Summerland Key, Florida Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Summerland Key, Florida on RentalSaver.com!

Summerland Key Rentals

From $260 per night (USD)
VRBO
Open Water Views 35' Dockage with Kayak & Bikes - Venture Out Unit 335
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Open Water Views 35' Dockage Centrally Located 2Bd/1Ba Walk to PoolThis newly renovated, freshly painted vacation home i ...
From $260 per night (USD)
VRBO
$REEL ESCAPE - 4 Bedroom \/ 2 Bathroom w\/ Pool & Deep Water Access$
From $550 per night (USD)
Expedia
REEL ESCAPE - 4 Bedroom \/ 2 Bathroom w\/ Pool & Deep Water Access
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Impeccably designed and maintained canal front home in Summerland Cove with a Pool! This fully fenced and gated para ...
From $550 per night (USD)
Expedia
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Expedia
Island Dreams in Paradise! - Venture Out Unit 537
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Island Dreams in Paradise! Lovely Vacation Home with Large Enclosed Porch! This beautiful newly remodeled home is a trop ...
Click For Pricing
Expedia
From $217 per night (USD)
Expedia
Breezy Palm 2 bedroom with pool, hot tub, tennis courts, and boat access.
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Perfect spot for fishing, lobstering, and snorkeling. Parking for one vehicle, but we have a free overflow lot if you ne ...
From $217 per night (USD)
Expedia
From $295 per night (USD)
VRBO
FL Keys Cottage with Ocean Views - Venture Out Unit 395
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Tropical Island Oasis! Tropical Breezes Across from the Marina! A perfect oasis with beautiful views all day, every day. ...
From $295 per night (USD)
VRBO
From $239 per night (USD)
VRBO
LIVING IN BEAUTIFUL PARADISE
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Enjoy the view from the large porch overlooking a deep, wide, crystal blue, clear canal with quick boating access to bot ...
From $239 per night (USD)
VRBO
From $180 per night (USD)
VRBO
Nice home on Atlantic side of Cudjoe Key!
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
This home would be the perfect vacation spot for a small family or a group of friends. There are plenty of fun restauran ...
From $180 per night (USD)
VRBO
From $275 per night (USD)
Expedia
Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This oceanside property has 2 beds 2 baths and sleeps 6 with all updated appliances and furniture. There are kayaks and ...
From $275 per night (USD)
Expedia
From $1000 per night (USD)
VRBO
Summerland Breeze - Three house retreat, perfect for multiple families
Bedrooms:
5
Bathrooms:
7
Sleeps:
14
Breathtaking property located on desirable Summerland Key right on the ocean. There are three structures on the property ...
From $1000 per night (USD)
VRBO
From $225 per night (USD)
Expedia
Beautiful Ocean view with 35' private seawall, 80' Heated Pool, Hottub
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Gorgeous stilt home with beautiful ocean views. This Lobstering paradise is just 1 house down from open water on a deep ...
From $225 per night (USD)
Expedia
From $575 per night (USD)
VRBO
Blue Pearl of Summerland Key 4 Bedrooms, 3 Baths with Dock, Heated Pool and Spa
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Welcome to this Florida Keys gem, The Blue Pearl. The Blue Pearl is a beautiful, updated waterfront home with pool in a ...
From $575 per night (USD)
VRBO
From $352 per night (USD)
Expedia
**MERMAID MAGIC @ VENTURE OUT** Waterfront Home & Slip + LAST KEY SERVICES…
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Looking to ma ...
From $352 per night (USD)
Expedia
From $339 per night (USD)
VRBO
**POSTCARD POINT @ VENTURE OUT** New Waterfront Home + LAST KEY SERVICES…
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! What could be ...
From $339 per night (USD)
VRBO
$Views! Waterfront Niles Channel Pool\/dock Industerial Ice Maker$
From $700 per night (USD)
VRBO
Views! Waterfront Niles Channel Pool\/dock Industerial Ice Maker
Bedrooms:
5
Bathrooms:
5
Sleeps:
8
Welcome to Paradise at the End of The Road. This home is so secluded you will think you are on your own private island. ...
