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 $200 per night (USD)
VRBO
Family Friendly 2 Bedroom 1 Bath, 32' Seawall, 4 Bike, 3 Kayak, WiFi, large pool
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
For your next Florida Keys vacation, reserve a stay at this waterfront home located on a canal with easy access to eithe ...
From $200 per night (USD)
VRBO
From $285 per night (USD)
VRBO
35' Seawall Sparkling , 30min from Keywest, WIFI, BBQ Grill, Pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Sparkling clean and bright 2Bd/2Ba vacation home in Venture Out Residential Condominium! Is located on a 60' wide canal ...
From $285 per night (USD)
VRBO
From $175 per night (USD)
VRBO
Cozy and modern island living, Cudjoe Key
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Unit #617 Bright, modern, 2bed, 2bath, midrise home. Across from canal and common area. Open floor plan, hardwood, c ...
From $175 per night (USD)
VRBO
From $375 per night (USD)
VRBO
Oceanfront Sunsets in the Florida Keys
Bedrooms:
6
Bathrooms:
4
Sleeps:
8
FOLSOM'S FOLLY... Summerland Key, Florida Interesting architecture with breezy views of the water. All rooms beautiful ...
From $375 per night (USD)
VRBO
From $268 per night (USD)
VRBO
Springs Venture Out Dolphin House (#386) with beautiful open water views
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This Home has some of the absolute best views of the Ocean; sitting on your deck watching nature at its best. Our 35ft s ...
From $268 per night (USD)
VRBO
From $211 per night (USD)
VRBO
Ocean view home -Private launch & breath taking sunset views-min 28 day rentals
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Minimum Rental is 28 Days to a single family or party (no subleases allowed). Simply Breathtaking VIEWS of the sunset ...
From $211 per night (USD)
VRBO
From $301 per night (USD)
VRBO
Views Views! Direct Oceanfront, Beautiful Inside!
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
View, views, views! Totally beautiful modern home has a very large balcony which provides an opportunity for endless d ...
From $301 per night (USD)
VRBO
From $400 per night (USD)
VRBO
The edge of the river of Poseidon
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Neptune’s End is the perfect island getaway home. This home sits ocean front and has unobstructed views of Cudjoe Bay ou ...
From $400 per night (USD)
VRBO
From $240 per night (USD)
VRBO
Fishermen’s Paradise 🎣
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
This is a water lover or a Fisherman’s Paradise. This waterfront home can sleep 6. The house is fully furnished with a ...
From $240 per night (USD)
VRBO
From $335 per night (USD)
VRBO
Beautiful Lagoon view on canal pool home Summerland
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Home has high vaulted ceiling and 30 feet of sliding glass windows which over looks the canal, lagoon and ocean. On quie ...
From $335 per night (USD)
VRBO
From $231 per night (USD)
VRBO
A slice of paradise
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Wanna go on vacation but feel Cozy as if your home? 🦎 We got the place for you! 2 bedroom,1 bathroom with living room, ...
From $231 per night (USD)
VRBO
From $420 per night (USD)
VRBO
Spectacular sunsets and open water views at this 3 BR 3 BA
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Spectacular sunsets and open water views at this 3 BR 3 BA home on Summerland Key. Brand new dock for your large boat ...
From $420 per night (USD)
VRBO
From $337 per night (USD)
VRBO
BIG BLUE waits for you in the sunny Keys
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Our vacation home in the Lower Keys awaits your arrival! We live here during the winter so our home is available spring ...
From $337 per night (USD)
VRBO
From $203 per night (USD)
VRBO
Oceanside, heated pool, near Key West, space for 20-25 ft boat. Book fall 2024!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
3 bedroom/2 bath home, sleeps 8. Enjoy early morning coffee or evenings gazing at the stars from the cozy balcony. Dow ...
