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Florida Snowbird Vacation Rentals

(3307 rentals)

Welcome to Florida, where your month-long getaway awaits! Whether you're a snowbird seeking sunny winters, a family on a seasonal retreat, or a digital nomad in search of a work-friendly stay, Florida offers an extensive range of accommodations. From budget-friendly options to luxury escapes, find your perfect monthly rental today.

Panama City Beach Townhome
Sleeps 6, 2 bedrooms, 1 bathroom
22 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

→ MONTHLY STAYS - Message Us for Great, Long Term Snowbird and Travel Nurse Rental Rates Throughout the Fall and Winter Months!Escape to our bright 2-story townhouse in the heart of Panama City's premier Gulf Highlands resort! This updated two-story townhouse sleeps up to 6. Enjoy a fully...

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$96
avg per night
New
Naples Apartment
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • WiFi

About this property

Enjoy this 3-bedroom, 2-bath condo in The Reserve. This third-floor unit offers a quiet and welcoming atmosphere with access to a resort-style pool, workout facilities, and clubhouse. Just minutes from Naples’ beautiful beaches, Fifth Avenue, and local dining, you’ll find the perfect balance...

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$100
avg per night
Fort Myers Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Pool
  • Rentals by owner
  • WiFi

About this property

This condo is located in the Venetian Palms neighborhood in Beautiful Ft Myers Florida! It is centrally located and within 1o minutes from stores, shops, pharmacies, restaurants, and only 20 minutes to Ft Myers Beach, Sanibel and Captiva Islands, Matlacha Artist Village, RSW Airport, Downtown...

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$77
avg per night
Naples Condo
Sleeps 4, 2 bedrooms, 2 bathrooms
6 reviews

Distance to beach: 5 miles to Naples Pier

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Beautifully decorated and completely turnkey, sunny and bright 2 bedroom/2 bath condo with cathedral ceilings and spacious lanai overlooking lake with lighted water fall. Second floor END unit with your own private garage in a GATED community. Free WI-FI and Cable TV/Infinity, SmartTV/Stream Netflix/Prime/Pandora/FUBO/Spotify...

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Featured review

"A last minute vacation"

We had a rough winter and decided at the last minute to see if we could get a place to stay in Naples. We had never been and it all worked out real well. We really enjoyed the Falling Water’s condo....

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$138
avg per night
Key West House
Sleeps 10, 4 bedrooms, 3 bathrooms
5 reviews

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

The home (also known as Margaux's Hideaway) was built in 1890's, with a farmhouse charm, and porches off of every bedroom. It is light and airy, with gorgeous and comfortable indoor and outdoor living spaces. It's perfect for family gatherings, or just a quiet escape. Each room is sunny...

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Featured review

"The Perfect Home"

I came to this house with friends, completely unsure what to expect from Key West. The island itself moves at this fascinating, slightly calm/chaotic pace, but stepping into this rental felt like entering...

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$777
avg per night

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Marco Island Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
5 reviews

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

Enjoy our gorgeous 10th floor, beachfront Marco Island getaway with Northern exposure. Take in the spectacular views - especially at sunset – from throughout the apartment and from the spacious balcony. You can enjoy stunning views of Tigertail and Hideaway Beaches.Our non-smoking, 2-bedroom,...

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Featured review

"Nice quiet stay"

Great view from balcony.owner is excellent to deal with had an issue and he had it taken care of right away.condo was clean n was a perfect stay.And are rebooking for next year.

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$261
avg per night
The Villages Villa
Sleeps 4, 3 bedrooms, 2 bathrooms

Distance to park: 45 miles to Disney

Key Amenities

  • Air conditioning
  • Pet friendly
  • Pool
  • Rentals by owner
  • WiFi

About this property

Property Details Address: 7664 Rutherford lane The Village of Shady Brook The Villages, FL This is a Brand new fully furnished cottage villa that is the perfect blend of Courtyard villa and cottage home, which allows for creating a personal outdoor oasis. This beautiful spacious closed cottage...

