Southwest Florida holiday homes

We found 49,128 holiday rentals — enter your dates for availability

Holiday rentals with weekly discounts – Southwest Florida

Showing deals for:18 Dec - 25 Dec

dining room with seating for 8
Four barstools and large area for eating
Interior
Living area
Exceptional
(87 reviews)

Large pool/spa home minutes from beach with arcade games and canal for fishing.

Bradenton

7% off
NZ$5,618
for 7 nights, 1 home
NZ$803 per night
includes taxes & fees
Large pool/spa home minutes from beach with arcade games and canal for fishing.
Terrace/patio
Private kitchen
Exterior detail
Room
Exceptional
(84 reviews)

Centrally located! 6 miles to Siesta and St. Armands. 2 miles to downtown.

Sarasota

8% off
NZ$3,273
for 7 nights, 1 home
NZ$468 per night
includes taxes & fees
Centrally located! 6 miles to Siesta and St. Armands. 2 miles to downtown.
Shopping on Anna Maria Island is like discovering hidden gems!
Anna Maria, Florida's ocean is your ultimate fun zone!
Living, lounging, cooking—our space does it all.
Your ideal mix of style, convenience, and comfort is ready and waiting for you.
Exceptional
(56 reviews)

Luxury Family Escape: Spacious 4BR, Pool, Close to AMI, Dining & Attractions!

Bradenton

8% off
NZ$8,959
for 7 nights, 1 home
NZ$1,280 per night
includes taxes & fees
Luxury Family Escape: Spacious 4BR, Pool, Close to AMI, Dining & Attractions!
Manatee River with 120 ft dock
Kitchen
Rainbow at The Cut House
Landscaping behind the Cut House
Exceptional
(64 reviews)

Snead Island Cut Home - Oceanfront near Anna Maria , Boat docking, pet friendly

Palmetto

8% off
NZ$4,796
for 7 nights, 1 home
NZ$685 per night
includes taxes & fees
Snead Island Cut Home - Oceanfront near Anna Maria , Boat docking, pet friendly
Terrace/patio
Interior
Room
Living area
Wonderful
(49 reviews)

🌴 Peaceful Sarasota Home with Patio, 2BR, 2BA Near Lido Beach & Downtown

Sarasota

7% off
NZ$2,059
for 7 nights, 1 home
NZ$294 per night
includes taxes & fees
🌴 Peaceful Sarasota Home with Patio, 2BR, 2BA Near Lido Beach & Downtown
Exterior
Pool
Interior
Private kitchen
Exceptional
(26 reviews)

Casa Bonita by the Sea. Unique upscale experience for the discerning vacationer

Bonita Springs

8% off
NZ$5,443
for 7 nights, 1 home
NZ$778 per night
includes taxes & fees
Casa Bonita by the Sea. Unique upscale experience for the discerning vacationer
Property grounds
Pool
Living area
Outdoor dining
Exceptional
(29 reviews)

Great Family Vacation, Waterfront Pool Home

Cape Coral

8% off
NZ$5,962
for 7 nights, 1 home
NZ$852 per night
includes taxes & fees
Great Family Vacation, Waterfront Pool Home
Property grounds
Miscellaneous
Exterior
Exterior detail
Exceptional
(6 reviews)

Your property to relax - "Oak on the Water", Waterfront, Golf, Fishing, Bike

Rotonda West

7% off
NZ$4,159
for 7 nights, 1 villa
NZ$594 per night
includes taxes & fees
Your property to relax - "Oak on the Water", Waterfront, Golf, Fishing, Bike
Terrace/patio
Interior
Pool
kitchen
Exceptional
(33 reviews)

Waterfront Paradise in Marco Island

Marco Island

8% off
NZ$23,356
for 7 nights, 1 home
NZ$3,337 per night
includes taxes & fees
Waterfront Paradise in Marco Island
Room
Property grounds
Dining
Exterior
Exceptional
(64 reviews)

Cozy Luxury Suite In The Heart Of Fort Myers Close To Everything!

