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Florida Snowbird Vacation Rentals

(3348 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.

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

At Kelly Greens you will have private access to outdoor pool and hot tub and enjoy access to tennis court. Kelly Greens community has 5 miles of private, lighted sidewalks with benches along the way and streets for walking, jogging or biking along with many clubs and activities (water aerobics, yoga,...

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$67
avg per night
Punta Gorda Condo
Sleeps 5, 2 bedrooms, 2 bathrooms

Key Amenities

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

About this property

Where Relaxation Meets Paradise! Welcome to your serene escape in beautiful Heritage Landing, Punta Gorda, Florida! Our Tropical Sunset Oasis is perfect for families or friends seeking a relaxing retreat in a picturesque setting.Property Highlights: 2 Bedrooms, 2 Bathrooms: Spacious and comfortable...

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$74
avg per night
Miramar Beach House
Sleeps 7, 2 bedrooms, 2.5 bathrooms
1 review

Key Amenities

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

About this property

⭐ TOP LOCATION! 5-Min WALK to Miramar BEACH ⭐ FREE BEACH GEAR – 6 chairs, tent, umbrella, wagon & toys; 2 bicycles ⭐ PET-FRIENDLY – Fenced yard, one of the largest in the complex ⭐ Sparkling POOL for Family Fun & Relaxation ⭐ Fully Equipped KITCHEN with Everything You...

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Featured review

"Perfect for Family and Pets!"

We had a wonderful Spring Break stay at this townhome. The location is fantastic—just a five‑minute walk to the beach—and the home itself is extremely well‑appointed. The kitchen was fully stocked...

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$327
avg per night
Islamorada House
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • WiFi

About this property

Mile Marker 74 – Bayfront – Beachfront – Handicap Assessable – Dockage for 30′ boatThis amazing beachfront home is a must see! Located on one of the few white sand beaches in the Florida Keys, Gulfview is a private home located on Lower Matecumbe Key in Islamorada in...

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$433
avg per night
Bonita Springs House
Sleeps 6, 3 bedrooms, 2 bathrooms
1 review

Key Amenities

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

About this property

A beautiful detached home in a gated golf course community with 24/7 security.Wonderful community filled with welcoming neighbours.Hunters Ridge has a large community pool including golf privileges, tennis courts, pickleball, bocce ball, walking and bike trails.Community events and a restaurant...

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Featured review

"Hunters Ridge"

Great location and very nice property. Gated and nice amenities, good location overall for community and this rental. Walking distance to pool and clubhouse.Nice layout, with primary suite separated...

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$118
avg per night

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Fort Myers Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Distance to beach: 5 miles to Fort Myers

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

Modern two bed, two bath condo in a private, and gated community. This property features many amenities, including a spacious community pool, fully equipped fitness center, picnic area with grills, a clubhouse that hosts endless activities, and walking path surrounding a private lake. Close to everything...

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$68
avg per night
New
Fort Myers Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Distance to beach: 1 miles to Bunche Beach

Key Amenities

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

About this property

Welcome to this spacious and professionally designed first-floor condo (1,674 sq. ft.) located in the sought-after Sanibel View gated community. Thoughtfully updated and beautifully furnished, this 2-bedroom + den residence lives like a 3-bedroom and offers the perfect blend of comfort, style, and location. The...

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$93
avg per night
Orlando Condo
Sleeps 5, 3 bedrooms, 2 bathrooms
14 reviews

Distance to park: 20 miles to Disney World

Key Amenities

  • Air conditioning
  • Rentals by owner

About this property

Preferred Jupiter Equestrian family community is a way of life that isn’t available anywhere else. It is common to see residence riding horses or driving a golf cart alongside the road. The community offers space and tranquility, Sidewalks, Nature Trails, Wildlife, Hiking, Biking, Playground, Country...

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Featured review

"Great house"

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. Ben (the owner) even let our dog stay. We'll visit again!

