Best Vacation Homes in Madeira Beach
House
10.0(2 Reviews)
6 Bedrooms
6 Baths
16 Guests
Balcony/Terrace
Pet Friendly
Kitchen
Air Conditioner
R14,237/Night
7 Nights - R99,653
House
10.0(5 Reviews)
2 Bedrooms
4 Baths
10 Guests
1463.89 ft²
Hot Tub
Fireplace/Heating
Pool
View
R6,740/Night
7 Nights - R47,182
Condo
9.2(5 Reviews)
1 Bedroom
1 Bath
Oceanfront- Fireplace/Heating
- Pool
Ocean View
R6,633/Night
7 Nights - R46,440
New
House
6 Bedrooms
3 Baths
18 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Pet Friendly
R8,841/Night
7 Nights - R61,898
House
10.0(5 Reviews)
2 Bedrooms
2 Baths
6 Guests
1205.56 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
R4,235/Night
7 Nights - R29,647
New
Condo
3 Bedrooms
2 Baths
6 Guests
1110 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
R8,277/Night
7 Nights - R57,943
New
Condo
2 Bedrooms
2 Baths
6 Guests
1300 ft²
- Fireplace/Heating
- Air Conditioner
Internet
Child Friendly
R6,318/Night
7 Nights - R44,232
New
House
2 Bedrooms
1 Bath
5 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R6,266/Night
7 Nights - R43,853
Madeira Beach Luxury Rentals
House
6 Bedrooms
6 Baths
20 Guests
3950.35 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
R40,815/Night
7 Nights - R285,710
House
10 Bedrooms
8 Baths
24 Guests
5263.55 ft²
- Fireplace/Heating
- Pool
- View
Parking
R39,545/Night
7 Nights - R276,811
Villa
7 Bedrooms
7 Baths
24 Guests
3164.59 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- View
R34,959/Night
7 Nights - R244,708
House
1 Bedroom
8 Baths
30 Guests
2400.35 ft²
- Fireplace/Heating
- View
- Air Conditioner
- Internet
R34,010/Night
7 Nights - R238,067
House
10.0(2 Reviews)
4 Bedrooms
3 Baths
14 Guests
2500 ft²
Private Pool- Oceanfront
- Hot Tub
- Fireplace/Heating
R33,710/Night
7 Nights - R235,974
House
6 Bedrooms
6 Baths
20 Guests
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
R30,903/Night
7 Nights - R216,313
House
10 Bedrooms
8 Baths
24 Guests
5268 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
R28,885/Night
7 Nights - R202,190
House
6 Bedrooms
6 Baths
16 Guests
3676 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R28,786/Night
7 Nights - R201,498
Madeira Beach Pet Friendly Vacation Rentals
Condo
3 Bedrooms
2 Baths
7 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R5,458/Night
7 Nights - R38,200
House
10.0(4 Reviews)
3 Bedrooms
1 Bath
6 Guests
1194.79 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
R5,587/Night
7 Nights - R39,106
House
4 Bedrooms
2 Baths
10 Guests
- Fireplace/Heating
- Pool
- Pet Friendly
- Kitchen
R7,152/Night
7 Nights - R50,066
Apartment
10.0(120 Reviews)
1 Bedroom
1 Bath
3 Guests
1150 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
R5,494/Night
7 Nights - R38,447
House
10.0(2 Reviews)
3 Bedrooms
3 Baths
8 Guests
1603.82 ft²
- Fireplace/Heating
- Pool
- View
- Pet Friendly
R8,421/Night
7 Nights - R58,948
Apartment
10.0(36 Reviews)
1 Bedroom
1 Bath
4 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R3,410/Night
7 Nights - R23,863
Apartment
10.0(24 Reviews)
1 Bedroom
1 Bath
4 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R3,410/Night
7 Nights - R23,863
Apartment
10.0(16 Reviews)
1 Bedroom
1 Bath
4 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- View
R3,460/Night
7 Nights - R24,225
Madeira Beach Large Vacation Homes
Villa
10.0(7 Reviews)
2 Bedrooms
2 Baths
4 Guests
1200 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
R5,168/Night
7 Nights - R36,173
House
10.0(3 Reviews)
3 Bedrooms
6 Baths
14 Guests
1496.18 ft²
- Fireplace/Heating
- Pool
- View
- Parking
R7,176/Night
7 Nights - R50,230
House
5 Bedrooms
4 Baths
14 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
R14,624/Night
7 Nights - R102,372
Villa
10.0(2 Reviews)
5 Bedrooms
4 Baths
12 Guests
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
R14,824/Night
7 Nights - R103,773
Apartment
10.0(2 Reviews)
3 Bedrooms
3 Baths
10 Guests
1496.18 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
R10,881/Night
7 Nights - R76,169
House
10.0(1 Review)
1 Bedroom
5 Baths
10 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R17,703/Night
7 Nights - R123,928
Condo
10.0(52 Reviews)
3 Bedrooms
3 Baths
10 Guests
1800 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
R6,648/Night
7 Nights - R46,539
House
10.0(30 Reviews)
4 Bedrooms
3 Baths
16 Guests
3288 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R16,957/Night
7 Nights - R118,704
Why Choose Rent By Owner for your Madeira Beach Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Popular Areas for Madeira Beach Vacation Rentals
Where are the best neighborhoods to stay in Madeira Beach?
