Cottages at Madeira Beach


Properties Available 441 properties available
Top Reasons to Book this Land's End Condo: * Beachfront Condo with Beautiful Updates Throughout* Private Balcony with Stunning Views* Gated Community* Amenities: Beach Access, Heated Pool, Hot Tub, Tennis and Pickleball, Shuffleboard, Sand Volleyball* Professionally ManagedStay more, SAVE more! We offer lower nightly rates on extended stays f
Specials Tag 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.



Land's End 11-302 Beach Front - Premier
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 5 guests
Rating 5 (11 Reviews)
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 2 bedroom, 2 bath
Land's End 6-302 Beach Front - Premier
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 4 guests
Rating 5 (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:* Beachfront Townhouse with Amazing Gulf Views from Multiple Balconies* Large Outdoor Covered Terrace Perfect for Relaxing and Soaking in the Sunsets* Additional
Specials Tag 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.



Seaclusion Beach Townhome
House Pet Friendly
Bedrooms 4 bedrooms
Bathrooms 3 Full, 1 Half
Guests 17 guests
Rating 4.9 (103 Reviews)
Top Reasons To Book This Condo:* Awesome Onsite Amenities - Beach Access, Large Heated Pool, 2 Hot Tubs, Kiddie Pool, Workout Room, Charcoal Grills, Beach Bar and Cafe* Private Balcony with Access from Living Room and Master Bedroom * Open Concept Living Area - 2 Bedroom, 2 Full Bathroom Condo* Professionally Managed, 24/7Welcome to Sunset Vist
Specials Tag 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.



Sunset Vistas 205S
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 4.8 (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 This Condo:* Location, Location, Location: Next to John's Pass and directly across from the sugar sand beach, with safe access via the pedestrian crosswalk light.*
Specials Tag 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.



Madeira Bay Resort I 1505
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 4.9 (109 Reviews)
Top Reasons To Book This Condo:* Private Balcony Overlooking the Gulf, Beach, and Pool Deck—Perfect for Sunsets!* Easy Beach Access Just Steps From Your Front Door* Beachside Heated Pool, Hot Tub, Pool Deck with Lounge Chairs* Beautiful and Spacious Beachfront Condo at San Remo in Redington Shores* Professionally Managed, 24/7Welcome to San Re
Specials Tag 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.



San Remo 206
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 5 (9 Reviews)
Top reasons to Book:• Private and beautifully furnished balcony overlooking the marina!• Just a block from beautiful, white sand Madeira Beach!• Wonderful amenities such as a pool and spa as well as free Wi-Fi, secured parking, and an in-unit washer and dryer!• Beautifully decorated throughout to reflect coastal comfort.•The location is great too!
Specials Tag 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.



The Harbor Condo 305 - Premier
Condo
Bedrooms 4 bedrooms
Bathrooms 3 Full
Guests 8 guests
Rating 5 (15 Reviews)
Top Reasons To Book Caddy's Cottage: * Just Steps from Sunset Beach in Beautiful Treasure Island* Walk to Caddy's Treasure Island for Beachfront Dining, Live Music, Volleyball, and Sunset Cocktails* Charming 2-bedroom, 1.5-bath Property with Open Living Space* Professionally Managed, 24/7Welcome to Caddy's Cottage, a charming coastal getaway just
Specials Tag 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.



Caddy's Cottage #1
Condo
Bedrooms 2 bedrooms
Bathrooms 1 Full, 1 Half
Guests 6 guests
 New Property!
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 #15:* Close to Beach Access* Private Balcony* Beautifully Landscaped Grounds* Onsite Heated Pool and Shuffleboard* Fishing Dock on Intracoastal Waterway* P
Specials Tag Special
Hot Summer Savings Are Here!


Enjoy 10% off your summer escape when you stay between June 2 and September 1, 2026. Book 3 nights or more and make the most of peak season for less.

Use code HOTDEALS at checkout.

*New online bookings only. Minimum stay required. Restrictions apply.



Sea Club #15 - Sand Dollar
Condo
Bedrooms 1 bedrooms
Bathrooms 1 Full
Guests 2 guests
Rating 5 (6 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: • Take in unforgettable panoramic beachfront views and warm sunshine from your private balcony. • Short drive to St Petersburg- loaded with great museums, shops and
Specials Tag Special
Hot Summer Savings Are Here!


Enjoy 10% off your summer escape when you stay between June 2 and September 1, 2026. Book 3 nights or more and make the most of peak season for less.

Use code HOTDEALS at checkout.

*New online bookings only. Minimum stay required. Restrictions apply.



Emerald Isle 401 - Premier
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 4 guests
Rating 4.9 (84 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 Townhouse: * Newly Updated Throughout - 2025* Beachfront with Direct Access to Sunset Beach* Dogs Welcome! (Fees and Restrictions Apply)* Great Space for
Specials Tag 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.



Serenity By The Sea
Townhouse Pet Friendly
Bedrooms 5 bedrooms
Bathrooms 4 Full
Guests 14 guests
Rating 4.9 (141 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: • Enjoy The low density and well-maintained beachside complex with beach access. • Very close proximity to many well know restaurants in the area. • Brand new kit
Specials Tag 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.



Pelican Pointe 2A
Townhouse
Bedrooms 2 bedrooms
Bathrooms 2 Full, 1 Half
Guests 6 guests
Rating 4.9 (69 Reviews)

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