
Holiday rentals with a pool in Madeira Beach
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Top-rated rentals with a pool in Madeira Beach
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

Perfect Ocean Sunset view Madeira Beach/Johns Pass
Excellent location for families or couples traveling to the beach! The building is BRAND NEW in late 2020. Beautiful private condo, a great view of the Gulf with perfect sunsets from the 6th-floor balcony. Master bedroom with an excellent view of the beach from bed. Steps away are the beach and John's Pass shopping district-with excellent restaurants and shopping. King size master with private en-suite bath. Private covered parking in attached garage. Heated pool with baja shelf and hot tub.

Pearl of the Sea, 1 BDRM, 2 min walk to the beach
Please note, the gym, jacuzzi, and hot tub are temporarily closed(hurricane damage) Completely remodeled, beach theme decorated, a beautifully furnished second-floor condo just steps away from the white silky sandy beach! Ideal for romantic vacations, honeymoon escapes, and getaways! Located in Madeira Beach Yacht Club, a private gated community, free parking, high-speed WI-FI, TV cable, Netflix, 2 outdoor heated swimming pools, and fishing piers. Please, book at least 7 days before your arrival

Stunning Views Beach Front Condo
Beautifully updated 4th floor 3 bedroom beach front condo! Enjoy gorgeous views of the Gulf of Mexico from a large screened in balcony! Gulf view from both the living room and master bedroom. A large updated kitchen is perfect for the whole family. This condo sleeps 6 comfortably. Cable and WIFI are available as well as beach necessities. A view of the Bay from the front door. Walking distance to John’s Pass. Due to the hurricane, there is still minor repairs being done around the building/town.

Spectacular beach to bay views from this resort.
Our condo has spectacular water views from the Bay to the Beach. We have a large one of a kind kitchen that is unique to our resort, with granite counter tops, hardwood cabinets, and all stainless steel appliances. Everything you need to prepare a meal is provided along with basic spices and condiments, Coffee, creamer, and sugar. The master bedroom has a new king size bed and walk in closet with all beach gear also available for your use. We have 2 - 50" flat screen TV's with cable as well.

40ft Floating Bungalow with Resort Perks
Unmatched Scenic Serenity: Imagine waking up to stunning sunrises and gentle ocean breezes. Your houseboat becomes a floating oasis, providing the comforts of a hotel but floating. Exclusive access to the resort across the street on the beach. Where you can use the heated pool and hot tub. Outdoor grilling area with corn hole boards are available to entertain you while you cook at the Beach Resort. No Grill on the Boat. *Boat is stationary at dock. **MOTION SICKNESS?? PLEASE DO NOT BOOK**

Beautiful Tampa Bay Pool Home Near Gulf Beaches
A beautiful Gulf Coast residence with many amenities to offer. Bright and open furnished spaces, for relaxing and entertaining up to 10 guests. A quiet, upscale neighborhood , your just 6 minutes from Madeira Beach and many other Gulf of Mexico beaches. Or, fun & sun in the private pool outback. 20 minutes from Downtown St Pete, which offers restaurants, museums, the new Pier, and excellent night life. Very close to countless restaurants, shopping, coffee shops, and grocery stores.

Penthouse Water View, Pool, @ Johns Pass!
Penthouse corner unit with stunning water view from the living room, bedrooms and balcony! This waterfront condo is in prime location. A block away from Johns Pass Boardwalk (#1 tourist destination in the county) and RIGHT across from the pristine white sands & sunsets of the Gulf of Mexico. The property offers a heated pool, hot tub, fitness room & event center. Our condo has everything you need including fully stocked kitchen, laundry in unit, high speed wifi & beach equipment.

Beach Front Madeira Beach
PLEASE NOTE: SEVERAL UNITS UNDER CONSTRUCTION in the building. And our swimming pool is currently closed for renovations as well. Expected completion by May 31. Amazing beachfront condo, newly remodeled on the second floor. Vinyl plank flooring throughout, No CARPET. 2 Bedroom, 2 Bath. Completely unobstructed views of the beach. It is centrally located less than 1 mile from World Famous Johns Pass. Enjoy breathtaking sunsets from your living room with the water just feet away.

Beachfront Condo in Exclusive Resort
The most stunning views from this brand new condo directly on Treasure Island Beach. This lovely unit is on the 4th, 5th, or 6th floor and provides sweeping views of the ocean. This units has 2 bedrooms and 2 full bathrooms. The inviting open concept living area has one of the best views of the ocean, especially when the retractable sliding doors are opened. The dining table on your private balcony provides a perfect dining area, with the ocean providing a beautiful backdrop.

