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South West Florida Vacation Rentals

From Anna Maria Island to Fort Myers and Marco Island

Southwest Florida Vacation Rentals By Owner

Discover the laid-back luxury of Southwest Florida with our carefully curated vacation rentals by owner. From Gulf-front condos to charming coastal cottages, explore our selection and secure your ideal retreat, offering the perfect blend of relaxation and the natural beauty of the Gulf Coast. Start your search below.

Cities in South West FL Vacation Rentals

Featured
Anna Maria Island - 3 bedroom - 2 pools - Hot Tub
Last Minute!
From/Per night$167

Anna Maria Island - 3 bedroom - 2 pools - Hot Tub

Bradenton Vacation Rentals
3/BR 2/BA SLEEPS 7
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Featured
Private Pool & Hot Tub - House close to Beach and Bridge Street
Last Minute!
From/Per night$399

Private Pool & Hot Tub - House close to Beach and Bridge Street

Bradenton Beach Vacation Rentals
4/BR 3.5/BA SLEEPS 10
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Featured
Anna Maria Island -walk to the beach!
Last Minute!
From/Per night$105

Anna Maria Island -walk to the beach!

Holmes Beach Vacation Rentals
2/BR 2/BA SLEEPS 6
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Avalon
From/Per night$539

Avalon

Holmes Beach Vacation Rentals
4/BR 3.5/BA SLEEPS 8
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Large Heated Pool, 2 Master-Bedroom suites, Very Close to Gulf Beach
From/Per night$520

Large Heated Pool, 2 Master-Bedroom suites, Very Close to Gulf Beach

Anna Maria Vacation Rentals
4/BR 3.5/BA SLEEPS 8
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Englewood Cottage ~ Quaint Beach Cottage on the Gulf
From/Per night$575

Englewood Cottage ~ Quaint Beach Cottage on the Gulf

Manasota Key Vacation Rentals
3/BR 2/BA SLEEPS 8
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STUNNING 3/2 Pool/Spa/Lake Home, Brand New Furniture, Fully Stocked, Lanai, Peaceful & Private
From/Per night$250

STUNNING 3/2 Pool/Spa/Lake Home, Brand New Furniture, Fully Stocked, Lanai, Peaceful & Private

Naples Vacation Rentals
3/BR 2/BA SLEEPS 7
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Blissful Paradise
From/Per night$358

Blissful Paradise

Holmes Beach Vacation Rentals
4/BR 4.5/BA SLEEPS 8
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Oasis on Canal - Pefect location, walk to Beach, Restaurants, Shops, Movie Theatre, Mini Golf, Icecream & More
From/Per night$450

Oasis on Canal - Pefect location, walk to Beach, Restaurants, Shops, Movie Theatre, Mini Golf, Icecream & More

Marco Island Vacation Rentals
3/BR 2/BA SLEEPS 8
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Sea Oats
From/Per night$413

Sea Oats

Holmes Beach Vacation Rentals
6/BR 4.5/BA SLEEPS 12
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Walk to Beach, JW Marriott, Upscale Montego Paradise
From/Per night$495

Walk to Beach, JW Marriott, Upscale Montego Paradise

Marco Island Vacation Rentals
3/BR 3/BA SLEEPS 6
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Seaside Escape
From/Per night$688

Seaside Escape

Bradenton Beach Vacation Rentals
7/BR 6/BA SLEEPS 16
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Beach to Bay
From/Per night$721

Beach to Bay

Bradenton Beach Vacation Rentals
6/BR 5.5/BA SLEEPS 18
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Starfish
From/Per night$242

Starfish

Holmes Beach Vacation Rentals
3/BR 2.5/BA SLEEPS 6
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TRADEWINDS Premium Beach Location & Gulf View - 11th Floor Renovated Condo
From/Per night$184

TRADEWINDS Premium Beach Location & Gulf View - 11th Floor Renovated Condo

Marco Island Vacation Rentals
2/BR 2/BA SLEEPS 4
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GULF ACCESS HOME WITH HEATED POOL
From/Per night$169

