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Cottage vacation rentals in Gulfport

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Top-rated cottage rentals in Gulfport

Guests agree: these cottages are highly rated for location, cleanliness, and more.

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Cottage in Clearwater

4.73 out of 5 average rating, 259 reviews

Clearwater cottage

welcome to our Clearwater cottage located just minutes drive away from the world-renowned Clearwater Beach and just a short bike ride down to the waterfront where you can take in breathtaking sunsets and fishing the Pinellas trail is a 45 mile long biking/walking trail it is right around the corner from the house, there are two bikes available at no additional charge. the house has been renovated and comes completely furnished, pots pans silverware.. 6ft privacy fence, outdoor barbecue. pets ok.

Cottage in Tampa

4.98 out of 5 average rating, 168 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

Cottage in Indian Rocks Beach

4.89 out of 5 average rating, 264 reviews

Vintage Florida Beach Cottage B

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

Cottage in Pass-a-Grille Beach

4.96 out of 5 average rating, 128 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.

Cottage in Madeira Beach

4.84 out of 5 average rating, 127 reviews

Family Friendly Beach Cottage in Madeira Beach, FL

Mad Beach Cottage is a single family home in the Surf Song Resort on Madeira Beach 60 flip-flop steps to SAND! No streets, boardwalks or stairs! You'll enjoy a heated pool, 3 Weber grills, shuffleboard and sundeck with lounge chairs for gazing at spectacular sunsets every night. It's located across from famous John's Pass Fishing Village Boardwalk for shopping, dining, ice cream, coffee, live music, brew pubs, dolphin/fishing/sunset/pirate boat cruises, wave runner/kayak rentals. 5* LOCATION!

Cottage in Gulfport

4.95 out of 5 average rating, 262 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!

Cottage in Dunedin

4.78 out of 5 average rating, 116 reviews

Serene French Country Cottage near everything

Unwind in this rustic French provençal, Extra Cosy Cottage w/ Unique Decor in Charming, Artsy Dunedin. Fenced in yard. Free Parking&Wifi. CENTRAL LOCATION Close to Clearwater Beach, Honeymoon Island. Short walk to Downtown Dunedin, Pinellas Trail, Blue Jay Stadium & Beautiful sunsets! Perfect location for Walkers, Runners and Bikers! A home away from home in a very convenient location for quality shopping, dining, nature explorations and beaches! A short walk or Uber away from everything!

Cottage in Indian Shores

4.96 out of 5 average rating, 126 reviews

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.

Cottage in Bayshore Beautiful

4.76 out of 5 average rating, 139 reviews

Good Vibes Cozy Cottage on Million $ Row

Great location for this cottage one block from Infamous Bayshore Blvd. Smart Tv's and quiet back porch with fire pit makes this location perfect for vacationers. Short walk to Bayshore blvd with scenic views of downtown Tampa and beautiful Tampa Bay water ways. Come and enjoy biking, running, skating or just walking along this 4 miles continuous waterfront walkway. You will have views of Tampa Bay on one side and views of multi-million dollar homes on the other during your stroll.

Cottage in Clearwater Beach

4.88 out of 5 average rating, 107 reviews

Mermaid Cottage

Located in a three unit 'Olde Florida Style Complex' and just 45 steps to Clearwater Beach! The Mermaid Cottage is located on the 1st floor at the back of the complex. This Florida style unit is adorned wood floors and charming island decor. Open to an outdoor patio with furniture. The cottage has two bedrooms, two full baths and an outdoor shower! Living room has a queen pull-out bed. The patio area is completely fenced for private use. Nice, park like charcoal grill.

Cottage in Treasure Island

5 out of 5 average rating, 191 reviews

Island Time Stay: Happy Hour

Check out our large studio cottage located on Gulf Blvd in Treasure Island, Florida. It is located less than 300 steps from the beautiful sand of Treasure Island Beach and 5 blocks from the world famous boardwalk, shopping and restaurants of John’s Pass Village in Madeira Beach. We have a crosswalk conveniently located in front of the property. You can stop traffic with the push of a button to safely walk across the street toward the boardwalk.

