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Florida Snowbird Vacation Rentals

(3360 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.

Key West House
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

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

About this property

When they say it's all about the location, this home says it all!By city ordinance, you must rent this property for 29 days or longer!!Welcome to this beautifully restored, remodeled second-floor 1933 Key West home on Caroline Street.A stairway decorated with wainscoting will lead you...

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$587
avg per night
Fort Myers Townhome
Sleeps 5, 2 bedrooms, 2 bathrooms

Distance to beach: 7 miles to Fort Myers Beach, Sanibel Island

Key Amenities

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

About this property

Bright and spacious 2 bedroom, plus den upper townhouse unit in a quiet gated community. Maximum of 5 person occupancy please. Sorry, no pets, no smoking and no vaping. All living space is on one floor with a minimum 3 month rental required. Open concept design with high ceilings, large windows and screened-in...

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Cocoa Beach Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
2 reviews

Distance to beach: 50 feet to You're on it.

Key Amenities

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

About this property

Ocean front condo directly on the beach with heated swimming pool. Two bedroom, two bathroom first floor unit with amazing views of the ocean and beach. Walk 50 feet from rear patio to step onto the beach sand. Our unit is located in a small 3 story building with 9 units total. You will have access to...

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Featured review

"Fantastic"

Was a wonderful condo. Perfect location. I hope we can return again. We were a group of 4 girls and it was a great escape for us all. The decor was so comfy, cozy. I brought items I thought we would...

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$287
avg per night
Bradenton Condo
Sleeps 5, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Welcome to Castaway in Margaritaville! Short drive to the World Class Beaches of Anna Maria Island Close proximity to Lakewood Ranch, Sarasota, and Tampa Gated community with pool and amenities ​​​​​​​Walk to Floridays or take a stroll around Robinson Preserve Fully stocked kitchen...

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$301
avg per night
Fort Myers Condo
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

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

About this property

New address: GOOGLE 15430 Bellamar Cir FT Myers, Fl 33908 BELLAMAR COMMUNITY SOUTH FT MYERS BY BEACHES. A 3 BED 2 BATH CONDO, 2ND FLOOR. FURNISHED SUMMER FALL SHORT TERM $1600 a month, APRIL TO DEC END. OR HIGH SEASON IS $3400 A MONTH JANUARY 1 TO APRIL 1, 2027. 1 King & 1 Queen, 1 Bunk Bed, washer...

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$53
avg per night

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Vero Beach Condo
Sleeps 2, 1 bedroom, 2 bathrooms

Distance to beach: 7 miles to South Beach

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Beautiful golf-side condo in Vero Beach available for seasonal rental. Ground floor, fully furnished, 1 bedroom, 2 full baths, washer & dryer, covered parking. Newly painted, tiled and carpeted. Overlooks the 10th hole at Vista Plantation. Vista Plantation is a quiet, friendly 55+ active community....

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Lynn Haven Townhome
Sleeps 4, 2 bedrooms, 2.5 bathrooms
2 reviews

Distance to beach: 12 miles to Panama City Beach

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

Pelican's Roost is a new townhome centrally located in Lynn Haven, Florida. Close to the bay, the beaches (20 minutes), shopping and outdoor activities. Fully equipped kitchen, new comfortable beds, and a quiet neighborhood. Perfect for a place to relax and explore the Emerald Coast. Because there...

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Featured review

"Nice Communication"

Kind folks who made sure to get back to me as soon as they could and also made sure tp accurately answer any and all questions I had.

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$80
avg per night
Venice Cottage
Sleeps 2, 1 bedroom, 1 bathroom

Distance to beach: 0.3 miles to Venice Beach

Key Amenities

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

About this property

Lovely Casita in the beautiful Island of Venice. Perfect for 1 person or 2 with a pet. Fenced yard, 2 blocks from the beach, 4 blocks from gorgeous downtown. Great shopping & restaurants are a walk-away. Churches, grocery store, post office, library, tennis courts nearby, just like Mayberry in the...

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$116
avg per night
Punta Gorda Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Lease this Luxury Birkdale, 2-bedroom, and 2-bathroom, on the desired top floor of the Terrace Condominiums; located in the beautiful, secured with gated entrance at Heritage Landing.Heritage Landing is a brand-new Golf Country Club Community in the beautiful Punta Gorda, Florida. Current amenities...

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$107
avg per night
Fort Lauderdale Apartment
Sleeps 6, 2 bedrooms, 2 bathrooms
4 reviews

Key Amenities

  • Air conditioning
  • Pet friendly
  • Pool
  • WiFi

About this property

Enjoy your time in Fort Lauderdale in a clean, cozy, and spacious apartment in the center of the action. With cozy & beachy furniture and all the comforts of home, you can live like a local on your next trip. Enjoy the communal pool, and park your car on your free parking spot and forget about it....

