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 $347 per night (USD)
VRBO
Oceanfront house private beach & protected 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 $347 per night (USD)
VRBO
From $233 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 $233 per night (USD)
Expedia
From $189 per night (USD)
VRBO
SHANGRI-LA June / July Mini Lobster Season - Discount rate for long term renters
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 $189 per night (USD)
VRBO
From $765 per night (USD)
Expedia
Summerland Nest - Ocean view with private beach and pool
Bedrooms:
4
Bathrooms:
7
Sleeps:
14
Fabulous resort-style living & incredible open water views over Niles Channel at this 7 BR 5 BA home on Summerland Key. ...
From $765 per night (USD)
Expedia
From $621 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 $621 per night (USD)
VRBO
From $350 per night (USD)
VRBO
Summerland Key Oceanfront
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Our longtime winter tenant who has rented our house from November through April for the last 7 years has bought his own ...
From $350 per night (USD)
VRBO
From $329 per night (USD)
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 ...
From $329 per night (USD)
VRBO
From $293 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 $293 per night (USD)
VRBO
From $140 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 $140 per night (USD)
VRBO
From $383 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 $383 per night (USD)
Expedia
From $183 per night (USD)
VRBO
Love Shack | Charming 2 bed/1 bath cottage on Summerland Key
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 $183 per night (USD)
VRBO
From $346 per night (USD)
Expedia
Relaxing Waterfront Escape Near Key West - Venture Out Unit 410
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
VO410 Relaxing Waterfront Escape Near Key West – 35' Dock, Kayaks and bikes included. Access to beautiful pool and hot t ...
From $346 per night (USD)
Expedia
From $668 per night (USD)
VRBO
Relax at Keys Time – 2BR Waterfront Rental w/ Kayaks, Bikes, and Boat Dock
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Keys Time – Canalfront 2BR Vacation Rental in Cudjoe Key | Pet-Friendly, Kayaks, Dock & More Welcome to Keys Time, your ...
From $668 per night (USD)
VRBO
From $618 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 $618 per night (USD)
VRBO
From $477 per night (USD)
VRBO
**CAREFREE ON CUDJOE @ THE BAY** Waterfront Home & Pool + LAST KEY SERVICES…
Bedrooms:
3
Bathrooms:
3
Sleeps:
9
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! From the mome ...
From $477 per night (USD)
VRBO
From $355 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 $355 per night (USD)
Expedia
From $190 per night (USD)
VRBO
Lake It Easy: Relax in This Beautiful 3BR Canal Front Home on Summerland Key, Dockage & Dog-Friendly
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
County zoning requires a minimum rental period of 28 nights, and no exceptions can be made. Please review additional pol ...
From $190 per night (USD)
VRBO
From $58 per night (USD)
Expedia
RV resort site/rvsite/spot/lot Cudjoe Florida mm23 Key West MONTHLY DISCOUNT
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
RV RESORT SPOT. BIG Rig Friendly discount per month when booking 1ST to the 1ST of the month RV RESORT SITE ...
From $58 per night (USD)
Expedia
From $469 per night (USD)
VRBO
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, only. We own: Flats Boat - 17 ft Ranger with E Tech 75 ...
From $469 per night (USD)
VRBO
From $684 per night (USD)
Expedia
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 $684 per night (USD)
Expedia
From $216 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 $216 per night (USD)
VRBO
$PALM COTTAGE \nSummer vacation Lobster and Fishing season!\nsleeps 4$
From $250 per night (USD)
Expedia
PALM COTTAGE \nSummer vacation Lobster and Fishing season!\nsleeps 4
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
The Palm Cottage is a standalone unit which is next to the pool and near the outdoor shower. It has been recently reno ...
From $250 per night (USD)
Expedia
From $466 per night (USD)
VRBO
Mad Mahi Canal with pool
Bedrooms:
3
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 $466 per night (USD)
VRBO
From $223 per night (USD)
Expedia
Sea La Vie: Your Oceanfront Escape in Cudjoe Key, Florida 3BD/3BA
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Sea La Vie: Oceanfront Vacation Rental in Cudjoe Key, Florida Looking for the perfect oceanfront getaway in the Florida ...
