5
House Pet Friendly
Bedrooms 5 bedrooms
Bathrooms 3 Full
Guests 14 guests
Rating 5 (26 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
NEW YEAR 2026

Get 10% OFF select  properties when you stay 7-14 nights between 1/2/26-4/3/26! Book by January 17, 2026.


Use code: "NEWYEAR2026" at checkout.


Offer is valid on new online bookings only when you book by January 17, 2026 for 7-14 night stays from January 2, 2026 - April 3, 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 : • Short proximity to the onsite heated pool. • All the fabulous amenities including two Hot Tubs, Charcoal BBQ Grills, Community Gazebos, Shuffleboard, Volleyball
Land's End 8-403 Beach Front - Premier
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 4 guests
Rating 4.9 (53 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: •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
Specials Tag Special
NEW YEAR 2026

Get 10% OFF select  properties when you stay 7-14 nights between 1/2/26-4/3/26! Book by January 17, 2026.


Use code: "NEWYEAR2026" at checkout.


Offer is valid on new online bookings only when you book by January 17, 2026 for 7-14 night stays from January 2, 2026 - April 3, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.  

Amadeus 5
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 4 guests
Rating 4.9 (79 Reviews)

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