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
- Anna Maria Island Vacation Rentals
- Ave Maria Vacation Rentals
- Bonita Beach Vacation Rentals
- Bonita Springs Vacation Rentals
- Bradenton Vacation Rentals
- Cape Coral Vacation Rentals
- Cortez Vacation Rentals
- Englewood Vacation Rentals
- Estero Vacation Rentals
- Fort Myers Vacation Rentals
- Grove City Vacation Rentals
- Longboat Key Vacation Rentals
- Manasota Key Vacation Rentals
- Marco Island Vacation Rentals
- Naples Vacation Rentals
- Nokomis Vacation Rentals
- North Captiva Island Vacation Rentals
- North Fort Myers Vacation Rentals
- North Port Vacation Rentals
- Palm Island Vacation Rentals
- Parrish Vacation Rentals
- Pine Island Vacation Rentals
- Port Charlotte Vacation Rentals
- Punta Gorda Vacation Rentals
- Rotonda West Vacation Rentals
- Sanibel Island Vacation Rentals
- Sarasota Springs Vacation Rentals
- Sarasota Vacation Rentals
- Siesta Key Vacation Rentals
- Venice Vacation Rentals
Luxury Private Vacation Estate on Sanibel
Sanibel Island Vacation RentalsPUTTING GREEN. DISC GOLF. SHUFFLEBOARD. HTD POOL. KIDS THEMED BUNK ROOM. CHAIR LIFT
Bradenton Vacation RentalsHyde Park Buttercup - Sarasota Affordable Condo Rental
Sarasota Vacation Rentals2/2 MAY-DECEMBER $2250 CLOSE TO SIESTA, PET FRIENDLY/YARD/ POOL/GYM WALK TO BAY&RESTAURANTS
Sarasota Vacation RentalsNew! Waterfront Views w/Private Heated Pool/Spa & Luxury Resort Amenities Sleeps 16
Anna Maria Vacation Rentals1/1 JUNE-DECEMBER $1999 CLOSE TO SIESTA KEY, PET FRIENDLY/YARD/ POOL/GYM WALK TO BAY&RESTAURANTS
Sarasota Vacation RentalsPRIME LOCATION ON AMI ** DIRECTLY ON WHITE SUGAR SAND BEACH ** HEATED POOL
Bradenton Beach Vacation RentalsBridge Escape in North Fort Myers, FL
North Fort Myers Vacation RentalsCREEKSIDE PALMS: 4 mi. to ANNA MARIA ISLAND, Sleeps 14, Heated Pool, Fishing, Kayak and Beach Gear!
Bradenton Vacation RentalsAVAILABLE 2025 Season - 2 Bedroom Beach-front Condo
Naples Vacation RentalsVilla Niccola - Cape Coral Waterfront Dock Boat Lift Heated Pool - Paradise!
Cape Coral Vacation RentalsCute Pool Home in Venice Close to Beach with Bikes and Kayaks!
Venice Vacation RentalsComforts of Home in Secure Gated Community Over Bridge from AMI Now Available Feb 17 2025!
Anna Maria Vacation RentalsWELCOME SNOWBIRDS! New Listing Bring Fido*!
Englewood Vacation RentalsEntire Duplex W/2 Golf Carts and Pool on Anna Maria Island
Bradenton Beach Vacation RentalsSol y Mar - Anna Maria Vacation Rental
Holmes Beach Vacation RentalscabAnna Maria Beach Block 4 bedroom4.5 Bathroom Private PoolSpa
Anna Maria Vacation RentalsCanal Front! Bring or rent a boat, close to IMG/AMI
Bradenton Vacation RentalsTHE MEADOWS 1 BED - 1 BATH CONDO WITH GOLF COURSE VIEW
Sarasota Vacation RentalsLovely and comfortable place in Englewood (A)
Grove City Vacation RentalsMISTY BEACH - Pet Friendly Bungalow Steps to Beaches - Anna Maria Island Vacation Rentals
Holmes Beach Vacation RentalsPRIVATE LUXURY VILLA WITH AMAZING WATER VIEWS AND HEATED POOL CLOSE TO BEACHES AND SHOPPING
Port Charlotte Vacation RentalsSea Life Retreat Vacation Rental on Anna Maria Island at Runaway Bay
Bradenton Beach Vacation RentalsCASA POSADA - So Close to Beach You Hear the Waves! Updated Clean Beach Cottage, Start $180n
Anna Maria Vacation RentalsVilla Costa - Cape Coral Vacation Rental with Dock
Cape Coral Vacation RentalsLakewood National Golf Club 2 Bedroom 2 Bath 1st Floor Condo
Lakewood Ranch Vacation RentalsAnna Maria Aloha - Renovated, Designer Inspired, Ground Level Home on Beach Block Just Steps to Pristine Beaches of Anna Maria Island!