Fort Myers

7% off
NZ$1,175
for 7 nights, 1 apartment
NZ$168 per night
includes taxes & fees
Cozy Luxury Suite In The Heart Of Fort Myers Close To Everything!
Pool
Private kitchen
Interior
Room
Exceptional
(11 reviews)

Pet Friendly Canal Front 3-Bedroom Grand Villa with Pool, Linai and Dock

Port Charlotte

7% off
NZ$3,700
for 7 nights, 1 villa
NZ$529 per night
includes taxes & fees
Pet Friendly Canal Front 3-Bedroom Grand Villa with Pool, Linai and Dock
Interior
5 minute drive to Sun Splash Family Waterpark.
Exterior
Interior
Wonderful
(23 reviews)

Fenced Yard & Pool · BBQ & Kayaks

Cape Coral

28% off
NZ$7,035
for 7 nights, 1 villa
NZ$1,005 per night
includes taxes & fees
Fenced Yard & Pool · BBQ & Kayaks
2nd Floor Master w/Sliding door out to 2nd story Balcony
Resort Styled 5-bdrm waterfront w/Pool/Spa/FirePit/Putting Grn/Boat/Jet Ski Lift
Dinning Room Table that Seats 10!
Exterior
Wonderful
(15 reviews)

Waterfront 5BR Luxury Home – Pool, Spa, Boat Lift, Putting Green, Fire Pit

Bradenton

8% off
NZ$11,231
for 7 nights, 1 home
NZ$1,604 per night
includes taxes & fees
Waterfront 5BR Luxury Home – Pool, Spa, Boat Lift, Putting Green, Fire Pit
Dining
Exterior
Room
Pool
Exceptional
(9 reviews)

Fly South Florida-near beaches, fishing, boating, shops. Private heated pool.

Rotonda West

8% off
NZ$3,879
for 7 nights, 1 home
NZ$554 per night
includes taxes & fees
Fly South Florida-near beaches, fishing, boating, shops. Private heated pool.
Living area
Private kitchen
Room
Terrace/patio
Exceptional
(111 reviews)

75 ft Canal Front Anna Maria House, Great for Boaters, Newly Renovated

Anna Maria

8% off
NZ$5,764
for 7 nights, 1 home
NZ$823 per night
includes taxes & fees
75 ft Canal Front Anna Maria House, Great for Boaters, Newly Renovated
Private kitchen
Pool
Living area
Property grounds
Exceptional
(45 reviews)

New Luxurious Coastal Resort 3-Beedroom 2 Bath Private Pool

Venice

7% off
NZ$3,464
for 7 nights, 1 home
NZ$495 per night
includes taxes & fees
New Luxurious Coastal Resort 3-Beedroom 2 Bath Private Pool
Dining
Outdoor dining
Private kitchen
Pool
Exceptional
(158 reviews)

CBR Nov & Dec DISCOUNTED! AMIsland White Sand Beaches BOAT DOCK & LAUNCH on site

Cortez

6% off
NZ$4,716
for 7 nights, 1 home
NZ$674 per night
includes taxes & fees
CBR Nov & Dec DISCOUNTED! AMIsland White Sand Beaches BOAT DOCK & LAUNCH on site
Arial view of the building - right on the beach!
Beach
Living area
Interior
Exceptional
(24 reviews)

Good Vibrations- Stay right ON the beach in Siesta Key! Sleeps 6

Siesta Key

8% off
NZ$6,439
for 7 nights, 1 apartment
NZ$920 per night
includes taxes & fees
Good Vibrations- Stay right ON the beach in Siesta Key! Sleeps 6
Pool
Private kitchen
Living area
Terrace/patio
Exceptional
(65 reviews)

Ila's Beach House: Near IMG-Heated Salt Pool- Pets OK-Modern Organic Smart Home

Bradenton

8% off
NZ$7,037
for 7 nights, 1 home
NZ$1,005 per night
includes taxes & fees
Ila's Beach House: Near IMG-Heated Salt Pool- Pets OK-Modern Organic Smart Home
Outdoor fire pit. Please note guests are responsible for refilling propane
additional bar area seating
sliding door in kitchen leads to patio area
Front (living) room
Exceptional
(129 reviews)

HEATED pool, bike to Siesta, quiet street, 1 MILE to SK beach, kayaks & bikes

Sarasota

5% off
NZ$5,478
for 7 nights, 1 home
NZ$783 per night
includes taxes & fees
HEATED pool, bike to Siesta, quiet street, 1 MILE to SK beach, kayaks & bikes
Exterior
Room
Interior
Private kitchen
Exceptional
(10 reviews)

