Venture Out Resort holiday rentals
We found 192 holiday rentals — enter your dates for availability
Holiday rentals with weekly discounts - Venture Out Resort
Showing deals for:19 Sept - 26 Sept
Image gallery for Emerald Seas - Florida Keys Ocean Front Paradise!
1010 out of 10 rating
Exceptional
(15 reviews)
Emerald Seas - Florida Keys Ocean Front Paradise!
Summerland Key, FL
8% off
Price is AU$5,289
AU$5,289
AU$756 per night
includes taxes & fees
Image gallery for A slice of paradise
9.09.0 out of 10 rating
Wonderful
(96 reviews)
A slice of paradise
Summerland Key, FL
8% off
Price is AU$2,807
AU$2,807
AU$401 per night
includes taxes & fees
Image gallery for Paradise in the Lower Keys!
8.68.6 out of 10 rating
Excellent
(19 reviews)
Paradise in the Lower Keys!
Summerland Key, FL
5% off
Price is AU$3,947
AU$3,947
AU$564 per night
includes taxes & fees
Image gallery for Family Friendly 2 Bedroom 1 Bath, 32' Seawall, 4 Bike, 3 Kayak, WiFi, large pool
9.49.4 out of 10 rating
Exceptional
(93 reviews)
Family Friendly 2 Bedroom 1 Bath, 32' Seawall, 4 Bike, 3 Kayak, WiFi, large pool
Summerland Key, FL
7% off
Price is AU$2,967
AU$2,967
AU$424 per night
includes taxes & fees
Image gallery for Cozy and modern island living, Cudjoe Key
9.29.2 out of 10 rating
Wonderful
(87 reviews)
Cozy and modern island living, Cudjoe Key
Summerland Key, FL
14% off
Price is AU$2,204
AU$2,204
AU$315 per night
includes taxes & fees
Image gallery for Fishermen’s Paradise
9.29.2 out of 10 rating
Wonderful
(95 reviews)
Fishermen’s Paradise
Summerland Key, FL
8% off
Price is AU$3,159
AU$3,159
AU$451 per night
includes taxes & fees
Image gallery for ISLAND PARADISE
1010 out of 10 rating
Exceptional
(32 reviews)
ISLAND PARADISE
Summerland Key, FL
8% off
Price is AU$2,933
AU$2,933
AU$419 per night
includes taxes & fees
Image gallery for water at your back door
8.88.8 out of 10 rating
Excellent
(34 reviews)
water at your back door
Summerland Key, FL
8% off
Price is AU$3,946
AU$3,946
AU$564 per night
includes taxes & fees
Image gallery for Crystal Clear Water Getaway!
9.89.8 out of 10 rating
Exceptional
(70 reviews)
Crystal Clear Water Getaway!
Summerland Key, FL
8% off
Price is AU$3,191
AU$3,191
AU$456 per night
includes taxes & fees
Image gallery for Mini lobster available! Open Water View from porch , dock, bikes, kayaks
9.89.8 out of 10 rating
Exceptional
(119 reviews)
Mini lobster available! Open Water View from porch , dock, bikes, kayaks
Summerland Key, FL
8% off
Price is AU$3,616
AU$3,616
AU$517 per night
includes taxes & fees
Image gallery for Comfortable Waterfront Vacation Rental
9.49.4 out of 10 rating
Exceptional
(157 reviews)
Comfortable Waterfront Vacation Rental
Summerland Key, FL
5% off
Price is AU$2,462
AU$2,462
AU$352 per night
includes taxes & fees
Image gallery for Waterfront home with numerous amenities on popular Cudjoe Key!
9.49.4 out of 10 rating
Exceptional
(18 reviews)
Waterfront home with numerous amenities on popular Cudjoe Key!
Summerland Key, FL
15% off
Price is AU$2,735
AU$2,735
AU$391 per night
includes taxes & fees
Image gallery for WATERFRONT Seaside Sanctuary in the Keys with 35' SEAWALL FOR YOUR BOAT!
1010 out of 10 rating
Exceptional
(9 reviews)
WATERFRONT Seaside Sanctuary in the Keys with 35' SEAWALL FOR YOUR BOAT!