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$127
avg per night
Delray Beach House
Sleeps 8, 4 bedrooms, 4.5 bathrooms
11 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Breathtaking waterfront 4 bedroom / 4.5 bath luxury property is picturesquely located on a deep water canal just 1/2 block from the Intracoastal. This dream home has a resort style waterfront backyard with a pool, jacuzzi, built-in grill, outdoor bar, patio furniture and plenty of seating for relaxing...

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Featured review

"Exceeded our expectations."

Exceeded our expectations. The location is amazing - the beach is on the doorstep! This is a great family-friendly condo with a stunning pool and wonderful hot tub.

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$1,282
avg per night
New
Madeira Beach Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Distance to beach: 0.2 miles to Madeira Beach Public Access

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • Rentals by owner
  • WiFi

About this property

Live on a private six-acre island. Unit 405W is a 2026 ground-up renovation on a gated, 24-hour-secured island at the north end of Treasure Island — you cross your own bridge to get home, with water on every side.THE VIEW. From the fourth floor, the balcony looks out over the canal, John's...

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$147
avg per night
Fort Myers Townhome
Sleeps 7, 3 bedrooms, 2.5 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

A beautiful townhome on a lake filled with water birds. A huge master suite with 2 walk-in closets and 2 other pretty bedrooms with their private bath. A laundry room upstairs and a large upstairs area for exercising or reading. There is a garage and parking for another car in the driveway Sail Harbour...

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Featured review

"Wonderful owner!"

I would like to share with you what a wonderful owner Pat is to work with! Highly recommend her unit!

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$94
avg per night
New
Fort Myers Beach Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to Batiki West 609! Our fully renovated 2BR/2BA condo offers Gulf & Back Bay views + easy island living right in the heart of Fort Myers Beach. Located just STEPS from the beach, and easy walking distance to Times Square, Margaritaville, and all the local favorites! Enjoy our private balcony...

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$297
avg per night
Bonita Springs Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

Experience true beachfront living at Dolphin Way, one of Bonita Beach’s most sought-after Gulf-front communities. This beautifully maintained 2-bedroom, 2-bath residence offers sweeping, unobstructed Gulf views from a desirable third-floor position, allowing for the perfect balance of elevation...

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$229
avg per night
Anna Maria Island Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pool

About this property

PLEASE EXCUSE THE CURRENT PICTURES. We are just finishing the condo and we don't have the bedding or the tvs yet. Just remodeled and ready to go starting February 1st, 2026! Everything you need is here for you. This well appointed condo on Anna Maria is ready for rent! Pack some clothes and come...

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$285
avg per night
Vero Beach House
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Luxury Beachside Retreat • Heated Pool • Walk to Beach • Seasonal Stays Welcome Villa Maris – Your Coastal Winter Retreat on the Barrier IslandNestled in a quiet, lush neighborhood on the barrier island, Villa Maris offers the perfect blend of luxury, comfort, and coastal charm....

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$286
avg per night
Naples Condo
Sleeps 4, 2 bedrooms, 2 bathrooms
3 reviews

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Welcome to Naples' Forest Lakes community! This cozy ground floor level condo is located in a 2-story condo building with swimming pool/club house and 2 tennis court access for our condo residence/guests. This two-bedroom and two-bathroom condo sleeps four people. A parking spot is assigned to the...

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Featured review

"Beautiful Condo"

A beautiful apartment with everything you need for an enjoyable holiday in beautiful Naples. Very close to supermarkets, shops and restaurants. Also Agnes has a provided a-good manual on places to visit...

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$114
avg per night
Punta Gorda Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Relax & Unwind in Our Modern Golf & Sunset View CondoWelcome to your getaway at Heritage Landing! This stylish 4th-floor condo (with elevator access) blends comfort, convenience, and stunning views—perfect for relaxation, golfing, or simply soaking in Florida sunsets.Sleep in ComfortMaster...

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$123
avg per night
Special Offer
Panama City Beach Townhome
Sleeps 6, 2 bedrooms, 1.5 bathrooms
15 reviews

Distance to beach: 100 yards to Front Beach Rd / Gulf Highlands Beach Club

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Gulf Highlands Beach Resort is located near the Beach in a gated community with 24-hour security making for a very safe family friendly complex. The resort offers a private Beach Club and beachside swimming pool directly on beautiful White Sandy Beaches with its own snack bar / restaurant overlooking...