GULF ACCESS HOME WITH HEATED POOL

Cape Coral Vacation Rentals
3/BR 2/BA SLEEPS 8
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Cape coral, Florida villa, heated pool and hot tub
From/Per night$200

Cape coral, Florida villa, heated pool and hot tub

Cape Coral Vacation Rentals
3/BR 2/BA SLEEPS 8
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A Coastal Paradise
From/Per night$171

A Coastal Paradise

Bradenton Vacation Rentals
3/BR 2/BA SLEEPS 7
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Southwest Florida Vacation Rentals

Florida's south west offers old fashioned Florida villages of Anna Maria Island to the beachcombers and boaters delights of Fort Myers, Marco Island, Sanibel and Captiva Islands. From sun soaked beaches to nature preserves and the everglades. This diverse region has something for everyone. Great for beach combers and shelling!

Is Southwest Florida a good place to rent a Vacation Rental?

Southwest Florida is a fantastic place to rent a vacation rental! With its beautiful beaches, warm weather, and abundance of activities, it is a popular destination for tourists from all over the world. Here are a few reasons why Southwest Florida is a great place to rent a vacation rental:

1. Beautiful Beaches - Southwest Florida is known for its stunning beaches, including Naples Beach, Sanibel Island Beach, and Lovers Key State Park. Visitors can relax on the soft white sand, swim in the clear blue water, and soak up the sun.

2. Warm Weather - With an average temperature of 75 degrees Fahrenheit, Southwest Florida offers a warm and inviting climate year-round. Visitors can enjoy outdoor activities such as fishing, kayaking, and golfing without worrying about the weather.

3. Abundance of Activities - From shopping and dining to fishing and boating, there is always something to do in Southwest Florida. Visitors can explore the area's natural beauty by hiking or biking, or take in a cultural event at one of the many theaters or art galleries.

4. Family-Friendly - Southwest Florida is a great place for families to vacation. With attractions such as the Naples Zoo and Sun Splash Family Waterpark, there are plenty of activities for children of all ages to enjoy.

If you are looking for a relaxing and fun-filled vacation, Southwest Florida is the perfect destination. Book your vacation rental today and start exploring all that this beautiful area has to offer!

What do I need to know to rent a vacation home in Southwest Florida?

If you're planning to rent a vacation home in Southwest Florida, there are a few things you should know to ensure a smooth and enjoyable experience. Here are some key factors to consider:

1. Location - Southwest Florida is a large area that includes popular destinations such as Naples, Fort Myers, and Sanibel Island. Consider the location carefully and choose a vacation home that is close to the attractions and activities you want to experience. If you're interested in beach activities, choose a home that is within walking distance or a short drive to the beach.

2. Rental Costs - Rental costs can vary significantly depending on the location, size, and amenities of the vacation home. Make sure you understand the total cost of renting the home, including any additional fees, taxes, and security deposits. Some vacation rental websites also charge a service fee, so be sure to factor that into your budget.

3. Amenities - Amenities can make a big difference in the quality of your vacation rental experience. Consider what amenities are important to you and make sure the vacation home you choose meets your needs. Some common amenities include a pool, outdoor grill, and access to beach equipment.

4. Rental Agreement - Be sure to carefully read the rental agreement and understand the terms and conditions of the rental. This includes the check-in and check-out procedures, cancellation policy, and any restrictions or rules that apply to the vacation home.

5. Property Management - Look for a vacation rental with a reputable property management company or host/owner who is responsive and available to address any issues or concerns that may arise during your stay. FLARBO verifies each host prior to listing publication so you can feel comfortable booking a rental.

Renting a vacation home in Southwest Florida can be a wonderful way to experience the area's beauty and charm. By considering these factors and doing your research, you can find the perfect vacation home for your needs and enjoy a memorable vacation.

What are the typical stay periods for rentals in Southwest Florida?

Vacation rentals in this region of the sunshine state can be rented as follows depending on the municipal zone restrictions and the host's preference.

  • nightly
  • weekly
  • monthly

What are the typical rental rates for short term rentals in Southwest Florida?

Rental Price Information

  • Low range from $42 per night - $294 per week - $1,176 per month
  • High range from $2,000 per night - $14,000 per week - $60,000 per month

Booking Window

The Southwest Florida region is a very popular location for visitors. The best vacation rentals book 1 year or more in advance. On average the booking window for this region is 5 - 6 months in advance. Plan ahead to secure your favorite property!