From $223 per night (USD)
Expedia
From $365 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 $365 per night (USD)
VRBO
From $1075 per night (USD)
VRBO
~Reel Em' Inn~ Luxury Oceanfront Summerland Key home with deep water and pool!
Bedrooms:
4
Bathrooms:
4
Sleeps:
14
Completely remodeled, high-end Summerland Key home! Meticulously designed vacation property with exquisite furnishings t ...
From $1075 per night (USD)
VRBO
From $371 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 $371 per night (USD)
VRBO
From $129 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 $129 per night (USD)
VRBO
From $335 per night (USD)
VRBO
Sun Bake @ Sponge Cake, 64' Sea Wall,
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Canal front home in a gated community. Large screened in porch. Sleeps 4 comfortably + a queen sleeper sofa if needed. ...
From $335 per night (USD)
VRBO
From $240 per night (USD)
Expedia
Sunshine 23 | Dog-friendly 2 bed/2 bath canalfront boating home on Cudjoe Key
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
All the comforts of home, with none of the cold weather! Dog-friendly 2 bed/2 bath monthly vacation rental on a boating ...
From $240 per night (USD)
Expedia
From $505 per night (USD)
VRBO
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 $505 per night (USD)
VRBO
Click For Pricing
Expedia
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 ...
Click For Pricing
Expedia
From $328 per night (USD)
VRBO
Venture Out Million Dollar Ocean View
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 $328 per night (USD)
VRBO
From $161 per night (USD)
Expedia
Oceanfront RV Lot with 40' Seawall
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Bring your own RV and experience the majestic beauty of the Florida Keysat this beautiful Oceanfront RV Lot! Lot feature ...
From $161 per night (USD)
Expedia
From $188 per night (USD)
VRBO
Canal front lot only. No house or RV. You need to bring your RV.
Bedrooms:
1
Bathrooms:
0
Sleeps:
0
Canal front lot with 35’ dock. Cleats , fish cleaning table, 110 volts,50 and 30 amp hook up and sewer service on site. ...
From $188 per night (USD)
VRBO
From $129 per night (USD)
VRBO
RV Lot 621 Venture Out
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Experience the tranquility of this freshly landscaped RV lot nestled within Venture Out. This spacious 35' by 70' lot fe ...
From $129 per night (USD)
VRBO
From $390 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 $390 per night (USD)
VRBO
From $253 per night (USD)
Expedia
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 $253 per night (USD)
Expedia
From $392 per night (USD)
VRBO
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 $392 per night (USD)
VRBO
From $309 per night (USD)
Expedia
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 $309 per night (USD)
Expedia
From $396 per night (USD)
VRBO
Piece Of Eight - Venture Out 279
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Piece Of Eight - Venture Out 279 Stilt 2Bd/2Ba 35' Dockage Close to Everything! Recently updated 2 BR/2 BA stilt home ...
From $396 per night (USD)
VRBO
From $300 per night (USD)
Expedia
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 $300 per night (USD)
Expedia
From $353 per night (USD)
VRBO
Florida Keys Paradise!
Bedrooms:
3
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 $353 per night (USD)
VRBO
Click For Pricing
Expedia
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 ...
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Expedia
From $594 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 $594 per night (USD)
VRBO
From $323 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 $323 per night (USD)
VRBO
Click For Pricing
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
From $322 per night (USD)
Expedia
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 $322 per night (USD)
Expedia
From $292 per night (USD)
VRBO
Summerland Cove..MM25 Summerland Key, Fl..Canal front-one street from open water
Bedrooms:
2
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 $292 per night (USD)
VRBO
From $286 per night (USD)
Expedia
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 ...
From $286 per night (USD)
Expedia
$Waterfront RV Lot w 35' dock in \Venture Out\. Utility hookups & beautiful views$
From $111 per night (USD)
VRBO
Waterfront RV Lot w 35' dock in \"Venture Out\". Utility hookups & beautiful views
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
35' dock on a canal in Venture Out! This is a RV lot only, there is no house. Simply drive up with your travel trailer/R ...
