Resort Rentals

We invite you to take a tour of our properties to find the perfect Florida vacation rental for your Florida beach vacation. You can check our rates and policies conveniently online. Our dedicated team of professionals is just a click away to assist you in planning your Florida family beach vacation and to provide the support you need to enjoy our tropical islands in one of our comfortable vacation rentals.


Please note that during certain months such as: February, March, June, July, and August, availability may be limited to Saturday-Saturday stays. For the best search results, please select "Flex Dates" in your search to see all possible options for your stay


Properties Available 440 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: • Spacious screened balcony featuring breathtaking views of the Gulf of Mexico. • Shared covered lounge chairs and access to the heated swimming pool during your vi
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.



Villa Madeira 206
Condo
Bedrooms 3 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 4.9 (61 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 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
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 Livin 1 - 1 Bedroom Downstairs
Condo Pet Friendly
Bedrooms 1 bedrooms
Bathrooms 1 Full
Guests 3 guests
Rating 5 (18 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 #20:* Close to Beach Access* Private Balcony* Beautifully Landscaped Grounds* Onsite Heated Pool and Shuffleboard* Fishing Dock on Intracoastal Waterway* P
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.



Sea Club #20 - Salty Vibes
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 5 (17 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: • You’ll love the beautiful décor, and comfortable furnishings throughout this unit • As you enter, you'll be greeted by floor to ceiling sliding glass doors and
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.



Trillium 5B - Premier
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 4.9 (78 Reviews)
Top Reasons To Book This Madeira Beach Condo:* Beachfront, End Unit Condo on 5th Floor with Amazing Gulf and Beach Views* Direct Beach Access, Heated Pool, Hot Tub, Shuffleboard, Tiki Bar, and Large Pool Deck all On Grounds* Great Location - Walk to John’s Pass Village and Boardwalk, Restaurants, Shops, or Hop on the Trolley!* Private Balcony off L
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.



Ocean Sands 1-501
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 4 guests
Rating 5 (5 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.



Land's End 7-402 Beach Front - Premier
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 4.9 (50 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.



Land's End 8-301 Beach Front
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 4 guests
Rating 5 (50 Reviews)
Top Reasons to Book La Vistana #A503:* Stunning Gulf Views from you Private Balcony* Large Pool Deck with Heated Pool and Hot Tub* Fitness Center On Grounds* Private Cabana for Use* Spacious Condo, Great for Families or Friends Traveling Together* Great Longer Term Rental Option* Professionally Managed, 24/7Welcome to your dream beachfront e
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 Vistana #A503
Condo
Bedrooms 3 bedrooms
Bathrooms 3 Full
Guests 7 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: * 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.



Shore Thing
House
Bedrooms 1 bedrooms
Bathrooms 1 Full
Guests 2 guests
Rating 5 (13 Reviews)
Top Reasons To Book This Condo:* Close to Beach Access - About 400ft Away!* Onsite Heated Pool and Shuffleboard* Private Balcony with View of Intracoastal Waterway and Pool Deck* Beautifully Landscaped Grounds - Fishing Pier* Professionally Managed, 24/7Welcome to Sea Club #42 – Stellar Escape, a spacious and inviting 2-bedroom, 2-bathroom condo
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.



Sea Club #42 - Stellar Escape
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 5 (1 Reviews)
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.



Sunset Vistas 403S
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 5 (18 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
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.



Oceana 301 East
Condo Pet Friendly
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 5 (50 Reviews)

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