From $700 per night (USD)
VRBO
From $400 per night (USD)
VRBO
Torchview Lookout- Secluded Waterfront Retreat With 240’ Dock On Niles Channel
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
We invite you to come and relax at Torchview Lookout, your own private waterfront retreat! This 3 bedroom / 2 bathroom ...
From $400 per night (USD)
VRBO
From $250 per night (USD)
Expedia
Waterfront home with numerous amenities on popular Cudjoe Key!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Crystal Clear Canal front home with open water view! Home is located in a desirable community called Venture Out. Fully ...
From $250 per night (USD)
Expedia
From $319 per night (USD)
VRBO
Island Oasis ~ YOUR Paradise awaits in Venture Out Resort!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Enjoy our little peace of paradise! Come and make memories at this laid back and family-friendly waterfront home. Locate ...
From $319 per night (USD)
VRBO
From $450 per night (USD)
Expedia
Pool, tiki hut, easy ocean access canal, dock, prime location 30m to Key West
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Relax! Swim! Boat! Bike! Kayak! Hike! Pickle Ball, yes even that. Just a short distance to Key West with quick and easy ...
From $450 per night (USD)
Expedia
From $250 per night (USD)
VRBO
Oceanfront house private beach & protected canal dockage for up to 36' boat
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
The Key-ver beach house is an oceanfront vacation rental in the world-famous Florida Keys on the southern end of Summerl ...
From $250 per night (USD)
VRBO
From $197 per night (USD)
Expedia
Relaxing and Inviting home in gated community
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
The community charges a security/registration fee upon arrival to the renter. The fee will be $116.28 plus $8.72 in ta ...
From $197 per night (USD)
Expedia
From $175 per night (USD)
VRBO
WATERFRONT GETAWAY IN PARADISE...FISH~RELAX~ENJOY!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to 'Shangri-La' This is where you can RELAX and ENJOY the TRANQUIL beauty of the sun, sea & sand of the Florida ...
From $175 per night (USD)
VRBO
From $715 per night (USD)
VRBO
Summerland Nest - Oceanfront with pool
Bedrooms:
5
Bathrooms:
7
Sleeps:
12
Fabulous resort-style living & incredible open water views over Niles Channel at this 7 BR 5 BA home on Summerland Key. ...
From $715 per night (USD)
VRBO
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VRBO
Come stay and play in the Florida Keys!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This colorful, tropical vacation home has two bedrooms, one bath, with new 2022 central air conditioning, and is locate ...
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VRBO
From $960 per night (USD)
VRBO
Luxurious, Private, Oceanfront, Gated Home
Bedrooms:
5
Bathrooms:
4
Sleeps:
12
Stunning 1 acre oceanfront gated estate with lush landscaping, beach and extreme privacy due to the adjacent wildlife re ...
From $960 per night (USD)
VRBO
From $540 per night (USD)
VRBO
Beautiful Oceanfront Villa with Pool and near Key West, Florida
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Make some memories at this unique and family-friendly place. Beautiful, custom designed concrete waterfront pool home wi ...
From $540 per night (USD)
VRBO
From $300 per night (USD)
VRBO
Summerland Key Oceanfront
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Please check out the new updated photos of all the repairs and updates. The house now has new impact windows and doors, ...
From $300 per night (USD)
VRBO
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VRBO
Cudjoe Key Home with a View
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
We are so excited to share our little piece of paradise with you! Our unit is located a short walk away from all the ame ...
Click For Pricing
VRBO
$Tropical Island Paradise W \/ Open Water Views!$
From $220 per night (USD)
VRBO
Tropical Island Paradise W \/ Open Water Views!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Please see our other property if you do not see your dates available! Property # 2092236 https://www.vrbo.com/2092236?ad ...
From $220 per night (USD)
VRBO
From $95 per night (USD)
VRBO
Cudjoe Key, FL RV Resort RV Lot
Bedrooms:
1
Bathrooms:
0
Sleeps:
0
RV lot in Cudjoe Key, FL RV Resort, 35×70, full hook-up. Beautiful community, great relaxing location, close to shopp ...
From $95 per night (USD)
VRBO
From $374 per night (USD)
Expedia
Atlantic Ocean Views - Venture Out 579
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Atlantic Ocean Views - Venture Out 579 Lovely Stilt 2Bd/2Ba with 35' Dockage This beautiful sparkling clean 2Bd/2Ba stil ...