Cottage in Ruskin

4.91 out of 5 average rating, 102 reviews

Little Manatee River Cottage

This cottage is located on the Little Manatee River. Sun City Center 10 min Aquatic rentals walking distance. The cottage is updated. Abundant fishing charters, Little Harbor, manatee viewing center and Simmons Park all within minutes. Fully furnished, linens, kitchen utensils; bath towels; blankets pillows comfy furnishings. View sunsets out on the river, on the dock or at Little Harbor sipping your favorite drink.

Vacation rentals for every style

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Popular amenities for Gulfport cottage rentals

Free parking on premises

Air conditioning

Cottage rentals with a hot tub

Cottage in Safety Harbor

4.96 out of 5 average rating, 172 reviews

Harbor Oasis with Hot Tub

Cottage in Clearwater Beach

4.77 out of 5 average rating, 137 reviews

Pink Gulfside Cottage, Steps to Beach, Pets OK

Cottage in Dunedin

5 out of 5 average rating, 11 reviews

1000 Oaks Cottage 3bed/2bath with hot tub

Cottage in Largo

5 out of 5 average rating, 32 reviews

Family FUN~Pool, GameRoom+Bikes, Near Beach/Trail

Cottage in Crystal Beach

4.83 out of 5 average rating, 90 reviews

Happy Camper Cottage | Cozy Oasis with Hot Tub

Cottage in Historic Old Northeast

4.99 out of 5 average rating, 72 reviews

"TROPI COTTAGE"

Cottage in Largo

4.96 out of 5 average rating, 79 reviews

Hidden Oasis #1, high&dry near the beach

Cottage in Tampa

5 out of 5 average rating, 5 reviews

Traveler's Sanctuary

Pet-friendly cottage rentals

Cottage in Largo

4.78 out of 5 average rating, 60 reviews

Cottage by the Coast 2 bd - Pet Friendly

Cottage in Clearwater

4.99 out of 5 average rating, 67 reviews

Amazing! Coastal Home+ 10 Mins to Dunedin & Beach

Cottage in Indian Shores

5 out of 5 average rating, 54 reviews

Private beach access, Dog-friendly home

Cottage in Crystal Beach

4.96 out of 5 average rating, 47 reviews

Mango Cottage, pet friendly, steps to gulf

Cottage in Indian Rocks Beach

4.88 out of 5 average rating, 42 reviews

Backyard Oasis with sand and private pool

Cottage in St. Petersburg

4.95 out of 5 average rating, 43 reviews

Old Florida Paradise Secret Lair Cottage

Cottage in Dunedin

4.96 out of 5 average rating, 47 reviews

The Cook Cottage sleeps 4 in Dunedin

Cottage in Tampa

4.94 out of 5 average rating, 35 reviews

Carriage House 1893

Private cottage rentals

Cottage in Indian Shores

4.87 out of 5 average rating, 95 reviews

Your Beach Paradise Awaits!

Cottage in Dunedin

4.96 out of 5 average rating, 69 reviews

Adorable Villa 1 min to Downtown Dunedin

Cottage in Dunedin

4.97 out of 5 average rating, 72 reviews

Private and Romantic I The Highland Hideaway

Cottage in Indian Shores

4.89 out of 5 average rating, 53 reviews

Just Steps To The Gulf We Mermaid For The Beach

Cottage in Clearwater Beach

5 out of 5 average rating, 30 reviews

NEW! 2BR/2BA Finest Vacation Home Steps to Beach

Cottage in Indian Rocks Beach

5 out of 5 average rating, 93 reviews

Sol Cottage, managed by owners- No Chores

Cottage in Madeira Beach

4.79 out of 5 average rating, 98 reviews

Water Front Super Chic 2BD/ 1 bath - Cottage Wi-Fi

Cottage in Indian Rocks Beach

4.9 out of 5 average rating, 94 reviews

Historic Florida Beach Cottage steps from the sand

Quick stats about cottage rentals in Gulfport

Total rentals
10 properties
Nightly prices starting at
$80 before taxes and fees
Total number of reviews
1.2K reviews
Family-friendly rentals
10 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace

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