Southwest Florida holiday rentals

We found 49,124 holiday rentals — enter your dates for availability

Holiday rentals with weekly discounts – Southwest Florida

Showing deals for:18 Dec - 25 Dec

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

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

Bradenton

7% off
AU$4,461
for 7 nights, 1 home
AU$637 per night
includes taxes & fees
Large pool/spa home minutes from beach with arcade games and canal for fishing.
Dining
Private kitchen
Exterior detail
Terrace/patio
Exceptional
(84 reviews)

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

Sarasota

8% off
AU$2,634
for 7 nights, 1 home
AU$376 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.
Pool
Exceptional
(56 reviews)

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

Bradenton

8% off
AU$7,202
for 7 nights, 1 home
AU$1,029 per night
includes taxes & fees
Luxury Family Escape: Spacious 4BR, Pool, Close to AMI, Dining & Attractions!
Rainbow at The Cut House
Kitchen
View of River from house
Manatee River with 120 ft dock
Exceptional
(64 reviews)

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

Palmetto

8% off
AU$3,808
for 7 nights, 1 home
AU$544 per night
includes taxes & fees
Snead Island Cut Home - Oceanfront near Anna Maria , Boat docking, pet friendly
Terrace/patio
Interior
Living area
Room
Wonderful
(49 reviews)

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

Sarasota

7% off
AU$1,645
for 7 nights, 1 home
AU$235 per night
includes taxes & fees
🌴 Peaceful Sarasota Home with Patio, 2BR, 2BA Near Lido Beach & Downtown
Interior
Pool
Terrace/patio
Private kitchen
Exceptional
(26 reviews)

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

Bonita Springs

8% off
AU$4,320
for 7 nights, 1 home
AU$617 per night
includes taxes & fees
Casa Bonita by the Sea. Unique upscale experience for the discerning vacationer
Property grounds
Pool
Outdoor dining
Private kitchen
Exceptional
(29 reviews)

Great Family Vacation, Waterfront Pool Home

Cape Coral

8% off
AU$4,761
for 7 nights, 1 home
AU$680 per night
includes taxes & fees
Great Family Vacation, Waterfront Pool Home
Terrace/patio
Interior
Pool
kitchen
Exceptional
(33 reviews)

Waterfront Paradise in Marco Island

Marco Island

8% off
AU$18,863
for 7 nights, 1 home
AU$2,695 per night
includes taxes & fees
Waterfront Paradise in Marco Island
Dining
Property grounds
Interior
Exterior
Exceptional
(64 reviews)

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

Fort Myers

7% off
AU$937
for 7 nights, 1 apartment
AU$134 per night
includes taxes & fees
Cozy Luxury Suite In The Heart Of Fort Myers Close To Everything!
Living area
Private kitchen
Pool
Room
Exceptional
(11 reviews)

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

Port Charlotte

8% off
AU$2,981
for 7 nights, 1 villa
AU$426 per night
includes taxes & fees
Pet Friendly Canal Front 3-Bedroom Grand Villa with Pool, Linai and Dock
Exterior
5 minute drive to Sun Splash Family Waterpark.
Interior
Interior
Wonderful
(23 reviews)

Fenced Yard & Pool · BBQ & Kayaks

Cape Coral

28% off
AU$5,630
for 7 nights, 1 villa
AU$804 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
Exterior
Dinning Room Table that Seats 10!
Wonderful
(15 reviews)

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

Bradenton

8% off
AU$8,909
for 7 nights, 1 home
AU$1,273 per night
includes taxes & fees
Waterfront 5BR Luxury Home – Pool, Spa, Boat Lift, Putting Green, Fire Pit
Pool
Exterior
Living area
Room
Exceptional
(9 reviews)

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

Rotonda West

8% off
AU$3,133
for 7 nights, 1 home
AU$448 per night
includes taxes & fees
Fly South Florida-near beaches, fishing, boating, shops. Private heated pool.
Living area
Private kitchen
Marina
Room
Exceptional
(111 reviews)