From $374 per night (USD)
Expedia
From $126 per night (USD)
VRBO
Love Shack | 2 Bed, 1 Bath
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
While not directly waterfront, this retreat boasts convenient access to a nearby boat ramp, making it ideal for boating ...
From $126 per night (USD)
VRBO
From $348 per night (USD)
Expedia
Fisherman's Delight! - Venture Out Unit 410
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
VO410 Fisherman's Delight! 35' Dockage 2Bd/2Ba with Covered Porch! This sparkling clean and beautiful canalfront home f ...
From $348 per night (USD)
Expedia
$Keys Time - Unit 437 Venture Out 2Bed\/2Bath Canal Front Home$
From $315 per night (USD)
VRBO
Keys Time - Unit 437 Venture Out 2Bed\/2Bath Canal Front Home
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to Keys Time!! Slow it down. Unwind. Enjoy the Island Life! This Beautifully furnished 2 bedroom 2 bath canal ...
From $315 per night (USD)
VRBO
$Paradise Views: Oceanfront\/Boating$
From $650 per night (USD)
VRBO
Paradise Views: Oceanfront\/Boating
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Enjoy one of Florida's most tranquil oceanfront settings. A romantic interlude and tropical adventure where absolutely e ...
From $650 per night (USD)
VRBO
From $152 per night (USD)
VRBO
Tropical Island Sanctuary
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to our beautiful tropical island retreat! Enjoy all the the splendor the lower Keys have to offer from our home ...
From $152 per night (USD)
VRBO
From $498 per night (USD)
Expedia
**CAREFREE ON CUDJOE @ THE BAY** Waterfront Home & Pool + LAST KEY SERVICES…
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! From the mome ...
From $498 per night (USD)
Expedia
From $200 per night (USD)
VRBO
Sailfish Dream on Cudjoe Key
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
This 2'nd floor 2 bedroom/2 bath home is your tropical getaway. The home is at MM 23 giving you Key West or Marathon eq ...
From $200 per night (USD)
VRBO
From $250 per night (USD)
Expedia
Peaceful ocean front cottage.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This classic keys cottage is tucked among the palm trees on the open water of Niles Channel. Enjoy the breath taking sun ...
From $250 per night (USD)
Expedia
From $177 per night (USD)
VRBO
Recently Renovated Home With Deepwater Canal
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Amazing canal front 3 bed conch style house located in prestigious community of Summerland Key Cove. It is the first can ...
From $177 per night (USD)
VRBO
From $242 per night (USD)
Expedia
Lake It Easy: Relax in This Beautiful 3BR Canal Front Home on Summerland Key, Dockage & Dog-Friendly
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Welcome to 'Lake It Easy' – Your Canal Front Oasis on Summerland Key! Indulge in the laid-back Florida Keys lifestyle in ...
From $242 per night (USD)
Expedia
$RV resort site\/rvsite\/spot\/lot Cudjoe Florida mm23 Key West MONTHLY DISCOUNT 25%$
From $70 per night (USD)
VRBO
RV resort site\/rvsite\/spot\/lot Cudjoe Florida mm23 Key West MONTHLY DISCOUNT 25%
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
RV RESORT SPOT. BIG Rig Friendly 25% discount per month RV RESORT SITE 25% DISCOUNT PER MONTHLY rental /CAMPSI ...
From $70 per night (USD)
VRBO
From $270 per night (USD)
Expedia
Summerland Keys Upgraded Waterfront Home
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Relax with the whole family at this peaceful oasis on the water with plenty of room for your boat and trailer! With 50 f ...
From $270 per night (USD)
Expedia
From $421 per night (USD)
VRBO
Keys Island Villa - Venture Out Home 354
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Exquisite waterfront home in the exclusive family friendly Venture Out Community. Keys Island Paradise is a boaters para ...
From $421 per night (USD)
VRBO
From $393 per night (USD)
Expedia
SOUTHERN SUNSET - As seen on House Hunters-S228 E6 - Family Time in the FL Keys
Bedrooms:
2
Bathrooms:
4
Sleeps:
12
BOAT RENTAL: We offer to rent our personal boats to our guests. We offer a Flats Boat, Bay Boat, and 28-ft Ocean Runner ...
