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Holiday Isle Vacation Rentals
 
If you haven't been to Holiday Isle, you're in for a treat. A peninsula surrounded by The Gulf of Mexico and Destin Harbor, it is a serene, little oasis within the heart of Destin with two and a half miles of paved trails for walking and biking. Surrounded by quiet neighborhoods, it is perfect for exploring on a bike ride with the family. It is just minutes away from restaurants, shopping, boat docks, fishing, golf, and amusements.

Destinations within Holiday Isle

Destin on the Gulf Condominiums is located directly on the beach in exclusive Holiday Isle in Destin, Florida, which is a peninsula surrounded by the Gulf of Mexico and Destin Harbor. This low rise, 6-story complex offersRead More.
East Pass Towers features a beachfront pool, hot tub, two levels of sundecks with chairs and loungers, and a full exercise room with kitchen and barstools. The beach at East Pass Towers is steps away from the condo and uniquelyRead More.
Holiday Surf & Racquet Club is located directly on the beach on exclusive Holiday Isle. Vacation rentals here enjoy an elevator located in the lobby for convenience, this destination is sure to please. Holiday Surf & RacquetRead More.
Jetty East is a mid-rise, 6 story condominium located on Holiday Isle. Jetty East is equipped with 4 elevators, covered parking, and 24-hour security. Resort amenities include a seasonally heated beachfront pool that is 5Read More.
You can't beat this location on pristine Holiday Isle. Vacation rentals at Shoreline Towers enjoy being within minutes from restaurants, shopping, water sports, fishing and golf. The amenities offered at this well-managedRead More.
The Islander is located on Holiday Isle, which is a peninsula surrounded by the Gulf of Mexico and Destin Harbor. This destination is sure to please! The Islander features Two Pools, Two Hot Tubs, Lighted Tennis Courts,Read More.
Waterview Towers is a beachfront, gated complex on Holiday Isle with only 33 units! Enjoy the water, boating, tennis, shopping, dining, and all that the Destin lifestyle has to offer. Amenities include fitness center, tennisRead More.

Featured Holiday Isle Rentals

Book for Spring Break!

Shoreline Towers Townhome#4-4

FROM: $140/NT
  • 8
  • 3
  • 3
 
$1450/mo for Winter - Lake Front - Walk to Beach - Peaceful Lake Views
Book for Spring Break!

Beach Side- Harbor View

FROM: $105/NT
  • 7
  • 2
  • 2.5
 
Harbor Views ~ 200 feet to Beach Access ~ Holiday Isle ~ $1500/mo Jan & Feb
Feb 27- March 6 $1294!

Hol. Surf & Racquet Club 707

FROM: $119/NT
  • 6
  • 2
  • 2
 
Heated Pool~ AMAZING 7th Floor Views~ Holiday Isle~ $1500/Mo for Winter
Watch the Boats From The Balcony!

East Pass 308

FROM: $170/NT
  • 6
  • 3
  • 2
 
Gulf & Harbor Views ~ Beachfront Pool ~ Hot Tub ~ Fitness Room ~ $1900/mo 4 Winter
FROM: $110/NT
  • 6
  • 2
  • 2
 
Walk 2 Beach~ Gulf Views~ Pool~ Holiday Isle~ $1500/mo for Winter
New to Program!

Destin on the Gulf 401

FROM: $130/NT
  • 8
  • 2
  • 2
 
Recently Renovated - Gulf Front Pool - Fitness Room - Shuffleboard - $1300/mo for Winter
FROM: $215/NT
  • 8
  • 3
  • 2
 
$1900/mo for Winter - Gulf Front views from Balcony - Ideal Destin Location!
FROM: $114/NT
  • 6
  • 2
  • 2
 
$1500/Mo for Winter * 5*Reviews! Gulf Views w/ Balcony!
FROM: $125/NT
  • 8
  • 3
  • 3
 
Lake Front - Walk to Beach - Heated Pool - Tennis
March 4-7 $956!