Guest Retention

Many travelers fall in love with this location in the USA and return to it every year with families, as snowbirds or digital nomads which also increases the demand to book early.

High Season - Southwest Florida - December through April

High season for travelers booking vacation rentals in Southwest Florida typically runs from December through April. This is the time of year when the weather is warm and sunny, and many people are looking to escape the colder climates up north. During this time, vacation rentals in Southwest Florida can be in high demand, and rental prices may be higher than during other times of the year.

If you're planning to visit Southwest Florida during high season, it's recommended that you book your vacation rental well in advance to ensure availability and secure the best rates. Additionally, be prepared for larger crowds and potentially longer wait times for popular attractions and restaurants. Despite the crowds, however, high season is a fantastic time to visit Southwest Florida and enjoy all the area has to offer, including its beautiful beaches, outdoor activities, and cultural events.

Low Season - Southwest Florida - May through November

Low season for travelers booking vacation rentals in Southwest Florida is typically from May through November. During this time, the weather can be hotter and more humid, with the occasional afternoon thunderstorm. While this may not be the ideal weather for some visitors, there are still plenty of advantages to visiting Southwest Florida during the low season.

Summer months are more popular with nearby visitors to the coastal regions of Florida. Keep in mind that Floridians travel within their state on holiday during the months of June through to mid-August while school's out.

One of the biggest advantages is that vacation rental prices are typically lower during this time, making it a great option for budget-conscious travelers. Additionally, there are fewer crowds, which means you can enjoy popular attractions and beaches with more space and fewer lines. Some businesses may also offer special deals and discounts during the low season to attract visitors.

If you're planning to visit Southwest Florida during the low season, it's important to be prepared for the weather and plan activities accordingly. For example, plan to spend time outdoors in the morning or evening when the temperatures are cooler, and take advantage of indoor activities during the hottest part of the day. Overall, visiting Southwest Florida during the low season can be a great way to save money and enjoy a more relaxed and uncrowded vacation experience.

Southwest Florida Monthly Stays - Snowbird Rentals

Many winter travelers are looking for monthly or seasonal rental options. Choosing the long term suitability filter renders 134 rental options ion Southwest Florida for snowbirds.

Southwest Florida Pet Friendly Rentals

There are many dog parks found in the region as well as pet-friendly fenced in rentals to let your pooch roam free. In some cases dogs are not permitted on the beaches so check with the local restrictions. If you bring your pet you may want to look at rentals with shady areas as well as nearby walking routes. There are currently 149 pet friendly vacation rentals for Southwest Florida.

Large Group rentals in Southwest Florida

Renting a vacation rental is a great option for large groups. It provides more space and comfort than multiple hotel rooms, with amenities such as multiple bedrooms, bathrooms, and full kitchens. Vacation rentals also offer unique decor and local touches, making for a personalized experience. Additionally, staying in a vacation rental can help save money on dining expenses, as guests can prepare meals themselves. Overall, renting a vacation rental is a convenient and comfortable way for large groups to enjoy their time together in Southwest Florida. The search renders 69 vacation rentals suitable for large groups in Southwest Florida.

Southwest Florida Rentals with Pools and Hot Tubs

A vacation rental with a pool can offer several benefits for visitors to Southwest Florida. Firstly, it provides a refreshing way to cool off from the hot and humid climate. Having a pool right on the property allows guests to take a dip at any time of day, without having to travel to a beach or public pool. Additionally, having a pool can provide a fun activity for families and friends to enjoy together, with options for swimming, pool games, and relaxation. Vacation rentals with pools may also have outdoor areas for lounging, grilling, and dining, making for a complete outdoor living experience. Overall, a vacation rental with a pool can provide a luxurious and convenient way to fully enjoy all that Southwest Florida has to offer, while also providing a refreshing and fun way to stay cool during the warmer months.

Southwest Florida Rentals by Property Type

There is an abundance of Southwest Florida vacation rental dwelling types, the majority ranging from condos to private homes: 


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