Condo
10.0(198 Reviews)
2 Bedrooms
6 Guests
Oceanfront
Hot Tub
Parking
Pool
US $394/Night
7 Nights - US $2,755
Madeira Beach Holiday Rentals
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Compare Holiday Rentals, Villas & Resorts in Madeira Beach
10.0
US $409/Night
7 Nights - US $2,863
Condo
9.2(26 Reviews)
1 Bedroom
2 Guests
Private Pool- Oceanfront
- Hot Tub
- Parking
US $216/Night
7 Nights - US $1,512
Condo
10.0(190 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
US $557/Night
7 Nights - US $3,896
House
10.0(5 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Parking
- Pool
Ocean View
US $257/Night
7 Nights - US $1,799
Condo
10.0(187 Reviews)
1 Bedroom
3 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
US $530/Night
7 Nights - US $3,712
New
Cottage
10.0(136 Reviews)
2 Bedrooms
4 Guests
- Parking
- Ocean View
Balcony/Terrace
View
US $318/Night
7 Nights - US $2,223
Apartment
10.0(127 Reviews)
1 Bedroom
3 Guests
- Private Pool
- Oceanfront
- Parking
- Pool
US $370/Night
7 Nights - US $2,592
Condo
10.0(122 Reviews)
1 Bedroom
2 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Parking
US $353/Night
7 Nights - US $2,470
Luxury Holiday Rentals in Madeira Beach
Over 2246+ Luxury Holiday Rentals in or Near Madeira Beach
Unlock the Best Price
Condo
10.0(6 Reviews)
11 Bedrooms
30 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $2,590/Night
7 Nights - US $18,131
US $2,400/Night
7 Nights - US $16,797
House
1 Bedroom
30 Guests
- View
Air Conditioner
Internet
Sports/Activities
US $2,222/Night
7 Nights - US $15,557
Villa
7 Bedrooms
24 Guests
- Oceanfront
- Ocean View
- View
- Air Conditioner
US $2,121/Night
7 Nights - US $14,849
House
10.0(1 Review)
6 Bedrooms
16 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $1,841/Night
7 Nights - US $12,885
US $1,803/Night
7 Nights - US $12,619
House
10.0(2 Reviews)
4 Bedrooms
14 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $1,755/Night
7 Nights - US $12,282
House
Ultimate Beachfront Escape for Families & Groups. Beach& Swim Spa. Tickets to Top Attractions Daily.
10.0(2 Reviews)
8 Bedrooms
16 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $1,525/Night
7 Nights - US $10,674
Top-Rated Holiday Rentals with a Pool in Madeira Beach
Over 1566+ The Best Private Villas and Holiday Rentals in Madeira Beach with a Pool
Condo
10.0(123 Reviews)
3 Bedrooms
8 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
US $525/Night
7 Nights - US $3,674
Condo
10.0(114 Reviews)
3 Bedrooms
9 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
US $450/Night
7 Nights - US $3,151
Condo
10.0(109 Reviews)
3 Bedrooms
8 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
US $578/Night
7 Nights - US $4,045
Condo
10.0(107 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
US $312/Night
7 Nights - US $2,183
House
10.0(107 Reviews)
1 Bedroom
2 Guests
- Parking
- Pool
- Balcony/Terrace
Kitchen
US $284/Night
7 Nights - US $1,985
House
10.0(99 Reviews)
3 Bedrooms
6 Guests
- Private Pool
- Parking
- Pool
- Ocean View
US $466/Night
7 Nights - US $3,260
Condo
10.0(99 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
US $297/Night
7 Nights - US $2,080
Condo
10.0(98 Reviews)
3 Bedrooms
9 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $475/Night
7 Nights - US $3,322
Condo
10.0(96 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
US $411/Night
7 Nights - US $2,877
Pet-Friendly Holiday Rentals in Madeira Beach
Over 318+ Pet-Friendly Holiday Rentals in or Near Madeira Beach
Cottage
10.0(75 Reviews)
1 Bedroom
2 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $289/Night
7 Nights - US $2,024
House
10.0(4 Reviews)
3 Bedrooms
6 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $339/Night
7 Nights - US $2,373
House
4 Bedrooms
10 Guests
- Parking
- Pool
- Kitchen
- Air Conditioner
US $434/Night
7 Nights - US $3,038
Apartment