When planning your stay in Madeira Beach, Florida, exploring the different neighborhoods can enhance your vacation experience. Each area offers unique surroundings, from lively beachfront communities to quiet, family-friendly spots near the Gulf Coast. Choosing the right neighborhood allows you to enjoy easy access to the beautiful beaches, local dining, and recreational activities that make Madeira Beach a popular destination. Whether you're seeking vibrant nightlife or tranquil seaside retreats, you'll find a variety of trustworthy vacation rentals in the perfect neighborhood to suit your preferences for an unforgettable getaway.
South Pinellas Community Council
Choosing a stay in this area places you close to vibrant community events and local culture, enhancing your experience of the region. Here, you'll enjoy easy access to diverse amenities and scenic views that make your visit memorable.
View 69+ Rentals in South Pinellas Community CouncilBest Times to Visit Madeira Beach
When should you plan your Vacation Rentals stay?
Timing your visit to Madeira Beach for optimal weather and local events can enhance your experience, so consider the seasons and climate patterns here when booking your ideal vacation rental in this charming coastal region.
Peak Season Highlights
Spring (March to May)
During this period, you can enjoy warm weather and lively local events, making it an ideal time to explore the region's natural beauty and vibrant atmosphere.
Average Temperature Daytime: around 75-82°F - Nighttime: around 60-68°F
Summer (June to August)
This is the busiest season when the area experiences high visitor influx, perfect for sunbathing, water activities, and enjoying long sunny days.
Average Temperature Daytime: around 85-90°F - Nighttime: around 75-78°F
Off-Season Highlights
Fall (September to November)
During these months, you’ll find fewer crowds and pleasant temperatures, providing a more relaxed experience while still enjoying the region's coastal charm.
Average Temperature Daytime: around 75-83°F - Nighttime: around 64-70°F
Winter (December to February)
In winter, the area sees a quieter atmosphere with milder weather, ideal if you prefer a peaceful getaway with fewer tourists and lower rates.
Average Temperature Daytime: around 65-71°F - Nighttime: around 52-58°F
Weekly Weather Forecast for Madeira Beach
How to Book Your Madeira Beach Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Madeira Beach
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy outdoor swimming pools available directly on the property, perfect for relaxing after a day at the beach.
- Take advantage of private or shared patios and decks to unwind and soak up the sunshine.
- Benefit from access to lush gardens and landscaped outdoor spaces that enhance your stay in the region.
- Make use of shaded lounging areas and hammocks to relax outdoors in comfort.
- Utilize outdoor grilling facilities and picnic areas for enjoyable meals under the sun or stars.
- Embrace water activities such as kayak or paddleboard rentals commonly found nearby, ideal for exploring the local coastline.
- Find convenient parking options with designated outdoor parking spaces for easy access during your visit here.
Top Attractions Around Madeira Beach
What attractions are nearby?
Enjoy a variety of outdoor activities nearby, from relaxing on pristine beaches to exploring scenic parks and engaging in water sports right here in this vibrant coastal area.
Family Activities
- Johns Pass Village and Boardwalk: Explore this vibrant waterfront shopping, dining, and entertainment area that offers family-friendly activities and scenic views along the coast.
- Beach Activities at Madeira Beach: Enjoy relaxing days on the soft sandy shores with opportunities for swimming, building sandcastles, and soaking up the Florida sunshine.
- Gulf Boulevard Water Sports: Experience exciting water adventures such as paddleboarding, jet skiing, or parasailing that provide fun for all ages in this coastal destination.
- Sunset Dolphin Cruises: Embark on a guided boat tour to spot playful dolphins and witness breathtaking sunsets over the peaceful waters surrounding this beach town.
Adult Activities
- Sunset Cruises: Embark on a relaxing sunset cruise to enjoy breathtaking views over the Gulf, providing a memorable experience in the region’s tranquil waters.
- Fishing Charters: Book a fishing charter to test your skills in the abundant waters, making for an exciting day of angling along this popular destination.
- Beachfront Watersports: Engage in watersports such as paddleboarding and jet skiing right on the shoreline, perfect for active adults seeking adventure here.
- Dining Along the Coast: Savor fresh seafood and local cuisines at beachfront restaurants, offering a delicious way to unwind after a day of exploring.
Other Places to Stay in Madeira Beach, FL
Clearwater-St. Pete Beaches
Seewinter
Hubbards Marina
John's Pass Village & Boardwalk
Alligator Attraction
Archibald Beach Park
Bay Pines VA Medical Center
War Veteran Memorial Park
Madeira Beach Travel Tips
How Can You Make the Most of Your Stay?
- Plan Ahead for Waterfront Activities: Book your vacation rentals near the water early to enjoy easy access to the area's renowned beaches and engage in popular aquatic adventures.
- Explore Local Dining Options: Take advantage of the region’s fresh seafood and charming eateries by choosing accommodations close to dining hotspots, enhancing your culinary experience here.