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Featured review

"What a wonderful time"

What a wonderful time I had. This lovely townhouse is perfect for one or your entire family to stay. Situated just a few blocks from the beach and many restaurants and fun places you will thank your lucky...

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$148
avg per night
New
Naples House
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Brand-New Coastal Villa - Seven Shores Luxury Community - Near Naples and Marco IslandPerfect luxury extended stay, snowbird rental, or executive seasonal rental Naples FL. 90-day minimum for refined Seasonal Continuity.Experience ultra-luxury seasonal living in this brand-new 2025 never-lived-in...

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$158
avg per night
Naples House
Sleeps 9, 3 bedrooms, 3 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Naples beach retreat will put a smile on adults and children! Located ONE MILE to Vanderbilt beach this newly updated home has a brand new kitchen fully stocked for any cook to enjoy with brand new appliances and wine fridge. Children of all ages will be delighted with the game room with Pac Man arcade...

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Featured review

"Awesome place!"

Super friendly and helpful hosts, everything you could need for a perfect beach vacation. All the towels, sheets, hot tub, heated pool, beach toys - even the bike tires were fully inflated and ready to...

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$514
avg per night
Destin Condo
Sleeps 6, 1 bedroom, 1.5 bathrooms
34 reviews

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

Please Call Tami to book this newly remodeled, well equipped, clean unit! Sugar white sand and emerald green waters are right outside the door of this lovely oceanfront condo.This ground floor, non-smoking unit walks out to a private tiled patio...

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Featured review

"Beach Front"

Wonderful beach front condo! We enjoyed sitting on the porch and watching the surf. In a short 3 days we saw so much marine life with highlights including a Manatee swimming east, Mobula rays jumping in...

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$263
avg per night
Ponce Inlet House
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Hot tub
  • Private pool
  • WiFi

About this property

Escape to this beautifully furnished 2-bedroom, 2-bathroom condo in the sought-after Harbour Village community. Located on the 4th floor, this spacious unit overlooks the tranquil marsh and Intracoastal Waterway—perfect for enjoying peaceful sunsets and nature views.The primary suite features...

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$116
avg per night
Cape Coral House
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • Rentals by owner
  • WiFi

About this property

SW Cape Coral 3 Beds 2 Bath - Heated Pool and Hot Tub - near Cape Harbour. One of the most popular areas in Cape Coral, as far as vacation homes go, is the SW part of town below Cape Coral Pkwy, and that is where you will find this beautiful home. When renting this home, you rent a piece of this paradise....

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$221
avg per night
Naples Condo
Sleeps 5, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Rentals by owner

About this property

2 Bedroom , 2 bath with a pull out sofa available as a seasonal rental as of April 5th thru the end of 2026. Any month you like, 1 month minimum duration. 2nd Floor Unit.Newly renovated, very clean, near beach with a lot of new upgrades and a Lanai with a beautiful view.10mins to Delnor...

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$91
avg per night
Naples Apartment
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Perfectly located vacation home in the heart of Olde Naples offers a peaceful and private retreat. Available January - April 2026. This highly desirable pet-free boutique building with only 18 units is just a three block walk to the white-sand beaches of the Gulf of Mexico.Fully renovated and decorated...

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$300
avg per night
New Smyrna Beach Condo
Sleeps 4, 2 bedrooms, 2 bathrooms
8 reviews

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

The Inlet at Minorca offers the best panoramic, beachfront views of any condo in New Smyrna Beach. Your breath will be taken away by the incredible view from this spacious 13th floor 2/2 vacation condo, located at the northernmost point of New Smyrna Beach island, adjacent to Smyrna Dunes Park. This...

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Featured review

""Perfect home away from home beach front condo""

Owner was, professional, prompt, and courteous, condo had everything we needed. Will rent again.

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$263
avg per night
Englewood House
Sleeps 8, 3 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • Rentals by owner

About this property

Relax in this bright coastal home with a private solar heated pool (Electric heater for an Additional Fee)and fully fenced yard. ( We have a wifi pool alarm for child safety).This three bedroom retreat also offers a pullout couch, full kitchen and comfortable living space. Located in a quiet Englewood...

