Location

Dates

Guests

Vacation rentals in Madeira Beach, Florida, United States

Seagate #107

3 bedrooms·2 baths

Indian Rocks Beach • Florida

$2,649.04 USD total for 7 nights

Sep 7 – 14, 2026

Seagate #205

3 bedrooms·2 baths

Indian Rocks Beach • Florida

$2,987.73 USD total for 7 nights

Sep 7 – 14, 2026

Seagate #208

3 bedrooms·2 baths

Indian Rocks Beach • Florida

$2,987.73 USD total for 7 nights

Sep 7 – 14, 2026

Seagate #506

3 bedrooms·2 baths

Indian Rocks Beach • Florida

$2,987.73 USD total for 7 nights

Sep 7 – 14, 2026

Master bedroom, balcony access, king bed

Master, king bed

Master, king bed

Master bathroom, access from master and main living area

Master bathroom

Sea Gate 206 Beautiful Beach Front Condo/3 BR - 2 BTH

3 bedrooms·2 baths

Indian Shores • Florida

5(180 reviews)

$1,339.05 USD total for 3 nights

Oct 5 – 8, 2026

Free cancellation

Bayshore Yacht & Tennis Club #803

Bayshore Yacht & Tennis Club #803

Bayshore Yacht & Tennis Club #803

Bayshore Yacht & Tennis Club #803

Bayshore Yacht & Tennis Club #803

Bayshore Yacht & Tennis Club #803

2 bedrooms·2 baths

Indian Shores • Florida

$1,646.92 USD total for 7 nights

Sep 7 – 14, 2026

Bay Shores Yacht & Tennis Club

Bay Shores Yacht & Tennis Club

Bay Shores Yacht & Tennis Club

Bay Shores Yacht & Tennis Club

Bay Shores Yacht & Tennis Club

Bay Shores Yacht & Tennis Club

2 bedrooms·2 baths

Indian Shores • Florida

$1,778.62 USD total for 7 nights

Sep 7 – 14, 2026

Golden-hour fire pit at Sun Oasis — teal Adirondack chairs, real wood flames, lush tropical palms, and a screened pool glowing in the background. The perfect Florida evening.

Game room open to the main living area at Sun Oasis — foosball table in the foreground, dartboard on the wall, and a seamless view through to the coastal living room and kitchen beyond.

Screened-in private pool at Sun Oasis, a vacation rental in St. Petersburg, FL — crystal-clear water, lounge chairs, and lush tropical landscaping in a fully fenced backyard.

Open-concept living room at Sun Oasis with a large smart TV, fireplace credenza, coastal turtle artwork, beachy blue-and-white decor, and views straight through to the fully equipped kitchen.

lounge out in yard under the sun for some summer relaxation

Sun Oasis | Game Room, Pool, Fire Pit | Near Beach

3 bedrooms·2 baths

St. Petersburg • Florida

5(72 reviews)

$179 – $359/ night(excl. fees & taxes)

Private 2bdrm Suite/Kitchen/Laundry/Sunroom/Grill

Private 2bdrm Suite/Kitchen/Laundry/Sunroom/Grill

Private 2bdrm Suite/Kitchen/Laundry/Sunroom/Grill

Private 2bdrm Suite/Kitchen/Laundry/Sunroom/Grill

Private 2bdrm Suite/Kitchen/Laundry/Sunroom/Grill

Private 2bdrm Suite/Kitchen/Laundry/Sunroom/Grill

2 bedrooms·1 bath

St. Petersburg • Florida

5(4 reviews)

$750.00 USD total for 5 nights

Sep 7 – 12, 2026

Flamingo House Tropical Oasis Bike Trail Tennis ct

Flamingo House Tropical Oasis Bike Trail Tennis ct

Flamingo House Tropical Oasis Bike Trail Tennis ct

Flamingo House Tropical Oasis Bike Trail Tennis ct

Flamingo House Tropical Oasis Bike Trail Tennis ct

Flamingo House Tropical Oasis Bike Trail Tennis ct

3 bedrooms·1 bath

St. Petersburg • Florida

4.63(19 reviews)

$3,949.00 USD total for 30 nights

Sep 7 – Oct 7, 2026

Private Guest suite/Patio/Laundry/Parking/Beach

Private Guest suite/Patio/Laundry/Parking/Beach

Private Guest suite/Patio/Laundry/Parking/Beach

Private Guest suite/Patio/Laundry/Parking/Beach

Private Guest suite/Patio/Laundry/Parking/Beach

Private Guest suite/Patio/Laundry/Parking/Beach

1 bedroom·1 bath

St. Petersburg • Florida

4.46(13 reviews)

$625.00 USD total for 7 nights

Sep 7 – 14, 2026

The Beautiful Treasure

The Beautiful Treasure

The Beautiful Treasure

The Beautiful Treasure

The Beautiful Treasure

The Beautiful Treasure

2 bedrooms·1 bath

St. Petersburg • Florida

5(26 reviews)

