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, 137 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.

Guest favourite

Cottage in Treasure Island

4.97 out of 5 average rating, 153 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.

Guest favourite

Cottage in Gulfport

4.96 out of 5 average rating, 137 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...!

Guest favourite

Cottage in Indian Rocks Beach

4.99 out of 5 average rating, 156 reviews

Cottage w/ Private Patio | 3 Min Walk to the Beach

Escape to paradise @sunshineescapes! Welcome to #CocoPalmsIRB, nestled in the heart of Indian Rocks Beach (IRB). This hidden gem radiates a whimsical, small-town charm, evoking nostalgic memories of carefree childhood summers by the shore. Just two blocks away, the Gulf of Mexico beckons, offering pristine fluffy sands and unforgettable sunsets. As the sister cottage of Mango, #CocoPalmsIRB invites you to immerse yourself in the laid-back beachy vibes of IRB. Your perfect beach getaway awaits!

Guest favourite

Cottage in St. Petersburg

4.92 out of 5 average rating, 126 reviews

Private Guesthouse- walk to downtown St. Pete!

Modern guest house in historic neighborhood-walking distance to downtown St. Pete! This space has an open floor plan with a bedroom loft accessed by an antique library ladder. Full kitchen and washer/dryer within space. This guesthouse is on host’s property, although the guesthouse has separate private alley parking, access, and entrance. Walking distance to nearby hospitals for medical professionals- short-term lease options available. **Ladder will need to be climbed to access bedroom**

Guest favourite

Cottage in Madeira Beach

4.92 out of 5 average rating, 119 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.

Guest favourite

Cottage in Gulfport

4.95 out of 5 average rating, 244 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!

Guest favourite

Cottage in St. Petersburg

4.95 out of 5 average rating, 101 reviews

Artsy guest house; near downtown w/ private patio

This uniquely decorated guest house is a private oasis with a lovely, private patio. The house is decorated with Latin American art from the owner's collection & travels. Only 11 blocks to downtown and very close to grocery stores, art galleries and all the night light life St. Pete offers. The home has a full kitchen and a very comfortable bedroom for one or two people. A perfect location for those that want to experience a comfortable and relaxing place. Only 12 block walk to Tropicana.

Guest favourite

Cottage in Indian Shores

4.96 out of 5 average rating, 113 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.

Guest favourite

Cottage in Indian Rocks Beach

4.93 out of 5 average rating, 182 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.

Guest favourite

Cottage in Madeira Beach

4.78 out of 5 average rating, 167 reviews

Quaint Madeira Beach Cottage with 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.

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**