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Naples Apartment
Sleeps 4, 2 bedrooms, 2 bathrooms
3 reviews

Distance to beach: 4 miles to Vanderbilt Beach

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Our property is a newly renovated 2-bedroom, and 2-bathroom unit located on the first floor of Cypress Woods Golf & Country Club. Cypress Woods is a hidden gem in North Naples offering a Golf course with narrow fairways and challenging greens, plus a dining room and banquet facility. There are two...

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Featured review

"Outstanding Condo – Truly a Gem"

This condo was the perfect place to unwind and enjoy everything the Naples area has to offer. The space feels calm, fresh, and very intentionally put together—nothing cluttered, nothing overlooked. It...

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$100
avg per night
Bonita Springs Condo
Sleeps 5, 2 bedrooms, 2 bathrooms
2 reviews

Distance to beach: 1 miles to Barefoot Beach

Key Amenities

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

About this property

Bonita Village is a luxury gated condominium community located in beautiful Bonita Springs, Florida just minutes from some of the best beaches in the world. With both our large Resort Pool and tranquil Quiet Pool, relaxation is all but guaranteed! Fancy a workout? Our Island House Clubhouse offers a state-of-the-art...

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Featured review

"Perfect Atmosphere"

Spent two weeks in Bonita Village condo and didn’t want to leave. Friendly guests, owners and staff made us feel welcome. Pool and bar plus 5 minute shuttle service to Barefoot Beach make this an ideal...

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$210
avg per night
Bonita Springs Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Pool
  • WiFi

About this property

Heated Pool - All Season! The Best of Both Worlds - North Naples and Beautiful Bonita Springs Enjoy your morning coffee overlooking the peaceful lake view, in a prime spot right on the border of these 2 Coastal Paradises Just minutes from Barefoot and Vanderbilt Beaches, this condo is in the quiet,...

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$134
avg per night
Longboat Key House
Sleeps 6, 3 bedrooms, 2.5 bathrooms

Distance to beach: 0.5 miles to Longboat

Key Amenities

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

About this property

Completely renovated Island home located 4 houses off Tarawitt point on a large 90x125ft lot. Coveted lifestyle and location on a deep water canal in the heart of Longboat Key. This waterfront home has 125ft of seawall docking for a boat up to 30 ft. boat plus a jet ski lift and room for other water toys....

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Naples House
Sleeps 8, 4 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

The Three Palms is a unique courtyard style pool home with all of the amenities you would expect from new construction. Courtyard style pool home features 4 bedrooms and 3 baths. Reclaimed heart pine floors throughout. Gourmet kitchen features oversized Island, 48" Sub zero fridge and Wolf 6 burner...

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$843
avg per night
Panama City Beach Condo
Sleeps 8, 4 bedrooms, 3 bathrooms

Key Amenities

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

About this property

This is beachfront luxury at its finest! This 4-bedroom, 3-bathroom Ocean Reef condominium on the 8th floor offers over 1,500 square feet of coastal living space. The fully equipped kitchen features granite countertops and stainless-steel appliances. The living room offers ample, comfortable seating,...

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$375
avg per night
Summerland Key House
Sleeps 6, 3 bedrooms, 2 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

This home is the ideal getaway for the whole family! The interior of the home is super spacious with an updated kitchen that looks out over the canal and large pool.There are three bedrooms, two bathrooms, and a large family area with a big screen television for your entertainment. Not to be outdone,...

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Featured review

"Outstanding location for fishing, boating, & diving!"

Stayed at this gem before and after Lobster mini season. The pool was perfectly refreshing after a day in the sun on the water. There are several free boat ramps nearby. Great proximity to the Looe key...

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$289
avg per night
Davenport Villa
Sleeps 10, 5 bedrooms, 5 bathrooms
6 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Enjoy beautiful Florida sunsets at this west facing pool and spa villa and grillWelcome to our beautiful 5 Bed, 5 Bath, West Facing Pool Villa located in the quiet gated community of VistaPark. Only 15 mins from Disney, 5 mins to great Shops and Restaurants.This home has all the necessary amenities...