Rejuvenate by the Ocean & Mineral Springs

North Port

8% off
NZ$1,033
for 7 nights, 1 apartment
NZ$148 per night
includes taxes & fees
Rejuvenate by the Ocean & Mineral Springs
Living area
Beach
Dining
Pool
Exceptional
(33 reviews)

NewToVRBO RELAX- Own Home Private Pool, Hot Tub, near Beaches, Golf & Pickleball

Rotonda West

16% off
NZ$4,743
for 7 nights, 1 home
NZ$678 per night
includes taxes & fees
NewToVRBO RELAX- Own Home Private Pool, Hot Tub, near Beaches, Golf & Pickleball
Pool
Desk/office space
Bonus sun room with cute fireplace (non-functional!)
Large dinning room
Exceptional
(63 reviews)

Amazing heated pool & spa just minutes from Anna Maria Island

Bradenton

7% off
NZ$4,563
for 7 nights, 1 home
NZ$652 per night
includes taxes & fees
Amazing heated pool & spa just minutes from Anna Maria Island
Exterior
Marina
Living area
Property grounds
Exceptional
(40 reviews)

Siesta Key Beachside Condo-direct beach access

Siesta Key

8% off
NZ$4,794
for 7 nights, 1 apartment
NZ$685 per night
includes taxes & fees
Siesta Key Beachside Condo-direct beach access
  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Why visit Southwest Florida

  • Pristine Beaches: Enjoy sun-kissed sandy shores perfect for a laid-back family holiday, beachcombing, and water sports.
  • Outdoor Adventures: Explore vibrant nature parks and serene preserves ideal for hiking and wildlife spotting.
  • Urban Vibe: Experience the blend of coastal charm with lively urban parks and local culture.
  • Rich History: Immerse yourself in Florida’s heritage as you discover charming towns and historical sites.
  • Relaxation & Adventure: Unwind in tranquil settings or seek thrilling activities for an unforgettable getaway.

Top attractions near Southwest Florida

Southwest Florida offers a perfect mix of coastal fun and urban charm for families, couples, and groups. With pristine beaches, vibrant urban parks and serene preserves, visitors can enjoy a variety of outdoor activities and beach experiences. Whether you're catching waves or exploring the local nature, Southwest Florida is an ideal destination for those seeking an authentic blend of beach and city life.

  • Barefoot Beach: A stunning stretch of coastline known for its soft, white sands and tranquil atmosphere, perfect for sunbathing and beachcombing.
  • Quail West Golf and Country Club: This exclusive golf course offers a friendly environment and excellent facilities, ideal for both seasoned golfers and newcomers looking to enjoy a round.
  • Riverside Park: A charming urban park that provides a family-friendly atmosphere with scenic walking paths, playgrounds, and lovely picnic spots amidst beautiful greenery.

Things to do recommended for couples

Seeking a romantic escape in Southwest Florida? Enjoy a sunset cruise along the coast and explore quaint local eateries. Wander hand in hand on scenic beaches, and create cherished memories in this charming destination.

Things to do recommended for families

Families visiting Southwest Florida can enjoy interactive marine exhibits at local aquariums and spend a sunny day at kid-friendly beaches, exploring nature trails and spotting native wildlife along the way.

Things to do recommended for groups

Groups visiting Southwest Florida can experience thrilling airboat rides through the Everglades, enjoy sun-soaked days on pristine beaches, and explore the vibrant local markets in Naples. Don't miss the chance to indulge in fresh seafood dining while soaking up the stunning Gulf Coast sunsets.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation around Southwest Florida

When planning your trip—whether with a group, family, or pets, or if you’re seeking longer stays—be sure to use the appropriate filters that align with your priorities. Here are some helpful Vrbo booking tips for you.

  • Traveling to Southwest Florida with a group: Think about how many bedrooms you'll require, as well as features like a full kitchen or outdoor area for group gatherings. Luckily, you can easily filter for all these options and more on Vrbo.
  • Traveling to Southwest Florida with young kids: Traveling with little ones can present its challenges. You need to prioritise their comfort and safety, along with ensuring access to age-appropriate facilities, like a private swimming pool. It’s also wise to consider how close you are to family-friendly attractions.
  • Taking your pets with you to Southwest Florida: For many families, a holiday wouldn’t be the same without their furry companions. If this resonates with you, explore Vrbo properties that welcome pets. Many of these pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Southwest Florida: If you're after holiday rentals with discounts for month-long stays or more, you've come to the right place. By using the correct filter, you can easily discover and save on monthly rentals. You might also want to consider including a parking space, a good kitchen, or even a private pool in your search.

