Treasure Island

Properties Available 215 properties available
Top Reasons To Book Bungalows #9:* Onsite Heated Pool and Large Pool Deck with Chairs and Umbrellas* Great Common Space with Charcoal Grills, Tables and Chairs and Family Fun Outdoor Game Area* Charming Property Across the Street from Beach Access - Only 400 ft away!* Spacious and Bright Studio* Dogs Allowed - 1 Dog, 50lb Max. Fees Apply* Pr
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.



🌴 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.

The Bungalows #9
The Bungalows #9
Studio Pet Friendly
Bathrooms 1 Full
Guests 2 guests
Rating 4.8 (7 Reviews)
Top Reasons To Book This Suite:* Pool-Facing Suite – Enjoy Views of the Heated Pool* 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 #54, a fres
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.



🌴 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.

Tropic Terrace Suite 54
Tropic Terrace Suite 54
Studio
Bathrooms 1 Full
Guests 3 guests
 New Property!
Top Reasons To Book Sunset Vistas #403S:* Awesome Onsite Amenities - Large Heated Pool, Hot Tub, Fitness Center, Snack Bar, Kiddie Pool and More! * Bright and Spacious Condo with Private Balcony and Gulf Views* Beachfront Property with Direct Beach Access Onsite* Located One Mile From John's Pass Village and Boardwalk, Loaded With Tons of Shop
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.



🌴 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.

Sunset Vistas 403S
Sunset Vistas 403S
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 5 (24 Reviews)
Top Reasons To Book This Suite:* Beach Views – Enjoy the Gulf Coast Right from Your Suite* Resort Amenities – Shuffleboard, Cornhole, Grills, and Recreation Room* Heated Pool – Perfect for Relaxing After a Day at the Beach* Separate Living Area with Sleeper Sofa – Room to Spread Out* Professionally ManagedWelcome to Tropic Terrace Suite #27, a fres
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.



🌴 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.

Tropic Terrace Suite 27
Tropic Terrace Suite 27
Condo
Bedrooms 1 bedrooms
Bathrooms 1 Full
Guests 4 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 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.



🌴 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.

Serenity By The Sea
Serenity By The Sea
Townhouse Pet Friendly
Bedrooms 5 bedrooms
Bathrooms 4 Full
Guests 14 guests
Rating 4.9 (149 Reviews)
****NOTICE OF ROOF WORK - BUILDING 7. ROOF WORK WILL BEGIN JUNE 1ST 2026 FOR APPROX 6 WEEKS. *** 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 fabul
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.



🌴 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 7-405 Beach Front - Premier
Land's End 7-405 Beach Front - Premier
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 4 guests
Rating 5 (15 Reviews)
*** 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 : • Short proximity to the
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.



🌴 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 4-404 Bay Front - Premier
Land's End 4-404 Bay Front - Premier
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 4.9 (20 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 Sunset Chateau #506:* Beachfront Building with Direct Access to Sunset Beach! * Fresh Updates Done in 2025/2026* Cozy 1 Bedroom Condo * Onsite Heated Pool* Prof
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.



🌴 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.

Sunset Chateau 506 - Premier
Sunset Chateau 506 - Premier
Condo
Bedrooms 1 bedrooms
Bathrooms 1 Full
Guests 4 guests
Rating 5 (45 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.Stay more, SAVE more! We
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.



🌴 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 6-203 Beach Front
Land's End 6-203 Beach Front
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 4.9 (48 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.Stay more, SAVE more! We offer
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.



🌴 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 11-305 Beach Front - Premier
Land's End 11-305 Beach Front - Premier
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 4.9 (26 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.Stay more, SAVE more! We
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.



🌴 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 11-307 Beach Front - Premier
Land's End 11-307 Beach Front - Premier
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 4.9 (29 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. Stay more, SAVE more! We
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.



🌴 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 8-401 Beach Front
Land's End 8-401 Beach Front
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 4 guests
Rating 5 (34 Reviews)

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