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Featured review

"Feb. Vacation"

Only a few things were not up to par but not enough of a problem to stop us from renting again. Hope to stay again next year.

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$228
avg per night
Daytona Beach Shores Condo
Sleeps 8, 3 bedrooms, 3 bathrooms
4 reviews

Key Amenities

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

About this property

Vacationers and Snowbirds, welcome to the luxury condominium located on the 9th floor of Towers Grande. Located right on the beach this condo is complete with 3 bedrooms and 3 full bathrooms, one for each bedroom. Master Bedroom w/queen bed. 2nd bedroom w/Queen Bed. Third bedroom twin bed/trundle that...

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Featured review

"Absolutely Fabulous"

I cannot say enough about how wonderful this property is. We looked all over FL, but were so surprised to find Smy and Shane. They were so helpful and extremely accommodating, from booking through to the...

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$199
avg per night
Fort Lauderdale House
Sleeps 10, 4 bedrooms, 3 bathrooms
3 reviews

Distance to beach: 9 miles to Hollywood Beach

Key Amenities

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

About this property

**Calendar & Rates are updated** See complete availability and book direct at Use code FLORIDA10 for an additional 10% off our lowest direct booking ratesIdeal for Short & Long-Term Stays – Comfort, Luxury & Convenience Await You! Sleeps up to 12 Our luxurious 4-bedroom villa...

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Featured review

"Family friendly home"

We recently stayed here, we were in town for a volleyball tournament at Broward convention center. It was a quick 25 min commute away. This house was in a quiet neighborhood but just mins away from shopping...

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$591
avg per night
Miami Beach Condo
Sleeps 4, 2 bedrooms, 2 bathrooms
14 reviews

Distance to beach: 50 feet to Miami Beach

Key Amenities

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

About this property

Beautifully renovated and stylishly furnished direct oceanfront apartment on the 6th floor of the Pavilion, located on Miami Beach's Millionaire's Row. An artfully decorated and air conditioned apartment, available for monthly or seasonal rentals (sorry, no nightly or one-week rentals). Apartment...

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Featured review

"All about the view"

As soon as you walk into the apartment you are taken in by the view onto the beach and ocean. The view is visible from the entire apartment and is all I needed to be happy every day. Sitting out on the...

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$250
avg per night
Big Torch Key House
Sleeps 14, 3 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Oceanfront
  • Pet friendly
  • Pool
  • WiFi

About this property

Welcome to Barefoot Retreat, where you will feel as though you are on your own private island! As you drive through the remote, lush tropical island road to access the estate, drive slow as you might be greeted by the quite friendly protected Key Deer, roaming free about the property.As you approach...

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$833
avg per night
Rotonda West House
Sleeps 5, 3 bedrooms, 2 bathrooms
16 reviews

Distance to beach: 8 miles to Englewood Beach

Key Amenities

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

About this property

*Availability: June-October 2024 (Please check the calendar for available weeks.)This spacious, bright, and open living concept, pool home affords plenty of privacy and lots of room for both you and your guests. Vaulted ceilings in the large living room, recessed lighting in the kitchen, and seamless...

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Featured review

"Winter retreat"

The few issues that came up were immediately addressed. We enjoyed your property and look forward to staying there next year

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$100
avg per night
Nokomis Townhome
Sleeps 6, 3 bedrooms, 2.5 bathrooms
2 reviews

Distance to beach: 2 miles to Nokomis Beach

Key Amenities

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

About this property

Brand new luxury Townhouse available for annual or short term rental. This is a 3 bedroom 2,5 bathroom unit with lake view, one car garage and a private driveway. All bedrooms on the second floor are carpeted and have access to the laundry closet. The living are and the kitchen feature ceramic tile...

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Featured review

"Beautiful home in upscale community"

We stayed in this home for 3 months this past winter. It is a very roomy house with a nice screened lanai and large garage. We used the pickleball courts and pool almost everyday when we were not biking...

