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 463 properties available
*** NOTICE OF ROOF WORK - BUILDING 4. ESTIMATED COMPLETION TIME IS CURRENTLY END OF SEPTEMBER, 2026 - NOT EXACT AND DATES MAY VARY. ***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
Specials Tag Special
Stay Longer on the Beach & Save 5%

Book your long-term Florida beach getaway now and take advantage of 5% savings on stays of 28+ nights. Use STAYLONGER5 on travel between October 1, 2026 and January 31, 2027 at select condos and homes.


*Offer is valid on new online bookings when you book by January 1, 2027, for stays of 28 nights or more with travel between October 1, 2026 and January 31, 2027. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.




🌴 Save Up to 10% on Your Florida Getaway 🌴



Save up to 10% on qualifying stays of 4 nights or more at Resort Rentals when you book by September 25, 2026. Travel August 22–December 31, 2026, and use code ENDOFYEAR10 at checkout.


Plan the beach getaway, family vacation, or end-of-year retreat you’ve been waiting for.


*Offer is valid on new online bookings when you book by September 25, 2026, for 4-night minimum stays from August 22 through December 31, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.

Land's End 4-304 Bay Front - Premier
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 4.9 (51 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. Open and airy with lots of beach front charm. This large south corner condo has everything you need for a perfect vacation. It is completely remodeled.... Rows of windows open the space t
Specials Tag Special
Stay Longer on the Beach & Save 5%

Book your long-term Florida beach getaway now and take advantage of 5% savings on stays of 28+ nights. Use STAYLONGER5 on travel between October 1, 2026 and January 31, 2027 at select condos and homes.


*Offer is valid on new online bookings when you book by January 1, 2027, for stays of 28 nights or more with travel between October 1, 2026 and January 31, 2027. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.




🌴 Save Up to 10% on Your Florida Getaway 🌴



Save up to 10% on qualifying stays of 4 nights or more at Resort Rentals when you book by September 25, 2026. Travel August 22–December 31, 2026, and use code ENDOFYEAR10 at checkout.


Plan the beach getaway, family vacation, or end-of-year retreat you’ve been waiting for.


*Offer is valid on new online bookings when you book by September 25, 2026, for 4-night minimum stays from August 22 through December 31, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.

Land's End 8-201 Beach Front - Premier
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 4 guests
Rating 5 (39 Reviews)
If you plan a 3 months plus stay on our beautiful beaches, this condo is for you! Minimum rental period required by the association is 3 months! This is a lovely 2 bedroom/2 bath condo in a great location in St. Pete Beach. The view from the water front balcony is absolutely stunning! The kitchen comes fully equipped with stainless steel applianc
Specials Tag Special
Stay Longer on the Beach & Save 5%

Book your long-term Florida beach getaway now and take advantage of 5% savings on stays of 28+ nights. Use STAYLONGER5 on travel between October 1, 2026 and January 31, 2027 at select condos and homes.


*Offer is valid on new online bookings when you book by January 1, 2027, for stays of 28 nights or more with travel between October 1, 2026 and January 31, 2027. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.




🌴 Save Up to 10% on Your Florida Getaway 🌴



Save up to 10% on qualifying stays of 4 nights or more at Resort Rentals when you book by September 25, 2026. Travel August 22–December 31, 2026, and use code ENDOFYEAR10 at checkout.


Plan the beach getaway, family vacation, or end-of-year retreat you’ve been waiting for.


*Offer is valid on new online bookings when you book by September 25, 2026, for 4-night minimum stays from August 22 through December 31, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.

St. Pete Beach Yacht and Tennis Club 503
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 Crystal Palms 201: * Steps From the Warm Sand and Sparkling Waters of the Gulf of Mexico* Spacious Pool Deck with Cozy Lounge Chairs, Heated Pool, and Hot Tub* Sout
Specials Tag Special
Stay Longer on the Beach & Save 5%

Book your long-term Florida beach getaway now and take advantage of 5% savings on stays of 28+ nights. Use STAYLONGER5 on travel between October 1, 2026 and January 31, 2027 at select condos and homes.


*Offer is valid on new online bookings when you book by January 1, 2027, for stays of 28 nights or more with travel between October 1, 2026 and January 31, 2027. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.




🌴 Save Up to 10% on Your Florida Getaway 🌴



Save up to 10% on qualifying stays of 4 nights or more at Resort Rentals when you book by September 25, 2026. Travel August 22–December 31, 2026, and use code ENDOFYEAR10 at checkout.


Plan the beach getaway, family vacation, or end-of-year retreat you’ve been waiting for.


