Poolside Properties


Properties Available 393 properties available
Top Reasons To Book This Beachfront Condo:* Beachfront Condo with Breathtaking Gulf Views from the Private Balcony * Resort-Style Amenities – Enjoy a Beachside Heated Pool, Relaxing Hot Tub, Shared BBQ Area, and a Spacious Pool Deck — All Just Steps from your Door!* Perfect Location – Close to Family-Friendly Activities, Top-Rated Restaurants, and
Specials Tag Special
NEW YEAR 2026

Get 10% OFF select  properties when you stay 7-14 nights between 1/2/26-4/3/26! Book by January 17, 2026.


Use code: "NEWYEAR2026" at checkout.


Offer is valid on new online bookings only when you book by January 17, 2026 for 7-14 night stays from January 2, 2026 - April 3, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.  

Sand Castle II #2602 - Premier
Condo
Bedrooms 3 bedrooms
Bathrooms 2 Full
Guests 8 guests
Rating 5 (2 Reviews)
*** NOTICE: THE POOL AND GRILLS AT SUNSET CHATEAU ARE CURRENTLY NOT AVAILABLE. *** Top Reasons To Book:* Beautiful Beaches Right Across the Street* Access to Beach Front Pool and Grills Across the Street* Nightly Sunsets to Watch Just a Few Steps Away* Less Than 3 Miles to John's Pass Village* Walking Distance to Caddy's on the BeachEscape to th
Harbor House 37
Condo
Bedrooms 1 bedrooms
Bathrooms 1 Full
Guests 2 guests
Rating 4.8 (22 Reviews)
Stay more, SAVE more! We offer lower nightly rates on extended stays from Sept-Mar. No coupon code needed! Just enter your dates, at least 14 nights, for pricing. Top Reasons to Book Sea Club #12:* Close to Beach Access* Private Balcony* Beautifully Landscaped Grounds* Onsite Heated Pool and Shuffleboard* Fishing Dock on Intracoastal Waterway* P
Specials Tag Special
NEW YEAR 2026

Get 10% OFF select  properties when you stay 7-14 nights between 1/2/26-4/3/26! Book by January 17, 2026.


Use code: "NEWYEAR2026" at checkout.


Offer is valid on new online bookings only when you book by January 17, 2026 for 7-14 night stays from January 2, 2026 - April 3, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.  

Sea Club #12 - The Dancing Dolphin
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 5 (4 Reviews)
Stay more, SAVE more! We offer lower nightly rates on extended stays from Sept-Mar. No coupon code needed! Just enter your dates, at least 14 nights, for pricing. **CONSTRUCTION NOTICE: Please note that restoration work is underway. Parking is limited onsite. Noise may be experienced while work is ongoing. Beach Access and Pool are OPEN! ***
Specials Tag Special
NEW YEAR 2026

Get 10% OFF select  properties when you stay 7-14 nights between 1/2/26-4/3/26! Book by January 17, 2026.


Use code: "NEWYEAR2026" at checkout.


Offer is valid on new online bookings only when you book by January 17, 2026 for 7-14 night stays from January 2, 2026 - April 3, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.  

Villa Madeira 305
Condo
Bedrooms 3 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 5 (40 Reviews)
Stay more, SAVE more! We offer lower nightly rates on extended stays from Sept-Mar. No coupon code needed! Just enter your dates, at least 14 nights, for pricing. Top Reasons to Book The Intercoastal #205:*Intercoastal water views*Upgraded appliances*Beautifully decorated* Private, Screened in Balcony* Professionally Managed, 24/7Escape to The I
Specials Tag Special
NEW YEAR 2026

Get 10% OFF select  properties when you stay 7-14 nights between 1/2/26-4/3/26! Book by January 17, 2026.


Use code: "NEWYEAR2026" at checkout.


Offer is valid on new online bookings only when you book by January 17, 2026 for 7-14 night stays from January 2, 2026 - April 3, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.  

The Intercoastal #205 - Beachy Chic
Condo Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 2 Full
Guests 8 guests
Rating 5 (30 Reviews)
Top Reasons To Book The Pointe #401:* Beachfront Corner Condo with AMAZING Gulf Views* Private Balcony with Seating and Sunset Views* Spacious, Updated Living with Coastal Décor* Professionally Managed, 24/7Welcome to your dream getaway at The Pointe in Indian Shores, FL! This beautifully updated 2-bedroom, 2-bathroom beachfront condo sits on t
Specials Tag Special
NEW YEAR 2026

Get 10% OFF select  properties when you stay 7-14 nights between 1/2/26-4/3/26! Book by January 17, 2026.


Use code: "NEWYEAR2026" at checkout.


Offer is valid on new online bookings only when you book by January 17, 2026 for 7-14 night stays from January 2, 2026 - April 3, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.  