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Featured review

"Amazing trip!"

My husband and I decided on a quick trip to the area and found this amazing house and Englewood Florida Home & Vacation rentals! Their customer service was amazing and everything was set up quickly! They...

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$116
avg per night
Anna Maria Island Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

Welcome to Tiffany Place 205 on beautiful Holmes Beach on Anna Maria Island! This spacious 2 bedroom, 2 full bath condo has been totally remodeled in a coastal inspired décor, is meticulously clean and well organized and has everything you need to enjoy your vacation directly on the beach.Tiffany...

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$259
avg per night
Deerfield Beach Condo
Sleeps 4, 1 bedroom, 1 bathroom
13 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • Rentals by owner
  • WiFi

About this property

You will find the best weather in Florida here! Warmest n the winter and coolest in the summer! Unique location in that you can park your car and leave it! Everything including the beach, fishing pier, and 10-12 restaurants are within a 2 minute walk!! Boasts one of the best beaches in Florida and a beautifulmeasured...

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Featured review

"Buccaneer"

What a wonderful place. Clean and so close to the beach! Has everything that you could possibly need!

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$103
avg per night
Big Pine Key House
Sleeps 8, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Discover your own private escape with this beautiful canal-front home, perfectly positioned for those who love nature, boating, and peaceful coastal living. Backcountry & Ocean Access Enjoy direct canal access leading to incredible backcountry waters ideal for kayaking, paddleboarding, and world-class...

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$316
avg per night
Naples House
Sleeps 8, 4 bedrooms, 2 bathrooms
5 reviews

Distance to beach: 1 miles to Vanderbilt Beach

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

500 Block Location!! A TOTAL REMODEL OF THIS HOME HAS JUST BEEN COMPLETED - (all floors, kitchen, baths, doors, closet organizers, etc and pool patio enlarged and freshly painted inside and out) - don't wait to book this home especially in this desirable location. . . . Heated pool, fully fenced...

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Featured review

"We really enjoyed our stay at Last Mango!!!"

We absolutely loved the house, the pool, the bikes, and the location. There was plenty of room for the four of us and the pool was heated just right. We were close to the beach, shopping, and dining. Ellie...

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$252
avg per night
Special Offer
Englewood East Condo
Sleeps 4, 2 bedrooms, 2 bathrooms
1 review

Distance to beach: 3 miles to Boca Grande, Palm Island South, Manasota Key

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

2 Bedroom 2 Bath open floor plan, Lania, Pickleball, Pool and minutes to the Beach!TwoMorrows Treasure: Englewood Charm 2 Bedroom Condo Whether you are looking to explore our beautiful beaches and parks, working up an appetite for the local restaurants or you just want to relax poolside with a cocktail...

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Featured review

"Location, Location, Location"

Spent the Winter (Jan-March 2026) at David’s Condo) We had a Great Time. Owner was very attentive and had great communication with Us. Condo was very well appointed, organized, and perfect for all...

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$97
avg per night
Tavernier House
Sleeps 8, 4 bedrooms, 3 bathrooms

Distance to beach: 4 miles to Founders Park

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to Island Time!This newly constructed canal front residence located in the heart of Plantation Key is sure to help boost your serotonin and ensure complete relaxation. This impressive home can comfortably accommodate eight adults with four bedrooms and three bathrooms.The main living...

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$521
avg per night
Naples Condo
Sleeps 4, 2 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

Located in the Heart of Naples, Beautiful 2 bedroom 2 bath condo, with canal and boat dock availability. The canal leads to the Gordon River, to the bay and eventually the Gulf.The unit is located on second floor of 2 story building. Wi-Fi and cable are include. The condo is located 1 mile to the...

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Featured review

"Excellent vacation experience"

We had an excellent vacation experience at this property. The condo was exactly as depicted and promised. It was a soothing comfortable space to stay with spacious snd spotless rooms that provided adequate...

