Check out our Florida Monthly Rentals By Owner Top 10 List of Monthly vacation rentals under $2,000! Bonus! We’ve added more vacation rentals to our list.
Updated Feb 7, 2025
Snowbird is a term for “a northerner who moves to a warmer southern state in the winter”. It’s not just a tradition but a way of life for people who reside in Canada and the northern United States. Who wouldn’t want to escape the frigid winters? Snowbird season in Florida runs from October until around late April.
Florida is the perfect spot for people and seniors who want to get away from the cold in search of Monthly Rentals By Owner. It can be quite difficult to find a suitable vacation rental that’s budget friendly. Not to worry, we’ve found some great Florida rentals under $2,000 per month! Just perfect for Florida snowbirds looking to get away from the cold on a tight budget.
No longer just for seniors, monthly Florida rentals are ideal for digital nomads who can work from home and kids who are web learning or homeschooling. You might also want to find resources online to help me with my homework – especially for kids who are web learning or homeschooling. Just be sure to ask about wifi connection when renting a home by the month in Florida.
A Top 10 List of the Best Florida Snowbird Rentals under $2,000 per Month
- Beachside Condo – Holmes Beach
- Lakeside Gated Community Condo Rental – Naples
- Waterfront Condo Rental – Dunedin
- Long Term Stay Snowbird Condo Rental – Clearwater
- Charming Cottage Retreat – Jupiter
- The Cutest Cottage Rental – Gulfport
- Centrally-Located Condo Rental – Sarasota
- Tropical Cottage Getaway – Gulfport
- Pet-Friendly Cottage Vacation Rental – Sarasota
- Boat-Friendly Monthly Rental – Punta Gorda
- Affordable Monthly Rental – Fort Myers
Beachside Condo Vacation Rental – Holmes Beach, Florida
Escape to a 5-star beachfront haven on Anna Maria Island! Indulge in breathtaking Gulf views from a 22-foot lanai, relish designer decor in this 2-bed, 2-bath + den condo. With a 7-day minimum stay, immerse yourself in tranquility. Professionally decorated, enjoy a fully equipped kitchen, 4 TVs, and free WiFi. Sunsets, sandy strolls, and the serene Gulf await—this idyllic retreat promises an unforgettable escape. Find your monthly rental for a slice of paradise.
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Lakeside Gated Community Condo Rental – Naples, Florida
Discover your “Happy Place” in this pet-friendly, fully renovated Coach House in Carlton Lakes, North Naples. Boasting a spacious 3-bed, 2-bath layout, this 1,700 sqft gem exudes luxury with oak floors, quartz countertops, and high-end furnishings. Enjoy breathtaking lake views from dual lanais and experience Naples’ best with Carlton Lakes’ tennis courts, pools, and more. With beach gear, high-speed internet, and two bikes included, create lasting memories in this ideal Naples retreat. Your perfect vacation awaits!
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Waterfront Condo Vacation Rental – Dunedin, Florida
Paradise at Dolphin Point condos, where this 1-bedroom unit offers modern luxury and breathtaking water views. Newly renovated, the colorful condo boasts fresh floors, furniture, granite countertops, and more. Enjoy the heated pool, fishing pier, and kayak racks. Explore nearby attractions like Honeymoon Island, the Pinellas Trail, and Dunedin’s charming town just 2 miles away. With golf courses, boat tours, and stunning sunsets, Dolphin Point is your ideal retreat. Experience a month of bliss—book now and make sunshine-filled memories now!
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Long Term Stay Snowbird Condo Rental – Clearwater, Florida
A 1 bedroom and 2.5 bath condo is perfect for a snowbird couple looking for a long-term monthly Florida rental. At $30 per night and with a minimum stay of 3 months, that works out to just $900 per month! The high season rate is only $1,995 per month. This gated resort community boasts a community Olympic-sized heated swimming pool with a hot tub, and tennis courts for day or night time use. Right in the heart of Clearwater, parks, dining and the beach are all within your grasp.
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Charming Cottage Retreat – Jupiter, Florida
Step into the charm of historic Jupiter with a stay in this lovingly preserved 20th-century gem. Nestled in the heart of old Jupiter, this 2 bedroom and 1.5 bath home offers a retreat to bygone Florida, just minutes from the Loxahatchee waters and pristine beaches. Enjoy the tranquility of green surroundings and the nostalgic allure of a clean, modernized interior. With spacious rooms, a well-equipped kitchen, and a flourishing garden, it’s the perfect retreat for families, couples, or anyone seeking timeless Florida magic. Fall in love with this enchanting home and its unique neighborhood!