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$120
avg per night
Special Offer
Naples Condo
Sleeps 7, 2 bedrooms, 2 bathrooms
2 reviews

Distance to beach: 3 miles to The Naples Beach and Pier

Key Amenities

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

About this property

This is a top floor condo with soaring cathedral ceilings and some of the best views in the community. The cathedral ceilings in the living room, dining room, sitting room and kitchen add a lot to the feeling of openness you get when you walk through the door. You will love the wide open views from your...

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Featured review

"Home Away From Home!"

We had a wonderful 3-month stay in this ideally located, quiet, 3rd floor condo that overlooks a 7th green and beautiful water view. The accommodation is very clean, has a well-equipped kitchen, and new...

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$121
avg per night
Big Pine Key House
Sleeps 4, 2 bedrooms, 1 bathroom
1 review

Key Amenities

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

About this property

Welcome to Kokomo Palms – Your Island Escape!Discover the perfect slice of paradise at Kokomo Palms, a charming 2-bedroom, 1-bath vacation home nestled in Big Pine Key. Located in a peaceful canal-front neighborhood, this getaway offers everything you need for a relaxing and adventurous stay....

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Featured review

"The Keys have never been better!"

We had a great time - the rental was terrific! Best clostet space we've ever encoutered. Clean laundry set. Accomadotions were top shelf all around. Nicely seculed & quiet location. And we saw Key deer...

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$107
avg per night
New Smyrna Beach Condo
Sleeps 6, 3 bedrooms, 2 bathrooms
20 reviews

Key Amenities

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

About this property

This condo is your vacation home away from home located in New Smyrna Beach a beautiful ,quaint and peaceful seaside community . Stay at this beautiful contemporary large 3/2 resort style, family friendly condo. Located just across the street from the beautiful New Smyrna NO-Drive portion of the beach...

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Featured review

"Fantastic Ocean Walk Condo – Clean, Comfortable, and Perfectly Located"

We had a fantastic stay at this beautiful condo in Ocean Walk (Building 11, Unit 305) in New Smyrna Beach. The unit was spotless, spacious, and extremely comfortable—perfect for relaxing after a day at...

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$144
avg per night
Last Minute Deal
Panama City Beach Condo
Sleeps 5, 1 bedroom, 2 bathrooms
79 reviews

Key Amenities

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

About this property

The condo accommodates 5 comfortably with 1 bedroom, bunk area, queen sleeper sofa and 2 full baths.Den & bedroom furniture were won on “The Price Is Right” game show!Amenities Fully equipped kitchen-from cookware to corkscrew Linens and Towels provided Hairdryers in each...

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Featured review

"Wonderful relaxing stay"

Place was comfortable and has fantastic beach view and access. The owner is a pleasure to work with as well! We will certainly re-book if we find ourselves in PCB again.

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$243
avg per night
Marathon House
Sleeps 8, 3 bedrooms, 3.5 bathrooms
1 review

Distance to beach: 2 miles to Sombrero

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

Start planning your perfect escape to the Florida Keys! Flamingo Palms Cottage is ideally located on a deep-water canal with 35’ of dockage and easy access to world-class fishing in the Atlantic and the Gulf. Enjoy all the amenities needed for a perfect island vacation: airy open living areas, cozy...

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Featured review

"Blue Ocean Bungalow"

The home was very comfortable, and clean, it was so nice to look out the windows and see the water. Everything you need for cooking in is provided as far as dishes and pots and pans. Also, the Canopy...

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$339
avg per night
Key Colony Beach House
Sleeps 6, 3 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to Reel Therapy, a beautifully updated three-bedroom, three-bathroom ground-level half duplex located on the tranquil side of 9th Street. The spacious bedrooms include a master suite with a king-size bed, a queen bed in the second bedroom, and two doubles in the third bedroom. Entertainment is...