From $393 per night (USD)
Expedia
From $325 per night (USD)
VRBO
Spanish Queen @Venture Out, Cudjoe Key
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Experience the beautiful Florida Keys and stay at the popular Venture Out Private Community at Cudjoe Key. Newly furnish ...
From $325 per night (USD)
VRBO
$3\/2 Home on Canal with Dock and Ocean Access$
From $185 per night (USD)
VRBO
3\/2 Home on Canal with Dock and Ocean Access
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
On canal with ocean access to Atlantic and Gulf sides. 3 bedroom 2 full bath renovated canal front Cudjoe Key beach home ...
From $185 per night (USD)
VRBO
From $199 per night (USD)
VRBO
THE NEW HIDDEN HAMMOCK RESORT - Green Cottage - Sleeps 4
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
The Green Cottage is a standalone unit which is next to the pool and near the outdoor shower. It has been recently reno ...
From $199 per night (USD)
VRBO
From $310 per night (USD)
VRBO
Rise-N-Shine with spectacular sunrise views!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Perfect spot for fishing, lobstering, and snorkeling with a spectacular sunrise view! There is room to park one vehicle, ...
From $310 per night (USD)
VRBO
From $520 per night (USD)
VRBO
Mad Mahi - Deep Water Canal
Bedrooms:
5
Bathrooms:
4
Sleeps:
10
This Summerland Key home is perfect for the avid fisherman. Deep Water Canal with easy access to both the Gulf and Atl ...
From $520 per night (USD)
VRBO
$Sea La Vie - Monthly Vacation Rental - Oceanfront 3BD\/3BA RealKeyWest$
From $234 per night (USD)
Expedia
Sea La Vie - Monthly Vacation Rental - Oceanfront 3BD\/3BA RealKeyWest
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Welcome to Sea La Vie, an elevated oceanfront paradise available for rent. Nestled in the picturesque Cudjoe Bay, this 3 ...
From $234 per night (USD)
Expedia
From $280 per night (USD)
VRBO
Ocean View Splendor on Summerland Key
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Enjoy the beautiful waterfront elevated home in the Florida Keys overlooking the Atlantic Ocean. Relax in the screened ...
From $280 per night (USD)
VRBO
From $900 per night (USD)
VRBO
~Reel Em' Inn~ Luxury Oceanfront Summerland Key home with deep water and pool!
Bedrooms:
5
Bathrooms:
4
Sleeps:
14
Completely remodeled, high-end Summerland Key home! Meticulously designed vacation property with exquisite furnishings t ...
From $900 per night (USD)
VRBO
From $305 per night (USD)
VRBO
Waterfront Venture Out Home
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Mandatory $125 Fee paid to Venture Out Community upon arrival. Waterfront home with concrete seawall for boat dockage. ...
From $305 per night (USD)
VRBO
$RV Lot Venture Out, 35x69' Accommodates Large\/Oversized RVs$
From $97 per night (USD)
VRBO
RV Lot Venture Out, 35x69' Accommodates Large\/Oversized RVs
Bedrooms:
1
Bathrooms:
0
Sleeps:
6
Welcome to this remarkable and generously spacious RV Lot nestled within the beautiful community of Venture Out on Cudjo ...
From $97 per night (USD)
VRBO
From $395 per night (USD)
VRBO
Open water pool home 25miles from Key West
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Relax by the pool with heater/chiller, jets and sundeck. Over 100' of seawall on deep water. Kayaks on-site. Second flo ...
From $395 per night (USD)
VRBO
From $350 per night (USD)
VRBO
Sun Bake @ Sponge Cake, 64' Sea Wall, Great Seating, Fish Gulf or Atlantic
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Canal front home in a gated community. Large screened in porch. Freshly updated deck furniture, docking post, and fish c ...
From $350 per night (USD)
VRBO
From $179 per night (USD)
VRBO
Sunshine 23 | 2 Bed, 2 Bath
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
All the comforts of home, with none of the cold weather! Dog-friendly 2 bed/2 bath monthly vacation rental on a boating ...