The Pointe #401
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 8 guests
Rating 5 (1 Reviews)
Stay more, SAVE more! We offer lower nightly rates on extended stays from Sept-Mar. No coupon code needed! Just enter your dates, at least 14 nights, for pricing. Top Reasons to Book this Awesome Townhouse:* Newly Built in 2025 - Everything is Brand New!* 4 Story Townhouse with Private Rooftop Deck* Approx. 300ft to the Beach - Easy Walk!* O
Specials Tag Special
NEW YEAR 2026

Get 10% OFF select  properties when you stay 7-14 nights between 1/2/26-4/3/26! Book by January 17, 2026.


Use code: "NEWYEAR2026" at checkout.


Offer is valid on new online bookings only when you book by January 17, 2026 for 7-14 night stays from January 2, 2026 - April 3, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.  

Azul Townhomes A4 - Sunset
Madeira Beach
Bedrooms 5 bedrooms
Bathrooms 4 Full
Guests 12 guests
Rating 5 (4 Reviews)
Stay more, SAVE more! We offer lower nightly rates on extended stays from Sept-Mar. No coupon code needed! Just enter your dates, at least 14 nights, for pricing. Top Reasons to book: • You’ll love the beautiful décor, and comfortable furnishings throughout this unit • As you enter, you'll be greeted by floor to ceiling sliding glass doors and
Specials Tag Special
NEW YEAR 2026

Get 10% OFF select  properties when you stay 7-14 nights between 1/2/26-4/3/26! Book by January 17, 2026.


Use code: "NEWYEAR2026" at checkout.


Offer is valid on new online bookings only when you book by January 17, 2026 for 7-14 night stays from January 2, 2026 - April 3, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.  

Trillium 5B - Premier
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 4.9 (75 Reviews)
Stay more, SAVE more! We offer lower nightly rates on extended stays from Sept-Mar. No coupon code needed! Just enter your dates, at least 14 nights, for pricing. Top Reasons to Book this Home:* 180 ft from Public Beach Access* Private Entrance with 1 Parking Space Any extra-large vehicles may have to park in city overflow due to restricted spac
Specials Tag Special
NEW YEAR 2026

Get 10% OFF select  properties when you stay 7-14 nights between 1/2/26-4/3/26! Book by January 17, 2026.


Use code: "NEWYEAR2026" at checkout.


Offer is valid on new online bookings only when you book by January 17, 2026 for 7-14 night stays from January 2, 2026 - April 3, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.  

Beach Livin 1 - 1 Bedroom Downstairs
Condo
Bedrooms 1 bedrooms
Bathrooms 1 Full
Guests 3 guests
Rating 5 (11 Reviews)
Stay more, SAVE more! We offer lower nightly rates on extended stays from Sept-Mar. No coupon code needed! Just enter your dates, at least 14 nights, for pricing. Top Reasons to book: • You’ll love the beautiful décor, and comfortable furnishings throughout this unit • As you enter, you'll be greeted by floor to ceiling sliding glass doors and
Specials Tag Special
NEW YEAR 2026

Get 10% OFF select  properties when you stay 7-14 nights between 1/2/26-4/3/26! Book by January 17, 2026.


Use code: "NEWYEAR2026" at checkout.


Offer is valid on new online bookings only when you book by January 17, 2026 for 7-14 night stays from January 2, 2026 - April 3, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.  

Trillium 1B - Premier
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 5 (69 Reviews)
Stay more, SAVE more! We offer lower nightly rates on extended stays from Sept-Mar. No coupon code needed! Just enter your dates, at least 14 nights, for pricing. Top Reasons to Book: •Walking distance to a wide variety of local restaurants and entertainment. •Located just a block from the easy beach access. •Includes access to a shared dock on
Specials Tag Special
NEW YEAR 2026

Get 10% OFF select  properties when you stay 7-14 nights between 1/2/26-4/3/26! Book by January 17, 2026.


Use code: "NEWYEAR2026" at checkout.


Offer is valid on new online bookings only when you book by January 17, 2026 for 7-14 night stays from January 2, 2026 - April 3, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.  

Amadeus 6
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 5 guests
Rating 4.9 (68 Reviews)
Stay more, SAVE more! We offer lower nightly rates on extended stays from Sept-Mar. No coupon code needed! Just enter your dates, at least 14 nights, for pricing. ***NOTICE: ROOF WORK CURRENLTY IN PROGRESS ON BUILDING 1. ESTIMATED COMPLETION MID DECEMBER 2025, COULD VARY BASED ON WORK. PLEASE CALL FOR DETAILS. **** Top Reasons to book : • Sh
Specials Tag Special
NEW YEAR 2026

Get 10% OFF select  properties when you stay 7-14 nights between 1/2/26-4/3/26! Book by January 17, 2026.


Use code: "NEWYEAR2026" at checkout.


Offer is valid on new online bookings only when you book by January 17, 2026 for 7-14 night stays from January 2, 2026 - April 3, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.  

Land's End 1-307 Gulf View
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 5 (37 Reviews)

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