From $111 per night (USD)
VRBO
$OCEAN BREEZE HOUSE \nSummer Vacation bring the family. Fishing and Lobster season$
From $396 per night (USD)
Expedia
OCEAN BREEZE HOUSE \nSummer Vacation bring the family. Fishing and Lobster season
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 $396 per night (USD)
Expedia
From $189 per night (USD)
VRBO
SEA SHELL COTTAGE, Sleeps 2 - Summer Vacation, Fishing & Lobster Season is Here!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
The Sea Shell Cottage UNIT #2 has efficiency kitchen with refrigerator, sink, microwave oven and toaster oven. The main ...
From $189 per night (USD)
VRBO
$FLAMINGO COTTAGE - Summer vacation\nLobster and Fishing season- sleeps 4$
From $224 per night (USD)
Expedia
FLAMINGO COTTAGE - Summer vacation\nLobster and Fishing season- sleeps 4
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
The Flamingo Cottage is a studio unit that includes a Queen-sized bed in the bedroom area, a full kitchen, bathroom with ...
From $224 per night (USD)
Expedia
From $235 per night (USD)
VRBO
Summerland Cottage- Our Little Piece of Paradise with an Old School Key Vibe!
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 $235 per night (USD)
VRBO
From $223 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 August ...
From $223 per night (USD)
VRBO
From $666 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 $666 per night (USD)
VRBO
From $210 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 $210 per night (USD)
VRBO
From $268 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 $268 per night (USD)
VRBO
From $480 per night (USD)
Expedia
COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
CUDJOE CUTIE WITH AMENITIES GALORE… Sweeping views of the dazzling turquoise waters of the Florida Keys will ignite your ...
From $480 per night (USD)
Expedia
From $352 per night (USD)
VRBO
Sunset Views, oceanfront
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Enjoy the sunsets on Sarcarma Bay from this rustic home in a tropical setting with an open waterfront and canal access. ...
From $352 per night (USD)
VRBO
From $378 per night (USD)
Expedia
Large 5 Bedroom Canal Home in Summerland Key, FL with Pool
Bedrooms:
3
Bathrooms:
5
Sleeps:
11
Welcome to Palm Mansion! This large family home with 5 bedrooms and 3 full baths is located on a wide, deep canal suited ...
From $378 per night (USD)
Expedia
From $330 per night (USD)
VRBO
Lime in the coconut
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
You put the "LIME IN THE COCONUT" and add a little fun! Great times to be had in this very nice 3 bedroom 2 bath custom ...
From $330 per night (USD)
VRBO
From $366 per night (USD)
Expedia
Waterfront Retreat: Bikes, Paddle-boards, and Fishing Amenities Included
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This beautiful house located in Cudjoe Key, one of the most beautiful and relaxing keys in the area with a canal and acc ...
From $366 per night (USD)
Expedia
From $325 per night (USD)
VRBO
Amazing 2 BR Home in Summerland w/ Great Boating Access & Private Heated Pool!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Summerland Key House! This amazing 2 bedroom home on Summerland Key is a perfect Keys vacation home! It has e ...
From $325 per night (USD)
VRBO
From $352 per night (USD)
VRBO
Spectacular Sunsets, 3 bed, 2 bath with pool
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Escape completely in this open and airy 3 bedroom 2 bath oceanfront pool home. Situated on the northern shore of Sarcarm ...
From $352 per night (USD)
VRBO
From $566 per night (USD)
VRBO
Windswept Beach
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Welcome to our newly renovated 3 bedroom, 3 bathroom home with stunning open water views! This modern home is perfect fo ...
From $566 per night (USD)
VRBO
From $420 per night (USD)
Expedia
Tropical Island Getaway - Venture Out Unit 196
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
VO196 2B/2Ba Tropical Island Getaway! Ocean Views with 35' Seawall! Enjoy breathtaking ocean views from this midrise ...
From $420 per night (USD)
Expedia
From $658 per night (USD)
VRBO
3 Bedroom 3 Bath Pool Home with Gorgeous Atlantic Views
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Welcome to the Prestigious neighborhood of Summerland Key Isles!! This gorgeous 3 bedroom 3 bath property has one of the ...
From $658 per night (USD)
VRBO
From $271 per night (USD)
Expedia
Beautiful 3 bed 2 bath deep water canal front home
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Beautiful 3 bedroom 2 bath canal front home on Summerland Key. This home features deep water dockage, great access to th ...