10.0(40 Reviews)
1 Bedroom
4 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $261/Night
7 Nights - US $1,830
US $460/Night
7 Nights - US $3,221
Apartment
10.0(5 Reviews)
1 Bedroom
4 Guests
- Parking
- Ocean View
- View
- Kitchen
US $218/Night
7 Nights - US $1,527
Apartment
10.0(5 Reviews)
2 Bedrooms
4 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $198/Night
7 Nights - US $1,388
Condo
10.0(4 Reviews)
2 Bedrooms
6 Guests
- Hot Tub
- Parking
- Pool
- Ocean View
US $366/Night
7 Nights - US $2,561
Apartment
10.0(4 Reviews)
1 Bedroom
4 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $180/Night
7 Nights - US $1,257
Large Holiday Rentals and Private Villas in Madeira Beach
Over 150+ Large Holiday Rentals and Private Villas in or Near Madeira Beach
Villa
9.8(9 Reviews)
2 Bedrooms
3 Guests
- Ocean View
- Balcony/Terrace
- View
- Kitchen
US $305/Night
7 Nights - US $2,133
US $377/Night
7 Nights - US $2,638
House
5 Bedrooms
14 Guests
- Pool
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $887/Night
7 Nights - US $6,212
Condo
10.0(60 Reviews)
3 Bedrooms
10 Guests
- Private Pool
- Parking
- Pool
- Ocean View
US $411/Night
7 Nights - US $2,880
Apartment
10.0(2 Reviews)
3 Bedrooms
10 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $544/Night
7 Nights - US $3,809
House
10.0(30 Reviews)
4 Bedrooms
16 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $1,260/Night
7 Nights - US $8,818
Condo
10.0(27 Reviews)
3 Bedrooms
10 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $536/Night
7 Nights - US $3,755
House
10.0(25 Reviews)
3 Bedrooms
12 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $1,035/Night
7 Nights - US $7,243
House
10.0(23 Reviews)
4 Bedrooms
10 Guests
- Private Pool
- Parking
- Pool
- Ocean View
US $795/Night
7 Nights - US $5,567
Wheelchair Accessible Holiday Homes in Madeira Beach
Over 845+ Wheelchair Accessible Holiday Homes in or Near Madeira Beach
Condo
10.0(92 Reviews)
2 Bedrooms
7 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
US $437/Night
7 Nights - US $3,058
US $378/Night
7 Nights - US $2,643
Condo
9.2(5 Reviews)
1 Bedroom
- Oceanfront
- Parking
- Pool
- Ocean View
US $403/Night
7 Nights - US $2,818
Condo
10.0(87 Reviews)
2 Bedrooms
7 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
US $416/Night
7 Nights - US $2,910
Resort
9.1(500 Reviews)
20 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $150/Night
7 Nights - US $1,050
Condo
10.0(70 Reviews)
2 Bedrooms
6 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Parking
US $207/Night
7 Nights - US $1,450
Condo
10.0(62 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
US $395/Night
7 Nights - US $2,766
Condo
10.0(50 Reviews)
2 Bedrooms
5 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $417/Night
7 Nights - US $2,916
Condo
10.0(48 Reviews)
3 Bedrooms
6 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
US $227/Night
7 Nights - US $1,587
Madeira Beach Private Villas and Holiday Homes Under $200
Over 480+ Madeira Beach Private Villas and Holiday Homes Under $200
Condo
10.0(62 Reviews)
1 Bedroom
2 Guests
- Parking
- Pool
Spa- Ocean View
US $182/Night
7 Nights - US $1,275
House
10.0(5 Reviews)
1 Bedroom
4 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $174/Night
7 Nights - US $1,218
US $187/Night
7 Nights - US $1,308
Condo
10.0(38 Reviews)
1 Bedroom
4 Guests
- Parking
- Ocean View
- View
- Kitchen
US $189/Night
7 Nights - US $1,323
House
10.0(4 Reviews)
1 Bedroom
4 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $171/Night
7 Nights - US $1,194
Condo
10.0(35 Reviews)
2 Bedrooms
6 Guests
- Hot Tub
- Parking
- Pool
- Spa
US $176/Night
7 Nights - US $1,229
Condo
10.0(32 Reviews)
2 Bedrooms
6 Guests
- Parking
- Pool
- Ocean View
- View
US $195/Night
7 Nights - US $1,365
Apartment
10.0(30 Reviews)
1 Bedroom
2 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $198/Night
