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Properties Available 50 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 this Townhouse: • Direct Beach Access Path • Just a short stroll to relax on the beautiful white sands of Treasure Island! • Low density complex, still close to all
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 September 25, 2026. Travel August 22–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 September 25, 2026, for 4-night minimum stays from August 22 through December 31, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.

Sand Dunes Townhome C1
Sand Dunes Townhome C1
House
Bedrooms 2 bedrooms
Bathrooms 2 Full, 1 Half
Guests 6 guests
Rating 4.9 (65 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 Fabulous House:* 3BR Family Home with Bay Views* Two Large, Private Balconies * Great Space for Larger Families or Couples * Walkable to Restaurants, Shopping,
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 September 25, 2026. Travel August 22–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 September 25, 2026, for 4-night minimum stays from August 22 through December 31, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.

Hippie Haven
Hippie Haven
House
Bedrooms 3 bedrooms
Bathrooms 3 Full
Guests 6 guests
Rating 5 (45 Reviews)
Top reasons to book this Townhouse: • Direct Beach Access Path • Just a short stroll to relax on the beautiful white sands of Treasure Island! • Low density complex, still close to all the action and entertainment! • EV-Electric Vehicle Charger available for our guests! The Sand Dunes Townhome has many interior upgrades with every possible amen
Sand Dunes Townhome C2
Sand Dunes Townhome C2
House
Bedrooms 2 bedrooms
Bathrooms 2 Full, 1 Half
Guests 8 guests
Rating 5 (16 Reviews)
Top Reasons To Book this Home: * Walking distance to Sunset Beach, one of the BEST beaches on Treasure Island!* Fresh New Updates - 2025 * Private Patio with Outside Seating and Gas Grill * Quiet Residential Neighborhood - Single Family Home all to Yourself * Beautiful, Fully Stocked Kitchen* Professionally Managed 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 September 25, 2026. Travel August 22–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 September 25, 2026, for 4-night minimum stays from August 22 through December 31, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.

Good Vibrations - Beach House
Good Vibrations - Beach House
House
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 4 guests
Rating 5 (20 Reviews)
Top Reasons To Book This Beautiful Home:* Single Family Home with Pool* Spacious Outdoor Living Area Beautifully Landscaped* Prime Location Just A Short Drive to Upham Beach and Treasure Island Beaches - About a Mile! * Fully Fenced Yard—Perfect for Dogs (Fees/Restrictions Apply)* Professionally Managed, 24/7Welcome to Sunset Dreams, a relaxing co
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 September 25, 2026. Travel August 22–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 September 25, 2026, for 4-night minimum stays from August 22 through December 31, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.

Sunset Dreams
Sunset Dreams
House Pet Friendly
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 5 guests
Rating 5 (2 Reviews)
Top Reasons to Book This Fabulous House:* Beautiful Views from the balcony of the Intracoastal Waterway* Great Space for Larger Families or Couples * Short Drive to Beach Access * Walking Distance to Great Restaurants and Entertainment* Professionally Managed; 24/7 Service*This property is NOT AVAILABLE for rent to those under the age of 25. No Exc
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 September 25, 2026. Travel August 22–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 September 25, 2026, for 4-night minimum stays from August 22 through December 31, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.

Paradise Along Boca Ciega Bay
Paradise Along Boca Ciega Bay
House
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 8 guests
Rating 5 (7 Reviews)
Top Reasons To Book John's Pass-Time Beach Cottages:* Beachfront Property with Direct Beach Access* Full Property to Yourself - Both Cottages - Great for Larger Families or Friends Traveling Together* Great Private Backyard Beach with Hammock, Grill and Picnic Table* 2 Private Entrances, 2 Great Deck/Patio Spaces* Gulf Views From the Upper Lev
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 September 25, 2026. Travel August 22–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 September 25, 2026, for 4-night minimum stays from August 22 through December 31, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.

John's Pass-Time Beach Cottage #1 and #2
John's Pass-Time Beach Cottage #1 and #2
House
Bedrooms 4 bedrooms
Bathrooms 2 Full
Guests 8 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: * Quiet Neighborhood Location in Treasure Island* Quick Drive to the Beach, Only 2 Minutes! * Easy Access on and off the Island* Great Spot for Couples * Pr
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.



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 September 25, 2026. Travel August 22–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 September 25, 2026, for 4-night minimum stays from August 22 through December 31, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.

Shore Thing
Shore Thing
House
Bedrooms 1 bedrooms
Bathrooms 1 Full
Guests 2 guests
Rating 5 (14 Reviews)
Top Reasons to Book Gulfside Retreat: * Gorgeous 3-Story Single Family Home with Private Elevator* Easy Walk to the Beach - About 350 Yards* 2 Spacious, Private Balconies with Seating* Quiet Neighborhood Location* Bright, Beautiful and Modern Home* Professionally ManagedWelcome to Gulfside Retreat! This stunning 3-story single-family home bo
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 September 25, 2026. Travel August 22–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 September 25, 2026, for 4-night minimum stays from August 22 through December 31, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.

Gulfside Retreat
Gulfside Retreat
House
Bedrooms 4 bedrooms
Bathrooms 3 Full
Guests 9 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 Paradise Cove:* AMAZING Single Family Home with Private Pool and Hot Tub (Heating options at an additional cost)* Covered Outside Deck with Couches, TV and Dining T
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 September 25, 2026. Travel August 22–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 September 25, 2026, for 4-night minimum stays from August 22 through December 31, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.

Paradise Cove
Paradise Cove
House
Bedrooms 4 bedrooms
Bathrooms 3 Full
Guests 10 guests
Rating 5 (15 Reviews)
Top Reasons to Book this Home: * Easy Walk to Beach Access - .1 Mile/3 Minutes!* Single Family Home to Yourself* 2 Private Decks* Great Location - Walking Distance to Restaurants and Shopping* Professionally ManagedWelcome to Beach Please! This spacious and inviting two-story single-family home offers 3 bedrooms and 3 full bathrooms, comfort
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 September 25, 2026. Travel August 22–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 September 25, 2026, for 4-night minimum stays from August 22 through December 31, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.

Beach Please
Beach Please
House
Bedrooms 3 bedrooms
Bathrooms 3 Full
Guests 6 guests
Rating 5 (1 Reviews)
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 Patio Space Perfect for Grilling and Sunbathing* Dog Friendly (2 small dogs or 1 large dog, Additional Fees Apply)* Lower-Level Game Room with Foosball Table, Dart
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 September 25, 2026. Travel August 22–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 September 25, 2026, for 4-night minimum stays from August 22 through December 31, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.

Seaclusion Beach Townhome
Seaclusion Beach Townhome
House Pet Friendly
Bedrooms 4 bedrooms
Bathrooms 3 Full, 1 Half
Guests 17 guests
Rating 4.9 (107 Reviews)

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