Cottage vacation rentals in Madeira Beach

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Top-rated cottage rentals in Madeira Beach

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Guest favorite

Cottage in Madeira Beach

4.96 out of 5 average rating, 134 reviews

BEACHFRONT FAIRWINDS Cottage Lower

Bright, tropical-themed beach house located directly on Madeira Beach 1/2 block from John's Pass Village. This cozy 2 bedroom & 1 bath downstairs getaway has a huge covered 400 sq. ft. deck & ocean views. Toes hit the sand off the deck & just past the dunes is the Gulf! 1 wk stay for holidays + holiday rates. Decorative items removed due to COVID. Pics are preCovid, but cottage is still very cute! If guest loses house key, guest responsible for expense of locksmith, new locks, and new keys.

Oct 31 – Nov 7

G$56,224 GYD per night

Guest favorite

Cottage in Treasure Island

4.97 out of 5 average rating, 150 reviews

Peacock Beach Cabana beach in 100 steps

Escape to a cozy retreat! The Peacock Beach Cabana at The Mermaid Beach Cottages, in Treasure Island is a bright 1938 Florida style boutique cottage. Professionally remodeled and decorated. This cabana offers accommodations for two guests. It is located 100 steps from the beach and walking distance to restaurants, beach bars and live music. No detail has been overlooked and we hope you enjoy our little piece of We are also 1.5 hour drive from Walt Disney World and 45 minutes from Busch Gardens.

Jul 29 – Aug 5

G$38,481 GYD per night

Guest favorite

Cottage in Gulfport

4.96 out of 5 average rating, 134 reviews

The Pelicans Roost / Gulfport

The Pelicans Roost is a remodeled home, with a new fully stocked kitchen with all your cooking and entertaining needs. All new furnishings, a screened in back porch and a patio with an outside table and grill. The yard is completely fenced and lined with tropical plants and trees for your privacy. This spacious and comfortable home is clean and in a quiet neighborhood just 5 blocks from all that downtown Gulfport has to offer- the Marina,Beach,Restaurants, Shops, Fishing, Galleries and more...!

Aug 12 – 19

G$24,478 GYD per night

Guest favorite

Cottage in Indian Rocks Beach

4.89 out of 5 average rating, 241 reviews

Vintage Florida Beach Cottage

Just a short walk to the beach makes this a great beach getaway for couples or families. On your way you can stop at the Cooky Coconut for lunch, an awesome milkshake or a variety of snacks. With a totally new renovation in 2019, this unit is in updated, very clean and worry free condition. This cottage is located in a quiet residential neighborhood and a great place to relax. Common laundry on shared screened porch. Dogs allowed (extra $45 cleaning). Easy refund policy. Level 2 EV charger

Nov 20 – 27

G$31,881 GYD per night

Guest favorite

Cottage in Indian Shores

4.86 out of 5 average rating, 161 reviews

*GROUND FLOOR DIRECT BEACHFRONT COTTAGE!!*

Step out the door and into the sand! Ground floor DIRECT beachfront one- bedroom/one-bath cottage nestled in the sand directly on the Gulf of Mexico with awesome amenities for the perfect Gulf Beach getaway! Enjoy a cozy bedroom, living/dining area, fully-equipped kitchen, beachfront patio and private beach area with lounge chairs and umbrellas. Conveniently located near a trolley stop for easy access to local restaurants, shops, and attractions. Book now for an unforgettable beach vacation!l

Aug 15 – 22

G$64,315 GYD per night

Guest favorite

Cottage in Madeira Beach

4.91 out of 5 average rating, 113 reviews

Flipper's @ Mad Beach Cottage

Flipper's at Mad beach is a few steps away from the sugary sands of Madeira Beach, and close by the famous John's Pass Village & Boardwark where shopping and entertainment is always great. Completely renovated with light porcelain tile, nice furniture, queen bed with memory Thempur-Pedic mattress, exquisite modern shower, tall kitchen cabinets with plenty of storage. Huge private paved fenced backyard with gazebo, great for entertainment and outdoor grilling. You will love the beach decor.

