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 366 properties available
**NOTICE AS OF 9/26/25 - ELEVATOR CURRENTLY OUT OF SERVICE - NO ETA ON COMPLETION***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
Trillium 1A - Premier
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 4.9 (76 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 Hot Tub, Charcoal BBQ Grills, Community Gazebos, Shuffleboard, Volleyball, Te
Specials Tag Special
Land's End for Less


Stay at Land's End for Less! Get 10% OFF select Land's End properties when you stay 7+ nights.


Use code: "LANDSEND10" at checkout.


Offer is valid on new online bookings only. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties. Resort Rentals has the right to change or end this promotion as they choose. 

Land's End 10-302 Beach Front - Premier
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 4 guests
Rating 4.9 (65 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. About this Land's End Condo:This top floor 2 bedroom, 2 bathroom has been nicely updated and is ready for you! The kitchen has been beautifully updated and is fully equipped and ready
Specials Tag Special
Land's End for Less


Stay at Land's End for Less! Get 10% OFF select Land's End properties when you stay 7+ nights.


Use code: "LANDSEND10" at checkout.


Offer is valid on new online bookings only. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties. Resort Rentals has the right to change or end this promotion as they choose. 

Land's End 3-404 Bay Front
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 4 guests
Rating 4.9 (22 Reviews)
**NOTICE AS OF 9/26/25 - ELEVATOR CURRENTLY OUT OF SERVICE - NO ETA ON COMPLETION***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
Trillium 4A - Premier
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 4.9 (95 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,
Specials Tag Special
Land's End for Less


Stay at Land's End for Less! Get 10% OFF select Land's End properties when you stay 7+ nights.


Use code: "LANDSEND10" at checkout.


Offer is valid on new online bookings only. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties. Resort Rentals has the right to change or end this promotion as they choose. 

Land's End 8-204 Beach Front - Premier
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 4 guests
Rating 4.9 (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 : • 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
Land's End for Less


Stay at Land's End for Less! Get 10% OFF select Land's End properties when you stay 7+ nights.


Use code: "LANDSEND10" at checkout.


Offer is valid on new online bookings only. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties. Resort Rentals has the right to change or end this promotion as they choose. 

Land's End 4-406 Bay Front
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 4.9 (45 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: Major exterior renovation project beginning December 1st, 2025 and to last approx. 10 months. Noise will be associated with the work. Access to areas on grounds/parking wil
Bayshore Yacht & Tennis 216
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 4.8 (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 beautiful 2-bedroom, 2-b
Land's End 1-408 Bay Front
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 4 guests
Rating 4.9 (10 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
Land's End for Less


Stay at Land's End for Less! Get 10% OFF select Land's End properties when you stay 7+ nights.


Use code: "LANDSEND10" at checkout.


Offer is valid on new online bookings only. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties. Resort Rentals has the right to change or end this promotion as they choose. 

Land's End 1-304 Bay Front - Premier
Condo
Bedrooms 1 bedrooms
Bathrooms 1 Full
Guests 2 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 : • 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
Land's End for Less


Stay at Land's End for Less! Get 10% OFF select Land's End properties when you stay 7+ nights.


Use code: "LANDSEND10" at checkout.


Offer is valid on new online bookings only. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties. Resort Rentals has the right to change or end this promotion as they choose. 

Land's End 10-203 Beach Front - Premier
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 4 guests
Rating 4.9 (38 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: Please note that restoration work is underway. Parking is limited onsite. Noise may be experienced while work is ongoing. Beach Access and Pool are OPEN! ***To
Villa Madeira 207 - Premier
Condo
Bedrooms 3 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 4.9 (69 Reviews)
Top Reasons to Book this Gulf Front Condo:* Amazing Views of The Gulf of Mexico and Sunset Beach* Wrap Around Private Balcony* Gated Community and Onsite Amenities* Spacious and Luxurious * Professionally Managed; 24/7 ServicetWelcome to Mansions By the Sea, a stunning 2-bedroom, 2-bathroom beachfront condo offering luxury, space, and breathta
Mansions By The Sea 903B - Premier
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 4 guests
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