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$162
avg per night
Englewood Condo
Sleeps 2, 1 bedroom, 1 bathroom
2 reviews

Distance to beach: 1 miles to Manasota Beach

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

**Escape to Paradise in Southwest Florida!**Why use a hotel when you can cook at home and enjoy this beautiful property located just a few short miles from Manasota Key and Venice/Nokomis beaches!Discover the ultimate getaway in this beautifully refurbished 1-bedroom, 1-bath condo, perfectly nestled...

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Featured review

"Quaint Condo - Perfect location"

Great condo! Everything I needed was provided and the king size bed was very comfortable. Very clean; furniture and appliances appear to be new. I liked the location, not far from three different beaches,...

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$133
avg per night
Hollywood Bungalow
Sleeps 8, 4 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Beautifully renovated 4-bedroom, 3-bathroom home located in a quiet, family-friendly neighbourhood. This spacious property features modern finishes throughout, including an updated kitchen and bathrooms, with plenty of natural light.Enjoy the convenience of being just a 3-minute drive to the beach...

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$250
avg per night
Big Pine Key House
Sleeps 13, 5 bedrooms, 4 bathrooms
4 reviews

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Welcome to our 5 bedroom with optional 6th bedroom home, “Reel’em Inn” Big Pine Key, an excellent location for a relaxing vacation with family and friends 31 miles from Key West’s Mile Marker 0. This spacious 5-bedroom home is on a double lot with plenty of parking and 150 feet...

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Featured review

"We love this place!"

We've stayed in this home for a month for 3 years, 2025 being our 4th year we added a month. We stayed in the home before Jeff and Christine bought it and loved it then. They've made so many improvements...

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$400
avg per night
Sarasota Condo
Sleeps 4, 2 bedrooms, 2 bathrooms
6 reviews

Distance to beach: 1 miles to Siesta Key

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

OUR RATES:May-November 2026 2025 $2000 December 2026 $3000 January 2027 $4500 February 2027 $5000 March 2027 $5500 April 2026 $3000*Calendar months only. *Ask for our 6-month plus special rate *Pet Friendly, Community pool and gym boutique-style condominium community that offers:WELCOME...

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Featured review

"Great stay at Oasis on Osprey"

It was a pleasure working with Ana (and her husband). The unit was clean, modernized, and comfortable. The area was very nice, quiet, friendly neighbors and kept clean. Location was good, plenty of restaurants...

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$89
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
15 reviews

Distance to beach: 1 miles to Crescent Beach

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

E91 is a completely renovated, First floor Condo, steps to the pool. Master bedroom has a King bed with on-suite bathroom and walk-in closet. Second bedroom has a Queen bed and twin bunk beds. Fully equipped kitchen provides state-of-the art appliances. There is washer and dryer conveniently by the kitchen. Ammenities...

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Featured review

"Best Condo EVER !!"

The HOST of this unit (E91) was the most prepared HOST of all time. She had every box checked inside the condo to make our stay effortless. The grand-children loved the bunk beds in the second bedroom...

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$183
avg per night
New
Fort Myers Beach Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Pool
  • WiFi

About this property

Enjoy the ultimate beachfront getaway in this beautifully remodeled 5th-floor corner condo, perfectly situated directly on the white sands of Fort Myers Beach along Estero Boulevard. Wake up to the soothing sound of the waves, then relax on your private lanai overlooking the lush, beautifully landscaped...

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$386
avg per night
New
Naples House
Sleeps 6, 3 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • WiFi

About this property

Modern 3-Bedroom Home with Private Pool in Naples, FLThis private single-level home in a quiet Naples neighborhood was completely remodeled in 2024 with modern design and luxury Arhaus furnishings. Featuring a private heated pool, hot tub, and lush landscaped yard, it’s perfect for guests seeking...

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$443
avg per night
Key Largo Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
5 reviews

Distance to beach: 3 miles to John Pennekamp State Park

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

Enjoy the panoramic view this tropically decorated, fifth-story unit has to offer of the Atlantic Ocean and the adjacent Wildlife Sanctuary. The unit affords its guests the spectacular sunsets the Florida Keys are famous for, right from your balcony and living room.Kawama Yacht Club is situated at...

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Featured review

"Boys week"

Great atmosphere, two minutes to the Atlantic. Jose great host, very clean. Thank you Jose for sharing your home.

