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Properties Available 46 properties available
Top Reasons To Book the La Barra Triplex: * Full Property - Great for Larger Families or Friends Traveling Together * 3 Individual Condos with Separate Entrances - All on Same Grounds* Easy Walk to the Beach, 350FT, and Nearby Restaurants* 3 Private Bedrooms, 5 Living/Sleeping Areas, 4 Full Bathrooms Total* 4 Private Patios Total* Historic
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.



La Barra - Full Property
House
Bedrooms 3 bedrooms
Bathrooms 4 Full
Guests 14 guests
Rating 5 (4 Reviews)
Top Reasons to book this Dreamy Beach Escape:• Brand new, luxurious beach house with a super cool vibe• Roof top terrace with loungers and a breathtaking view of the Gulf of Mexico.• Large private balcony hot tub with an attached comfy outdoor seating area• 75" TV in living area• Easy access to an additional bonus room featuring a Queen size bed, a
Sunset Point Beach House
House
Bedrooms 4 bedrooms
Bathrooms 3 Full
Guests 10 guests
Rating 4.9 (33 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 Home:* Single Family Home all to Yourself* 2 Blocks from the Beach!* Awesome Wrap Around Deck* Dogs Welcome (2 max. Fees Apply)* Private Yard Fully Fence
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.



Bates Avenue House
House Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 2 Full
Guests 8 guests
Rating 5 (37 Reviews)
Top Reasons to Book Sailfish + Jellyfish:* Beachfront Home on Sunset Beach* Two Connected Townhomes: Ideal for Multi-Family Trips* 6 Bedrooms + 4 Full Baths + 2 Half Baths* Two Full Kitchens, Living Rooms + Laundry Areas* Expansive Beachfront Deck + Covered Patio* Gulf Views + Sunset Balconies* Walk to Caddy’s + Ka’Tiki* Dog Friendly: Fees + Restri
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.



Sailfish AND Jellyfish
House Pet Friendly
Bedrooms 6 bedrooms
Bathrooms 4 Full, 2 Half
Guests 16 guests
 New Property!
Top Reasons To Book This Home: * Just a short 3–4 minute walk to Sunset Beach* Rooftop deck with Intracoastal Waterway views* 3 spacious bedrooms, each with its own bathroom* Easy access to St. Pete Beach and Madeira Beach* Professionally ManagedWelcome to Salty Smiles, a 3 bedrooms and 3.5 bathrooms home in the Sunset Beach neighborhood of be
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.



Salty Smiles
House
Bedrooms 3 bedrooms
Bathrooms 3 Full, 1 Half
Guests 6 guests
 New Property!
Top Reasons To Book This Fabulous House:* Only 400ft to Public Beach Access* 4BR Family Home with Awesome Bay Views* Two Large, Private Balconies * Great Space for Larger Family or Couples * Walkable to Restaurants, Shopping, and a ParkStay more, SAVE more! We offer lower nightly rates on extended stays from Sept-Mar. No coupon code needed! Just en
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.



Gulfport Getaway
House
Bedrooms 4 bedrooms
Bathrooms 3 Full
Guests 8 guests
Rating 5 (27 Reviews)
Welcome to Rocking Sunset Beach House, your luxury coastal retreat in the heart of Sunset Beach—one of Treasure Island's most desirable neighborhoods. Just a 2–3 minute walk to the sugar-white sands of the Gulf of Mexico, this beautifully renovated 3-bedroom home, PLUS Loft and Bonus room combines upscale comfort, thoughtful amenities, and an unbea
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.



Rocking Sunset Beach House
House
Bedrooms 3 bedrooms
Bathrooms 2 Full, 1 Half
Guests 10 guests
Rating 5 (3 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: • 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.



Sand Dunes Townhome C1
House
Bedrooms 2 bedrooms
Bathrooms 2 Full, 1 Half
Guests 6 guests
Rating 4.9 (68 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.



Beach Please
House
Bedrooms 3 bedrooms
Bathrooms 3 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 this Awesome House: * Huge Outdoor Space with 2 Putt-Putt Pads* Quick and Easy Walk to Beach Access * Outside Dining and Firepit* Open and Spacious Single Famil
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.



Indian Rocks Retreat
House
Bedrooms 3 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 5 (9 Reviews)
Top Reasons To Book John's Pass-Time #2:* Beachfront Property with Direct Beach Access* Gulf Views from your Private Balcony* Shared Beachfront Area with Picnic Table, Hammock and Charcoal Grill* Great Location - Walk To John's Pass Village and Boardwalk* Professionally Managed, 24/7Welcome to John's Pass-Time Beach Cottage #2, a peaceful 2-be
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.



John's Pass-Time Beach Cottage #2
House
Bedrooms 2 bedrooms
Bathrooms 1 Full
Guests 4 guests
Rating 5 (12 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.



Sunset Dreams
House Pet Friendly
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 5 guests
Rating 5 (2 Reviews)

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