Language and Currency

Select your language and currency preferences for the site. Please note that all transactions will be processed in USD

Calendar View
  • Dates
    Any
  • Occupancy
    Any
    - +
    - +
    - +
  • Rooms
    Any
  • Price Range
    Any
  • Amenities
    Any
  • List
  • Map
  • Calendar

Madeira Beach Vacation Rentals

1 - 42 of 269 rentals
  PrevNext  
Sun 27 May Mon 28 May Tue 29 May Wed 30 May Thu 31 May Fri 1 Jun Sat 2 Jun Sun 3 Jun Mon 4 Jun Tue 5 Jun Wed 6 Jun Thu 7 Jun Fri 8 Jun Sat 9 Jun Sun 10 Jun Mon 11 Jun Tue 12 Jun
Madeira Bay Resort: The Baysider  - Madeira Beach, FL Vacation Rental
- - 97 101 90 - - - - - - - - - - 94 99
Bay Breeze - Anna Maria, FL Vacation Rental

Bay Breeze

Anna Maria, FL
4 Bed 3 Bath Sleeps 8
- - - - - - 353 385 - - - - - - - - -
Turquoise Paradise East  - Holmes Beach, FL Vacation Rental
- - - - - - 150 173 177 167 - - - - 185 201 200
Island Nestaway - Holmes Beach, FL Vacation Rental

Island Nestaway

Holmes Beach, FL
3 Bed 2 Bath Sleeps 6
- - - - - - - - - - - - - - - - -
Palm Tree Beach House  - Holmes Beach, FL Vacation Rental
169 160 158 158 159 159 162 160 163 162 161 160 160 166 179 185 184
La Casa Poulos - Holmes Beach, FL Vacation Rental

La Casa Poulos

Holmes Beach, FL
3 Bed 3 Bath Sleeps 8
- - - - - - - - - - - - - - - - -
La Casa Karen - Holmes Beach, FL Vacation Rental

La Casa Karen

Holmes Beach, FL
3 Bed 2.5 Bath Sleeps 6
- - - - - 309 331 327 333 331 329 327 327 338 363 373 371
Coquina Beach Club 204 - Bradenton Beach, FL Vacation Rental
- - - - - - - - - - - - - - - - -
LaMedeira 305 Unit A - Holmes Beach, FL Vacation Rental

LaMedeira 305 Unit A

Holmes Beach, FL
3 Bed 3 Bath Sleeps 6
- - - 200 212 211 216 213 217 215 203 - - - - - -
211 Elm A  - Anna Maria, FL Vacation Rental

211 Elm A

Anna Maria, FL
2 Bed 1 Bath Sleeps 6
- 131 137 136 128 - - - - - 146 153 130 - - - -
Serenity Now - Holmes Beach, FL Vacation Rental

Serenity Now

Holmes Beach, FL
2 Bed 2 Bath Sleeps 6
173 172 170 171 171 171 173 172 174 173 172 172 172 176 188 192 191
Turquoise Paradise West - Holmes Beach, FL Vacation Rental
- - - 155 164 163 167 165 168 158 - - - - - - -
Starfish Beach Cottage #3 - Holmes Beach, FL Vacation Rental
- 141 147 147 148 147 150 148 151 150 149 148 126 - - - -
Salt Shack - Holmes Beach, FL Vacation Rental

Salt Shack

Holmes Beach, FL
3 Bed 2 Bath Sleeps 6
- - - - - - - - - - - - - - - - -
Bay View Inn 101-308 2nd St  - Bradenton Beach, FL Vacation Rental
- - - - - - - - - - - - - - - - -
North Beach Village 72 - Holmes Beach, FL Vacation Rental

North Beach Village 72

Holmes Beach, FL
3 Bed 2.5 Bath Sleeps 6
208 198 195 196 197 167 - - - - - - - 166 - - -
Sundance Cottage - Anna Maria, FL Vacation Rental

Sundance Cottage

Anna Maria, FL
3 Bed 2 Bath Sleeps 6
- - - - - - - - - - - - - - - - -
Casa Bonita - Anna Maria, FL Vacation Rental

