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 397 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 Lovely Condo: * Spacious Balcony with Pool Views and Electric Grill* Private, Charming Community, Close to Great Area Attractions* Fabulous Resort Amenities: H
Specials Tag Special
NEW YEAR 2026

Get 10% OFF select  properties when you stay 7-14 nights between 1/2/26-4/3/26! Book by January 31, 2026.


Use code: "NEWYEAR2026" at checkout.


Offer is valid on new online bookings only when you book by January 31, 2026 for 7-14 night stays from January 2, 2026 - April 3, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.  

Vista Verde East 250
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 4 guests
Rating 5 (8 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 Townhome: - Directly on the Beach- Dog Friendly (Additional Costs Apply) - Two Balconies- Wine Fridge, Large TVs throughout- Close to Restaurants- Professional
Specials Tag Special
NEW YEAR 2026

Get 10% OFF select  properties when you stay 7-14 nights between 1/2/26-4/3/26! Book by January 31, 2026.


Use code: "NEWYEAR2026" at checkout.


Offer is valid on new online bookings only when you book by January 31, 2026 for 7-14 night stays from January 2, 2026 - April 3, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.  

Beach Haven #C7
Treasure Island Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 2 Full, 1 Half
Guests 8 guests
Rating 4.9 (73 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
NEW YEAR 2026

Get 10% OFF select  properties when you stay 7-14 nights between 1/2/26-4/3/26! Book by January 31, 2026.


Use code: "NEWYEAR2026" at checkout.


Offer is valid on new online bookings only when you book by January 31, 2026 for 7-14 night stays from January 2, 2026 - April 3, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.  

Land's End 8-401 Beach Front
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 4 guests
Rating 5 (31 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
NEW YEAR 2026

Get 10% OFF select  properties when you stay 7-14 nights between 1/2/26-4/3/26! Book by January 31, 2026.


Use code: "NEWYEAR2026" at checkout.


Offer is valid on new online bookings only when you book by January 31, 2026 for 7-14 night stays from January 2, 2026 - April 3, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.  

Land's End 9-304 Beach Front - Premier
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 4 guests
Rating 4.9 (48 Reviews)
***NOTICE - WATER PARK CLOSURE. Splash Harbour Water Park will be temporarily closed for annual maintenance from January 19th to January 31st, 2026. Dates could vary due to weather or work delays. *** 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 nigh
Specials Tag Special
NEW YEAR 2026

Get 10% OFF select  properties when you stay 7-14 nights between 1/2/26-4/3/26! Book by January 31, 2026.


Use code: "NEWYEAR2026" at checkout.


Offer is valid on new online bookings only when you book by January 31, 2026 for 7-14 night stays from January 2, 2026 - April 3, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.  

Harbourside 7718- Premier
Condo
Bedrooms 3 bedrooms
Bathrooms 2 Full
Guests 10 guests
Rating 4.9 (183 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 : • Completely remodeled 2022/2023 • Short proximity to the onsite heated pool. • All the fabulous amenities including two Hot Tubs, Charcoal BBQ Grills, Community
Specials Tag Special
NEW YEAR 2026

Get 10% OFF select  properties when you stay 7-14 nights between 1/2/26-4/3/26! Book by January 31, 2026.


Use code: "NEWYEAR2026" at checkout.


Offer is valid on new online bookings only when you book by January 31, 2026 for 7-14 night stays from January 2, 2026 - April 3, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.  

Land's End 4-204 Bay Front - Premier
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 4 guests
Rating 5 (8 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: THE POOL IS CURRENTLY CLOSED. Work is still ongoing and hopeful to be complete by March 2026 - Dates could vary. ***Top Reasons to Book: • Take in unforgettable panoramic
Specials Tag Special
NEW YEAR 2026

Get 10% OFF select  properties when you stay 7-14 nights between 1/2/26-4/3/26! Book by January 31, 2026.


Use code: "NEWYEAR2026" at checkout.


Offer is valid on new online bookings only when you book by January 31, 2026 for 7-14 night stays from January 2, 2026 - April 3, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.  

Emerald Isle 104
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 4 guests
Rating 4.8 (57 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: • Direct waterfront views from your private dock! • The location- Walking distance to the sugary white sands of Madeira Beach. • Plenty of comfortable outdoor furn
Specials Tag Special
NEW YEAR 2026

Get 10% OFF select  properties when you stay 7-14 nights between 1/2/26-4/3/26! Book by January 31, 2026.


Use code: "NEWYEAR2026" at checkout.


Offer is valid on new online bookings only when you book by January 31, 2026 for 7-14 night stays from January 2, 2026 - April 3, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.  

Coconut Paradise
House
Bedrooms 3 bedrooms
Bathrooms 1 Full
Guests 8 guests
Rating 4.9 (57 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 (31 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
NEW YEAR 2026

Get 10% OFF select  properties when you stay 7-14 nights between 1/2/26-4/3/26! Book by January 31, 2026.


Use code: "NEWYEAR2026" at checkout.


Offer is valid on new online bookings only when you book by January 31, 2026 for 7-14 night stays from January 2, 2026 - April 3, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.  

Beach Livin 2 - 1 Bedroom Downstairs
Condo
Bedrooms 1 bedrooms
Bathrooms 1 Full
Guests 3 guests
Rating 5 (19 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 Beautiful Condo:* Easy Beach Access Just Across the Street, Approx. 300 ft* Onsite Heated Pool and Hot Tub* Dog Friendly! (Fees and Restrictions Apply)* Wa
Specials Tag Special
NEW YEAR 2026

Get 10% OFF select  properties when you stay 7-14 nights between 1/2/26-4/3/26! Book by January 31, 2026.


Use code: "NEWYEAR2026" at checkout.


Offer is valid on new online bookings only when you book by January 31, 2026 for 7-14 night stays from January 2, 2026 - April 3, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.  

Madeira Bay Resort II - 309
Condo Pet Friendly
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 5 (6 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: • All the property amenities- Outdoor heated pool, shuffleboard, tiki huts, a shared grilling area, bike racks and complementary in unit Wi-Fi.• You are not limit
Specials Tag Special
NEW YEAR 2026

Get 10% OFF select  properties when you stay 7-14 nights between 1/2/26-4/3/26! Book by January 31, 2026.


Use code: "NEWYEAR2026" at checkout.


Offer is valid on new online bookings only when you book by January 31, 2026 for 7-14 night stays from January 2, 2026 - April 3, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.  

Friendly Native 507
Condo
Bedrooms 1 bedrooms
Bathrooms 1 Full
Guests 4 guests
Rating 4.8 (38 Reviews)

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