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$371
avg per night
Babcock Ranch Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Distance to beach: 30 miles to Fort Myers Beach

Key Amenities

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

About this property

Welcome to this cool condo in Babcock Ranch. This terrific rental features 2 bedrooms, 2 bathrooms, and a range of convenient amenities like a fitness room, AC, Golf and WiFi. Guests can unwind in the tranquil atmosphere of this property, whether they're lounging in the cozy living space or taking...

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$67
avg per night
Fort Lauderdale Condo
Sleeps 3, 1 bedroom, 1 bathroom
1 review

Distance to beach: 500 yards to Sunrise Ft Lauderdale Beach

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Amazing LOCATION; 1074sq Ft CONDO building near EVERYTHING, SUNRISE BEACH (10 min walk). Publix (30 sec walk , Galleria mall (1 min walk) , Beach is 10 min walk , Resturants , Seasons 52, PF Chang’s, Capital Grill, are 3 min walk. Condo was completely renovated a couple years ago with new...

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Featured review

"Awesome place to stay"

My husband & I so enjoyed staying here for our vacation. I think my favorite thing is how close it is to the beach. Just a few minutes walk & BOOM there you are. We took many walks along the beach &...

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$82
avg per night
Key West House
Sleeps 8, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Oceanfront
  • Pet friendly
  • WiFi

About this property

The welcoming views at Coral Cove are waiting for you! This brand new two-bedroom, two-bathroom home is located on the open water and canal on Saddlebunch Key, just a stone’s throw from the famous “Baby’s Coffee.” You’re at Milemarker 15 and Key West is just minutes away!This...

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$150
avg per night
Islamorada House
Sleeps 10, 3 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • WiFi

About this property

This quaint Keys-style home offers timeless charm in a premier waterfront setting on an ocean-access canal. The open-concept living, kitchen, and dining area flows effortlessly through the terrace to the backyard, where a private dock invites boating and fishing, and an outdoor bar and dining area offer...

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$436
avg per night
Last Minute Deal
Fort Myers Beach Condo
Sleeps 6, 3 bedrooms, 2 bathrooms
10 reviews

Key Amenities

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

About this property

Fabulous newly renovated end unit condo featuring 3 Bedrooms, 2 Bathrooms, and a full view of the marina from an enclosed lanai. Condo is equipped with a king bed, queen bed, and 2 twins, so there is no need for your guests to sleep on a sofa! Condo has new flat screen tv's (living room and master...

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Featured review

"Beautiful!"

This unit and the property are beautiful! Everything went smoothly during our stay. The property was clean and well maintained. We will definitely consider returning to this complex and specifically this...

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$171
avg per night
Fort Pierce House
Sleeps 6, 3 bedrooms, 2.5 bathrooms

Distance to beach: 0.2 miles to Private Beach at Ocean Village

Key Amenities

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

About this property

2026 Season Rental - Prime Golf Course Location Experience the ultimate Florida getaway in this meticulously maintained private home Nestled on the 3rd hole of Ocean Village's picturesque golf course and just a 3-minute stroll to pristine white sands, this spectacular privately owned residence offers...

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Delray Beach Apartment
Sleeps 3, 1 bedroom, 1 bathroom

Key Amenities

  • Air conditioning
  • WiFi

About this property

Walk to everything, steps to the avenue. Beautiful downtown Delray Beach, Fl. The most popular downtown. beach on the east coast. The main street is lined with restaurants, bars, trendy shops, and crowds. Fun and excitement for every age. Only steps to the heart of all the action. No smokers, no pets,...

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$67
avg per night
Kissimmee Apartment
Sleeps 5, 2 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

2bd/2ba with the Best View in the amazing community of Storey Lake. Located 10 minutes from Disney Come in and enjoy a unique experience. There is a beautiful waterpark in the community center for you to enjoy. It is the perfect place to relax, have a good time and enjoy all that Orlando has to offer. This...