Shoreline Towers 3061

FROM: $159/NT
  • 8
  • 3
  • 2
 
$2100/mo for Winter - Floor to Ceiling Gulf & Lake Views - Steps 2 Beach
FROM: $165/NT
  • 6
  • 2
  • 2
 
2BR Gulf Front Condo ~ Updated ~ Gulf Views ~ Winter $1700/mo ~ Seasonally Heated Pool
Beautiful Views

Shoreline Towers 1092

FROM: $122/NT
  • 8
  • 2
  • 2
 
Beautifully Updated! ~ 2BR Gulf Front Condo ~ Gulf Views ~ Seasonally Heated Pool
March 4-7 $746!

Shoreline Towers 2052

FROM: $120/NT
  • 6
  • 2
  • 2
 
Gulf Front Beauty* Steps 2 Beach * Pool-Tennis-Sauna-Fitness Center
Feb 12-15 $647 Total!

Jetty East 114B

FROM: $115/NT
  • 6
  • 2
  • 2
 
Jetty & East Pass Views ~ Beachfront Pool ~ Hot Tub ~ Beachside Sun Deck & Pavilion
Feb 27- March 6 $1237!

Blue Paradise

FROM: $100/NT
  • 8
  • 2
  • 2
 
Walk to Beach ~ Two Balconies & Porch with Harbor Views ~ $1500/mo for Winter*
FROM: $167/NT
  • 6
  • 2
  • 2
 
Gulf Views * Balcony * Steps 2 Beach * $1400/mo for Winter * Comm. Pool & Tennis Courts
Seasonally Heated Pool!

Shoreline Towers 3026

FROM: $165/NT
  • 8
  • 3
  • 2
 
$1700/mo for Winter - Beach Service - Gulf Views - 300 Steps to the Beach!
Feb 27- March 6 $1184!

The Islander 211

FROM: $115/NT
  • 8
  • 2
  • 2
 
$1300/mo 4 Winter ~ Walk to the Beach ~ 2 Pools ~ 2 Hot Tubs ~ Tennis
Beautiful Views

Destin on the Gulf 206

FROM: $120/NT
  • 8
  • 2
  • 2
 
Beachfront for 6 - Gulf Front Pool - $1300/mo for Winter - Fitness Room - Shuffleboard
Great Views!

East Pass 208

FROM: $155/NT
  • 6
  • 2
  • 2
 
HUGE Balcony w/ Views of East Pass & Harbor - Holiday Isle - $1700/Mo for Winter
FROM: $132/NT
  • 4
  • 2
  • 2
 
$1900/Mo for Winter -Gulf Views -Long Balcony -Beach Side Pool
FROM: $135/NT
  • 6
  • 2
  • 2
 
2BR w/Fantastic Gulf Views ~ Free Beach Service ~ Pool ~ Tennis ~ Fitness Room ~ $1625/mo Winter
FROM: $120/NT
  • 5
  • 1
  • 1
 
Fully Renovated! $1300/mo for Winter - Gulf Views - Holiday Isle
Book for Spring Break!

The Islander 416

FROM: $115/NT
  • 6
  • 2
  • 2
 
Gulf Views on Holiday Isle ~ Two Pools & Hot Tubs ~ $1200/mo for Winter
FROM: $105/NT
  • 8
  • 2
  • 2
 
Pool and Gulf Views from Balcony! $1350/mo 4 Winter
Feb 12-15 $544!

Jetty East 114A

FROM: $95/NT
  • 4
  • 1
  • 1
 
East Pass Views ~ Beachfront Pool ~ Hot Tub ~ Beachside Sun Deck & Pavilion
FROM: $110/NT
  • 6
  • 2
  • 2
 
* Fully Updated Condo * $1350/mo for Winter * Walk 2 Beach * Pool, Tennis, Fitness Room *
Feb 27- March 6 $1107!