Sep 29 – Oct 6

G$25,179 GYD per night

Guest favorite

Cottage in Gulfport

4.95 out of 5 average rating, 235 reviews

Gulfport Cottage STEPS to Beach & Restaurants

Calling all beach lovers! Fall in love with this unique Gulfport Beach Cottage! Colorful, light & bright. Located on a corner lot STEPS from popular Beach Blvd & Gulfport beach, fishing pier, eclectic Gulfport shops, cafes and everything FUN! Gulfport has artsy and quirky shops, fabulous waterfront restaurants and a thriving art scene. Gulfport is a funky community all its own. Gulfport has an Art Walk on the First Friday and Third Saturday and a Tuesday market every week. Don’t miss it!

Jun 23 – 30

G$38,795 GYD per night

Guest favorite

Cottage in Indian Shores

4.95 out of 5 average rating, 110 reviews

OPEN! Beautiful Beachfront Cottage on the Water

Renovated, romantic 1937 beach front cottage. Last of its kind in the quiet family setting of Indian Shores Florida, halfway between Clearwater Beach and Treasure Island/John's Pass. Truly an "Old Florida" experience with original pine floors, Florida room and covered porches, as well as updated kitchen and bathroom. This house, uniquely built near ground level, allows it to be waterfront on the beach while shaded by huge pine trees. You won't find a more tranquil setting on the beach.

Oct 30 – Nov 6

G$92,399 GYD per night

Guest favorite

Cottage in Indian Rocks Beach

4.93 out of 5 average rating, 178 reviews

Kooky Coconut Cottage, Indian Rocks Beach

Coconut Cottage only steps away from the beautiful beaches of Indian Rocks Beach. 2 bedroom,1 bath. The entire cottage has been renovated. Next door to the local famous Kooky Coconut Cafe. Perfect for couple, friends or small families. ONLY 3 GUESTS ALLOWED. NO sleeping on the sofa ALLOWED. If you bring more then 3 guests you will be charged $100.00 surcharge per night per extra guest. Due to cleaning restriction we DO NOT allow cooking with CURRY or FISH OIL in the cottage.

Apr 20 – 27

G$37,172 GYD per night

Guest favorite

Cottage in Madeira Beach

4.8 out of 5 average rating, 162 reviews

20% OFF Quaint Madeira Beach Cottage w Heated Pool

Enjoy a Gulf vacation in a private beach cottage located directly across the street from the beach. In less than a one minute walk from your doorstep you will be enjoying the sun on the white powdery sands of Madeira Beach. Our quaint resort grounds are meticulously taken care of and beautifully landscaped. You can swim in the large heated pool with plenty of seating and lounge chairs. A quiet shaded area with barbecue grills and tables are available to prepare and enjoy a nice meal.

Dec 13 – 20

G$28,998 GYD per night

Guest favorite

Cottage in Indian Rocks Beach

4.96 out of 5 average rating, 293 reviews

Private Heated pool/spa home!

ZERO Storm damage to this home! Pool heat available. Swim all year! FIVE STAR CLEAN. WIFI GAME STRONG. WORK REMOTE, KEEP KIDS BUSY, BREATHE CLEAN SALT AIR. BTR#1735 Come explore our gorgeous, resilient Gulf Coast:) Beach bungalow with all of the amenities. Have the house and pool with private oasis all to yourself. Just step out the front door and walk 7 homes to the sandy shores of Indian Rocks Beach. See hundreds of reviews to learn more about us, our place, our style.

Feb 23 – Mar 2

G$94,293 GYD per night

Guest favorite

Cottage in Largo

4.94 out of 5 average rating, 124 reviews

Fall special 3rd night free! “The Sweet”

Cozy, romantic, 1 king bed, super cute and super sweet! Just a short walk to beautiful Indian Rocks Beach, nature parks with trails, shopping, orange grove, and many restaurants and fun beach bars! Guests have private entrance, full bath, laundry facilities, large back yard with fire pit, bbq grill, beach chairs and cooler. With each stay guests receive a mini super rummy Island Rum Cake and a gift certificate PJ's Oyster Bar! **Fall Special stay 2 nights get 1 free**

Oct 15 – 22

G$27,742 GYD per night