Anna Maria Vacation RentalsA WAVE FROM IT ALL - Luxury Renovated Home! Heated Pool, Cabana, Hammock, Walk to Beach
Anna Maria Vacation RentalsFrom $75nt - Beautiful, Private Southwest Florida Townhouse
Fort Myers Vacation RentalsPeace River House - "Enjoy the adventure, Embrace the detours."
Punta Gorda Vacation RentalsTwin Palms: Big House Steps to the Beach, Kid/Infant/Pet Friendly, Lush Private Pool
Holmes Beach Vacation RentalsEsplanade at Lakewood Ranch Monthly Stays
Lakewood Ranch Vacation RentalsCatching Waves - Beautifully Updated w/Heated Pool, Covered Porches, Walk to Beach!
Anna Maria Island Vacation RentalsROOMY*SOUTHERN EXPOSURE POOL*LOCATION*DOG FRIENDLY*
Cape Coral Vacation RentalsCoral Palms - POOL & CANAL w/ quick Gulf access. 1.5 miles to Yacht Club & Beach
Cape Coral Vacation RentalsPrime Location, Top Amenities, and UNBELIEVABLE Discounts for Long-Term Stays (25-26 Season) - Hurry!
Fort Myers Vacation RentalsFound Your Sol Mate! Gorgeous Home w/ Pool, Spa, Steps to Bean Point, Dogs OK!
Anna Maria Vacation RentalsGORGEOUS AMI VILLA- STEPS TO THE BEACH, PRIVATE WATERFALL POOL, 3 PATIOS INCLUDING A ROOFTOP PATIO WITH A SWING
Holmes Beach Vacation RentalsNew331 N Washington Dr by FGC
Lido Key / St Armand's Vacation RentalsGriffins Island Getaway - Coastal Luxury with Private Heated Pool, Game Room, and Just Minutes from Anna Maria Island's Beaches!
Anna Maria Island Vacation RentalsLido Key & St Armands Family & Pet Friendly Pool Home - 232 S Boulevard of the Presidents
Lido Key / St Armand's Vacation RentalsVitamin Sea has everything! Heated pool & spa, elevator, rooftop deck, water views +++
Anna Maria Vacation RentalsOn Turtle Time - Beautifully Updated w/Heated Pool, Covered Porches, Walk to Beach!
Anna Maria Vacation RentalsIsland Garden Villas ~ 6 Private Cottages where Old Florida charm meets refreshing modern luxury
Holmes Beach Vacation RentalsCOZY CABANA EAST - GORGEOUS Renovated w/ Pvt. Pool, Backyard Oasis, Walk to Beach w Beach Gear!
Anna Maria Island Vacation RentalsSerenity Now - Newly Listed Holmes Beach Beauty. Heated Pool with Sun Shelf
Anna Maria Island Vacation RentalsChasing Waves - Steps from the beach, no roads to cross . AMI Perfect Beach House
Holmes Beach Vacation RentalsStarfish Isle 4 Bedroom3 Bath ~ Private HEATED Pool & Spa, Close to BEACH! Free WiFi
Holmes Beach Vacation RentalsNaples Happy Place! 3 BR2 BA; 2 Pets Any Size; Gated Community & Loads of Amenities!
Naples Vacation RentalsColony Don Pedro 422 - Palm Island Beachfront Condo Rental
Palm Island Vacation RentalsShe's Always Right - Holmes Beach Home w Pool & Spa, 1 Block to Beach & Shops
Anna Maria Island Vacation RentalsTHE COTTAGE ON PINE - Adorable Renovated Cottage w/Private Heated Pool, On Main Street of Anna Maria
Anna Maria Vacation Rentals3 BR / 2 Bath unfurnished golf optional condo
Babcock Ranch Vacation RentalsBeautiful condo on the Bradenton Riverwalk - Min 4 Month Stays - Snowbirds and Digital Nomads Welcome!
