Cottage vacation rentals in St Petersburg

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Top-rated cottage rentals in St Petersburg

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Guest favorite

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...!

Aug 12 – 19

G$24,478 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$38,665 GYD per night

Guest favorite

Cottage in St Pete Beach

4.95 out of 5 average rating, 109 reviews

Pass-a-Grille Historic Cottage Unit 2

PASS-A-GRILLE HISTORIC COTTAGE UNIT 2 A fully renovated historic beach cottage located in beautiful Pass a Grille, Florida. Steps from the Gulf of Mexico and Boca Ciega Bay. This is a duplex; Unit 2 - 2 bedroom/1 bath. Household linens, towels, cookware & dishes provided. Appliances include; dishwasher, washer/dryer, flat screen TVs and wi-fi. Vintage-style tiled bathroom and shower. High end window shades on all windows. Front and back patio area w/ BBQ grill. Private parking for 2 vehicles.

Jul 27 – Aug 3

G$75,874 GYD per night

Guest favorite

Cottage in Palm Harbor

4.78 out of 5 average rating, 167 reviews

Crystal Beach Cottage #1

Original MCM bungalow located 1 blk from the Crystal Beach park. This property has original windows, AC window units, renovated bath and kitchen and every six month upgraded soft goods. It is appointed with all the travelers' needs for a quick get-away or a vacation. Located in a quaint neighborhood setting conveniently located by the Pinellas trail so cyclist, runners & walkers have immediate access. Close to local towns near by & Palm Harbor's Restaurant/bars, & 10 min all the best beaches.

Jul 3 – 10

G$20,692 GYD per night

Guest favorite

Cottage in Tarpon Springs

4.99 out of 5 average rating, 136 reviews

Cooper Cottage: Cozy, Convenient and Comfortable

Cooper Cottage is for cyclists, boaters, beach goers or those who just want to relax! The Cottage is the front half of a duplex in downtown Tarpon with all the amenities including bikes and beach gear! Walk/bike to Restaurants, Churches, Museums and Parks in under 12 minutes or drive to Fred Howard Beach or Sunset Beach in 7 minutes! Due to allergies of visiting family & friends we do NOT ALLOW PETS OR COMPANION ANIMALS, so you can rest assured that animal allergens will NOT be an issue.

Sep 13 – 20

G$31,636 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 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!

May 10 – 17

G$25,224 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$27,776 GYD per night