Where to stay near Southwest Florida

Southwest Florida is a stunning destination perfect for beach lovers and outdoor enthusiasts, offering a laid-back atmosphere ideal for family holidays. Explore sun-kissed beaches, lush nature parks, and charming towns, where friendly locals welcome you. This region is the ultimate getaway for those seeking relaxation, adventure, and a taste of Florida's rich history. Whether you're basking in the sun or exploring vibrant local culture, Southwest Florida promises unforgettable experiences for every traveller.

  • Bonita Springs: Situated 13km from Southwest Florida, Bonita Springs is a vibrant city that offers a blend of beachside charm and outdoor adventure. Visitors will enjoy family-friendly attractions, from the sandy beaches to the nearby island, and a variety of activities at the local recreation centre and shopping mall centre. The town is perfect for those seeking a mix of relaxed coastal living and active pursuits in a scenic setting.
  • Corkscrew Swamp Sanctuary: Located 8km from Southwest Florida, Corkscrew Swamp Sanctuary is a natural park that invites travellers to immerse themselves in the great outdoors. Ideal for adventure and family-focused fun, this destination features activities like exploring the nature reserve and playing a round of golf in nearby recreational areas. The sanctuary is set near a national state park, where visitors can also enjoy the serene beach and abundant natural beauty.
  • Three Oaks: Just 10km from Southwest Florida, Three Oaks offers a unique blend of family warmth and city-themed excitement. This neighbourhood is well known for its vibrant outdoor scene and conveniently located attractions, including a modern college university and a sports facility stadium. With easy access to shopping centres and education hubs, Three Oaks is a great base for exploring local urban life and outdoor leisure.

Best time to go to Southwest Florida

If you're planning a trip to Southwest Florida, it's a good idea to check both the weather and property rates. The warmest month is August.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January65.7°F (18.7°C)No Rain (Dry)Mostly Sunny
February67.1°F (19.5°C)No Rain (Dry)Mostly Sunny
March70.3°F (21.3°C)No Rain (Dry)Sunny
April73.8°F (23.2°C)Light RainMostly Sunny
May78.8°F (26.0°C)Light RainMostly Sunny
June82.2°F (27.9°C)Light RainMostly Sunny
July83.1°F (28.4°C)Moderate RainMostly Sunny
August83.5°F (28.6°C)Moderate RainMostly Sunny
September82.4°F (28.0°C)Light RainMostly Sunny
October78.6°F (25.9°C)Light RainMostly Sunny
November73.0°F (22.8°C)No Rain (Dry)Mostly Sunny
December69.3°F (20.7°C)No Rain (Dry)Mostly Sunny

Booking with Vrbo is simple

Looking to save on your next holiday? Consider being flexible with your travel dates, as prices can fluctuate. Additionally, extending your stay often results in significant savings. To discover the ideal Vrbo property that fits your budget, utilise our filters to search by price, location, and type of holiday rental.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board provides a dedicated space for planning new adventures, picking up where you left off, or managing your existing bookings. Your saved and booked properties are neatly organised into Potential, Upcoming, or Current Trips. Discover more about Trip Boards by visiting: https://www.bookabach.co.nz/trips.

**Based on Vrbo properties bookings.

Delight in the picturesque landscape of Southwest Florida

The beaches and wildlife provide a pleasant backdrop to your holiday home in Southwest Florida. This city's bird watching, golfing and baseball games draw many visitors. Take in top local attractions such as Siesta Key Beach and Key West Express. Whether you're planning a family holiday, romantic stay or trip with friends, holiday rentals offer features like full kitchens and laundry facilities for a more convenient stay.