- Visit During Off-Peak Seasons: To make the most of your stay with fewer crowds, consider visiting during less busy times while still enjoying pleasant weather and local events.
- Use a Trusted Booking Platform: Secure your ideal vacation rentals through a dependable site to ensure a seamless and trustworthy booking process for your trip here.
Transportation Options
- Private Car Rentals: Opt for convenient car rentals to explore the region at your own pace and visit nearby attractions effortlessly.
- Public Transit Services: Use local buses for affordable and reliable transportation around the area, connecting you to key points of interest.
- Taxi and Rideshare Options: Hail taxis or book rides through popular services for quick and comfortable transit within this coastal destination.
- Bicycle Rentals: Rent a bicycle to enjoy scenic routes along the shoreline and discover hidden gems in the surrounding neighborhoods.
Local Customs Options
- Local Seafood Cuisine: You’ll find that enjoying fresh, locally caught seafood is a cherished tradition here, reflecting the region’s coastal roots.
- Beach Etiquette: Respect for sunbathers and maintaining cleanliness on the sandy shores exemplify the relaxed and friendly atmosphere of this destination.
- Boating and Water Sports: Engaging in boating or water activities aligns with the area's maritime culture, where leisure often revolves around the Gulf waters.
- Community Festivals: Participating in or observing local festivals highlights the region's vibrant community spirit rooted in its traditions and history.
Frequently Asked Questions About Madeira Beach?
1. What are the top vacation rentals in Madeira Beach?
There are a lot of options in Madeira Beach. If you plan on staying in the Madeira Beach area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Madeira Beach:
- REMODELED, immaculately designed, BEACHFRONT condo with gorgeous water views
- Enjoy beautiful sunsets from the top floor in this 2 bed, 2 bath condo!
- Listen to the Waves - Direct Gulf Front - WiFi, Parking Included
- Extra Clean, Fully Renovated Beachfront Three Bedroom Condo on Madeira Beach 🏖️
- Directly on the Beach
- Gulf Front Sunsets From the Balcony of This 3 BD/2 BA condo!
- Gulf-Side Beach House - Tiki Bar · Direct Beach Access · No Roads to Cross
- Paradise awaits you!
- Amazing Beachfront Condo 3BR/2BA - Spectacular View
- Amazing Beach Front w/Gulf & Ocean Views~Las Brisas 506
2. How many vacation rentals have private pools in Madeira Beach?
There are 178 vacation rentals with private pools near Madeira Beach. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Madeira Beach are best for families?
If you are looking for a family-friendly vacation home in Madeira Beach, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Madeira Beach:
4. How many Rentbyowner vacation rentals are available in Madeira Beach?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 2222 in the Madeira Beach area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Madeira Beach.
5. What is the cancellation policy for vacation rentals in Madeira Beach, Florida?
Cancellation policies vary by property. You should review the specific listing details or contact the property owner directly to understand the terms and any applicable fees before making your reservation.
6. Are there any additional fees I should expect when booking a vacation rental here?
Additional fees such as cleaning fees, service charges, or taxes can be included in the property listing. It's best to check the detailed description or contact the host for a complete breakdown of costs before confirming your booking.
7. How do I verify the safety and security features of the vacation rentals in the region?
Safety features are typically listed on each property page, including security systems, locks, and other amenities. For further assurance, you can reach out directly to the property owner or manager to inquire about specific safety measures.
8. Can I find pet-friendly vacation rentals in this area?
Many properties in Madeira Beach accommodate pets, but availability varies. Review each listing carefully to see if pets are allowed, or contact the property owner to confirm pet policies before booking.
9. What should I know about checking in and out of vacation rentals in Madeira Beach?
Check-in and check-out times are specified on each property listing. You can also communicate directly with the host for any special arrangements or questions regarding your arrival or departure procedures.
Madeira Beach Top Rated Vacation Rentals
Condo
10.0(183 Reviews)
2 Bedrooms
2 Baths
6 Guests
1120 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Ocean View
R7,239/Night
7 Nights - R50,675
Condo
10.0(180 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Hot Tub
- Fireplace/Heating
- Pool
- Ocean View
R8,380/Night
7 Nights - R58,668
Condo
10.0(172 Reviews)
2 Bedrooms
1 Bath
3 Guests
750 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Ocean View
R5,561/Night
7 Nights - R38,925
Condo
10.0(130 Reviews)
3 Bedrooms
2 Baths
6 Guests
1100 ft²
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
R7,268/Night
7 Nights - R50,873
Condo
10.0(115 Reviews)
3 Bedrooms
2 Baths
8 Guests
1300 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Ocean View
R7,449/Night
7 Nights - R52,142
Condo
10.0(113 Reviews)
1 Bedroom
1 Bath
2 Guests
860 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
R5,467/Night
7 Nights - R38,266
Condo
10.0(109 Reviews)
3 Bedrooms
2 Baths
9 Guests
1250 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Ocean View
R6,006/Night
7 Nights - R42,040
Condo
10.0(105 Reviews)
3 Bedrooms
2 Baths
8 Guests
1450 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
R6,716/Night
7 Nights - R47,017