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Featured review

"Vacation getaway"

Nice place it looked just how the pictures looked online. Safe location and easy access to local shopping.

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$60
avg per night
New
Longboat Key House
Sleeps 12, 4 bedrooms, 3 bathrooms

Distance to beach: 0.5 miles to Deeded Beach Access

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Luxury and Coastal Elegance! This Stunning Turnkey Canal-Front Pool Home was Built in 2015. Situated on the Highly Desired North End of Longboat Key. Featuring 120 Feet of Beautiful Canal Frontage, A 10,000lbs Boat Lift and Deeded Beach Access only Steps Away! Truly A Boater's Paradise! At Almost...

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$650
avg per night
New
Ave Maria Condo
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Experience luxury living at the National Golf and Country Club! Discover the exceptional Diangelo II Model, a haven of comfort and elegance, perfect for seasonal rental. Accommodating 4 to 6 guests, this home features a pull-out couch with an upgraded gel memory foam mattress, ensuring everyone enjoys...

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$210
avg per night
Fort Myers Condo
Sleeps 6, 3 bedrooms, 2.5 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Nestled in desirable south Fort Myers you'll find Sail Harbor - a private, gated community of town homes, just minutes from our beautiful Gulf beaches, the popular vacation islands of Sanibel and Captiva, and the shores of the Caloosahatchee River. As you enter the gates you'll be welcomed by...

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$105
avg per night
Bonita Springs Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Oceanfront
  • Pool
  • WiFi

About this property

Stunning Water views and Beautiful 2 BR, 2 BA fully equipped condo on Hickory Blvd, Bonita Springs, FL. Perfect for the Beach Lovers with only steps to the beach. Swimming Pool, Beach Equipment, Private Parking, Private Boat Dock and much more. Enjoy your morning coffee or tea and your evening cocktail...

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$333
avg per night
New
Panama City Condo
Sleeps 2, 1 bedroom, 1 bathroom

Key Amenities

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

About this property

Great end unit in this Bay and Beach Front Community. This beautiful 1 Bedroom/1 Bath with private balcony unit has large bedroom and walk in closet, ceiling fans, fully furnished, beautifully landscaped, updated and is located in this quiet gem of a community of Landmark on St Andrews Bay. This complex...

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$60
avg per night
New
Fort Myers Condo
Sleeps 6, 3 bedrooms, 4 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to Estero Pointe — Your Seasonal Retreat in Paradise! Available for the full season 2026, minimum 3 months. Discover the charm and ease of Southwest Florida living in this beautifully appointed home located in the exclusive gated community of Estero Pointe. This stunning seasonal rental...

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$260
avg per night
Cape Coral Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool

About this property

Contact for specific booking dates.Welcome to the Heart of SW Cape Coral Marina LIFEstyle living !Weekly 7 day = $1500 or 12 month annual = $2800 Or winter seasonal rent Options available!Annual Furished option! ***$2800 fully furnished annual rental starting april 1st** 30 min...

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$214
avg per night
Panama City Beach Townhome
Sleeps 6, 2 bedrooms, 1.5 bathrooms

Key Amenities

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

About this property

Located in Panama City Beach, this terrific canal-front 2 bedroom townhome offers a fun retreat for guests. With a king bed, two queen beds, and a cozy living room, this property provides plenty of space for relaxation. The balcony upstairs and the backyard patio below both offer beautiful water views...

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$247
avg per night
Jensen Beach Townhome
Sleeps 8, 3 bedrooms, 3 bathrooms

Key Amenities

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

About this property

Direct Ocean View - Book your Winter Home Away From HomeAvailable May 2025 and beyondCome in and immediately relax and enjoy your very own home away from home. This 2007 built 3-level townhome comes with a direct ocean view and a one-minute walk to private beach. Your own private elevator will...

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$279
avg per night
Naples House
Sleeps 12, 6 bedrooms, 5 bathrooms

Distance to beach: 2 miles to Lowdermilk park

Key Amenities

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

About this property

6-bedroom vacation home just 3 minutes to Naples Beach with 3 king ensuites.In the heart of Naples' charming neighborhood lies this beautiful 6-bedroom vacation house. Imagine yourself relaxing by the heated private pool, soaking up the sun and enjoying the refreshing breeze. With free WiFi,...