Activities and attractions in Southwest Florida

Are you hoping to discover attractions to visit in the area? Travellers enjoy fun activities like bird watching and golfing. Venture out of your holiday home and experience everything that makes Southwest Florida a fun place to get away to. These are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Fort Myers Country Club (7.2 mi / 11.6 km)
  • Sun Splash Water Park (11.7 mi / 18.8 km)
  • Stoneybrook Golf Club (17.1 mi / 27.6 km)
  • Sanibel Island Golf Club (23.2 mi / 37.3 km)
  • La Playa Golf Club (27.8 mi / 44.8 km)
  • Revolution Cable Park (3.2 mi / 5.2 km)

Exploring the beaches and other natural features in Southwest Florida

Southwest Florida is famous for its breathtaking sunsets, island views and wildlife. Whether you're looking for fun outdoor activities or just want to spend some time taking in the scenery, Southwest Florida is a great place to spend some time outside. These are a few of the area's most eye-catching natural features, all within 30 miles (48.2 km) of the city centre:

  • Centennial Park (5.6 mi / 9 km)
  • Four Mile Cove Ecological Preserve (9.2 mi / 14.8 km)
  • Cape Coral Yacht Club Beach (13.7 mi / 22 km)
  • Bunche Beach (17.8 mi / 28.7 km)
  • Bowditch Point Park (18.5 mi / 29.7 km)
  • Estero Boulevard Beach (18.7 mi / 30 km)

Transport options to and around Southwest Florida

Fly into Fort Myers, FL (RSW-Southwest Florida Intl.), the closest airport, located 11 mi (17.7 km) from the city centre. If you're unable to find a flight that fits your schedule, you could book a flight to Punta Gorda Airport (PGD), which is 20.4 mi (32.8 km) away.

Frequently asked questions

What is the best area to stay in Southwest Florida when booking a holiday home?
One of the more in-demand areas to choose a Bookabach holiday home in Southwest Florida is Cape Coral. Make your home away from home here and discover its much-loved attractions, such as Sun Splash Water Park and Cape Coral Yacht Club Beach.
What is the most popular type of holiday home accommodation in Southwest Florida?
The most sought-after types of holiday homes in Southwest Florida are houses. After something a little different? Bookabach has many options to match our guests' needs, so you'll see holiday homes in lots of sizes and shapes. The ideal fit is waiting for you — get hold of yours today.
How much does it cost to rent a holiday home in Southwest Florida?
Different things can influence how much you pay for a holiday home in Southwest Florida, such as the season, type of property and length of stay. However, all of our holiday homes have something in common — amazing value. Just enter your travel dates to find your dream escape.
How much does it cost to rent a beach house in Southwest Florida?
Prices for beach houses in Southwest Florida vary depending on the size and type of the property and time of year you're travelling. Simply enter your dates of travel into Bookabach and the number of guests to view holiday home options and prices. From there you can use our filter tool to refine your search by amenities, ratings, nearby activities and more.
What are popular home amenities in Southwest Florida?
When it comes to home amenities that people search for in Southwest Florida, a microwave oven, a washing machine and a fridge rank the highest. With Bookabach holiday homes, there are choices to suit your style and taste, whether you're holidaying with friends, family or even pets.
Are there large group holiday homes in Southwest Florida?
Southwest Florida has 1,706 holiday homes that can accommodate 10 or more guests. These stays come with plenty of space to share good times with family and friends.
What are the top attractions for families in Southwest Florida?
Keep the kids busy at these awesome family-friendly attractions in Southwest Florida:
  • St. Armands Circle
  • Siesta Key Beach
  • Lido Beach
Can I find two-bedroom holiday homes in Southwest Florida?
Pick from 10,478 two-bedroom holiday homes in Southwest Florida. Give the kids the second room or maybe fill it with a couple of your besties. There's enough space for whoever's lucky enough to be coming along.
Are there holiday homes with WiFi in Southwest Florida?
Whether you'd like to stay in touch with the news, check emails or surf social networks, there are 10,140 holiday homes with WiFi in Southwest Florida. Check the "WiFi" box when searching on Bookabach and stay connected on your holiday.
How old do you have to be to rent a holiday home in Southwest Florida?
The minimum age allowed can differ across properties on Bookabach, so be sure to check the rules of the holiday home in Southwest Florida you're considering. But normally, it's 16, 18 or 21.
How long can I rent a holiday home in Southwest Florida for?
How long you can rent a holiday home in Southwest Florida varies according to the property. Simply enter your desired dates to view a list of options offering extended stays. With loads of features such as washing machines and air conditioning, as well as some offering weekly or monthly discounted prices, you're sure to get a terrific place to call your home away from home in Southwest Florida.

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