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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.
Dolphin Point on Holiday Isle is a quiet, low-rise condominium complex of three buildings offering three different, gorgeous views. Enjoy the condominium pool, tennis court, and laundry facilities at the end of each hallRead 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 condominium 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 tennisRead 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

Open October 28-31!

Beach Side- Harbor View

FROM: $105/NT
  • 7
  • 2
  • 2.5
 
Harbor Views ~ 200 feet to Beach Access ~ Holiday Isle ~ $1950/mo Jan & Feb
FROM: $130/NT
  • 6
  • 2
  • 2
 
Gulf Views ~ Walk to Beach ~ Beach Service ~ Gated Community ~ Two Pools
OPEN October 28-31!

Shoreline Towers 3092

FROM: $123/NT
  • 6
  • 2
  • 2
 
Updated Interior ~Gulf Views~ Community Pool~ Tennis ~ $1800/mo 4 Winter
OPEN 4 Christmas!

Dolphin Point #605C

FROM: $130/NT
  • 6
  • 2
  • 2
 
Harbor Views ~ Renovated ~ Walk to Beach ~ Pool, Tennis Court, & Grills ~ $2000/mo for Winter
FROM: $130/NT
  • 12
  • 2
  • 3
 
Luxurious Décor ~ Quiet Lake Views ~ Pool ~ Walk 2 Beach ~ $2100/mo 4 Winter
Book 4 Winter!

East Pass 502

FROM: $140/NT
  • 6
  • 2
  • 2
 
Gulf & East Pass Views ~ Updated ~ Beachfront Pool & Hot Tub ~ $2250/mo for Winter
OPEN October 28-31!

Shoreline Towers 2061

FROM: $200/NT
  • 8
  • 3
  • 2
 
Partial Gulf Views ~ Remodeled ~ Tennis ~ Pool ~ Sauna ~ $2450/mo for Winter
OPEN October 28-31!

Sandpiper Cove 2019

FROM: $100/NT
  • 4
  • 1
  • 1
 
Pet Friendly ~ Harbor Views ~ 5 Pools + 3 Hot Tubs ~ Tennis Courts + Golf Course ~ $1700/mo 4 Winter
Great Winter Rates!

Jetty East 310B- Jetty Gem

FROM: $115/NT
  • 6
  • 2
  • 2
 
Jetty & East Pass Views ~ Beachfront Pool ~ Hot Tub ~ Beachside Sun Deck & Pavilion
NEW to our program!

Dolphin Point #406C

FROM: $130/NT
  • 6
  • 2
  • 2
 
Harbor & Pool Views ~ Walk to Beach ~ Pool, Tennis Court, & Grills ~ $1900/mo for Winter
OPEN October 28-31!

East Pass 306

FROM: $205/NT
  • 6
  • 2
  • 2
 
Beautiful Harbor & East Pass Views ~ Beachfront Pool & Hot Tub ~ $2500/mo for Winter
OPEN November 11-14!

Hol. Surf & Racquet Club 319

FROM: $105/NT
  • 5
  • 1
  • 1
 
Updated Furnishings- Gulf Views- Pool- Tennis- $1700/mo 4 Winter
FROM: $117/NT
  • 8
  • 3
  • 3
 
Lake Front - Walk to Beach - Heated Pool - Tennis
Book for Christmas!

Shoreline Towers 2025

FROM: $155/NT
  • 8
  • 2
  • 2
 
Gulf Front Views ~ Free Beach Service~ $1950/mo 4 Winter ~ Pool, Tennis ~ Updated
OPEN October 28-31!

Blue Paradise

FROM: $124/NT
  • 8
  • 2
  • 2
 
Walk to Beach ~ Two Balconies & Porch with Harbor Views ~ $1950/mo for Winter*
OPEN November 4-7!

Shoreline Towers 1085

FROM: $122/NT
  • 6
  • 2
  • 2
 
2BR w/Fantastic Gulf Views ~ Free Beach Service ~ Pool ~ Tennis ~ Fitness Room ~ $2000/mo Winter
Book for Thanksgiving!

Hol. Surf & Racquet Club 216

FROM: $124/NT
  • 6
  • 2
  • 2
 
Updated ~ Laptop Friendly ~ Amazing Views ~ Lighted Tennis Courts ~ Pool
Great Winter Rates!

Hol. Surf & Racquet Club 610

FROM: $105/NT
  • 8
  • 2
  • 2
 
Steps 2 Beach- Tennis- Pool and Gulf Views from Balcony- $1750/mo 4 Winter
Great Winter Rates!