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$343
avg per night
Miami Beach Condo
Sleeps 4, 0 bedrooms, 1 bathroom
2 reviews

Key Amenities

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

About this property

Comfortable and bright RENOVATED apartment, modern tiles and beautiful modern furniture Sleeps 4 comfortably 1 full bathroom Non smoking Free High speed internet -WiFi 55' Smart TV Balcony with 2 chairs and a coffee table Spectacular views of the ocean, the city, and the bay Kitchen has...

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Featured review

"Great place!"

This is absolutely wonderful place right on the beach. Great view and amenities. Amazing host and everything you need is inside. We would be happy to return here someday. Thank you for the vacation

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$140
avg per night
Bonita Springs Apartment
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • WiFi

About this property

This 2 Bedroom/2 Bath waterfront condo is located in a gated community with pool. Walk 50 yards to the beautiful white sandy beach on the gulf at the end of Little Hickory Island. The condo has been completely renovated and offers a king sized bed and TV in each bedroom, along with newly installed blackout...

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$191
avg per night
Daytona Beach Condo
Sleeps 5, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Oceanfront
  • Pool
  • WiFi

About this property

Experience the ultimate beach getaway in our 1st floor, direct oceanfront condo! This stunning two-bedroom retreat offers everything you need for an unforgettable stay:** Breathtaking Atlantic Ocean Views – Wake up to the soothing sounds of waves and watch spectacular sunrises from your private...

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$263
avg per night
Fort Myers Condo
Sleeps 5, 2 bedrooms, 2 bathrooms
5 reviews

Distance to beach: 5 miles to Fort Myers Beach

Key Amenities

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

About this property

This listing has a minimum 2-week occupancy. The condo is located on the 3rd floor in front of the elevator, it is very spacious and bright with vaulted ceilings and view of the golf course. Condo is a 6-minute drive from Fort Myers Beach and 1.5 miles from the bridge to Sanibel Island and Captiva. We...

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Featured review

"Lovely Condo"

Clean, lovely condo on the golf course. Great host communication and price point. Would recommend for those wanting to visit SWFL

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$97
avg per night
Naples Villa
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Our private peaceful renovated Villa with 17 foot ceilings and a relaxing water view at the back of the Villa await you. Regent Park Villas are a community of Villas and private homes in a very friendly, house proud community that is extremely well maintained by the association and the private home ownersThe...

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$125
avg per night
The Villages House
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Escape to this charming 3BR/2BA home in The Villages, FL! Enjoy a private heated pool & spa, perfect for relaxation. Walk to the nearby recreation center or take a short 1-mile ride to Eastport. This home includes a 4-person golf cart, making it easy to explore all The Villages has to offer. Comfortably...

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$222
avg per night
Ave Maria Condo
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

About this property

JANUARY AND APRIL OF 2026 IS STILL AVAILABLE FOR SEASON! You will not believe the incredible views from this GORGEOUS property. They are jaw-droppingly gorgeous. Beautifully decorated interior designed for your vacation comfort. Stunning Bromelia model features 2 bedrooms + den, 2 bathrooms and Front/back...

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$210
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

Direct ocean front condo with amazing sunrise views! Beautifully appointed 2/2 updated condo with all the comforts of home. Located on the 4th floor of a 12 story building, provides you with both a magnificent view AND low enough to hear the waves. 30 night minimum stay by order of the Condo Association....

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Featured review

"Nice Unit Excellent Landlord"

We have been going to Hutchinson Island for a number of winters now and just finished our 2nd year in this unit. The unit is well appointed, great kitchen as Ocean Harbor kitchens go and very comfortable....

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$120
avg per night
Cudjoe Key House
Sleeps 8, 3 bedrooms, 2 bathrooms
2 reviews

Distance to beach: 10 miles to Bahia Honda, Key West

Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

About this property

Wonderful, pet-friendly and beautifully decorated 3/2 home on the water that's perfect for a vacation or simply relaxation. It's located on beautiful Cudjoe Gardens with direct ocean access. There's a marina within walking or rowing distance. Check out the nearby Marvin Key video.Summary: •...

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Featured review

"Wonderful"

My husband and myself along with another couple rented this property for 28 days in September 2022. The home is clean, very comfortable and nice. There is a canal at the house which we used to dock 2 boats...

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$195
avg per night
Panama City Beach Condo
Sleeps 8, 2 bedrooms, 2 bathrooms
5 reviews

Distance to beach: 2 yards to Direct Oceanfront, WOW!

Key Amenities

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

About this property

For avail and other questions, best to call us at the number listed on contact owner vs email- phone is best as availability changes constantly.Some of our units now include Complementary Seasonal Beach Service for 2 for each night's stay(March 1 - Oct 31)!Long Beach Resort is a beautiful...