From $179 per night (USD)
VRBO
From $399 per night (USD)
Expedia
Emerald Seas - Florida Keys Ocean Front Paradise!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to our Florida Keys Ocean Paradise, Emerald Seas! Truly a special place to get away and relax. Enjoy the crystal ...
From $399 per night (USD)
Expedia
From $386 per night (USD)
VRBO
Tropical paradise on open water 35 ft seawall in beautiful Venture Out Community
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Ocean Front 35’ Seawall – Spectacular views from this 2 Bedroom 2 Bathroom ocean front stilt home! This home features a ...
From $386 per night (USD)
VRBO
From $265 per night (USD)
Expedia
Venture Out- Million Dollar Island Resort
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Oceanfront Home, Pool Access/50 Ft Dock Fresh & Fabulous best describes this island listing . This fantastic Ocean home ...
From $265 per night (USD)
Expedia
From $129 per night (USD)
VRBO
Oceanfront RV Lot with 40' Seawall
Bedrooms:
1
Bathrooms:
0
Sleeps:
6
Bring your own RV and experience the majestic beauty of the Florida Keys at this beautiful Oceanfront RV Lot! Lot featur ...
From $129 per night (USD)
VRBO
From $158 per night (USD)
Expedia
Water Lovers Paradise
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
This newly renovated vacation home on a canal in Cudjoe Key is a stunning retreat that offers the perfect blend of comf ...
From $158 per night (USD)
Expedia
From $172 per night (USD)
VRBO
Base Camp - Cudjoe Key 2 Bedroom, 2 Bath Wheelchair Accessible
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Escape to Base Camp in the Florida Keys – Your Canal Front Paradise Awaits! Indulge in the ultimate relaxation as vaca ...
From $172 per night (USD)
VRBO
From $149 per night (USD)
Expedia
Canal front RV lot quick access to Atlantic Ocean or Gulf
Bedrooms:
1
Bathrooms:
0
Sleeps:
0
Canal front RV lot with 35’ dock. Cleats , fish cleaning table, 110 volts,50 and 30 amp hook up and sewer service on sit ...
From $149 per night (USD)
Expedia
From $126 per night (USD)
VRBO
RV Lot 621 Venture Out
Bedrooms:
1
Bathrooms:
0
Sleeps:
6
Experience the tranquility of this freshly landscaped RV lot nestled within Venture Out. This spacious 35' by 70' lot fe ...
From $126 per night (USD)
VRBO
From $235 per night (USD)
Expedia
Blue Mind - Venture Out Unit 225
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
BLUE MIND - VO225 35' Dockage on Y-shaped Canal Sparkling Clean Kayak & WiFi This beautifully decorated vacation home is ...
From $235 per night (USD)
Expedia
From $292 per night (USD)
VRBO
Paradise Escape - Venture Out Unit 99
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
VO099 Spectacular Ocean View Stilted 2Bd/2Ba 35' Dockage Great Boating Property! This beautiful sparkling clean two bedr ...
From $292 per night (USD)
VRBO
From $286 per night (USD)
Expedia
Turtle Retreat - Venture Out Lot 329
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Turtle Retreat - Venture Out Lot 329 Expansive Water Views! 29' + 9' Seawall Pull up to a 40' seawall and rooms for kaya ...
From $286 per night (USD)
Expedia
From $320 per night (USD)
VRBO
Endless Water Views - Venture Out 526
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Endless Water Views - Venture Out 526 Newer Stilted 2Bd/2Ba Home with WIFI 35' Dockage Open Water Views! This newer cons ...
From $320 per night (USD)
VRBO
From $362 per night (USD)
VRBO
Paradise place located in a gated resort
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Island living. Waterfront home ground level , with boat dock/ seawall in your back yard. located Between the Atlantic ...
From $362 per night (USD)
VRBO
From $188 per night (USD)
VRBO
Cozy Venture Out Cottage
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
MANDATORY $125 FEE NOT INCLUDED, PAID TO VENTURE OUT COMMUNITY UPON ARRIVAL. One bedroom home with all that you need. ...