East Pass 407

FROM: $165/NT
  • 6
  • 2
  • 2
 
Updated- Huge Balcony w/ East Pass & Harbor Views ~ Beach Front Pool
Book for Winter!

Waterview Towers 202

FROM: $180/NT
  • 6
  • 2
  • 2.5
 
End of Holiday Isle * Upgrades! * Boat Slip * Huge balcony * Water views from all rooms!
Book for Spring Break!

East Pass 208

FROM: $135/NT
  • 6
  • 2
  • 2
 
HUGE Balcony w/ Views of East Pass & Harbor - Holiday Isle - $2100/Mo for Winter
Book for Thanksgiving!

Hol. Surf & Racquet Club 710

FROM: $114/NT
  • 6
  • 2
  • 2
 
Coastal Decor - Gulf Views w/ Balcony - $1950/Mo for Winter
Book 4 Winter!

East Pass 308

FROM: $170/NT
  • 8
  • 3
  • 2
 
Gulf & Harbor Views ~ Beachfront Pool ~ Hot Tub ~ Fitness Room ~ $2350/mo 4 Winter
Book 4 Winter!

East Pass 104

FROM: $130/NT
  • 6
  • 2
  • 2
 
Updated unit in East Pass * Harbor Views *Beachfront Pool & Hot Tub * $2100/mo for Winter *
OPEN October 28-31!

The Islander 302

FROM: $135/NT
  • 7
  • 2
  • 2
 
Walk to the Jetties ~ 2 Pools + 2 Hot Tubs ~ Tennis Courts + Fitness Center ~ $1950/mo 4 Winter
Book for Christmas!

Destin-A-tion on the Water

FROM: $260/NT
  • 10
  • 5
  • 4.5
 
Boat Slip - Golf Cart - Waterfront - Walk 2 Beach - 2 Available Bikes!
OPEN October 28-31!

The Islander 211

FROM: $115/NT
  • 8
  • 2
  • 2
 
$1700/mo 4 Winter ~ Walk to the Beach ~ 2 Pools ~ 2 Hot Tubs ~ Tennis
FROM: $122/NT
  • 6
  • 2
  • 2
 
Remodeled ~ Pool ~ Gulf Views ~ Sauna ~ Tennis ~ $1950/mo for Winter
Book for Christmas!

Shoreline Towers 3063

FROM: $129/NT
  • 6
  • 2
  • 2
 
* Fully Updated Condo * Walk 2 Beach * Pool, Tennis, Fitness Room * $1750/mo for Winter
FROM: $110/NT
  • 5
  • 2
  • 2
 
Balcony overlooking Gulf & Pool ~ Seasonally Heated Pool ~ Tennis Courts ~ $1950/mo 4 Winter
FROM: $221/NT
  • 8
  • 3
  • 2
 
Remodeled ~ Gulf Views ~ Tennis ~ Pool ~ Sauna
Spacious Floorplan!

Shoreline Towers 2056

FROM: $200/NT
  • 8
  • 3
  • 2
 
Gulf Front ~ Amazing Views from Balcony ~ Ideal Destin Location ~ $2450/mo for Winter
FROM: $110/NT
  • 6
  • 2
  • 2
 
Walk 2 Beach~ Gulf Views~ Pool~ Holiday Isle~ $1950/mo for Winter
Book for Christmas!

Shoreline Towers 3026

FROM: $159/NT
  • 8
  • 3
  • 2
 
Sunroom - Beach Service - Gulf Views - 300 Steps to the Beach - $2100/mo for Winter
Great Winter Rates!

Shoreline Towers 3021

FROM: $155/NT
  • 8
  • 3
  • 2
 
Sun Porch - 500 Steps to Beach - Heart of Destin - Newly Refurnished - $2150/mo for Winter
OPEN October 28-31!

Hol. Surf & Racquet Club 101

FROM: $114/NT
  • 7
  • 2
  • 2
 
Recently Remodel* Steps to the Beach* Ground Floor * $1950/mo 4 Winter * Private Patio
OPEN October 28-31!

Shoreline Towers 3074

FROM: $108/NT
  • 6
  • 2
  • 2
 
Heated Pool - FABULOUS Gulf Views - Steps to Beach-$1800/mo for Winter!
Sauna + Fitness Room!

Shoreline Towers 1092

FROM: $122/NT
  • 8
  • 2
  • 2
 
Beautifully Updated ~ Gulf Front Condo ~ Gulf Views ~ Seasonally Heated Pool
FROM: $169/NT
  • 6
  • 2
  • 2
 
Updated ~ Gulf Views ~ Seasonally Heated Pool ~ Winter $2100/mo
Book for Winter!