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$244
avg per night
Sarasota Condo
Sleeps 4, 1 bedroom, 1 bathroom
6 reviews

Distance to beach: 2 miles to Siesta Key beach

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

OUR RATES:May -November $1999 December $3000 January $4200 February-March $4500 April $2500*Calendar months only. *Pet Friendly, Private Yard, First Floor Unit. *Community pool and gym in Complex. *Ask for our 6-month plus special rate *Boutique-style condominium community that offers:WELCOME...

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Featured review

"1 Bed/1 Bath Oasis on Osprey"

We stayed here for a clinical rotation from July - October at the Oasis on Osprey. It was truly a wonderful experience. Ana was always so helpful and attentive whenever we needed something. The area surrounding...

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$80
avg per night
Marathon House
Sleeps 10, 4 bedrooms, 4 bathrooms
5 reviews

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Villa Sombrero – Private Waterfront Living with Sunset Views in the Florida KeysVilla Sombrero is a peaceful waterfront retreat overlooking Boot Key Harbor, offering breathtaking sunsets to the west and refreshing island breezes flowing in from the east through Sisters Creek. A natural waterway...

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Featured review

"Nice comfortable place..... Quiet except for construction work going on across the street."

It's the little things...... We had to call concerning changing the water filter on the refrigerator. The pool needed water added so that the filter and heater would work. The strainer was full of debris.......

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$640
avg per night
Punta Gorda Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
1 review

Distance to beach: 42 miles to Manasota Key Beach

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

This exceptional, highly sought-after Arabella II floorplan is a beautifully furnished end-unit condo offering the ultimate in comfort and style! It is the largest floorplan of the Verandas at 1569 sqft. Enjoy spacious living with vaulted ceilings and an abundance of natural light. This exquisite floorplan...

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Featured review

"Relax & Unwind in This Beautiful Punta Gorda Condo with sunrise view"

Perfect getaway we had such a relaxing stay. The sunrise views were incredible each morning. The decor is excellent and the space was so peaceful and relaxing. Amazing host, super responsive and easy to...

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$148
avg per night
Fort Myers Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Distance to beach: 4 miles to Sanibel Island

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Property Overview - Another piece of paradise in sought after Punta Rassa. Open concept, completely remodeled in 2026, master bath, guest bath, and kitchen, new tile throughout the unit, new electric and water lines, newer appliances. Raised panel doors, all windows have impact glass. The lanai with the...

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$250
avg per night
Matlacha House
Sleeps 5, 2 bedrooms, 1.5 bathrooms

Key Amenities

  • Air conditioning
  • WiFi

About this property

Two Bedroom, 1 1/2 bath house on Matlacha Island in a quiet neighborhood. Fully furnished with an outside shower house and a boat dock. Each bedroom has a TV. Cable and Internet are provided. House is on the water with direct access to the Gulf. Located within walking distance from eating and drinking...

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$200
avg per night
Plantation Key House
Sleeps 8, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Oceanfront
  • Pet friendly
  • Private pool
  • WiFi

About this property

Property #27839 - silverEscape to your own Keys hideaway with cozy island‑inspired home, coastal décor and a bright open living/kitchen area that flows onto a huge screened terrace. Relax in your own private pool, tiki hut-gazebo, shaded lounge areas and serene canal views, perfect for lazy mornings,...

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$400
avg per night
Cape Coral Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
5 reviews

Distance to beach: 2 miles to Cape Coral

Key Amenities

  • Air conditioning
  • Pet friendly
  • Pool
  • Rentals by owner
  • WiFi

About this property

Beautiful 2/2 First Floor, Waterfront, offering lots of privacy being an end unit, Located in Southeast Cape Coral, near downtown, and just 5 minutes from Yacht Club Beach. 20 minutes to the beaches of Fort Myers and Sanibel Island! Smaller, Pet friendly community. Covered Parking just steps outside...

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Featured review

"A home away from home"

Location We stay at the Condo for the Roy Hobbs World Series and it is quick and easy to get to Terry Park. the Twins Complex and Fenway South etc Cape Coral has a small beach on the river and Fort Myers...