Casa Bonita

Anna Maria, FL
4 Bed 4 Bath Sleeps 8
- - - - - - - - - - - - - - - - -
Pelican Landing AMI - Holmes Beach, FL Vacation Rental

Pelican Landing AMI

Holmes Beach, FL
3 Bed 2 Bath Sleeps 6
- - - - - - - - - - - - - - - - -
A Gulf Front Getaway - Holmes Beach, FL Vacation Rental

A Gulf Front Getaway

Holmes Beach, FL
1 Bed 1.5 Bath Sleeps 4
- - - 113 120 113 - - - - - - - 119 151 157 156
Coconut Tree - Anna Maria, FL Vacation Rental

Coconut Tree

Anna Maria, FL
3 Bed 2.5 Bath Sleeps 8
- - - 236 249 215 - - - - - - - - - - -
Vitamin Sea - Holmes Beach, FL Vacation Rental

Vitamin Sea

Holmes Beach, FL
4 Bed 3 Bath Sleeps 8
- - - - - 329 - - - - - - - 363 463 480 478
Hidden Cove Unit 3 - Holmes Beach, FL Vacation Rental

Hidden Cove Unit 3

Holmes Beach, FL
2 Bed 2.5 Bath Sleeps 4
- - - - - - 210 232 - - - - - - - - -
A Pirate's Cove - Bradenton Beach, FL Vacation Rental

A Pirate's Cove

Bradenton Beach, FL
2 Bed 1 Bath Sleeps 6
- - - - - - - - - - - - - - - - -
Palm Gables 106 - Holmes Beach, FL Vacation Rental

Palm Gables 106

Holmes Beach, FL
3 Bed 2.5 Bath Sleeps 6
- - - - - - - - - - - - - - - - -
Little Miss Magic - Holmes Beach, FL Vacation Rental

Little Miss Magic

Holmes Beach, FL
3 Bed 2 Bath Sleeps 6
- - - - - - - - - - - - - - - - -
Rest Assured - Holmes Beach, FL Vacation Rental

Rest Assured

Holmes Beach, FL
3 Bed 3 Bath Sleeps 6
- 343 343 343 343 343 343 343 343 343 343 343 343 343 343 343 343
7001 B Holmes Blvd - Holmes Beach, FL Vacation Rental

7001 B Holmes Blvd

Holmes Beach, FL
3 Bed 2 Bath Sleeps 6
- - - 215 - - - - - - - - - - - - -
Au Soleil - Anna Maria, FL Vacation Rental

Au Soleil

Anna Maria, FL
5 Bed 3 Bath Sleeps 10
- - - - - - - - - - - - - - - - -
West Winds - Holmes Beach, FL Vacation Rental

West Winds

Holmes Beach, FL
2 Bed 2 Bath Sleeps 4
184 180 179 179 179 179 181 179 182 181 180 179 179 185 198 203 203
Gulf Drive Duplex (Upstairs) - Holmes Beach, FL Vacation Rental
- - - - - - - - - - - - - 193 - - -
Holly Hideaway - Anna Maria, FL Vacation Rental

Holly Hideaway

Anna Maria, FL
2 Bed 2 Bath Sleeps 4
- - - - - - - - - - - - - - - - -
Paradise Pointe - Anna Maria, FL Vacation Rental

Paradise Pointe

Anna Maria, FL
3 Bed 2 Bath Sleeps 8
- - - 265 280 243 - - - - - - - 243 - - -
Neolinda 305 - Holmes Beach, FL Vacation Rental

Neolinda 305

Holmes Beach, FL
3 Bed 2 Bath Sleeps 6
- - - - 201 211 216 213 217 215 214 213 181 - - - -
Hidden Cove Unit 1 - Holmes Beach, FL Vacation Rental

Hidden Cove Unit 1

Holmes Beach, FL
2 Bed 2.5 Bath Sleeps 4
- - - - - - - - - - - - - - - - -
Tiffany Place - Holmes Beach, FL Vacation Rental

Tiffany Place

Holmes Beach, FL
2 Bed 2 Bath Sleeps 4
- - - - - - - - - - - - - - - - -
Blue Manatee Retreat - Holmes Beach, FL Vacation Rental