*Offer is valid on new online bookings when you book by September 25, 2026, for 4-night minimum stays from August 22 through December 31, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.

Crystal Palms 201
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 4 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: • All the Amenities! Large Heated Pool, Kiddie Pool, Hot Tub, Fitness Center, Bicycles, Beach Tiki Bar and Café all in one location! • One of very few handicapped ac
Specials Tag Special
Stay Longer on the Beach & Save 5%

Book your long-term Florida beach getaway now and take advantage of 5% savings on stays of 28+ nights. Use STAYLONGER5 on travel between October 1, 2026 and January 31, 2027 at select condos and homes.


*Offer is valid on new online bookings when you book by January 1, 2027, for stays of 28 nights or more with travel between October 1, 2026 and January 31, 2027. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.




🌴 Save Up to 10% on Your Florida Getaway 🌴



Save up to 10% on qualifying stays of 4 nights or more at Resort Rentals when you book by September 25, 2026. Travel August 22–December 31, 2026, and use code ENDOFYEAR10 at checkout.


Plan the beach getaway, family vacation, or end-of-year retreat you’ve been waiting for.


*Offer is valid on new online bookings when you book by September 25, 2026, for 4-night minimum stays from August 22 through December 31, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.

Sunset Vistas 206S
Condo
Bedrooms 2 bedrooms
Bathrooms 1 Full, 1 Half
Guests 6 guests
Rating 4.9 (82 Reviews)
Top Reasons To Book This Condo: * Direct Beach Access Just Steps Away—No Need to Drive or Find Parking* Shared Heated Pool with Lounge Chairs and Extra Outdoor Sitting Spaces* Well-Maintained Beachfront Community* Two Bedrooms Each With Attached Bathrooms - Added Privacy and Comfort* Professionally Managed, 24/7Welcome to View West #5, a beau
Specials Tag Special
Stay Longer on the Beach & Save 5%

Book your long-term Florida beach getaway now and take advantage of 5% savings on stays of 28+ nights. Use STAYLONGER5 on travel between October 1, 2026 and January 31, 2027 at select condos and homes.


*Offer is valid on new online bookings when you book by January 1, 2027, for stays of 28 nights or more with travel between October 1, 2026 and January 31, 2027. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.




🌴 Save Up to 10% on Your Florida Getaway 🌴



Save up to 10% on qualifying stays of 4 nights or more at Resort Rentals when you book by September 25, 2026. Travel August 22–December 31, 2026, and use code ENDOFYEAR10 at checkout.


Plan the beach getaway, family vacation, or end-of-year retreat you’ve been waiting for.


*Offer is valid on new online bookings when you book by September 25, 2026, for 4-night minimum stays from August 22 through December 31, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.

View West #5
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 4 guests
Rating 5 (1 Reviews)
*** NOTICE: At Harbor House there is still active work on grounds. Buildings have gates in place and there will be construction taking place, noise will be associated with this. Parking will vary. Onsite Laundry Room currently closed. ***Top Reasons To Book:* Beautiful Beaches Right Across the Street* Access to Beach Front Pool and Grills Acros
Harbor House 37
Condo
Bedrooms 1 bedrooms
Bathrooms 1 Full
Guests 2 guests
Rating 4.8 (22 Reviews)
**Please note that due to damage from the recent hurricanes the elevators may be in and out of service. **Top Reasons to Book this Beachfront Condo:* Beachfront Condo with Direct Views of the Gulf of Mexico* Open and Spacious Condo on 10th Floor* Large Pool Deck with Table and Chairs* Heated Pool, Hot Tub and Shuffleboard on Grounds * Central Locat
Specials Tag Special
Stay Longer on the Beach & Save 5%

Book your long-term Florida beach getaway now and take advantage of 5% savings on stays of 28+ nights. Use STAYLONGER5 on travel between October 1, 2026 and January 31, 2027 at select condos and homes.


*Offer is valid on new online bookings when you book by January 1, 2027, for stays of 28 nights or more with travel between October 1, 2026 and January 31, 2027. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.




🌴 Save Up to 10% on Your Florida Getaway 🌴



Save up to 10% on qualifying stays of 4 nights or more at Resort Rentals when you book by September 25, 2026. Travel August 22–December 31, 2026, and use code ENDOFYEAR10 at checkout.


Plan the beach getaway, family vacation, or end-of-year retreat you’ve been waiting for.


*Offer is valid on new online bookings when you book by September 25, 2026, for 4-night minimum stays from August 22 through December 31, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.