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Featured review

"Amazing views"

Everything in the Condo worked perfect. AC was cold, ceiling fan was fast, water pressure great. Furniture and decorations are a little blah and outdated, but functioned great. Easy check in.

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$289
avg per night
The Villages House
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • WiFi

About this property

Enjoy comfort and convenience in this 3BR/2BA home near The Villages’ new Eastport Square! Relax in the living room with a 65" TV or unwind in the main bedroom with a 55" TV and cozy nightstands. The fully stocked kitchen includes an air fryer, Keurig, and all cooking essentials. Each...

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$130
avg per night
Key West Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

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

About this property

Luxury island resort style living in Key West. 1800 Atlantic offers a private sandy sunning beach, Olympic style pool, gym, three tennis courts (one is clay), fitness center, community clubhouse, picnic areas and more. This condominium is updated and turnkey . Open living and dining spaces, eat-in kitchen...

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$177
avg per night
Fort Myers House
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

20514 Pebble Glen Drive is a fully furnished, turn-key residence located in the tranquil community of Verdana Village in Estero, Florida. This home features two bedrooms plus a den, two bathrooms, and spans 1,670 square feet. The property offers picturesque lake views from the backyard, enhancing the...

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$134
avg per night
Fort Pierce Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

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

About this property

Lovely remodeled "Old-Florida" condo directly on the beach in gated Community with Tennis , Pickleball, new Gym, heated Pools, Par 3 Golfcourse ,Restaurant on site , Shuffleboard, Tikibar, activities.Direct Ocean views from Livingroom and both bedrooms.Bed confirguration: Master...

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$160
avg per night
Punta Gorda Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Enjoy seasonal living in this brand-new, first-floor 2 bed + den / 2 bath home, located directly on the 10th tee of the Nicklaus Design course at Webb’s Reserve Golf & Country Club.Easy access with no stairs thanks to its convenient first-floor location.Outfitted with luxury home-grade...

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$117
avg per night
Babcock Ranch Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Enjoy resort style living! Gorgeous 2nd floor condo overlooking the 18th hole with views of Lake Babcock in the gated community of Babcock National. Enjoy this fully equipped condo with 2 bedrooms, 2 bathrooms, a den, 2 lanais and a garage. This unit is steps away from a satellite pool and around the...

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$104
avg per night
Islamorada Condo
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

PROPERTY NAME: Ocean Harbour K31 87851 Old Highway, Islamorada, FloridaLOCATION: Ocean Front CondoMINIMUM STAY: 28 Days, MILE MARKER: 87.8DETAILS: Gorgeous 3 bedroom ocean front condo with unobstructed ocean views from the screened balcony. Check out the photos! The kitchen was completely...

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$300
avg per night
Naples Condo
Sleeps 6, 3 bedrooms, 2 bathrooms
1 review

Distance to beach: 3 miles to Bonita Beach

Key Amenities

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

About this property

This condo is located in North Naples in the much sought out gated community of Sterling Oaks. CLOSE TO BEACHES. Unit consists of 3 bedrooms and 2 full baths, living room, dining area, large kitchen plus breakfast bar and an enclosed lanai. There’s covered parking at your door and additional parking...

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Featured review

"Two month stsy"

Susan was a great host. She met us at the condo and had little welcoming touches thoughout. The condo split layout worked great when our kids and grandkids visited. We enjoyed the community and amenities....

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$104
avg per night
Fort Myers Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
6 reviews

Key Amenities

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

About this property

Newly renovated ground floor condo on spectacular golf course just 5 Miles from Ft. Myers Beach and Sanibel/Captiva Island. Primary bedroom has a 2 queen beds with ensuite and walk-in closet. Spare bedroom has 2 double beds with own bathroom. Living room has a reclining sofa and a love seat. Bedding,...

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Featured review

"Comfortable, Clean and Quiet!"

Our stay could not have been made better. Irene was quick to respond to my first inquiry and was easy to contact during our stay. The kitchen is a big factor for me and hers is fully equipped with everything...

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$88
avg per night
Hutchinson Island Condo
Sleeps 4, 2 bedrooms, 2 bathrooms
13 reviews

Key Amenities

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

About this property

Welcome to "Serenity on the Sea - This updated and beautifully appointed 2 bedroom/2 bathroom 8th floor condo sits directly amongst the sandy dunes on a long private stretch of secluded beach on the north end of gorgeous Hutchinson Island. If you’re looking to spend some quiet time dozing on...

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Featured review

"Time to Exhale"

Nothing better than watching the sunrise, listening to ocean waves roll in. This will be the start of each day staying at this nicely decorated Condo. From the well-equipped kitchen to the comfy King...