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$129
avg per night
Special Offer
Naples Condo
Sleeps 6, 3 bedrooms, 2 bathrooms
4 reviews

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Beautiful Fully Renovated Condo in Gated Emerald Lakes Community Spacious 3-bedroom, 2-bathroom corner unit available:Seasonal or annual lease starting 7/15/2026.This beautifully updated condo features an open-concept floor plan with an enclosed lanai that extends the living space — perfect...

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Featured review

"Exceptional Condo and Owners"

We rented this condo for three months. It was beautiful and had every thing we needed. We have been seasonal renters for many years and this was at the top. We loved the location in North Naples. It was...

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$116
avg per night
Islamorada Condo
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

Welcome to Mother Ocean!This stunning ocean view condo boasts three bedrooms and two full bathrooms, making it perfect for a family or group of friends. It features modern amenities and coastal decor throughout, providing a comfortable and inviting atmosphere for your stay. The spacious living room...

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$417
avg per night
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FAQ

Cost & Budgeting

What are the most affordable cities in Florida for winter rentals?

Storage Cafe reports that Venice, Vero Beach, Fort Pierce, Naples, Fort Myers, Tarpon Springs, and Clermont are among the most affordable cities for winter rentals. These cities offer a variety of winter rentals in Florida for under $3,000 a month.

Are utilities typically included in monthly winter rentals in Florida?

Yes. Essential utilities such as air conditioning, heating, and Wi-Fi are listed under Amenities in a rental’s description.

How can I find hidden fees or extra costs associated with winter rentals?

Scroll through the property’s description to find the Fees section to find cleaning costs, management fees, resort fees, etc.

What is the average cost of a winter rental in popular Florida destinations like The Villages, Naples, or Siesta Key?

According to Zillow, the average cost of a winter rental in The Villages is $2400, and in Naples it’s $5000. In Siesta Key, the average cost of a winter rental is $7000.

Location & Lifestyle

Which Florida coast (Gulf or Atlantic) is better for affordable winter rentals?

Florida’s Gulf Coast is the more affordable option for winter rentals.

What are some of the best small towns in Florida for snowbirds on a budget?

Titusville, Melbourne Beach, Ponce Inlet, and Sebring are just a few of the best small communities in the Sunshine State for snowbirds on a budget.

What are the pros and cons of renting in a 55+ community for the winter?

One pro is that you have a gathering of potential friends close by. Also, many of these communities offer access to a clubhouse and exercise facilities as well as provide regular lawn maintenance. One downside is that most of these communities have a lot of rules to remember. Plus, the advertised features and services often come with extra fees to cover the costs.

What are some popular activities and attractions for winter visitors in Florida?

The Jacksonville Zoo hosts a Zoo Lights event in December. The Naples National Art Fair in February showcases a variety of artwork. The Marie Selby Botanical Gardens in Sarasota is a big draw for visitors in the wintertime. Fort Myers has 18-hole golf courses open to golfing enthusiasts year-round.

Logistics & Planning

When is the best time to book a snowbird rental in Florida for the best rates and availability?

It’s best to book a snowbird rental at least six months ahead of time. Booking six months ahead of peak snowbird season (October through April) allows you a larger selection of housing options while rental rates are still relatively low.

What are the typical lease terms for snowbird rentals in Florida (e.g., monthly, 3-month, 6-month)?

Typically, snowbird rentals in Florida have monthly lease terms. But some owners offer discounted rates if you agree to lease for a longer period of time.

What documents do I need to provide when applying for a snowbird rental?

When applying for a rental, you need your identification (driver’s license), social security number, contact information, proof of income, and personal references.

How far in advance should I start my search for a snowbird rental?

It’s wise to start your search one year ahead of time to take advantage of the largest number of options.

Accommodation & Amenities

What are the essential amenities to look for in a snowbird rental in Florida?

Some of the essential amenities to look for include air conditioning, heating, fast Wi-Fi, cable/satellite, parking, a washer/dryer, and a kitchen stocked with appliances and dishes.

How can I find fully furnished snowbird rentals in Florida?

Including the keywords “fully furnished” in your online search is an easy way to find these types of rental properties.

What are the differences between renting a condo, a single-family home, or a villa for the winter?