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The Cutest Cottage Snowbird Rental – Gulfport, Florida
Flamingo Cottage, a tropical 1 bedroom, 1 bath getaway in beautiful Gulfport. Leave the daily grind behind and immerse yourself in Old Florida’s charm. Wander amid palm trees and oaks, relax on your private patio, and bring your furry friends to roam the expansive yard. Just a short walk to Gulfport’s beaches, this pet-friendly retreat blends tranquility with world-class dining and vibrant community life. Indulge in a day of beach strolls, gallery visits, and cozy nights in a colorful cottage. Your Gulfport adventure awaits—book now for an enchanting getaway.
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Centrally-Located Condo Rental – Sarasota, Florida
Discover The Meadows, a top-rated neighborhood in the United States. Nestled in 1650 acres of lush greenery, this 1 bedroom and 1 bath, first-floor condo offers a perfect blend of natural beauty and modern convenience. With a breathtaking golf course view from the open kitchen, living room, and screened-in patio, you’ll enjoy a serene lifestyle. Pet-friendly and just 5 miles from downtown Sarasota, this retreat provides access to arts, cultural activities, dining, and more. Uncover the best of Florida living at this unbeatable location!
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Tropical Cottage Getaway – Gulfport, Florida
A tropical 1 bedroom, 1 bath, Fish Camp is the perfect retreat for a snowbird getaway. Surround yourself with lush greenery and soak up the Florida sunshine steps from Gulfport’s art galleries and restaurants. Enjoy the spacious screened porch, featuring floor-to-ceiling windows, where you can sip drinks, play cards, and take in the tropical surroundings. With a well-equipped kitchen, pet-friendly policy, and beach just three blocks away, Fish Camp promises an idyllic stay for two. Experience the charm of downtown Gulfport and create lasting memories in this cozy, well-appointed cottage!
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Pet-Friendly Cottage Rental – Sarasota, Florida
Comfort and convenience in this beautifully decorated 1 bedroom and 1 bath West of the Trail condo. Ideal for long-term travelers, enjoy a full kitchen with granite countertops, stainless steel appliances, and a serene screened-in lanai with garden views. With included utilities, this condo is a hassle-free retreat in an upscale, safe neighborhood close to Downtown Sarasota and a short distance to Siesta Key. Embrace the community pool, gym, and proximity to amenities. Find more pet friendly monthly rentals on FLARBO.
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Boat-Friendly Condo Rental – Punta Gorda, Florida
From $1400 per month, this is a boater and fisherman’s dream! This Punta Gorda condo has two bedrooms and two full baths with spacious rooms, and bathrooms are easily accessible with grab rails. Enjoy the pool and community center where you can gather with friends to watch TV favorites, play cards and participate with others in various activities.
This location boasts a 27 – hole golf course with restaurants, a marina, and a yacht club. Bring your boat and moor it in the marina or store in their dry full-service storage. There is a boat ramp at the marina as well as boat rentals and salt water fishing tours available.
If you are into boating, fishing, golfing relaxing in the sun, enjoying great new friends, then this Gulf coast community is for you.
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Affordable Fort Myers Monthly Rental
Starting at just $1,300 per month this Fort Myers monthly vacation rental is the best bet for budget-minded long term renters and snowbirds. The Heritage Pointe gated community is popular. This home is close to the beaches and hospital. Elevator access is a great choice for people with limited mobility issues. The condo has a master bedroom with a queen bed and a second bedroom with twin beds. Close to the community pool and clubhouse as well as the grilling facilities. Enjoy sunrises over the lake and sunset off the back walkway. Find more snowbird vacation rentals.
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No matter where you choose to stay in Florida, there’s a perfect place to get away from the cold at an affordable price. Whether you’re looking for adventure, fun or just need to unwind, there’s a perfect vacation rental for everyone on Florida Rental By Owners. For your long term trip to Florida, think about booking a vacation rental on a site that will allow you to “Florida monthly vacation rentals”.
If you like this article you might also enjoy our “6 Hot Florida Spots for Endless Summers” article.
Skip the traveler fees that are charged on other large online travel agency platforms like Aribnb, HomeAway, VRBO and Expedia. Reserve your vacation rental on FLARBO – Florida Rental By Owners where there are no booking fees for either traveler or property owners. FLARBO, it’s the best option for Florida travelers.
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You can view all Florida snowbird monthly vacation rental properties here. Get the whole house for a whole lot less!
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