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 380 properties available
Top Reasons to Book this Land's End Condo: * Beachfront Condo with Beautiful Updates Throughout* Private Balcony with Stunning Views* Gated Community* Amenities: Beach Access, Heated Pool, Hot Tub, Tennis and Pickleball, Shuffleboard, Sand Volleyball* Professionally ManagedStay more, SAVE more! We offer lower nightly rates on extended stays f
Land's End 11-302 Beach Front - Premier
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 5 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: • All the Amenities- Beachside heated pool, hot tub, shared BBQ area and a large pool deck- all onsite! • Direct panoramic views from your private balcony. • Sever
Sand Castle I #804
Condo
Bedrooms 3 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 4.9 (40 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
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 Madeira Bay Resort #1402:* Easy Beach Access Directly Across the Street* Private Balcony with Gulf Views* Walk to Restaurants, Bars, Ice Cream, Coffee, Bike Rent
Madeira Bay Resort I 1402
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 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 : • Short proximity to the onsite heated pool. • All the fabulous amenities including two Hot Tubs, Charcoal BBQ Grills, Community Gazebos, Shuffleboard, Volleybal
Land's End 6-301 Beach Front
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 4 guests
Rating 5 (52 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 5C - Premier
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 4.9 (71 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: SUNSET VISTAS WILL BE DOING A WALKWAY RESURFACING PROJECT THROUGH EACH BUILDING AND ON EACH FLOOR NOVEMBER 2025 - ESTIMATED END OF JANUARY 2026. SOME NOISE AND FLOOR CLOSURES
Sunset Vistas 302S
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 4.6 (35 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. This 2 bedroom, 2 bath
Land's End 6-302 Beach Front - Premier
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 4 guests
Rating 5 (26 Reviews)
Top Reasons To Book Bungalows #9:* 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* Charming Property Across the Street from Beach Access - Only 400 ft away!* Spacious and Bright Studio* Dogs Allowed - 1 Dog, 50lb Max. Fees Apply* Pr
Specials Tag Special
New Property Introductory Discount

New Property Introductory Discount 

Limited time only Promo Code NEW100

The Bungalows #9
Treasure Island Pet Friendly
Bathrooms 1 Full
Guests 2 guests
 New Property!
Top Reasons to Book this Condo: * Private Balcony with Awesome Views of Intracoastal Waterway* Easy Walk to Public Beach Access, about .3 Miles* Heated Pool Onsite* Beautifully Updated Condo with Stunning Details* Fishing Dock on Grounds* Professionally ManagedExperience relaxed coastal living in this beautifully updated 2-bedroom, 2- bathr
Palm Beach 602
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. 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
Land's End 3-402 Bay Front
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 4 guests
Rating 4.5 (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 : • Short proximity to the onsite heated pool. • All the fabulous amenities including two Hot Tubs, Charcoal BBQ Grills, Community Gazebos, Shuffleboard, Volleybal
Land's End 10-402 Beach Front - Premier
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 4 guests
Rating 4.9 (68 Reviews)

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