Luxury Home N/Heated Pool/Rooftop/Steps to Beach
New, 2000 sq ft/3 Bedroom/3 Full Bathrooms 2 living rooms/modern townhome with heated salt water POOL located near a canal and the gulf just two blocks from the beach. Please note the pool is shared with the other side of the duplex. You can enjoy full view of the canal and partial views of the gulf from the balconies and the rooftop! Walking distance to the beach, restaurants, and volleyball. Close to Johns Pass, 2 miles. Please ask for the golf cart availability and a fee.

*Shore Thing* Walk to Beach | Intercoastal Views
🏖️ Shore Thing Condo 🏖️ Experience the ultimate blend of Sunset Bliss at this stylish Treasure Island retreat. Just steps from powdery sands, ocean breezes and breathtaking sunsets. Keep an eye out for local wildlife as dolphins and manatees glide by. Inside, enjoy coastal vibes featuring modern beachy interiors. Whether you are preparing a meal in the luxury kitchen or diving into the intercoastal heated pool, my service ensures your comfort always comes first.

Lux Condo w/ 2 balconies, Ocean & Marina views
This luxury condo features 2 private balconies, w/ spectacular ocean & marina views. It's stylish decor, meticulously picked quality & comfortable furnishing/accessories are sure to please. It’s conveniently located just across the street from the pristine white sands and sunsets of the Gulf of Mexico. It is adjacent to the #1 tourist destination in the county, John's Pass Village. The property offers a heated swimming pool, hot tub, fitness room & event center.
Popular amenities for Madeira Beach rentals with a pool
House rentals with a pool

Insta Worthy Retreat -Arcade Room- Htd Pool- Golf

Ocean Dreaming: Waterfront Home with Heated Pool,

Coastal Pool Retreat *5 Min to Madeira Beach Sand

Heated Pool-Near Beaches-3 Bikes-Firepit-OutsideTV

Tiki House •Sleeps 12 •Walk to Beach + Heated Pool

Stunning views! Spot dolphins from the pool!

Redington Beach near beach on ICW w/pool & dock

Tranquil "Ocean Breeze Retreat"
Apartment rentals with a pool

Modern Condo | Remodeled, Beach Access, Sleeps 6

Beach Front Gulf View at John’s Pass Medeira Beach

Steps to beach with Marina Sunsets – 3 -Bed condo

Ideal beach getaway condo!

Five Star Beachfront Condo Newly Renovated

Ocean Breeze Madeira Beach; steps from the beach

Beach, dolphin/manatee sightings, fishing, sunsets

Stunning BEACH FRONT Condo, KING Size Bed, Balcony
Other holiday rentals with a pool

Luxury Penthouse Beach Condo

Bay-View 2BR / Heated Pool, Steps to Madeira Beach

Sandy Shores #204 - John's Pass, Pool, Gulf front!

Three Palms

Beachfront Madeira Norte - Gulf front - Pool

Beachside Bliss | Rooftop Gulf Views & Fun Vibes

Direct Beachfront Corner 3BR|GulfView Pool|Madeira

Stylish Stay At Ocean Sands
When is the best time to visit Madeira Beach?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | € 176 | € 214 | € 255 | € 188 | € 171 | € 178 | € 177 | € 157 | € 151 | € 158 | € 163 | € 170 |
| Avg. temp | 17°C | 18°C | 20°C | 23°C | 26°C | 28°C | 29°C | 29°C | 28°C | 25°C | 21°C | 18°C |
Quick stats about holiday rentals with a pool in Madeira Beach

Total holiday rentals
Explore 1,230 holiday rentals in Madeira Beach

Nightly prices starting at
Madeira Beach holiday rentals start at € 26 per night before taxes and fees

Verified guest reviews
Over 27,740 verified reviews to help you choose

Family-friendly holiday rentals
960 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 120 rentals that welcome pets

Rentals with dedicated workspaces
830 properties have a dedicated workspace

Wifi availability
1,220 of Madeira Beach holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Madeira Beach rentals

4.7 Average rating
Madeira Beach stays receive an average rating of 4.7 out of 5 from guests
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- Anna Maria Island
- Siesta Beach
- Raymond James Stadium
- Crescent Beach
- Busch Gardens Tampa Bay
- John's Pass
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