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
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
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.



Land's End 1-304 Bay Front - Premier
Condo
Bedrooms 1 bedrooms
Bathrooms 1 Full
Guests 2 guests
Rating 4.9 (50 Reviews)
Top Reasons To Book This Condo:* Close to Beach Access - About 400ft Away!* Onsite Heated Pool and Shuffleboard* Private Balcony with View of Intracoastal Waterway and Pool Deck* Beautifully Landscaped Grounds - Fishing Pier* Professionally Managed, 24/7Welcome to Sea Club #42 – Stellar Escape, a spacious and inviting 2-bedroom, 2-bathroom condo
Sea Club #42 - Stellar Escape
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 4 guests
 New Property!
Top Reasons To Book This Beautifully Updated Condo:* Direct Beachfront Location with Stunning, Unobstructed Gulf Views* Private 5th-Floor Balcony—Perfect for Sunsets and Morning Coffee* Direct Beach Access - Onsite Heated Pool* Beautifully Updated Interior with Modern Finishes Throughout* Professionally Managed, 24/7Welcome to Emerald Isle #501, a
Emerald Isle 501 - Premier
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 4 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 Sea Club #102:* Close to Beach Access* Private Balcony* Beautifully Landscaped Grounds* Onsite Heated Pool and Shuffleboard* Fishing Dock on Intracoastal Waterway*
Sea Club #102 - Another Day in Paradise
Condo
Bedrooms 1 bedrooms
Bathrooms 1 Full
Guests 2 guests
Rating 5 (18 Reviews)
***PLEASE NOTE: THE ELEVATOR WILL BE OUT OF SERVICE FOR A SHORT TIME FROM MAY 1ST, 2026 FOR APPROX 1 WEEK. SOME DAYS IN THAT WEEK MAY NOT BE AFFECTED AT ALL OR VERY LITTLE, SOME DAYS MAY HAVE NO ELEVATOR SERVICE FOR A FULL DAY. REPAIRS/UPDATES BEING DONE. DATES COULD VARY BASED ON WEATHER. PLEASE CALL FOR DETAILS **** Stay more, SAVE more! We o
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.



Oceana 204 East
Condo Pet Friendly
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 4.9 (54 Reviews)
*** NOTICE - THE POOL AND ONSITE BEACH ACCESS ARE CURRENTLY CLOSED!!! Open Beach Access Nearby! *** Top Reasons To Book This Townhome: * Elegant 3 Story Townhome With Direct Beach Access Onsite - Easy Come-and-Go from the Beach* 3 bedrooms • 3 Full Bathrooms — Ideal for Families or Groups* Community Pool - Perfect for Relaxing* 3 Private Bal
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.



El Mar Townhome - Unit D
Townhouse
Bedrooms 3 bedrooms
Bathrooms 3 Full
Guests 8 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: • Direct waterfront views from your private dock! • The location- Walking distance to the sugary white sands of Madeira Beach. • Plenty of comfortable outdoor furn
Coconut Paradise
House
Bedrooms 3 bedrooms
Bathrooms 1 Full
Guests 8 guests
Rating 4.9 (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 : • 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 1-405 Gulf View - Premier
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 4 guests
Rating 5 (27 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: * Top Floor Corner Unit with Bay Views * Onsite heated pool* All the fabulous amenities including two Hot Tubs, Charcoal BBQ Grills, Community Gazebos,
Land's End 3-406 Bay Front
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 4 guests
Rating 5 (18 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 directly across the street • Pet Friendly (30lbs Max, Additional Cost Apply) • Gym Available (Building II) • Short stroll away from many shops and r
Madeira Bay Resort I 1408
Condo Pet Friendly
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 4.9 (41 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 Sea Club #47:* Close to Beach Access!* Private Balcony* Beautifully Landscaped Grounds* Onsite Heated Pool and Shuffleboard* Fishing Dock on Intracoastal Waterway*
Sea Club #47 - Sea Haven
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 5 (15 Reviews)
Top reasons to Book: • All the Amenities-THREE luxurious swimming pools, hot tubs, an outdoor grilling area, fitness center, and beach access. • Direct panoramic views from your private balcony. • 10 minutes on the beach trolley to the well-known John’s Pass Village which is loaded with tons of shopping, restaurants, and entertainment! This condo
Tides 4-642
Condo
Bedrooms 3 bedrooms
Bathrooms 2 Full
Guests 5 guests
Rating 5 (11 Reviews)

Tell us what you're looking for and someone will contact you with available options.

I agree