Bradenton Vacation RentalsSaltair East Gorgeous 2 Bed 2 Bath with Pool! Sleeps up to 6
Holmes Beach Vacation RentalsParadise Found 6 bed 6.5 bath Heated Pool & Hot TUB Bikes Free Wifi
Holmes Beach Vacation RentalsEMERALD BAY 3 KING BEDROOMS & bunk room - COMES WITH BEACH GEAR AND BIKES
Holmes Beach Vacation RentalsSunrise & Sunset Views - Holmes Beach Monthly Vacation Rental
Holmes Beach Vacation RentalsCaribbean Surf PRIVATE POOL ONLY 3 MINUTE WALK TO BEACH -SLEEPS 6
Holmes Beach Vacation RentalsLOCATION LOCATION LOCATION large home only 2 houses away from the gulf
Holmes Beach Vacation RentalsPOINT'S HIDEAWAY - Beautiful Island Home w/ Rooftop Water Views on Bean Point! Pool, Bar, Foosball!
Anna Maria Vacation RentalsPerfect Anna Maria Island Location, GROUND FLOOR UNIT, Runaway Bay Condo135
Bradenton Beach Vacation RentalsBlue Heron - Palm Island Beach House Rental
Palm Island Vacation RentalsLuxury Home in AMI with Heated Pool and close to Beach
Holmes Beach Vacation RentalsTropical Acres 2 bedroom, pool, pond, pets and much more
Cape Coral Vacation Rentals“Calypso” an Anna Maria Island Private Oasis!
Holmes Beach Vacation RentalsPrivate and Modern 3br, 2.5bath Vacation Home with pool
Port Charlotte Vacation RentalsEscape to Paradise in this 2-bedroom 2-bath furnished Snowbird condo rental
Sarasota Springs Vacation RentalsCondo has the largest plan in the collection
Venice Vacation RentalsTradewinds Resort Cottage Rental - 1 bedroom-sleeps 4 -pet friendly-Welcome to Paradise!
Bradenton Beach Vacation RentalsReel Royale a Canal Home on Anna Maria Island
Holmes Beach Vacation RentalsConch Out Beach House! 4 bed 3 bath HUGE yard, heated pool & spa, gazebo
Holmes Beach Vacation RentalsVilla Cutrone - Perico Bay Vacation Rental Near the Beach! - 3 Month Minimum Stays
Bradenton Vacation RentalsCrosswind Cottages - Sprawling 3 bed 2.5 bath heated pool elevator FREE WIFI Sleeps 9
Holmes Beach Vacation RentalsBarefoot by the Bay at Bayside Bungalow
Anna Maria Vacation RentalsLA Buena Vida - Bright Beachy & Canal front! Steps to Beach, Pool/Spa, Dock, Dogs OK
Anna Maria Vacation RentalsNokomis Beach Bungalow 229 - Pet Friendly Florida Rental
Nokomis Vacation RentalsSUNSET MARGARITA - Luxury Condo, Pool, Bikes, Just 5 Mins to Anna Maria Gulf Beaches!
One Particular Harbour - Margaritaville Vacation RentalsTailwind South - Palm Island Waterfront Beach House Rental with Dock
Palm Island Vacation RentalsCOCONUT LAGOON - Lovely Historic Renovated Cottage w/Huge Heated Pool, Backyard Oasis/Cabana/Bar
Anna Maria Vacation RentalsIsland Girl East & West - Heated Pool, Covered Porches, Walk to Beach
Anna Maria Island Vacation RentalsBeautiful Townhouse Vacation Rental - Near Fort Myers Beach, Sanibel Bridge
Fort Myers Vacation RentalsSouthwest 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:
- 605 properties in Southwest Florida listed for rent
- 320 Southwest rentals are listed as "house" rentals, accounting for 53% of the accommodation types
- 194 Southwest rentals are listed as "condo" rentals, are another popular rental type accounting for 32% of the accommodation types
- 55 Southwest rentals are listed as "bungalows and villas"
- 11 Southwest rentals are listed as "townhouses"