From $271 per night (USD)
Expedia
From $233 per night (USD)
VRBO
Fishing, boating, lobstering from your backyard! Gorgeous Views & Super Private
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
**NEW TO VRBO & AIRBNB** Thank you for checking out the Key Lime Cottage - a cottage by no means!! This will be your Fl ...
From $233 per night (USD)
VRBO
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Expedia
Stunning Oceanfront Keys Home
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This 1,200-square foot home is a gorgeous ocean front property just minutes from back country and oceanside fishing. Tuc ...
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Expedia
$PEACEFUL PARADISE DEEP WATER CANAL! MINUTES TO OCEAN \nFishing and Lobster season$
From $420 per night (USD)
VRBO
PEACEFUL PARADISE DEEP WATER CANAL! MINUTES TO OCEAN \nFishing and Lobster season
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Nestled in the heart of Summerland Key, this 3-bedroom vacation home offers a tranquil escape for your Florida Keys geta ...
From $420 per night (USD)
VRBO
From $321 per night (USD)
VRBO
Summerland Key House Open Air Living
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summerland Key House is all about open air living. Cypress plank cathedral ceilings extend through the bedrooms, bathro ...
From $321 per night (USD)
VRBO
From $287 per night (USD)
VRBO
Pelican's Paradise #507 - Gated, Oceanfront Community!
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
<p>You'll find a kayak, bicycles, and more on site at this smoke-free vacation home. Venture Out Keys is within an easy ...
From $287 per night (USD)
VRBO
Click For Pricing
Expedia
Waterfront home with boat/canal access, screened lanai, & renovated interior
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Endless Summerland Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
Click For Pricing
Expedia
From $655 per night (USD)
VRBO
Beautiful Cottage & Amenities in Gated Community
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Our comfortable, beautifully decorated two bedroom/two bathroom home with full sized kitchen is located in the Venture O ...
From $655 per night (USD)
VRBO
From $389 per night (USD)
Expedia
Sunny Hideaway - Venture Out Unit 276
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Sunny Hideaway - Venture Out Unit 276 This beautifully decorated home is located on the water and is located within walk ...
From $389 per night (USD)
Expedia
From $549 per night (USD)
VRBO
Slow M'Ocean #54 - Oceanfront Home - Cudjoe Key
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Did you say you wanted something with a view? Look no further because this home has the most gorgeous, turquoise ocean w ...
From $549 per night (USD)
VRBO
From $387 per night (USD)
Expedia
Bluegill pool, larger boat allowed
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This 28 day minimum rental home has 3 bedroom 2 bath home has great boating access and dockage for up to a 39' boat. Bea ...
From $387 per night (USD)
Expedia
From $392 per night (USD)
VRBO
Waterfront Pool Home w/ Dock – Easy Access to Looe Key & Island Adventures!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Discover Your Ideal Florida Keys Getaway at Latitudes and Attitudes Welcome to Latitudes and Attitudes, a charming 3-be ...
From $392 per night (USD)
VRBO
From $261 per night (USD)
Expedia
Coconut Cottage #653 - Oceanfront Community
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Welcome to Coconut Cottage, your charming oasis nestled within the exclusive gated community of Venture Out in Cudjoe Ke ...
From $261 per night (USD)
Expedia
From $366 per night (USD)
VRBO
Beautifully Renovated with Stunning Sunset Views and Dockage!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Looking for a vacation rental to get away from it all in the Fabulous Florida Keys? Look no further than our beautifully ...
From $366 per night (USD)
VRBO
From $276 per night (USD)
Expedia
Venture Out RV lot 223
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
RV223 Beautiful RV Lot Open Water Views Expansive 55' Seawall, Amazing Location! OPEN WATER VIEWS with 55' concrete seaw ...
From $276 per night (USD)
Expedia
From $333 per night (USD)
VRBO
Endless Ocean Views - RV589
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
RV589 Endless Ocean Views! 64' Dockage Slice of Paradise! Panoramic Ocean Views from this fantastic location, perfect f ...
From $333 per night (USD)
VRBO
From $132 per night (USD)
Expedia
35'x70'WF RV Site on canal for rent for RV owners. Pet friendly gated community.
