Montgomery Cottages - Vacation Rentals in Bayfront

The Urban Cottage Downtown Sarasota From US $211
         

10.0 (5 Reviews)
Cottage
  • Air Conditioner
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  • TV
Lovely Cottage near the Beach and Downtown Sarasota From US $207
         

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9.5 (2 Reviews)
House
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  • Pet Friendly
Sunny Sarasota Home w/Private Yard & Fire Pit! From US $203
         

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New
Cottage
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Charming Beach Bungalow with Private Pool and steps away from the Beach! From US $593
         

Luxury Places to Stay in Bayfront

Over 2327+ Luxury Places to Stay in or Near Bayfront
Siesta Key Oceanfront Palace with Private Beach From US $5,933
         

9.6 (18 Reviews)
House
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  • Pet Friendly
All Decked Out From US $4,077
         

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7.0 (1 Review)
House
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  • Pet Friendly
  • Accessibility
Five Palms - 354 From US $3,556
         

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New
House
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  • Pet Friendly
  • View
The Ringling Estate From US $3,450
         

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New
House
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Top-Rated Vacation Rentals with a Pool in Bayfront

Over 1012+ Top-Rated Vacation Rentals with a Pool in or Near Bayfront
Island Vibes + Modern Comfort at Lido Beach! From US $379
         

10.0 (157 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
ST. ARMANDS CIRCLE, 3 Bedroom 3 Bath, Heated Pool! From US $718
         

1/10 mile to Lido Beach From US $517
         

10.0 (73 Reviews)
House
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  • Pool

Pet-Friendly Vacation Rentals in Bayfront

Over 910+ Pet-Friendly Vacation Rentals in or Near Bayfront
Lido Breeze Tropical Private Pool Home Near Beach & St. Armands From US $693
         

9.8 (92 Reviews)
House
  • Air Conditioner
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  • Pet Friendly
Modern & Fresh - Less than 3 miles to the Beach! From US $146
         

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8.5 (2 Reviews)
House
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  • Pet Friendly
voco Sarasota by IHG From US $346
         

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9.2 (1005 Reviews)
Hotel
  • Air Conditioner
  • Pet Friendly
  • Pool
Studio Apartment, Safe & Walkable area, Pet Friendly From US $253
         

8.8 (5 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV
"Updated & Charming Pool Home 1 Mile from Siesta Key " From US $487
         

9.8 (64 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
See More Pet-Friendly Vacation Rentals in Bayfront on PetFriendly.io

Large Vacation Homes & Villas in Bayfront

Over 313+ Large Vacation Homes & Villas in or Near Bayfront
Lido Beach Villa From US $989
         

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10.0 (4 Reviews)
Villa
  • Air Conditioner
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  • Pool
Lido Lux Beach House From US $597
         

10.0 (61 Reviews)
House
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  • Pet Friendly
Beach Views - Family-Friendly, Steps to Lido Beach! From US $1,526
         

10.0 (51 Reviews)
House
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  • Pet Friendly
Entire private house From US $546
         

10.0 (48 Reviews)
House
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  • Pool
Luxury Villa with Pool, Game Room, Near Beach From US $594
         

10.0 (33 Reviews)
Villa
  • Air Conditioner
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  • Pet Friendly

Wheelchair Accessible Vacation Homes in Bayfront

Over 321+ Wheelchair Accessible Vacation Homes in or Near Bayfront
Su Casa Sarasota From US $249
         

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10.0 (1 Review)
House
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  • TV
Art Ovation Hotel, Autograph Collection From US $376
         

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9.4 (1004 Reviews)
Hotel
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  • Parking
  • Pool
The Ringling Estate From US $2,589
         

10.0 (26 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
The Strand of Sarasota 509 From US $304
         

10.0 (19 Reviews)
Condo
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  • Pool

Bayfront Vacation Rentals and Airbnb Places to Stay Under $200

Over 628+ Bayfront Vacation Rentals and Airbnb Places to Stay Under $200
Jungalow Oasis From US $125
         

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New
House
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  • Balcony/Terrace
PERFECT LOCATION STEPS TO LIDO BEACH From US $111
         

10.0 (4 Reviews)
Apartment
  • TV
  • View
  • Ocean View
Sarasota Downtown, Best Location For Your Vacation! From US $190
         

7.0 (4 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Lido Beach Walk! One block to beach! From US $164
         

10.0 (123 Reviews)
House
  • Air Conditioner
  • Parking
  • TV

Instantly Bookable Vacation Homes in Bayfront

Over 1386+ Instantly Bookable Vacation Homes in or Near Bayfront
Waterfront Relaxation - Modern Comfortable Condo From US $251
         

10.0 (14 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pet Friendly
3 bedroom Home with Pool Near Downtown. From US $229
         

9.2 (53 Reviews)
House
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  • Pet Friendly
Comfy 3bed/2bath with pool close to Downtown From US $253
         

9.4 (37 Reviews)
House
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  • Parking
  • Pet Friendly
Best Location w/Fenced Yard & Private Pool From US $311
         

9.0 (26 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool

About Bayfront Vacation Rentals

With more than 61 Bayfront vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Montgomerycottages and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Bayfront.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Montgomerycottages Bayfront, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Bayfront. Places to stay near Bayfront are 663.8 ft² on average, with prices averaging $271 a night.

Montgomerycottages makes it easy and safe to find and compare vacation rentals in Bayfront with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Bayfront

Type Count
Cottages 52
Vacation Homes 9

Use these Quick Filters to Find a Vacation Rental in Bayfront

Pro Tip: Montgomerycottages makes it easy to compare the best listings on Montgomerycottages homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Montgomerycottages homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Bayfront.

Weather in Bayfront

View the weather forecast for Bayfront before booking your Bayfront Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Bayfront Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Bayfront?
How many vacation rentals are available in Bayfront?

Currently, the total number of properties listed in 2026 is over 61 in the Bayfront area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Bayfront.