Shoreline Towers 3074

FROM: $108/NT
  • 6
  • 2
  • 2
 
Heated Pool - FABULOUS Gulf Views - Steps to Beach-$1400/mo for Winter!
FROM: $115/NT
  • 6
  • 2
  • 2
 
Gulf Views from Balcony * Pool-Tennis-Sauna * $1400/mo for Winter
Coastal Decor!

East Pass 104

FROM: $132/NT
  • 6
  • 2
  • 2
 
Updated unit in East Pass * Harbor Views *Beachfront Pool & Hot Tub * $1700/mo for Winter *
FROM: $114/NT
  • 6
  • 2
  • 2
 
$1500/mo for Winter - Gulf, Pool & Tennis Views from 7th Floor!
March 13-19 $1551 Total!

Hol. Surf & Racquet Club 717

FROM: $99/NT
  • 8
  • 2
  • 2
 
Tennis Courts- Fitness Room- Pool and Gulf Views- $1350/mo for Winter
FROM: $190/NT
  • 6
  • 2
  • 2.5
 
End of Holiday Isle * Upgrades! * Boat Slip * Huge balcony * Water views from all rooms!
March 4-7 $764!

Shoreline Towers 1024

FROM: $122/NT
  • 6
  • 2
  • 2
 
Gulf Views - Tennis - Seasonally Heated Pool - $1450/Month for Winter
Book for Spring Break!

Shoreline Towers 2043

FROM: $135/NT
  • 6
  • 2
  • 2
 
*Gulf Front w/Sunroom * $1650/mo 4 Winter * Renovated! Pool-Tennis-Sauna-Fitness Center
March 5-8 $1182!

Shoreline Towers 3021

FROM: $155/NT
  • 8
  • 3
  • 2
 
Sun Porch - 500 Steps to Beach - Heart of Destin - Newly Refurnished - $1750/mo for Winter
Feb 27-March 6 $1162!

The Islander 214

FROM: $115/NT
  • 6
  • 2
  • 2
 
Updated - $1300/mo for Winter - Partial Gulf & Pool Views - Near Destin Harbor!
Feb 27 - March 6 $1255!

Hol. Surf & Racquet Club 101

FROM: $114/NT
  • 7
  • 2
  • 2
 
Recently Remodel* Steps to the Beach* Ground Floor * $1500/mo 4 Winter * Private Patio
Bk4Winter

East Pass 605

FROM: $199/NT
  • 8
  • 3
  • 2.5
 
2200 s.f. Penthouse * Gulf & Harbor Views * Master Suite has Jetted Tub * $2000/Mo in Winter
Book for Spring Break!

East Pass 102

FROM: $120/NT
  • 4
  • 2
  • 2
 
Huge Balcony ~ Holiday Isle ~ $1600/mo for Winter ~ Beachfront Pool
Book for Spring!

Waterview Towers 404

FROM: $250/NT
  • 9
  • 3
  • 2
 
Pool ~ Hot Tub ~ Tennis ~ Harbor and Gulf Views ~ 3BR on Holiday Isle ~ $2100/mo for Winter
Feb 27 - March 6 $1502!

East Pass 505

FROM: $140/NT
  • 6
  • 2
  • 2
 
Harbor & East Pass Views * Large Balcony * Holiday Isle * $1600/mo for Winter
Feb 27- March 6 $1251!

Hol. Surf & Racquet Club 212

FROM: $110/NT
  • 5
  • 2
  • 2
 
Balcony overlooking Gulf & Pool ~ Seasonally Heated Pool ~ Tennis Courts ~ $1500/mo 4 Winter
Walk 2 Beach!

East Pass 407

FROM: $150/NT
  • 6
  • 2
  • 2
 
Updated- Huge Balcony w/ East Pass & Harbor Views ~ Beach Front Pool
FROM: $125/NT
  • 6
  • 2
  • 2
 
$1400/mo for Winter - Gulf Views - Heart of Destin!
Book for Spring Break!

Shoreline Towers 2025

FROM: $165/NT
  • 8
  • 2
  • 2
 
Gulf Front Views ~ Free Beach Service~ $1500/mo 4 Winter ~ Pool, Tennis ~ Updated