$1,415.32 USD $1,047.03 USD total for 7 nights

Oct 17 – 24, 2026

Free cancellation

Holiday Villa II #103 Beachside Condo

Holiday Villa II #103 Beachside Condo

Holiday Villa II #103 Beachside Condo

Holiday Villa II #103 Beachside Condo

Holiday Villa II #103 Beachside Condo

Holiday Villa II #103 Beachside Condo

2 bedrooms·2 baths

Indian Shores • Florida

5(86 reviews)

$235 – $500/ night(excl. fees & taxes)

No Crossing the Street You are Staying ON THE BEACH

Miles of Powder White Sand

Jump in the Gulf When it's Time for Water Break

Play doubles or 3x3 or 6x6

Living Room w/Recliners

Beach Paradise w/Balcony+Pool

2 bedrooms·2 baths

Indian Rocks Beach • Florida

4.6(5 reviews)

$398/ night(excl. fees & taxes)

Family & pet friendly 4-bedroom home • heated pool image 1

Front of the house

Family & pet friendly 4-bedroom home • heated pool image 4

Family & pet friendly 4-bedroom home • heated pool image 5

Family & pet friendly 4-bedroom home • heated pool

4 bedrooms·2 baths

Largo • Florida

4.72(133 reviews)

$735.00 USD total for 3 nights

Sep 7 – 10, 2026

Comfy Living Room with 55" TV

Center Open view

Kitchen w/beverage fridge

Indian Rocks Beach only 2.5 miles - 4 bed & 2 bath

4 bedrooms·2 baths

Seminole • Florida

$1,401.75 USD total for 3 nights

Oct 16 – 19, 2026

Free cancellation

Paddle boarding just off the dock around mangroves.

Waterfront yard with dock for fishing and launching paddle boards and kayaks and turf for chilling

Mangrove Haven

3 bedrooms·3 baths

St. Petersburg • Florida

$388 – $1,619/ night(excl. fees & taxes)

Lakeside Retreat-4plex Sleeps 20

Lakeside Retreat-4plex Sleeps 20

Lakeside Retreat-4plex Sleeps 20

Lakeside Retreat-4plex Sleeps 20

Lakeside Retreat-4plex Sleeps 20

Lakeside Retreat-4plex Sleeps 20

9 bedrooms·5 baths

Largo • Florida

$1,833.99 USD total for 3 nights

Sep 7 – 10, 2026

We have it all - beautiful beach and comfortable accommodation

Living room with queen sofa bed and upgraded mattress. Comfortable rocking chairs. Smart TV - guests can use their Netflix, Amazon movie's, Hulu, etc. Basic cable is available in the living room TV as well.

Heated community pool for residents and guests only. Hours of operations: 9am-10pm.

The condo and the beach - very short walk across beach parking lot. St. Pete Beach - votes #1 beach in US by TripAdvisor in 2021.

Living room, kitchen and the coffee station

Condo in Beachfront Resort with Heated Pool

1 bedroom·1 bath

St. Pete Beach • Florida

5(29 reviews)

$614.72 USD total for 3 nights

Sep 13 – 16, 2026

Free cancellation

Welcome to the Lakeside Retreat -This tranquil estate awaits!

Nestled right on Lake Seminole, the backyard gazebo and pool area provide stunning views!

Our unique 4-plex floor plan gives your large group the ability to gather…

…while still having moments of privacy in their own suites.

Each suite is inspired by one of the 4 elements: Earth, Air, Fire, & Water

Lakeside Retreat-4plex Sleeps 20

9 bedrooms·5 baths

Largo • Florida

5(19 reviews)

$5,520.00 USD total for 3 nights

Sep 7 – 10, 2026

Floriday's Covered Patio Poolviews

Sea Club 18 Floridays Poolview

Floriday's Guest Bedroom

Floriday's Kitchen

Sea Club Community Pool

Sea Club Condo #18

2 bedrooms·2 baths

Indian Shores • Florida

Satly Vibes Living Room

Salty Vibes Kitchen Breakfast Bar

Salty Vibes Kitchen

Salty Vibes Queen Bed

Primary Bedroom - 2 Queen Beds

Sea Club Condo #20

2 bedrooms·2 baths

Indian Shores • Florida

Gone Coastal - One Bedroom Sleeps 4 Waterfront Condo

Gone Coastal Bedroom

Gone Coastal Living Room

Sea Club Community Swimming Pool

Indian Shores Beaches

Sea Club Condo #304

1 bedroom·1 bath

Indian Shores • Florida

Isle Be Back - Perfect View to Dolphin Watch

Dining & Living Space

Bedroom - 1 Queen / 1 Full

Bedroom - 1 Queen / 1 Full

Sea Club Condo #402

1 bedroom·1 bath

Indian Shores • Florida

$129/ night(excl. fees & taxes)