A furnished condo with multiple amenities is an affordable option for social snowbirds who want neighbors nearby. A furnished single-family home may not have the same types of amenities as a condo, but it offers more privacy. Villas offer much more luxurious surroundings than a condo or a single-family home. But villas are the least affordable of the three housing options.

Are there communities specifically designed for snowbirds in Florida?

Yes, there are communities specifically designed to meet the expectations of snowbirds in Florida.

General Information

What is the "high season" for winter rentals in Florida, and how does it affect pricing?

The high season for Florida winter rentals runs from October through April. During this time, rental rates are higher than in less busy times of the year.

What are some of the most popular destinations in Florida for winter rentals?

Fort Lauderdale, Orlando, Miami, St. Petersburg, and Boca Raton are some of the most popular destinations for Florida winter rentals.

What is the "high season" for winter rentals in Florida, and how does it affect pricing?

The high season for Florida winter rentals runs from October through April. During this time, rental rates are higher than in less busy times of the year.

What are some of the most popular destinations in Florida for winter rentals?

Fort Lauderdale, Orlando, Miami, St. Petersburg, and Boca Raton are some of the most popular destinations for Florida winter rentals.

What should I know about Florida's climate and weather during the winter months?

Florida has mild winters with very little rain. The high temperatures are between 60 and 70 degrees Fahrenheit, while the low temperatures sometimes fall to around 40 degrees.

What are the advantages of a winter rental in the Florida Panhandle versus South Florida?

The Florida Panhandle is more affordable than South Florida. Also, the beaches in the Panhandle are less crowded, and the atmosphere has more of a laid-back vibe than South Florida.

Finding & Booking

What are the most reliable websites and resources for finding winter rentals in Florida?

Vrbo, Florida Rental by Owners (FLARBO), and, of course, Florida Rentals are three reliable resources for locating winter rentals.

How can I avoid rental scams when looking for winter accommodation in Florida?

According to the FTC, you should be suspicious of a rental with extraordinary amenities that’s available at a very low rate. An owner who pushes you for a fast decision or asks for payment via a gift card or wire transfer is another red flag.

What are some tips for negotiating the price of a winter rental?

Research the rental rates of condos or homes in the surrounding area so you have an idea of what other property owners are charging. Express interest in renting for three months or more. The owner may agree to lower the rent in exchange for a long-term booking.

What are the cancellation policies for most winter rentals?

Generally, if you cancel less than 60 days before your scheduled arrival, you’re likely to lose your rental fee. Trip cancellation insurance can give you peace of mind if circumstances change.

Flexibility & Short-Term Stays

Can I find month-to-month rentals in Florida, or do I need to commit to a longer-term lease?

Month-to-month rentals and long-term leases are both available in Florida.

What are the pros and cons of a monthly rental versus a traditional annual lease in Florida?

One of the pros of monthly rentals in Florida is that you can try out different places before making a long-term commitment. Also, if you have to return home, you aren’t locked in a year-long lease. A downside of renting month-to-month is that someone else may book the property before you let the owner know you’d like to stay.

Are monthly rentals available in all parts of Florida, or are they more common in tourist areas?

Monthly rentals are available in all parts of Florida, but are especially common in tourist areas to accommodate people on different travel schedules.

How does the cost of a monthly rental compare to a weekly or nightly rental in Florida?

In many cases, going with a monthly rental is more affordable than shorter-term options.

For Different Needs

How can I find monthly rentals that are suitable for business travelers or digital nomads in Florida?

When looking for a monthly rental in Florida, include the keywords “business travelers” or “digital nomads” to narrow the search.

Are there monthly rentals available near major hospitals or medical centers in Florida?

Yes, there are monthly rentals located near medical facilities in Florida.

What are some options for temporary housing in Florida while relocating or searching for a permanent home?

Renting a condo on a month-to-month basis is one option if you need temporary housing. An Airbnb is another option when you’re in-between permanent addresses.

Can I find monthly rentals that include services like housekeeping or laundry?

You may be able to arrange for housekeeping or laundry services depending on the amenities offered by the property owner. Many monthly rentals in Florida include the use of a washer and dryer.