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Featured review

"2024 vacation"

The house was lovely.. lots of room, clean, bright The resort pool was absolutely beautiful.. my grandson loved his time in the pool .. lot of room to sit around and food at the pool area was really good

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$145
avg per night
Key West House
Sleeps 6, 3 bedrooms, 3.5 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner

About this property

A phrase the locals use quite often here in Key West is that we are "Living the Dream" - if you come and spend some time here you will see why! Steps away from the Key West Seaport and just a few blocks from world famous Duval Street this property is located on Eaton Street in Old Town Key...

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$500
avg per night
Marco Island Condo
Sleeps 4, 2 bedrooms, 3 bathrooms

Distance to beach: 1 miles to South Beach

Key Amenities

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

About this property

Escape to Marco Island in this updated 2-bedroom, 3-bathroom townhouse-style bright beautiful renovated condo. Located on the desirable south end, just steps from South Beach, this 1,075 sq. ft. two-story condo is part of Huron Cove, a quiet 10-unit community with a heated pool, boat docks, and canal...

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$209
avg per night
Hollywood Condo
Sleeps 6, 2 bedrooms, 1.5 bathrooms
5 reviews

Key Amenities

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

About this property

*** NEWLY REMODELED AND PROFESSIONALLY DECORATED DIRECT OCEANFRONT UNIT ***Relax and leave all your worries behind! You won't be disappointed in this spacious and tastefully decorated, fully furnished, 2 bedroom, 1.5 bathroom condo on the 7th floor. This ample unit is 1,236 square feet and has...

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Featured review

"Fantastic condo"

The condo has everything that you need and the view is fantastic. The beach and pool area is clean and very nice. We enjoyed our stay here very much

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$258
avg per night
Special Offer
Anna Maria Island Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
14 reviews

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Private pool
  • WiFi

About this property

Welcome to Cheerful Oasis – Your Bay-to-Beach Escape!Discover the ultimate island retreat at Cheerful Oasis, a delightful 2-bedroom, 2-bathroom condo perfectly situated for your next getaway. Nestled just off the walking trail to the Marina, Bridge Street, and Bradenton Beach, this serene haven...

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$227
avg per night
Estero House
Sleeps 6, 3 bedrooms, 2 bathrooms
1 review

Distance to beach: 14 miles to Barefoot Beach preserve

Key Amenities

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

About this property

Come stay in this private home on the lovely Stoney brook golf course. The property boasts a beautiful pool and lanai and is perfect for soaking up the sun. We are a close drive to several local shopping malls as well as the main beaches of Bonita springs. The home is located in Stoney Brook of Estero...

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Featured review

"Great stay!"

We really enjoyed our time in the house! It has all the amenities you need. The children especially loved the pool, where they spent hours. The landlady is very nice, helpful and answers questions immediately....

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$181
avg per night
Longboat Key Condo
Sleeps 5, 2 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Pet friendly
  • Private pool

About this property

NEW LISTING! Welcome to Bay Dream Believer, your luxurious bayfront escape on beautiful Longboat Key! This bright and beautifully upgraded condo offers breathtaking views of Sarasota Bay through massive picture windows and an enclosed patio that lets you soak in the scenery year-round. Located just across...

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Featured review

"Lovely views, great location"

Great location on Longboat Key…out of the crowds with great beaches. Windward Bay where this is located, is a lovely larger condominium community with excellent amenities. The pickleball group is awesome....

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$209
avg per night
Fort Myers Villa
Sleeps 4, 2 bedrooms, 2 bathrooms
1 review

Distance to beach: 20 miles to Ft. Myers, Beaches of Sanibel Isle, Bonita Beach

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

This Beautiful Resort Style Villa is waiting for you! The villa is fully equipped and ready for you to move right in. Inside, guests find a beautiful space featuring a gathering room, dining area, full kitchen, 2 bedrooms with one king bed and one queen bed, perfect for a restful night. An additional...

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Featured review

"Wonderful Villa"

Super clean, nicely decorated, comfortable bed, sunny, beautiful view, more than enough space, fully equipped kitchen, very nice pool and spa, pickle and tennis ball courts, safe , secure and quiet community...

