Treasure Island

215 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 : • Direct Beach and Gulf views • Easy access to the onsite heated pool and hot tub • Loads of onsite amenities • Gated community with 24 hour security • Nicely upd

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.

Land's End 9-204 Beach Front

Top Reasons to book : • Premier, updated condo in the gated beachfront community at Land's End • 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

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 1-401 Gulf View - 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 : • Short proximity to the onsite heated pool. • All the fabulous amenities including two Hot Tubs, Charcoal BBQ Grills, Community Gazebos, Shuffleboard, Volleybal

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 6-205 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:•All new updates completed this year, 2024•Amazing water views from every angle•Fully stocked kitchen with new appliances•Private balcony•Gated community with loads

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 5-201 Gulf-Bay Front - Premier

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

Top Reasons To Book This Suite:* Heated Pool – Perfect for Relaxing After a Day at the Beach* Beachfront Access – Steps from Beautiful Treasure Island Beach* Ground Floor Suite - No Stairs Required* Resort Amenities – Shuffleboard, Cornhole, Grills, and Recreation Room* Professionally ManagedWelcome to Tropic Terrace Suite #11, a charming ground-fl

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 11

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 Fabulous Beachfront Slice of Paradise • All the Amenities! Large Heated Pool, Kiddie Pool, Hot Tub, Fitness Center, Bicycles, Beach Tiki Bar and Café all in o

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.

*** NOTICE OF ROOF WORK - BUILDING 4. ESTIMATED COMPLETION TIME IS CURRENTLY END OF SEPTEMBER, 2026 - NOT EXACT AND DATES MAY VARY. *** 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 C

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 4-405 Bay Front - Premier

Top Reasons To Book Treasure Sands #502:* Beachfront Condo with Stunning Beach and Gulf of Mexico Views* Onsite, Beachfront Heated Pool with Spacious Deck, Tables, and Chairs* Shared Tiki Bar and Rec Room with Pool Table, Ping Pong, Cornhole, and TV* Spacious and Comfortable Layout* Professionally Managed, 24/7Welcome to Treasure Sands #502!

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 this Condo:* 180 ft from Public Beach Access* Private Entrance with 1 Parking Space Any extra-large vehicles may have to park in city overflow due to restricted spa

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.

Beach Livin 2 - 1 Bedroom Downstairs

**** CLOSURE NOTICE - THE POOL IS CURRENTLY CLOSED WHILE WORK CONTINUES ONSITE ****Top Reasons To Book This Stunning Condo:* Top, 12th-Floor Luxury Condo with Nearly 3,000 sq. ft. of Living Space* Spectacular Partial Wraparound Private Balcony with Stunning Gulf and Intracoastal Waterway Views* Awesome Onsite Amenities - Beach Access, Heated Poo

Mansions By The Sea 1201A - 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 this Premier Condo: * Private Balconies with Stunning Views* Close Proximity to the Onsite Heated Pool* Fabulous Amenities: 2 Hot Tubs, Charcoal BBQ Grills, and Com

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 5-203 Gulf-Bay Front - Premier

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