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 425 properties available
Top Reasons to Book Dolphin Key 504: * Top Floor Condo with Incredible Intracoastal Views* Easy Beach Access Across the Street* Huge Private Balcony + Beach Gear in Unit* Community Heated Pool + Spa * Grilling Area + Gazebo* Great Location in Indian Shores Beach* Professionally ManagedWelcome to Dolphin Key 504, the ideal waterfront retreat for you
Dolphin Key 504 - Premier
Condo
Bedrooms 3 bedrooms
Bathrooms 2 Full
Guests 8 guests
Rating 5 (1 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 2B - Premier
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 5 (87 Reviews)
Top Reasons To Book This Beautiful Home: * Single Family Home All To Yourself - 3 Story Home - 2 Large, Partial Wrap Around Balconies* Quick Walk to Sunset Beach Access - Less than 400ft!* Garage Converted into Game Room with Ping Pong, Corn Hole, Large Screen Smart TV, Mini Fridge, Games and More!* Gorgeous Updates and Top of the Line Finishes
Casa Solmar
House Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 3 Full
Guests 10 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. *** CONSTRUCTION NOTICE: Crystal Palms is currently undergoing a restoration project (entire building) and work will be taking place on grounds, noise will be associated with this. There
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.



Crystal Palms 405
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 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: • Spacious balcony featuring breathtaking views of the Gulf of Mexico. • Shared covered lounge chairs and access to the heated swimming pool during your visit. • Loc
Villa Madeira 305
Condo
Bedrooms 3 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 5 (43 Reviews)
**Please note that due to damage from the recent hurricanes the elevators may be in and out of service. **Top Reasons to Book:• Stunning Views of the Gulf of Mexico from the moment you enter the condo. • Enjoy the fabulous complex amenities such as the shared outdoor pool, lounge chairs and beach access. • Washer/Dryer in unit Welcome to Ocean Sand
Ocean Sands 1-708
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 5 (5 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 (70 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: Please note that due to damage from the recent hurricanes, this property temporarily has no access to onsite amenities. Parking is limited onsite. Elevators are currently out
Madeira Vista 201
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 4.7 (14 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 9-304 Beach Front - Premier
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 4 guests
Rating 4.9 (48 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: * Newly Updated Throughout - 2025* Beachfront with Direct Access to Sunset Beach* Dogs Welcome! (Fees and Restrictions Apply)* Great Space for
Serenity By The Sea
Townhouse Pet Friendly
Bedrooms 5 bedrooms
Bathrooms 4 Full
Guests 14 guests
Rating 4.9 (141 Reviews)
Top Reasons To Book Bungalows #3:* Large 2 Bedroom, Poolside Unit* Charming Property Across the Street from Beach Access - Only 400 ft away!* Dogs Allowed - 1 Dog, 50lb Max. Fees Apply* Onsite Heated Pool, Outside Games and Charcoal Grills* Small, Quaint Property - Only 10 Units Total* Professionally ManagedWelcome to The Bungalows #3! This
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.



The Bungalows #3
Condo Pet Friendly
Bedrooms 2 bedrooms
Bathrooms 1 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: • Short proximity to the onsite heated pool. • All the fabulous amenities including two Hot Tubs, Charcoal BBQ Grills, Community Gazebos, Shuffleboard, Volleyball
Land's End 3-405 Bay Front - Premier
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 4 guests
Rating 4.9 (30 Reviews)

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