The Islander 416

FROM: $129/NT
  • 6
  • 2
  • 2
 
Gulf Views on Holiday Isle ~ Two Pools & Hot Tubs ~ $1550/mo for Winter
Great Winter Rates!

Jetty East 114A

FROM: $95/NT
  • 4
  • 1
  • 1
 
East Pass Views ~ Beachfront Pool ~ Hot Tub ~ Beachside Sun Deck & Pavilion
FROM: $130/NT
  • 8
  • 3
  • 3
 
Lake Front - Walk to Beach - Peaceful Lake Views - Great Amenities - $1900/mo for Winter
Great Winter Rates!

Hol. Surf & Racquet Club 711

FROM: $114/NT
  • 6
  • 2
  • 2
 
Gulf- Pool & Tennis Views from 7th Floor - $1950/mo for Winter
Book for Winter!

Shoreline Towers 3083

FROM: $123/NT
  • 6
  • 2
  • 2
 
Tennis Courts - Walk 2 Beach -Gulf Views - Heart of Destin -$1800/mo for Winter
FROM: $122/NT
  • 6
  • 2
  • 2
 
Gulf Views - Tennis - Seasonally Heated Pool - $1900/Month for Winter
OPEN November 4-7!

Shoreline Towers 3061

FROM: $159/NT
  • 8
  • 3
  • 2
 
Floor to Ceiling Gulf & Lake Views ~ Steps 2 Beach ~ $2550/mo for Winter
OPEN October 28-31!

Shoreline Towers 3104

FROM: $115/NT
  • 6
  • 2
  • 2
 
Coastal Decor - Gulf Views from Balcony - Pool-Tennis-Sauna - $1800/mo for Winter
OPEN October 28-31!

Hol. Surf & Racquet Club 707

FROM: $119/NT
  • 6
  • 2
  • 2
 
Heated Pool~ AMAZING 7th Floor Views~ Holiday Isle~ $1950/Mo for Winter
Great Winter Rates!

East Pass 102

FROM: $149/NT
  • 4
  • 2
  • 2
 
Huge Balcony ~ Holiday Isle ~ Beachfront Pool ~ $2000/mo for Winter
OPEN October 28-31!

Jetty East 114B

FROM: $115/NT
  • 6
  • 2
  • 2
 
Jetty & East Pass Views ~ Beachfront Pool ~ Hot Tub ~ Beachside Sun Deck & Pavilion
Seasonal Beach Service!

Destin on the Gulf 401

FROM: $120/NT
  • 8
  • 2
  • 2
 
Recently Renovated - Gulf Front Pool - Fitness Room - Shuffleboard - $1700/mo for Winter
Book for Winter!

The Islander 214

FROM: $115/NT
  • 6
  • 2
  • 2
 
Updated - Partial Gulf & Pool Views - $1700/mo for Winter
FROM: $120/NT
  • 8
  • 2
  • 2
 
Beachfront for 6 - Gulf Front Pool - Fitness Room - Shuffleboard - $1700/mo for Winter
OPEN October 28-31!

Hol. Surf & Racquet Club 717

FROM: $99/NT
  • 8
  • 2
  • 2
 
Tennis Courts- Fitness Room- Pool and Gulf Views- $1750/mo for Winter
Great Winter Rates!

East Pass 505

FROM: $140/NT
  • 6
  • 2
  • 2
 
Harbor & East Pass Views * Large Balcony * Holiday Isle
OPEN October 28-31!

Shoreline Towers 3073

FROM: $170/NT
  • 6
  • 2
  • 2
 
Gulf Views * Balcony * Steps 2 Beach * Comm. Pool & Tennis Courts *$2700/mo for Winter
Book 4 Winter!

East Pass 207

FROM: $130/NT
  • 6
  • 2
  • 2
 
Gulf Views -Long Balcony -Beach Side Pool -$2350/Mo for Winter
Book for Spring Break!

East Pass 605

FROM: $189/NT
  • 8
  • 3
  • 2.5
 
2200 s.f. Penthouse * Gulf & Harbor Views * Master Suite has Jetted Tub * $2550/Mo in Winter
Gr8 Winter Rates!

Dolphin Point #602A

FROM: $130/NT
  • 6
  • 2
  • 2
 
Harbor Views ~ Renovated ~ Pool, Tennis Court, & Grills ~ Condominium Directly on the Destin Harbor