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$152
avg per night
Naples Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

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

About this property

This beautiful condo is located in the extremely desirable active Huntington Lakes, which is just minutes from all of the amazing shops, restaurants and the BEACH! This 2-bedroom condo, is fully FURNISHED and stocked with everything that is needed. It is a gated community with plenty of activities such...

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$67
avg per night
Hutchinson Island Condo
Sleeps 4, 2 bedrooms, 2 bathrooms
4 reviews

Key Amenities

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

About this property

The view will draw you in to this lovely 2 bedroom condo situated directly on the beach! This spacious two bedroom, two bath condo has been updated and furnished with everything you could desire. Enjoy the sound of the waves as you enjoy breakfast, lunch, or dinner from your private balcony. The primary...

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Featured review

"Beautiful place loved it!"

Beautiful clean place and wonderful people to work with! There are many wonderful outdoor activities in this area. Our home away from home! We can’t wait for our next visit! Thank you, JR and Sue

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$117
avg per night
Siesta Key House
Sleeps 6, 3 bedrooms, 2 bathrooms
5 reviews

Distance to beach: 400 feet to Siesta Beach

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Prime location, being only two minutes walk to Siesta Beach entrance from this attractive three bedroom, two bath florida ranch! You live around the ground level pool with large patio doors openings from the two living areas and kitchen/dinning area. The home has been freshened with a very nice decor...

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Featured review

"Fantastic place"

This home is absolutely beautiful and spotless! Has every amenity you could want and is so close to the beach! Working with the host was very easy and very accommodating. You would totally enjoy this stay,...

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$553
avg per night
Naples Cottage
Sleeps 2, 1 bedroom, 1 bathroom

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

Enjoy sunny Old Naples at reasonable rates, 75 yards to the beautiful beaches of Old Naples at a charming guest house efficiency on an estate property. This property is located in the heart of the most exclusive section of of Old Naples, steps to the Gulf of Mexico and the fine shops of Fifth Ave and...

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$133
avg per night
Englewood House
Sleeps 5, 2 bedrooms, 2 bathrooms
4 reviews

Distance to beach: 7 miles to Manasota Key Beach

Key Amenities

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

About this property

Come stay at our newly renovated 2-bedroom, 2-bath traditional Florida home! We’ve recently added a brand-new heated 14’ x 25’ saltwater pool—perfect for a refreshing morning dip or unwinding after a day of exploring.Located just a few blocks from the newly revitalized Dearborn...

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Featured review

"The Best!!"

We had the pleasure of renting this lovely home with a pool for a month in Englewood, our favourite Florida destination. The home was outfitted with everything you would need. It was most comfortable &...

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$156
avg per night
Naples Condo
Sleeps 4, 2 bedrooms, 2 bathrooms
1 review

Distance to beach: 6 miles to Naples Pier and Vanderbilt

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

Gorgeous hotel style suites. Penthouse, corner suite. This condo is suitable for one couple or a single person. You wont be disappointed. Best King size mattresses you'll ever sleep on. It's like sleeping on a cloud... What are you waiting for... contact us or book. It won't last! 2...

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Featured review

"Wonderful Rental Condo In Naples, Florida"

Positano Place is a gated, safe and quiet community. The condo has two spacious bedrooms with new mattresses that ensure a restful sleep. The furnishings are very comfortable. Two spacious bathrooms. The...

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$195
avg per night
Fort Myers Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
2 reviews

Distance to beach: 10 feet to Located on a private beach

Key Amenities

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

About this property

Located at Sanibel Harbour, Condo 431 in The Bayview Tower is the perfect get- away spot for relaxing at the beach and pool and enjoying all that the Florida Gulf coast has to offer.The unit was recently fully renovated including new easy gliding lania terrace slidersWatch the dolphins and...

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Featured review

"Birthday weekend"

Great accommodations, VERY clean, Quiet, comfortable beds, beautiful view!!! 5 stars!!! Wonderful host!!!!

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$261
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.