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$286
avg per night
Naples Condo
Sleeps 6, 3 bedrooms, 2 bathrooms
1 review

Key Amenities

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

About this property

Welcome to your Happy Place that checks all the boxes! Three bedroom, 2 bathroom “Coach House” in the North Naples Gated Community of Carlton Lakes - the Best Spot in Naples! It is one of the few areas in Naples that allow tenants to have UP TO TWO PETS ANY SIZE! We have TWO OTHER nearly...

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Featured review

"We loved the home and location"

I stayed at this location with my wife in December for 3.5 weeks and we miss it already, great location and pet friendly. Super friendly neighbors and a safe gated community. Walking distance to Seed To...

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$95
avg per night
Bonita Springs Townhome
Sleeps 6, 2 bedrooms, 2.5 bathrooms

Key Amenities

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

About this property

Enjoy the best Bonita Springs has to offer in our Spanish Villa oasis with waterfront lake views and a heated private pool! Just a quick ride to the sandy beaches of Bonita Beach, Fort Myers and Naples. Enjoy the quiet, serenity of our beautiful private heated pool, or sit and enjoy the cool breezes in...

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$128
avg per night
Daytona Beach Condo
Sleeps 6, 1 bedroom, 1 bathroom
9 reviews

Key Amenities

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

About this property

This Oceanfront Breathtaking Luxury is Located In Daytona's Most Sought After Complex On The World's Most Famous Beach In The No Drive Zone. Featuring phenomenal panoramic ocean views. Enjoy All The Resort Amenities Including 2 Full-Size Outdoor Pools, A Kiddie Pool Area & 2 Indoor Pools,...

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Featured review

"Florida trip"

Great rental! Perfect location! Great ocean view on the 7th floor! Our plan is to return to same condo next February! Very cordial hosts !

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$150
avg per night
Anna Maria Island House
Sleeps 8, 3 bedrooms, 2 bathrooms

Distance to beach: 50 feet to across the street

Key Amenities

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

About this property

Key Lime Cottage – 880 N Shore Drive, Anna Maria Island3 Bedrooms | 2 Bathrooms | Sleeps 8 | Pet Friendly | Private Hot Tub | Fenced BackyardWelcome to Key Lime Cottage, a charming slice of island life nestled along the coveted North Shore Drive on Anna Maria Island. With room for up to...

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$724
avg per night
Summerland Key House
Sleeps 8, 3 bedrooms, 3 bathrooms
3 reviews

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Keys Life Come on down to “Keys Life” and enjoy a great Florida Keys vacation. Located in one of the best deep-water boating areas. The crystal blue canals and superb deep-water boating will make your fishing days a dream. Great outside entertaining areas with a perfect pool to splash around...

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Featured review

"Keys life"

Enjoyed our stay at Keys Life. The home was beautiful. The weather was quite windy so we weren’t able to get out as much as we wanted in our boat but we were able to get some nice lobster! It was nice...

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$254
avg per night
Perdido Key Cottage
Sleeps 10, 3 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

See Videos, Specials and choice of 6 properties go to LenFarinaProperties com. Snow Birds recrive 48% discount Dec 12 to March 13, 2026Your custom built beach vacation cottage is just a few steps away from a gorgeous, resort style community pool with a kiddie wading area, and a short stroll to the...

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$456
avg per night
Hutchinson Island Apartment
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

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

About this property

Barclay Beach Club One of the most modern and beautiful condominiums in Hutchinson island, surrounded by amazing and peaceful Nature! Ocean front condo in Hutchinson Island Fl 1 hour and a half from orlando ,and 2 hours from miami Perfect place to relax ,Hot tub, heated pool. Billards,tennis courts...

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$104
avg per night
Ave Maria House
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Gorgeous vacation home! Much less expensive than a hotel and way more spacious with amenities! Great for family or a couple vacation getaway w/ loads of privacy. Prepare to enjoy the quintessential Seasonal Rental Home. Stunning Napoli II model situated on lovely golf course view with a right hand view...

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$400
avg per night
Venice Condo
Sleeps 5, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

**Charming 2-Bedroom Condo in Bird Bay Village, Venice, FL**Located in the heart of Bird Bay Village, this delightful 2-bedroom, 2-bathroom condo offers the perfect blend of relaxation and activity. Nestled in a serene setting with lush vegetation and serene waterways, this property is part of a resort-style...

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$81
avg per night
New
Englewood House
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

Relax with the whole family at our getaway. Our coastal home is clean, comfortable, and intentionally uncluttered, offering all the basic essentials for a simple, stress-free stay. It's warm, welcoming and a home. Thoughtfully set up—including wheelchair accessibility.

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$93
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.