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 424 properties available
Top Reasons To Book This Beachfront Condo:* Direct Beachfront Condo with Stunning Gulf Views* Heated Community Pool and Direct Beach Access Onsite* Private Balcony with Table and Chairs Overlooking the Beach* Great Location with Easy Trolley Access and Nearby Restaurants and Local Favorites* Professional Managed; 24/7Welcome to Gulf Shores #20
Gulf Shores #205
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 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 8-401 Beach Front
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 4 guests
Rating 5 (32 Reviews)
****NOTICE OF ROOF WORK - BUILDING 4. ROOF WORK WILL BEGIN MID JULY 2026 FOR APPROX 6 WEEKS. DATES MAY VARY. *** Top Reasons To Book This Beautiful Land's End Condo:* Beautifully Updated Corner Unit in the Gated Land’s End Community* Great Onsite Amenities - Large Heated Pool. 2 Hot Tubs. Shuffleboard. Tennis/Pickleball Courts. BBQ Grills
Land's End 4-201 Bay Front - Premier
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 4 guests
Rating 4.8 (7 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:• Stunning Beachfront Views!• Low Density and Well-Maintained Beachfront Complex with Beach Access• Single story layout!• Double adjoining balconies.• Very
Pelican Pointe 4C
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 5 (31 Reviews)
Top Reasons To Book John's Pass-Time Beach Cottages:* Beachfront Property with Direct Beach Access* Full Property to Yourself - Both Cottages - Great for Larger Families or Friends Traveling Together* Great Private Backyard Beach with Hammock, Grill and Picnic Table* 2 Private Entrances, 2 Great Deck/Patio Spaces* Gulf Views From the Upper Lev
John's Pass-Time Beach Cottage #1 and #2
House
Bedrooms 4 bedrooms
Bathrooms 2 Full
Guests 8 guests
Rating 5 (3 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 Chic Condo:* Beach Access Located Across the Street* Newly Renovated Unit* All the Amenities: Well Maintained, Seasonally Heated Pool + Large Sundeck* BBQ and
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.



Barefoot Beach Resort A202
Condo
Bedrooms 1 bedrooms
Bathrooms 1 Full
Guests 5 guests
Rating 4.9 (74 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: • Two private balconies, enjoy panoramic views of the sugary white sands of Indians Shores.• Beautifully decorated throughout to reflect beachside coastal comfort.
Pelican Pointe 3B
Townhouse
Bedrooms 2 bedrooms
Bathrooms 2 Full, 1 Half
Guests 4 guests
Rating 5 (14 Reviews)
Top Reasons to Book this Land's End Condo: * Private Balconies Facing Channel - Watch the Boats and Dolphins Coming and Going* Alexa-Enabled Throughout Entire Condo* Close Proximity to the Large, Heated Pool* Tons of Onsite Amenities - Heated Pool, Hot Tub, Tennis and Pickleball, Shuffleboard, Sand Volleyball Court, Gated Community, BBQ Grills*
Land's End 1-206 Bay Front-Premier
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 4.8 (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: • 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
Villa Madeira 408 - Premier
Condo
Bedrooms 3 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 5 (57 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
Sunset Vistas 403S
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 5 (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, Volleyball,
Land's End 10-202 Beach Front - Premier
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 4 guests
Rating 5 (43 Reviews)
Top Reasons To Book St. Pete Yacht and Tennis Club 404:* Gorgeous Unit with Incredible Water Views* Gated Waterfront Community* Incredible Amenities including Tennis Courts, Pool, Jacuzzi, Gym, and Sauna* Walking Distance to Restaurants and Activities* Professionally ManagedWelcome to St. Pete Yacht and Tennis Club 404! This beautifully decorated 2
St. Pete Beach Yacht and Tennis Club 404
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 4 guests
Rating 5 (1 Reviews)

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