Summerland Key, FL
8% off
Price is AU$6,792
AU$6,792
AU$970 per night
includes taxes & fees
Image gallery for NAUTILUS...ocean front cottage retreat ~
8.88.8 out of 10 rating
Excellent
(6 reviews)
NAUTILUS...ocean front cottage retreat ~
Summerland Key, FL
8% off
Price is AU$7,411
AU$7,411
AU$1,059 per night
includes taxes & fees
Image gallery for 20 MINUTES TO KEY WEST , BOATERS PARADISE
9.49.4 out of 10 rating
Exceptional
(57 reviews)
20 MINUTES TO KEY WEST , BOATERS PARADISE
Summerland Key, FL
8% off
Price is AU$2,749
AU$2,749
AU$393 per night
includes taxes & fees
Image gallery for Relax by Florida Keys Beaches, just a 7-min drive away
9.89.8 out of 10 rating
Exceptional
(192 reviews)
Relax by Florida Keys Beaches, just a 7-min drive away
Summerland Key, FL
8% off
Price is AU$3,181
AU$3,181
AU$454 per night
includes taxes & fees
Image gallery for Tropical Island Paradise W / Open Water Views!
9.69.6 out of 10 rating
Exceptional
(101 reviews)
Tropical Island Paradise W / Open Water Views!
Summerland Key, FL
8% off
Price is AU$3,298
AU$3,298
AU$471 per night
includes taxes & fees
Image gallery for ATLANTIS...Ocean Front Cottage Retreat!
9.89.8 out of 10 rating
Exceptional
(13 reviews)
ATLANTIS...Ocean Front Cottage Retreat!
Summerland Key, FL
6% off
Price is AU$11,475
AU$11,475
AU$1,639 per night
includes taxes & fees
Image gallery for 35' Seawall Sparkling , 30min from Keywest, WIFI, BBQ Grill, Pool
9.89.8 out of 10 rating
Exceptional
(129 reviews)
35' Seawall Sparkling , 30min from Keywest, WIFI, BBQ Grill, Pool
Summerland Key, FL
7% off
Price is AU$3,732
AU$3,732
AU$533 per night
includes taxes & fees
Image gallery for Enjoy Caribbean weather in the USA. Openings in July-Open lobster season!
9.49.4 out of 10 rating
Exceptional
(139 reviews)
Enjoy Caribbean weather in the USA. Openings in July-Open lobster season!
Summerland Key, FL
14% off
Price is AU$2,180
AU$2,180
AU$311 per night
includes taxes & fees
Image gallery for waterfront cottage near key west, sleeps 6
9.49.4 out of 10 rating
Exceptional
(22 reviews)
waterfront cottage near key west, sleeps 6
Summerland Key, FL
7% off
Price is AU$3,227
AU$3,227
AU$461 per night
includes taxes & fees
Image gallery for Island Therapy
9.89.8 out of 10 rating
Exceptional
(57 reviews)
Island Therapy
Summerland Key, FL
8% off
Price is AU$3,298
AU$3,298
AU$471 per night
includes taxes & fees
Image gallery for Lower Keys paradise
1010 out of 10 rating
Exceptional
(33 reviews)
Lower Keys paradise
Summerland Key, FL
8% off
Price is AU$3,169
AU$3,169
AU$453 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Venture Out Resort
Comfortable Waterfront Vacation Rental
Sleeps 4 · 1 bedroom · 1 bathroom
9.49.4 out of 10
Exceptionalexceptional
157 reviews(157 reviews)
Springs Venture Out Dolphin House (#386) with beautiful open water views
Sleeps 6 · 2 bedrooms · 2 bathrooms
9.29.2 out of 10
Wonderfulwonderful
96 reviews(96 reviews)
Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West
Sleeps 4 · 2 bedrooms · 2 bathrooms
9.09.0 out of 10
Wonderfulwonderful
207 reviews(207 reviews)
Waterfront Home
Sleeps 4 · 2 bedrooms · 2 bathrooms
8.88.8 out of 10
Excellentexcellent
164 reviews(164 reviews)
Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill
Sleeps 6 · 2 bedrooms · 2 bathrooms
9.89.8 out of 10
Exceptionalexceptional
222 reviews(222 reviews)
Relax by Florida Keys Beaches, just a 7-min drive away
Sleeps 5 · 2 bedrooms · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
192 reviews(192 reviews)
Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value