72+ Vacation Rentals Near Bay Island |
  1. USA
  2. Florida
  3. Sarasota
  4. Bay Island

Luxury Cruises - Vacation Rentals in Bay Island

Property Image From $699
         

9.4 (35 Reviews)
House
Casa Leone | Pet Friendly 🐶 on Siesta Key w/Private Heated Pool, Golf Cart, & Putting Green!
  • Air Conditioner
  • Parking
  • Pet Friendly

View Availability
Property Image From $1,078
         

|
10.0 (1 Review)
House
Family friendly with large pool
  • Air Conditioner
  • Parking
  • Pool

View Availability
Property Image From $642
         

|
10.0 (24 Reviews)
House
210 m² House ∙ 4 bedrooms ∙ 10 guests
  • 2263 ft² House
  • Air Conditioner
  • Parking
  • Pet Friendly

View Availability
Property Image From $1,379
         

10.0 (50 Reviews)
House
The Seagrape Villa -Family Friendly- Luxury Accommodation in Paradise
  • Air Conditioner
  • Parking
  • Pool

View Availability
Property Image From $728
         

|
10.0 (1 Review)
House
Palm Paradise - Pet Friendly Home on Siesta Key w/Large Heated Private Pool & Outdoor Area!
  • Parking
  • Pool
  • Security/Safety

View Availability
Property Image From $454
         

|
10.0 (12 Reviews)
House
178 m² House ∙ 3 bedrooms ∙ 8 guests
  • 1920 ft² House
  • Air Conditioner
  • Parking
  • Pool

View Availability
Property Image From $685
         

10.0 (29 Reviews)
House
The Beach Bungalow Siesta Key - 205
  • Air Conditioner
  • Parking
  • Pet Friendly

View Availability
Property Image From $599
         

|
9.7 (3 Reviews)
House
Hemingway House - 117
  • Parking
  • Pool
  • View

View Availability
Property Image From $405
         

|
10.0 (11 Reviews)
House
270 m² House ∙ 5 bedrooms ∙ 10 guests
  • 2900 ft² House
  • Air Conditioner
  • Parking
  • Pool

View Availability
Property Image From $1,320
         

10.0 (11 Reviews)
House
Your Personal Resort-7BR, Elevator, Pool, Bocce Ball, Boating & so much more!
  • Air Conditioner
  • Parking
  • Pet Friendly

View Availability
Property Image From $449
         

|
9.0 (2 Reviews)
House
Shell Beach - The Treehouse 210
  • Pool
  • Security/Safety
  • Sports/Activities

View Availability
Property Image From $1,943
         

10.0 (7 Reviews)
Villa
Private Indoor/Outdoor POOL & Waterfront Oasis on Siesta Key
  • Air Conditioner
  • Parking
  • Pool

View Availability
Property Image From $2,068
         

New
House
Your Personal Resort-7BR, Pool, Tennis, Boating &
  • Air Conditioner
  • Parking
  • Pet Friendly

View Availability
Property Image From $895
         

10.0 (4 Reviews)
House
Shore Thing | Luxe Pool Oasis, Hot Tub, Siesta Key Beach
  • Air Conditioner
  • Parking
  • Pet Friendly

View Availability
Property Image From $1,134
         

New
House
Shore Thing - 185
  • Parking
  • Pet Friendly
  • Pool

View Availability
Property Image From $470
         

10.0 (1 Review)
House
Sunset West | Private Pool, Spa, Near Siesta Key Beach & Siesta Key Village
  • Air Conditioner
  • Parking
  • Pool

View Availability
Property Image From $1,122
         

|
New
House
Sunset West - 3360
  • Pool
  • View
  • Security/Safety

View Availability
Property Image From $775
         

9.8 (122 Reviews)
House
Stunning Siesta Key, . , Walk to Shell Beach, HEATED POOL - Discounts
  • Air Conditioner
  • Parking
  • Pool

View Availability
Property Image From $847
         

|
New
House
Casa Leone - 3446
  • Parking
  • Pet Friendly
  • Pool

View Availability
Property Image From $651
         

9.8 (16 Reviews)
House
Hemingway House – Serene Siesta Key Getaway with Heated Pool, Pizza Oven
  • Air Conditioner
  • Parking
  • Pool

View Availability
Property Image From $351
         

9.8 (12 Reviews)
House
3 Bedroom House North End of Siesta Key - Short Walk To Shell Beach
  • Air Conditioner
  • Parking
  • TV

View Availability
Property Image From $1,243
         

|
9.8 (11 Reviews)
House
5 BR SIESTA KEY SPA GETAWAY WITH GOLF SIMULATOR, TURFED YARD, AND MANCAVE.
  • Air Conditioner
  • Parking
  • Pet Friendly

View Availability
Property Image From $822
         

9.8 (8 Reviews)
House
Luxurious Paradise with Tiki Bar and Heated Pool, Just Remodeled!
  • Air Conditioner
  • Parking
  • Pool

View Availability
Property Image From $661
         

9.6 (39 Reviews)
House
Tropical Siesta Key Home with Incredible Pool, Hot Tub, and Patio!
  • Air Conditioner
  • Parking
  • Pet Friendly

View Availability
★ Pro Tip: Luxurycruises makes it easy to compare the best listings on Luxurycruises homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Luxurycruises 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 Island.

Weather in Bay Island

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

Top Attractions Around Bay Island, FL

Luxurycruises offers a large selection of top attractions around Bay Island. Research things to do on your vacation before you visit Bay Island.


Lido Beach Siesta Key Beach St. Armands Circle Turtle Beach IMG Academy Nokomis Beach Sarasota Jungle Gardens Mote Marine Laboratory & Aquarium Sarasota Memorial Hospital John and Mable Ringling Museum of Art Crescent Beach Siesta Key Marina Sarasota Opera House Mall at University Town Center Marie Selby Botanical Gardens Marina Jack Ca dZan Longboat Key Beaches Sarasota Classic Car Museum University of South Florida Sarasota

Other Places to Stay Near Bay Island, FL


Bay Isle 49 Properties