Cottage holiday rentals in Bay Pines

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Top-rated cottage rentals in Bay Pines

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Guest favourite

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.

13 – 20 Sept

$3,304 AUD total

Guest favourite

Cottage in Tampa

4.99 out of 5 average rating, 140 reviews

Bay Lake Cottage

You’ll have the Entire 500sq ft Cottage & private entry, deck/dock, all to yourself. Located on a 37-acre private ski lake.Key-pad entry, private parking. 1 king bed, 1 bath, queen sofa bed, washer/dryer, smart TV’s, blackout curtains,shampoo/conditioner,hairdryer,WiFi. Fully stocked kitchen, smokeless grill, wine fridge upon request, k-cup/drip coffee machine. The lake has bass, we provide fishing poles/tackle box. Rentable Kayaks & Canoe. Pet fee $50. Elope/Proposal packages IG lakepossibility

19 – 26 Aug

$2,211 AUD total

Guest favourite

Cottage in Gulfport

4.96 out of 5 average rating, 135 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...!

12 – 19 Aug

$1,652 AUD total

Guest favourite

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.

29 Mar – 5 Apr

$2,563 AUD total

Guest favourite

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.

12 – 19 Aug

$1,607 AUD total

Guest favourite

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!

23 – 30 June

$2,367 AUD total

Guest favourite

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.

30 Oct – 6 Nov

$5,442 AUD total

Guest favourite

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.

21 – 28 Apr

$2,206 AUD total

Guest favourite

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.

13 – 20 Dec

$1,825 AUD total

Guest favourite

Cottage in St. Petersburg

4.87 out of 5 average rating, 142 reviews

Beachy St. Pete Cottage Retreat!

Fully immerse in a private oasis at this beachy cottage. Centrally located to Downtown St. Pete, all Gulf beaches, and surrounded by excellent shops, local restaurants, bars, and craft breweries, you can enjoy all this amazing city has to offer or bring some of that culture back to enjoy at home! Eclectic accents include unique artwork scattered throughout the home, and an emphasis on furniture with a modern/beachy esthetic. We can’t wait to welcome you to our stylish beach cottage!

10 – 17 May

$1,652 AUD total

Guest favourite

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.

26 Mar – 2 Apr

$5,457 AUD total

Guest favourite

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**

13 – 20 Mar

$1,782 AUD total