From $188 per night (USD)
VRBO
From $418 per night (USD)
Expedia
Shangri-la in the Keys! Enjoy the water views and a 45' dock space!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Shangri-la in the Keys! Enjoy the water views and a 45' dock space! VO unit 413 - 2Bd/2Ba Stilt Home Newly renovated s ...
From $418 per night (USD)
Expedia
From $256 per night (USD)
VRBO
Treasure Isle at Parks End - Venture Out 062
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Treasure Isle at Parks End - Venture Out 062 Southern Location Walk to Ocean! This sparkling clean and bright 2 Bedroom ...
From $256 per night (USD)
VRBO
From $409 per night (USD)
Expedia
Casa Dolphin - Venture Out 279
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Casa Dolphin - Venture Out 279 Stilt 2Bd/2Ba 35' Dockage Close to Everything! Recently updated 2 BR/2 BA stilt home ha ...
From $409 per night (USD)
Expedia
From $299 per night (USD)
VRBO
Pelican's Roost, Waterfront comfort at Venture Out
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
About this space Pelicans Roost is a waterfront home on the Atlantic side of Cudjoe Key with a 17’ dock. Only 20 miles f ...
From $299 per night (USD)
VRBO
From $338 per night (USD)
VRBO
Florida Keys Paradise!
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
Looking for the ultimate vacation experience? Our vacation home has everything you need to relax and have fun. We are lo ...
From $338 per night (USD)
VRBO
From $329 per night (USD)
VRBO
Dickey's Dockside Retreat
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Summary: Escape to Dickey's Dockside Retreat. This waterfront paradise in the Florida Keys offers a private dock, perfec ...
From $329 per night (USD)
VRBO
From $569 per night (USD)
VRBO
WATERFRONT Seaside Sanctuary in the Keys with 35' SEAWALL FOR YOUR BOAT!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Your WATERFRONT Keys getaway!! Updated appliances & fixtures, this 2BR/2BA elevated property that won’t disappoint! Full ...
From $569 per night (USD)
VRBO
$Waterfront Oceanside 200' Seawall 3\/2 Sleeps 6$
From $275 per night (USD)
VRBO
Waterfront Oceanside 200' Seawall 3\/2 Sleeps 6
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Hello ! My name is Debra and I run our VRBO account for our family. We love our salty slice of paradise and I look forwa ...
From $275 per night (USD)
VRBO
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VRBO
Waterfront Oceanside 200' Seawall efficiency Sleeps 4
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Hello ! My name is Debra and I run our account for our family. We love our salty slice of paradise and I look forward t ...
Click For Pricing
VRBO
$Ocean\/Canal Views 21ft Dock - Venture Out #357$
From $255 per night (USD)
VRBO
Ocean\/Canal Views 21ft Dock - Venture Out #357
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Beautiful Ocean/Canal Views 21' Dockage 2Bd/2Ba with Double Porches, Large Landscaped Yard! Island Breeze is a fabulous ...
From $255 per night (USD)
VRBO
From $186 per night (USD)
Expedia
Oceanfront Empty RV lot - 59' Seawall
Bedrooms:
1
Bathrooms:
0
Sleeps:
6
Stunning Oceanfront EMPTY RV LOT: Perfect for Boating Enthusiasts! Dive into an oceanfront experience like no other! Thi ...
From $186 per night (USD)
Expedia
From $283 per night (USD)
VRBO
Blue Lobster Lodge - Venture Out #543
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
BLUE LOBSTER LODGE VO 543 Comfortable 2 Bedroom 1.5 Bath Dry Lot This cozy 2 bedroom / 1.5 bath sleeps 6. It's a great p ...
From $283 per night (USD)
VRBO
From $300 per night (USD)
VRBO
Shore Thing at Venture Out With 50’ Private Dock, Bring Your Boat!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
NEW LISTING JULY 2023!!! Welcome to Shore Thing at Venture Out! This remarkable home features unparalleled Atlantic V ...
From $300 per night (USD)
VRBO
From $250 per night (USD)
VRBO
Summerland Cove..MM25 Summerland Key, Fl..Canal front-one street from open water
Bedrooms:
3
Bathrooms:
2
Sleeps:
5
Newly renovated 2 bedroom, 2.5 bath canal front home with pool in quite, safe neighborhood 25 miles from Key West. House ...
