Snowbirds & Winter Monthly Rentals

Resort Rentals, a trusted name in coastal getaways, offers the ultimate monthly winter rentals across the picturesque destinations of St. Pete Beach, Madeira Beach, and Treasure Island, and more. Our carefully selected vacation rentals, ranging from beachfront condos to luxurious vacation homes, serve as your home away from home, welcoming snowbirds looking to escape the winter’s chill. Immerse yourself in the laid-back beach lifestyle along these stunning shores, enjoying leisurely strolls, savoring fresh seafood, and taking in breathtaking sunsets. Resort Rentals ensures an unforgettable winter retreat, allowing you to make cherished memories in these sought-after Florida coastal gems.


Properties Available 371 properties available
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!
Treasure Sands #502
Condo
Bedrooms 2 bedrooms
Bathrooms 2 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. ***NOTICE: ROOF WORK CURRENLTY IN PROGRESS ON BUILDING 1. ESTIMATED COMPLETION MID DECEMBER 2025, COULD VARY BASED ON WORK. PLEASE CALL FOR DETAILS. **** Top Reasons to book : • Sh
Specials Tag Special
Land's End for Less


Stay at Land's End for Less! Get 10% OFF select Land's End properties when you stay 7+ nights.


Use code: "LANDSEND10" at checkout.


Offer is valid on new online bookings only. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties. Resort Rentals has the right to change or end this promotion as they choose. 

Land's End 1-405 Gulf View - Premier
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 4 guests
Rating 5 (25 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
Trillium 5A - Premier
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 4.9 (75 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:* 180 ft from Public Beach Access* Private Entrance with 4 Parking SpacesAny extra-large vehicles may have to park in city overflow due to restricted spac
Beach Livin - All
House
Bedrooms 5 bedrooms
Bathrooms 4 Full, 1 Half
Guests 11 guests
Rating 4.8 (11 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. ***NOTICE: ROOF WORK CURRENLTY IN PROGRESS ON BUILDING 1. ESTIMATED COMPLETION MID DECEMBER 2025, COULD VARY BASED ON WORK. PLEASE CALL FOR DETAILS. **** Top Reasons to book : • Sh
Specials Tag Special
Land's End for Less


Stay at Land's End for Less! Get 10% OFF select Land's End properties when you stay 7+ nights.


Use code: "LANDSEND10" at checkout.


Offer is valid on new online bookings only. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties. Resort Rentals has the right to change or end this promotion as they choose. 

Land's End 1-202 Bay Front
Condo
Bedrooms 1 bedrooms
Bathrooms 1 Full
Guests 2 guests
Rating 4.9 (43 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 : • Short proximity to the onsite heated pool. • All the fabulous amenities including two Hot Tubs, Charcoal BBQ Grills, Community Gazebos, Shuffleboard, Volleybal
Specials Tag Special
Land's End for Less


Stay at Land's End for Less! Get 10% OFF select Land's End properties when you stay 7+ nights.


Use code: "LANDSEND10" at checkout.


Offer is valid on new online bookings only. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties. Resort Rentals has the right to change or end this promotion as they choose. 

Land's End 10-201 Beach Front - Premier
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 4 guests
Rating 5 (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 Condo: * Private Balcony with Gulf Views* Across the Street from the Beach* Onsite Heated Pool* In-Unit Washer/Dryer* 1.5 Miles North of John's Pass Village a
La Coquina 102
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 4.9 (10 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: • Beach access is a short distance from the property, just across the street for your convenience. • Property includes an on-site pool (heated seasonally) • Also o
Sea Shell 24
House
Bedrooms 2 bedrooms
Bathrooms 2 Full, 1 Half
Guests 6 guests
Rating 4.9 (24 Reviews)
Top Reasons To Book Bungalows #8:* Spacious Studio Just Steps from the Beach - Only 400 ft!* 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* Dogs Allowed - 1 Dog, 50lb Max. Fees Apply * Professionally Managed; 24/7 ServiceWelcome to
Specials Tag Special
New Property Introductory Discount

New Property Introductory Discount 

Limited time only Promo Code NEW100

The Bungalows #8
Treasure Island Pet Friendly
Bathrooms 1 Full
Guests 2 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: • Covered parking for multiple vehicles underneath the home. • Two private gulf facing balconies as well as a private boardwalk for easy access to the beach. Para
Paradiso Al Mare Beach House
House
Bedrooms 3 bedrooms
Bathrooms 2 Full
Guests 10 guests
Rating 4.7 (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: •Walking distance to a wide variety of local restaurants and entertainment. •Located just a block from the easy beach access. •Includes access to a shared dock on
Amadeus 6
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 5 guests
Rating 4.9 (67 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 : •Totally Remodeled in 2024! • Short proximity to the onsite heated pool. • All the fabulous amenities including two Hot Tubs, Charcoal BBQ Grills, Community Gaze
Specials Tag Special
Land's End for Less


Stay at Land's End for Less! Get 10% OFF select Land's End properties when you stay 7+ nights.


Use code: "LANDSEND10" at checkout.


Offer is valid on new online bookings only. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties. Resort Rentals has the right to change or end this promotion as they choose. 

Land's End 7-406 Beach Front - Premier
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 4 guests
Rating 4.9 (49 Reviews)

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