7 Nights - US $1,386
Condo
10.0(26 Reviews)
2 Bedrooms
6 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $134/Night
7 Nights - US $938
Instantly Bookable Holiday Homes in Madeira Beach
Over 1421+ Instantly Bookable Holiday Homes in or Near Madeira Beach
Apartment
10.0(101 Reviews)
1 Bedroom
2 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $203/Night
7 Nights - US $1,419
US $379/Night
7 Nights - US $2,654
House
10.0(95 Reviews)
2 Bedrooms
4 Guests
- Parking
- Balcony/Terrace
- View
- Kitchen
US $541/Night
7 Nights - US $3,789
Apartment
10.0(92 Reviews)
1 Bedroom
2 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $266/Night
7 Nights - US $1,864
Apartment
10.0(64 Reviews)
1 Bedroom
2 Guests
- Parking
- Balcony/Terrace
- View
- Kitchen
US $349/Night
7 Nights - US $2,443
Cottage
10.0(60 Reviews)
1 Bedroom
4 Guests
- Hot Tub
- Parking
- Pool
- Ocean View
US $208/Night
7 Nights - US $1,456
Condo
10.0(48 Reviews)
1 Bedroom
2 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $325/Night
7 Nights - US $2,272
Condo
10.0(47 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $307/Night
7 Nights - US $2,147
Condo
10.0(45 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
US $472/Night
7 Nights - US $3,304
Book a Last Minute Place to Stay in Madeira Beach
About Casai's Private Villas and Holiday Rentals in Madeira Beach
Discover more than 2255 vacation rentals available in Madeira Beach. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Madeira Beach.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Madeira Beach, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Madeira Beach. On average, places to stay near Madeira Beach offer 790.57 ft², with nightly prices averaging US $330.
With Casai, finding and comparing holiday rentals in Madeira Beach is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
Other Places to Stay in Madeira Beach, FL
There are 2255 Madeira Beach, FL Holiday Rentals
- Prices for a holiday home in Madeira Beach start at US $89
- Top rated vacation home in Madeira Beach is REMODELED, immaculately designed, BEACHFRONT condo with gorgeous water views
- Most popular short term in Madeira Beach is Barefoot Beach Club
- Cheapest place to stay in Madeira Beach is Waterfront 2 bed/2 ba in 55+ resort, steps to pool & 1.5 mi to Madeira Beach!
- Most expensive holiday rental in Madeira Beach is Walk to the Beach | Sleeps 4 | Pool
Recently Booked Holiday Rentals in Madeira Beach
Frequently Asked Questions About Madeira Beach?
What are the top holiday rentals in Madeira Beach?
With numerous options available in Madeira Beach, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday 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
- Ocean Breeze - Cozy Beach Cottage across from the beach. Pet friendly!
- Gulf-Side Beach House - Tiki Bar · Direct Beach Access · No Roads to Cross
- Directly on the Beach
- Gulf Front Sunsets From the Balcony of This 3 BD/2 BA condo!
- Paradise awaits you!
- Amazing Beachfront Condo 3BR/2BA - Spectacular View
- Sweeping views from this 3 bed/2bath condo
How many holiday rentals have private pools in Madeira Beach?
Discover a selection of holiday rentals with private pools near Madeira Beach with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.
Which holiday homes in Madeira Beach are best for families?
If you're searching for a family-friendly holiday home in Madeira Beach, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Madeira Beach:
How many Casai.nz holiday rentals are available in Madeira Beach?
As of 2026, Casai boasts over 2255 properties listed in the Madeira Beach area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Madeira Beach.
Nearby Neighborhood (1)
| Neighborhood | Property Count |
|---|---|
| South Pinellas Community Council Vacation Rentals in Madeira Beach, Florida | 60 |