Ocean Sands 1-1002
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 5 (13 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:• Unobstructed view of the gulf from the private balcony• Beach access directly across the street (with crossing light for safety!) About 200 steps to the sand!• Gy
Specials Tag Special
Stay Longer on the Beach & Save 5%

Book your long-term Florida beach getaway now and take advantage of 5% savings on stays of 28+ nights. Use STAYLONGER5 on travel between October 1, 2026 and January 31, 2027 at select condos and homes.


*Offer is valid on new online bookings when you book by January 1, 2027, for stays of 28 nights or more with travel between October 1, 2026 and January 31, 2027. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.




🌴 Save Up to 10% on Your Florida Getaway 🌴



Save up to 10% on qualifying stays of 4 nights or more at Resort Rentals when you book by September 25, 2026. Travel August 22–December 31, 2026, and use code ENDOFYEAR10 at checkout.


Plan the beach getaway, family vacation, or end-of-year retreat you’ve been waiting for.


*Offer is valid on new online bookings when you book by September 25, 2026, for 4-night minimum stays from August 22 through December 31, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.

Madeira Bay Resort I 1504
Condo Pet Friendly
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 4.9 (61 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 Bayside Unit:• Dogs Allowed! (Fees and Restrictions apply)• Treasure Island’s newest, boutique condo-resort offers the best of both worlds; beachfront and bay
Specials Tag Special
Stay Longer on the Beach & Save 5%

Book your long-term Florida beach getaway now and take advantage of 5% savings on stays of 28+ nights. Use STAYLONGER5 on travel between October 1, 2026 and January 31, 2027 at select condos and homes.


*Offer is valid on new online bookings when you book by January 1, 2027, for stays of 28 nights or more with travel between October 1, 2026 and January 31, 2027. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.




🌴 Save Up to 10% on Your Florida Getaway 🌴



Save up to 10% on qualifying stays of 4 nights or more at Resort Rentals when you book by September 25, 2026. Travel August 22–December 31, 2026, and use code ENDOFYEAR10 at checkout.


Plan the beach getaway, family vacation, or end-of-year retreat you’ve been waiting for.


*Offer is valid on new online bookings when you book by September 25, 2026, for 4-night minimum stays from August 22 through December 31, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.

Oceana 305 East
Condo Pet Friendly
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 4.9 (49 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 i
Specials Tag Special
Stay Longer on the Beach & Save 5%

Book your long-term Florida beach getaway now and take advantage of 5% savings on stays of 28+ nights. Use STAYLONGER5 on travel between October 1, 2026 and January 31, 2027 at select condos and homes.


*Offer is valid on new online bookings when you book by January 1, 2027, for stays of 28 nights or more with travel between October 1, 2026 and January 31, 2027. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.




🌴 Save Up to 10% on Your Florida Getaway 🌴



Save up to 10% on qualifying stays of 4 nights or more at Resort Rentals when you book by September 25, 2026. Travel August 22–December 31, 2026, and use code ENDOFYEAR10 at checkout.


Plan the beach getaway, family vacation, or end-of-year retreat you’ve been waiting for.


*Offer is valid on new online bookings when you book by September 25, 2026, for 4-night minimum stays from August 22 through December 31, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.

Tides 6-563
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 5 (1 Reviews)
Top Reasons To Book This Premier Condo:* Directly On The Beach - Gulf Views from your Living Room* Steps from the Beach - Easy Access Right Onsite* Great Location on Sunset Beach in Treasure Island* Onsite Headed Pool * Professionally Managed, 24/7Welcome to Sunset Chateau #210, a comfortable and spacious 1-bedroom, 1-bath beachfront condo des
Specials Tag Special
Stay Longer on the Beach & Save 5%

Book your long-term Florida beach getaway now and take advantage of 5% savings on stays of 28+ nights. Use STAYLONGER5 on travel between October 1, 2026 and January 31, 2027 at select condos and homes.


*Offer is valid on new online bookings when you book by January 1, 2027, for stays of 28 nights or more with travel between October 1, 2026 and January 31, 2027. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.




🌴 Save Up to 10% on Your Florida Getaway 🌴



Save up to 10% on qualifying stays of 4 nights or more at Resort Rentals when you book by September 25, 2026. Travel August 22–December 31, 2026, and use code ENDOFYEAR10 at checkout.


Plan the beach getaway, family vacation, or end-of-year retreat you’ve been waiting for.


*Offer is valid on new online bookings when you book by September 25, 2026, for 4-night minimum stays from August 22 through December 31, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.

Sunset Chateau 210 - Premier
Condo
Bedrooms 1 bedrooms
Bathrooms 1 Full
Guests 4 guests
Rating 5 (48 Reviews)

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