Fall Into Savings with 15% Off

Fall into savings and plan your extended getaway with our FALLSTAY2026 offer!


Enjoy 15% off 7+ night stays between September 1 and December 15, 2026 when you book by May 31, 2026 using code FALLSTAY2026 at checkout. It’s the perfect time to unwind with fewer crowds, cooler temperatures, and all the beauty of the season.


**Offer is valid on new online bookings when you book by May 31, 2026, to receive 15% off for 7+ night stays from September 1, 2026 to December 15, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.


Properties Available 399 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 : • Completely remodeled 2022/2023 • Short proximity to the onsite heated pool. • All the fabulous amenities including two Hot Tubs, Charcoal BBQ Grills, Community
Specials Tag Special
Fall Into Savings with 15% Off

Fall into savings and plan your extended getaway with our FALLSTAY2026 offer!


Enjoy 15% off 7+ night stays between September 1 and December 15, 2026 when you book by May 31, 2026 using code FALLSTAY2026 at checkout. It’s the perfect time to unwind with fewer crowds, cooler temperatures, and all the beauty of the season.


**Offer is valid on new online bookings when you book by May 31, 2026, to receive 15% off for 7+ night stays from September 1, 2026 to December 15, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.

Land's End 4-204 Bay Front - Premier
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 4 guests
Rating 4.9 (11 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: • Spacious balcony featuring breathtaking views of the Gulf of Mexico. • Shared covered lounge chairs and access to the heated swimming pool during your visit. • Loc
Specials Tag Special
Fall Into Savings with 15% Off

Fall into savings and plan your extended getaway with our FALLSTAY2026 offer!


Enjoy 15% off 7+ night stays between September 1 and December 15, 2026 when you book by May 31, 2026 using code FALLSTAY2026 at checkout. It’s the perfect time to unwind with fewer crowds, cooler temperatures, and all the beauty of the season.


**Offer is valid on new online bookings when you book by May 31, 2026, to receive 15% off for 7+ night stays from September 1, 2026 to December 15, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.

Villa Madeira 305
Condo
Bedrooms 3 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 5 (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. 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
Fall Into Savings with 15% Off

Fall into savings and plan your extended getaway with our FALLSTAY2026 offer!


Enjoy 15% off 7+ night stays between September 1 and December 15, 2026 when you book by May 31, 2026 using code FALLSTAY2026 at checkout. It’s the perfect time to unwind with fewer crowds, cooler temperatures, and all the beauty of the season.


**Offer is valid on new online bookings when you book by May 31, 2026, to receive 15% off for 7+ night stays from September 1, 2026 to December 15, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.

Land's End 1-405 Gulf View - 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 this Bayside Unit:• Dogs Allowed! (Fees and Restrictions apply)• Treasure Island’s newest, boutique condo-resort offers the best of both worlds; beachfront and bay
Specials Tag Special
Fall Into Savings with 15% Off

Fall into savings and plan your extended getaway with our FALLSTAY2026 offer!


Enjoy 15% off 7+ night stays between September 1 and December 15, 2026 when you book by May 31, 2026 using code FALLSTAY2026 at checkout. It’s the perfect time to unwind with fewer crowds, cooler temperatures, and all the beauty of the season.


**Offer is valid on new online bookings when you book by May 31, 2026, to receive 15% off for 7+ night stays from September 1, 2026 to December 15, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.

Oceana 301 East
Condo Pet Friendly
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 5 (43 Reviews)
Top Reasons To Book This Beautiful Condo:* Extra-Long Private Balcony With Direct Water Views* Fully Renovated Top-to-Bottom With High-End Finishes* Beach Access Onsite - Quick and Easy Walk* End, Corner Unit With Extra Space and Privacy* Great Onsite Amenities - Large Heated Pool, 2 Hot Tubs, Tennis/Pickleball, Shuffleboard, Charcoal GrillsWe
Specials Tag Special
Fall Into Savings with 15% Off

Fall into savings and plan your extended getaway with our FALLSTAY2026 offer!


Enjoy 15% off 7+ night stays between September 1 and December 15, 2026 when you book by May 31, 2026 using code FALLSTAY2026 at checkout. It’s the perfect time to unwind with fewer crowds, cooler temperatures, and all the beauty of the season.


**Offer is valid on new online bookings when you book by May 31, 2026, to receive 15% off for 7+ night stays from September 1, 2026 to December 15, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.

Land's End 3-301 Bay Front - Premier
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 4 guests
Rating 4.9 (43 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! • 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-
Specials Tag Special
Fall Into Savings with 15% Off

Fall into savings and plan your extended getaway with our FALLSTAY2026 offer!


Enjoy 15% off 7+ night stays between September 1 and December 15, 2026 when you book by May 31, 2026 using code FALLSTAY2026 at checkout. It’s the perfect time to unwind with fewer crowds, cooler temperatures, and all the beauty of the season.


**Offer is valid on new online bookings when you book by May 31, 2026, to receive 15% off for 7+ night stays from September 1, 2026 to December 15, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.

Royal Orleans 117
Condo
Bedrooms 1 bedrooms
Bathrooms 2 Full
Guests 4 guests
Rating 5 (8 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 Shell 28:* Spacious Townhouse on the Intracoastal Waterway* Onsite Heated Pool, Deck with Lounge Chairs and Fishing Dock* 176 Yards to Beach Access* Private
Specials Tag Special
Fall Into Savings with 15% Off

Fall into savings and plan your extended getaway with our FALLSTAY2026 offer!