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Located at Venture Out on Cudjoe Key, 20 miles from Key West this gated community offers a heated saltwater pool overloo ...
From $132 per night (USD)
Expedia
From $168 per night (USD)
VRBO
Empty RV Lot with Amazing Views!
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Captivating Oceanfront Getaway with 35' Durable Seawall! This property is equipped with a robust seawall featuring dock ...
From $168 per night (USD)
VRBO
From $213 per night (USD)
VRBO
Ocean front home with 4 bedrooms, 4.5 baths and dock
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
You will be treated to gorgeous sunsets over Cudjoe Bay from this custom built 4 bedroom, 4 1/2 bath (master suite has h ...
From $213 per night (USD)
VRBO
From $317 per night (USD)
VRBO
Paradise Escape - VO466 35' Dockage
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
VO466 Paradise Escape! Perfect Location 35' Dockage! It's a wonderful time to enjoy Paradise! Enjoy endless expansive w ...
From $317 per night (USD)
VRBO
From $189 per night (USD)
Expedia
Cudjoe Escape – Luxury Island Stay #24
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Luxury 3BR Waterfront Pool Home – Cudjoe Key Escape Discover tropical luxury in this 3-bedroom waterfront pool home just ...
From $189 per night (USD)
Expedia
From $184 per night (USD)
VRBO
Seabreeze Escape WF RV Lot 489
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Seabreeze Escape WF RV Lot 489 Open Water Views! 35' Dockage with Tropical Landscaping!! Fish and swim right from your ...
From $184 per night (USD)
VRBO
From $308 per night (USD)
Expedia
Caribbean Cabana: Your Perfect 3BR Oceanfront Retreat with Dockage, Pool and Breathtaking Views!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
County zoning requires a minimum rental period of 28 nights, and no exceptions can be made. NO PETS. Please review addit ...
From $308 per night (USD)
Expedia
From $349 per night (USD)
VRBO
Truly sitting right on the ocean. Ocean's Edge has forever ocean views.
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Don’t be fooled by canal front listings. Lose yourself in the ever changing beauty of the Atlantic Ocean in this charmin ...
From $349 per night (USD)
VRBO
From $164 per night (USD)
VRBO
RV Lot 442 Venture Out, Canal Front, 35ftx69ft
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Welcome to RV Lot 442 in the exclusive gated community of Venture Out, located in stunning Cudjoe Key, Florida! This spa ...
From $164 per night (USD)
VRBO
From $291 per night (USD)
VRBO
Pelicans View - Venture Out Lot 318
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Pelicans View - VO318 Island Gem-Walk to POOL & Marina! Gorgeous Open Water Views! This beautifully remodeled midrise ...
From $291 per night (USD)
VRBO
From $219 per night (USD)
Expedia
Latitude Adjustment – Canalfront 3BR w/ Hot Tub, Tiki Hut & Boating Access
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Latitude Adjustment – Luxury 3BR Canal-Front Vacation Rental in Summerland Key, Florida Keys Welcome to Latitude Adjustm ...
From $219 per night (USD)
Expedia
From $221 per night (USD)
VRBO
Casa Morado - Bring your boat
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Imagine a charming retreat situated on a canal and right on the private airstrip in Summerland Key, Florida. This cozy 3 ...
From $221 per night (USD)
VRBO
From $426 per night (USD)
Expedia
Keys House - Venture Out Lot 220
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
VO220 Keys Home w/ 40' Dockage 2Bd/2Ba This beautiful home on stilts overlooks the open water with amazing views from ...
From $426 per night (USD)
Expedia
From $150 per night (USD)
VRBO
RV Lot 40 Venture Out, Lot dimentions - 35'x69'
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Welcome to your ideal RV lot in the vibrant Venture Out community on Cudjoe Key! This dry lot, measuring 35' x 69', offe ...
From $150 per night (USD)
VRBO
From $152 per night (USD)
VRBO
Canal Front RV LOT 451 Venture Out (40x23x70x31x35)
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Welcome to your dream canal front RV Lot with peekaboo ocean views. Situated on a quiet cul de sac, this picturesque lot ...
From $152 per night (USD)
VRBO

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Results: 282 Rentals