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

Anna Maria

8% off
AU$4,578
for 7 nights, 1 home
AU$654 per night
includes taxes & fees
75 ft Canal Front Anna Maria House, Great for Boaters, Newly Renovated
Living area
Pool
Dining
Property grounds
Exceptional
(45 reviews)

New Luxurious Coastal Resort 3-Beedroom 2 Bath Private Pool

Venice

7% off
AU$2,819
for 7 nights, 1 home
AU$403 per night
includes taxes & fees
New Luxurious Coastal Resort 3-Beedroom 2 Bath Private Pool
Private kitchen
Outdoor dining
Pool
Dining
Exceptional
(158 reviews)

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

Cortez

6% off
AU$3,745
for 7 nights, 1 home
AU$535 per night
includes taxes & fees
CBR Nov & Dec DISCOUNTED! AMIsland White Sand Beaches BOAT DOCK & LAUNCH on site
Dining
Private kitchen
Living area
Pool
Exceptional
(65 reviews)

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

Bradenton

8% off
AU$5,630
for 7 nights, 1 home
AU$804 per night
includes taxes & fees
Ila's Beach House: Near IMG-Heated Salt Pool- Pets OK-Modern Organic Smart Home
Pool
additional bar area seating
Outdoor fire pit. Please note guests are responsible for refilling propane
Front (living) room
Exceptional
(129 reviews)

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

Sarasota

5% off
AU$4,350
for 7 nights, 1 home
AU$621 per night
includes taxes & fees
HEATED pool, bike to Siesta, quiet street, 1 MILE to SK beach, kayaks & bikes
Private kitchen
Room
Exterior
Beach
Exceptional
(10 reviews)

Rejuvenate by the Ocean & Mineral Springs

North Port

8% off
AU$825
for 7 nights, 1 apartment
AU$118 per night
includes taxes & fees
Rejuvenate by the Ocean & Mineral Springs
Dining
Beach
Exterior
Living area
Exceptional
(33 reviews)

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

Rotonda West

16% off
AU$3,764
for 7 nights, 1 home
AU$538 per night
includes taxes & fees
NewToVRBO RELAX- Own Home Private Pool, Hot Tub, near Beaches, Golf & Pickleball
Pool
Desk/office space
Living area
Large dinning room
Exceptional
(63 reviews)

Amazing heated pool & spa just minutes from Anna Maria Island

Bradenton

7% off
AU$3,622
for 7 nights, 1 home
AU$517 per night
includes taxes & fees
Amazing heated pool & spa just minutes from Anna Maria Island
Private kitchen
Marina
Property grounds
Exterior
Exceptional
(40 reviews)

Siesta Key Beachside Condo-direct beach access

Siesta Key

8% off
AU$3,807
for 7 nights, 1 apartment
AU$544 per night
includes taxes & fees
Siesta Key Beachside Condo-direct beach access
Exterior
Beach
Living area
Dining
Exceptional
(128 reviews)

Stunning Modern beach front unit - completely renovated! Includes golf cart!

Captiva

8% off
AU$7,148
for 7 nights, 1 apartment
AU$1,021 per night
includes taxes & fees
Stunning Modern beach front unit - completely renovated! Includes golf cart!
Pool
Outdoor dining
Exterior
Room
Exceptional
(41 reviews)

Ellis' Hideaway! Cozy 2-bedroom pool home with WiFi, AC in enjoyable Cape Coral

Cape Coral

8% off
AU$1,734
for 7 nights, 1 home
AU$248 per night
includes taxes & fees
Ellis' Hideaway! Cozy 2-bedroom pool home with WiFi, AC in enjoyable Cape Coral
  • 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

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 Stayz 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? Stayz 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 Stayz 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 Stayz 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 Stayz 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 Stayz, 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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