Blue Manatee Retreat

Holmes Beach, FL
3 Bed 3 Bath Sleeps 6
- 233 242 242 243 215 - - - - - - - - - - -
Gulf Place - Holmes Beach, FL Vacation Rental

Gulf Place

Holmes Beach, FL
3 Bed 2 Bath Sleeps 6
- - - - - - - - - - - - - - - - -
Starfish Beach Unit 1 - Holmes Beach, FL Vacation Rental

Starfish Beach Unit 1

Holmes Beach, FL
2 Bed 2 Bath Sleeps 6
- - - - - - - - - - - - - - - - -
Anna Maria Island Club 40 - Bradenton Beach, FL Vacation Rental
- - - - - - - - - - - - - - - 212 209
Tropical Oasis - Holmes Beach, FL Vacation Rental

Tropical Oasis

Holmes Beach, FL
2 Bed 2 Bath Sleeps 6
- 172 - - - - - - - - - - 172 - - - -
Tina's Piece of Paradise - Holmes Beach, FL Vacation Rental
- - - - - - - - - - - - - - - - -
Page 1 of 7

About Madeira Beach

Home to year-round warm weather, world-renowned white sand beaches, and an eclectic seaside bazaar known as John’s Pass Village and Boardwalk, Madeira Beach is a hidden treasure on the western edge of Tampa Bay. From families and couples to seasonal residents and retirees, there's something for everyone in this oceanfront town and our Madeira Beach vacation rentals are the perfect home away from home for your next trip to the Sunshine State! 

Things to Do in Madeira Beach, FL

The area’s main draw are its white sand beaches that slope gently into the aquamarine waters of the Gulf of Mexico. With beautiful shoreline and tropical breezes, the beach at Madeira Beach will lull any beachgoer into a deep state of relaxation!

Looking for an adrenaline rush? Stop by one of the adventure outfitters on the boardwalk, like Eagle Parasailing or Dolphin Quest, and sign up your whole family for a thrilling day of flying high above the Gulf attached to a parachute or viewing native wildlife on the Intercoastal Waterway.

Guests of all ages and interests will love spending time at John's Pass Village and Boardwalk. From low-key dining options to charming souvenir shops to businesses providing tours of the Gulf and its plentiful wildlife, this half-mile shopping center on the south end of Madeira Beach offers a fun-filled day of sampling the local scene.

Kids (and those young at heart) will love hunting for the perfect souvenir to remind them of the beach in shops like Fun N Sun or Beach Fun and Games. After a long day soaking up the sun, the adults of the group will appreciate having some tropical cocktails and fresh seafood at laid-back restaurants like Bamboo Beach Bar & Grill or Sculley’s.

Day Trips from Madeira Beach, FL

Although the town itself is a quaint and quiet beach community, our Madeira Beach vacation rentals offer quick and easy access to the bustling and action-orientated activities of nearby Tampa. Enjoy the best of both worlds when you stay here! 

Load the kids in the car and drive 38 miles east for a fun family outing to Busch Gardens. They’ll love learning about exotic animals in exhibits like the Edge of Africa and Jambo Junction and zipping down roller coasters and other rides in this sprawling amusement park. 

Local sporting events in professional hockey, football, and baseball are also conveniently close -  it's just a 30-mile drive east to Tampa or south to St. Petersburg. The sports fans in your group can cheer on the Tampa Bay Rays MLB team at a home game in Tropicana Field Stadium or watch a puck fly by at Amalie Arena, home to the Tampa Bay Lightning NHL team. If you come in the fall, make sure to include a stop at the Raymond James Stadium for a home game of the NFL’s Tampa Bay Buccaneers. 

However you choose to fill your days and wherever you may roam, our Madeira Beach vacation rentals are the perfect place for beachside relaxation, adventure, and so much more! Book your trip today for the ultimate beachfront getaway on Florida’s Gulf Coast. 

Photo credit: Claudia Brauer via Flickr

  • Searching ...
  • 42 of 269
No results in this area. Move map or change filters for more rentals.
  • More Map
  • Less Map
Search Here