From $250 per night (USD)
VRBO
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VRBO
Stylish & Modern Summerland Key Private Retreat!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Discover the very best of the Florida Keys from the comfort & convenience of this upgraded waterfront retreat! Perfectly ...
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VRBO
$Waterfront RV Lot w 35' dock in \Venture Out\$
From $110 per night (USD)
VRBO
Waterfront RV Lot w 35' dock in \"Venture Out\"
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
35' dock on a canal in Venture Out! This is a lot only there is no house. Simply drive up with your travel trailer/RV/5t ...
From $110 per night (USD)
VRBO
From $299 per night (USD)
Expedia
OCEAN BREEZE COTTAGE AT HIDDEN HAMMOCKS
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Ocean Breeze is the largest of our 5 cottages at 1500 square feet. It's perfect for your family vacation, sleeping 7 pe ...
From $299 per night (USD)
Expedia
From $150 per night (USD)
VRBO
SEA SHELL COTTAGE UNIT #2
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Sea Shell Cottage UNIT #2 has efficiency kitchen with refrigerator, sink and microwave oven. Enjoy the communal outdoor ...
From $150 per night (USD)
VRBO
From $184 per night (USD)
VRBO
FLAMINGO COTTAGE UNIT #1
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
The Flamingo Cottage comes with TV, AC & WIFI. UNIT #1 has full kitchen, and it's own private space. Enjoy the communal ...
From $184 per night (USD)
VRBO
From $233 per night (USD)
VRBO
Summerland Cottage-Relax At Our Little Piece of Paradise!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
** Phone Meeting Required before booking approval!! Host Missy Proctor (561) 667-0160 *** Don't forget to check the VR ...
From $233 per night (USD)
VRBO
From $450 per night (USD)
VRBO
Come relax at Sandy Bottom Beach Cottage!!!!!
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
Beautiful Summerland Key!! Two houses from the Atlantic Ocean. Enjoy boating, kayaking, swimming in the 28' x 9' swim s ...
From $450 per night (USD)
VRBO
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VRBO
Waterfront villa with pool, outdoor areas, home gym, & fillet station
Bedrooms:
8
Bathrooms:
6
Sleeps:
14
Tarpon Ranch Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
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VRBO
$Relaxing 2\/2 Get Away in the Lower Keys! by RedAwning$
From $286 per night (USD)
Expedia
Relaxing 2\/2 Get Away in the Lower Keys! by RedAwning
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Spacious Canal Front Home with Fast WiFi, Central AC, & Private Hot Tub Chill at a spacious and recently renovated hom ...
From $286 per night (USD)
Expedia
From $190 per night (USD)
VRBO
Perfect Boating Access to Kemp Channel Cudjoe Key New POOL!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Perfect fishing and boating location on Kemp Channel between Cudjoe Key and Summerland Key. New Pool Installed June 20 ...
From $190 per night (USD)
VRBO
From $275 per night (USD)
Expedia
Bimini Breeze in Cudjoe Key
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Welcome to your dream vacation destination! This beautifully updated and remodeled 2-bedroom, 1-bathroom rental property ...
From $275 per night (USD)
Expedia
$Our Florida Keys \Sea-Cove\! Canal front, Boat dockage, Pool, Private!!$
From $270 per night (USD)
VRBO
Our Florida Keys \"Sea-Cove\"! Canal front, Boat dockage, Pool, Private!!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Make our happy place, your happy place! Escape to this canal front retreat and leave your worries behind. This 2-bedr ...
From $270 per night (USD)
VRBO
From $550 per night (USD)
VRBO
Beach Bliss, Oceanfront with pool
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Beach Bliss has everything you need for a spectacular vacation. The views inside and outside the home are mesmerizing. T ...
From $550 per night (USD)
VRBO
From $215 per night (USD)
VRBO
Coastal Oasis, Canal front
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
COASTAL OASIS is just for you. This three-bedroom two-bath canal-front home offers a comfortable base for your Keys adve ...
From $215 per night (USD)
VRBO
From $215 per night (USD)
VRBO
Cudjoe Bay Overlook
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This really nice custom Keys home is located in a very quiet area with good boating access to both the Atlantic with its ...
From $215 per night (USD)
VRBO

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