Montgomery Cottages - Vacation Rentals in Bay Isles

Luxury Places to Stay in Bay Isles

Over 775+ Luxury Places to Stay in or Near Bay Isles
Coastal Elegance by FVC From US $1,033
         

New
House
  • Air Conditioner
  • Parking
  • Pool

Top-Rated Vacation Rentals with a Pool in Bay Isles

Over 643+ Top-Rated Vacation Rentals with a Pool in or Near Bay Isles
Flash Sale Late OCT - NOV take a peek From US $413
         

10.0 (136 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Major Upgrades 1 of a kind home right on the beach From US $534
         

Direct Oceanview on LBK: Open Tuesday & Wednesday! From US $390
         

Client texted view crazy ON SALE From US $400
         

10.0 (96 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Unit #218 Sand Cay Beach Resort Gulf Front From US $571
         

10.0 (67 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool

Pet-Friendly Vacation Rentals in Bay Isles

Over 65+ Pet-Friendly Vacation Rentals in or Near Bay Isles
Beach Downtown Pet-friendly 1 BD @ The Park-633 From US $229
         

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7.7 (3 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Pet Friendly Longboat Key Condo with View of Gulf From US $120
         

9.6 (86 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pet Friendly
Longboat Key Condo w/Lanai: Walk to Beach & Shops From US $121
         

7.8 (7 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pet Friendly
Bay Haven Home on Longboat Key by RVA From US $355
         

6.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Bayview Paradise by FVC From US $636
         

New
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Large Vacation Homes & Villas in Bay Isles

Over 25+ Large Vacation Homes & Villas in or Near Bay Isles
1901 Harbour Links Circle #1 by RVA From US $262
         

Bright and Sunny Oceanfront Villa With Pool + Lanai | Hosts 6 From US $750
         

10.0 (1 Review)
Villa
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens
Villa Sereno Summary: From US $764
         

New
House
  • Air Conditioner
  • Parking
  • Pool

Wheelchair Accessible Vacation Homes in Bay Isles

Over 338+ Wheelchair Accessible Vacation Homes in or Near Bay Isles
Beachcomber unit 204 From US $424
         

10.0 (22 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
The Beach on Longboat Key #227 From US $519
         

Longboat Bay Club by Coolvacay From US $424
         

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10.0 (1 Review)
Condo
  • Air Conditioner
  • Parking
  • Pool
Beachcomber unit 202 From US $502
         

9.8 (18 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Beachcomber unit 303 From US $342
         

9.8 (42 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Beachcomber unit 205 From US $327
         

10.0 (15 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Unit #217 Sand Cay Beach Resort Gulf Front From US $689
         

9.8 (69 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool

Bay Isles Varoom and Airbnb Places to Stay Under $200

Over 96+ Bay Isles Varoom and Airbnb Places to Stay Under $200
Spectacular Sarasota Bay Views from all rooms From US $162
         

Sea Club I From US $193
         

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8.5 (142 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
Beachplace building 4 unit 503 by FVC From US $196
         

10.0 (3 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Beachplace 10-402 by FVC From US $193
         

10.0 (2 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Beachplace 11-305 (3BR) by FGC From US $199
         

8.0 (2 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Harbour Oaks 2121 by FVC From US $190
         

New
Condo
  • Air Conditioner
  • Parking
  • Pool
Beachplace 4 - 304 by FGC From US $186
         

New
Condo
  • Air Conditioner
  • Parking
  • Pool

Instantly Bookable Vacation Homes in Bay Isles

Over 454+ Instantly Bookable Vacation Homes in or Near Bay Isles
Beachcomber unit 501 From US $314
         

9.6 (20 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Longboat Key Private Beach Access Condo From US $266
         

New
Condo
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens
Beachcomber unit 403 From US $342
         

10.0 (3 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Beachcomber unit 305 From US $342
         

10.0 (10 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Unit #311 Sand Cay Beach Resort Pool and Garden View From US $471
         

Beachcomber unit 207 From US $328
         

9.4 (3 Reviews)
Condo
  • TV
  • View
  • Ocean View

About Bay Isles Vacation Rentals

With more than 775 Bay Isles 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 Bay Isles.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Montgomerycottages Bay Isles, 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 Bay Isles. Places to stay near Bay Isles

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

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 Bay Isles.

Weather in Bay Isles

View the weather forecast for Bay Isles before booking your Bay Isles 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