Enjoy 15% off 7+ night stays between September 1 and December 15, 2026 when you book by May 31, 2026 using code FALLSTAY2026 at checkout. It’s the perfect time to unwind with fewer crowds, cooler temperatures, and all the beauty of the season.


**Offer is valid on new online bookings when you book by May 31, 2026, to receive 15% off for 7+ night stays from September 1, 2026 to December 15, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.

Sea Shell 28
House
Bedrooms 2 bedrooms
Bathrooms 2 Full, 1 Half
Guests 6 guests
Rating 4.8 (9 Reviews)
*****NOTICE - The gym onsite is currently closed. *****Top Reasons To Book This Beachfront Condo: * 7th Floor Condo with Awesome Views of the Beach and Gulf of Mexico* Large Pool Deck with Lounge Chairs and Heated Beachside Pool Onsite* Spacious, Bright Interior with Lots of Natural Light* Private Balcony Accessible from Living Room and Maste
Specials Tag Special
Fall Into Savings with 15% Off

Fall into savings and plan your extended getaway with our FALLSTAY2026 offer!


Enjoy 15% off 7+ night stays between September 1 and December 15, 2026 when you book by May 31, 2026 using code FALLSTAY2026 at checkout. It’s the perfect time to unwind with fewer crowds, cooler temperatures, and all the beauty of the season.


**Offer is valid on new online bookings when you book by May 31, 2026, to receive 15% off for 7+ night stays from September 1, 2026 to December 15, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.

Redington Towers 7D
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 5 (2 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 #12:* Close to Beach Access* Private Balcony* Beautifully Landscaped Grounds* Onsite Heated Pool and Shuffleboard* Fishing Dock on Intracoastal Waterway* P
Specials Tag Special
Fall Into Savings with 15% Off

Fall into savings and plan your extended getaway with our FALLSTAY2026 offer!


Enjoy 15% off 7+ night stays between September 1 and December 15, 2026 when you book by May 31, 2026 using code FALLSTAY2026 at checkout. It’s the perfect time to unwind with fewer crowds, cooler temperatures, and all the beauty of the season.


**Offer is valid on new online bookings when you book by May 31, 2026, to receive 15% off for 7+ night stays from September 1, 2026 to December 15, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.

Sea Club #12 - The Dancing Dolphin
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 5 (4 Reviews)
Top Reasons To Book Bungalows #4:* 400ft away from Beach Access - Just Across the Street* Dogs Allowed - 1 Dog, 50lb Max. Fees Apply* Large 2 Bedroom, Poolside Unit* Onsite Heated Pool, Outside Games and Charcoal Grills* Professionally Managed, 24/7Welcome to The Bungalows #4! This updated 2-bedroom, 1-bathroom unit is the perfect spot for your
Specials Tag Special
Fall Into Savings with 15% Off

Fall into savings and plan your extended getaway with our FALLSTAY2026 offer!


Enjoy 15% off 7+ night stays between September 1 and December 15, 2026 when you book by May 31, 2026 using code FALLSTAY2026 at checkout. It’s the perfect time to unwind with fewer crowds, cooler temperatures, and all the beauty of the season.


**Offer is valid on new online bookings when you book by May 31, 2026, to receive 15% off for 7+ night stays from September 1, 2026 to December 15, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.

The Bungalows #4
Condo Pet Friendly
Bedrooms 2 bedrooms
Bathrooms 1 Full
Guests 6 guests
Rating 4.6 (3 Reviews)
Top Reasons To Book This Beachfront Condo:* Beautiful and Spacious Condo Directly on Madeira Beach* 3 Balconies - Main Balcony Overlooking the Beach and Gulf of Mexico* Onsite Heated Beachside Pool with Lounge Chairs * Direct Beach Access—Step Off the Pool Deck onto the Sand* Professionally Managed, 24/7Welcome to Trillium 2A, a beautiful and s
Specials Tag Special
Fall Into Savings with 15% Off

Fall into savings and plan your extended getaway with our FALLSTAY2026 offer!


Enjoy 15% off 7+ night stays between September 1 and December 15, 2026 when you book by May 31, 2026 using code FALLSTAY2026 at checkout. It’s the perfect time to unwind with fewer crowds, cooler temperatures, and all the beauty of the season.


**Offer is valid on new online bookings when you book by May 31, 2026, to receive 15% off for 7+ night stays from September 1, 2026 to December 15, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.

Trillium 2A - Premier
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 4.9 (90 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
Fall Into Savings with 15% Off

Fall into savings and plan your extended getaway with our FALLSTAY2026 offer!


Enjoy 15% off 7+ night stays between September 1 and December 15, 2026 when you book by May 31, 2026 using code FALLSTAY2026 at checkout. It’s the perfect time to unwind with fewer crowds, cooler temperatures, and all the beauty of the season.


**Offer is valid on new online bookings when you book by May 31, 2026, to receive 15% off for 7+ night stays from September 1, 2026 to December 15, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.

Land's End 3-206 Bay Front - Premier
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 4 guests
Rating 4.9 (31 Reviews)

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