From $203 per night (USD)
VRBO
From $300 per night (USD)
VRBO
LATITUDE ADJUSTMENT
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Need a “LATITUDE ADJUSTMENT”? Our spotless 2 BR, 2 BA stilt home on a 60’ wide canal in VO at MM23, on Cudjoe Key await ...
From $300 per night (USD)
VRBO
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
$Tropical Island Paradise W \/ Open Water Views!$
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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 ...
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VRBO
From $259 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 $259 per night (USD)
VRBO
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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 ...
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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
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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 ...
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VRBO
From $286 per night (USD)
VRBO
Paradise Found, Oceanfront with pool
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Escape completely in this open and airy 3 bedroom 2 bath oceanfront home, with a 10 x 14 ft pool. Situated on the northe ...
From $286 per night (USD)
VRBO
From $210 per night (USD)
VRBO
Ocean front home with 4 bedrooms, 4.5 baths and dock
Bedrooms:
5
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 $210 per night (USD)
VRBO
From $105 per night (USD)
VRBO
RV Lot 69Venture Out, Canal Front ,Lot Dimensions:35x69'
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Welcome to your slice of paradise in the breathtaking Florida Keys! Nestled in the vibrant community of Venture Out, thi ...
From $105 per night (USD)
VRBO
$The Lookout-2 bed\/2 bath Unit 659 Venture Out stilted Home$
From $294 per night (USD)
VRBO
The Lookout-2 bed\/2 bath Unit 659 Venture Out stilted Home
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to your tropical paradise getaway in Cudjoe Key, Florida! Nestled within a secure gated community, this charming ...
From $294 per night (USD)
VRBO
From $376 per night (USD)
Expedia
Beautifully Renovated, Open Water Sunset Views, Dockage, Direct Boating Access
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 $376 per night (USD)
Expedia
From $150 per night (USD)
VRBO
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 $150 per night (USD)
VRBO
From $195 per night (USD)
Expedia
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 $195 per night (USD)
Expedia
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VRBO
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 ...
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VRBO
From $140 per night (USD)
Expedia
Empty RV Lot with Amazing Views!
Bedrooms:
1
Bathrooms:
0
Sleeps:
6
Captivating Oceanfront Getaway with 35' Durable Seawall! This property is equipped with a robust seawall featuring dock ...
From $140 per night (USD)
Expedia
From $268 per night (USD)
VRBO
Bluegill - 3 bedroom 2 bath on canal. POOL COMING SUMMER 2024
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 35' boat. Th ...
From $268 per night (USD)
VRBO
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
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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 ...
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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 $169 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 $169 per night (USD)
VRBO
From $149 per night (USD)
VRBO
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)
VRBO
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)
VRBO
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)
VRBO
From $292 per night (USD)
Expedia
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)
Expedia
From $289 per night (USD)
VRBO
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 $289 per night (USD)
VRBO
From $429 per night (USD)
Expedia
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 $429 per night (USD)
Expedia
From $186 per night (USD)
VRBO
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)
VRBO
From $320 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 $320 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 $325 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 $325 per night (USD)
Expedia
From $392 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. We offer a Flats Boat, Bay Boat, and 28-ft Ocean Runner ...
From $392 per night (USD)
VRBO
From $164 per night (USD)
Expedia
EMPTY RV LOT - Sea Esta in Cudjoe Key!
Bedrooms:
1
Bathrooms:
0
Sleeps:
6
This RV LOT has it all! This is a great spot for those who want to enjoy open water views without having the hassle of g ...
From $164 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 $325 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 $325 per night (USD)
VRBO
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Expedia
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 ...
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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 $259 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 $259 per night (USD)
Expedia
From $158 per night (USD)
VRBO
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)
VRBO
From $367 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 $367 per night (USD)
VRBO
From $191 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 $191 per night (USD)
VRBO
From $317 per night (USD)
Expedia
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 $317 per night (USD)
Expedia
$RV Lot Venture Out, 35x69' Accommodates Large\/Oversized RVs$
From $105 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 $105 per night (USD)
VRBO
From $244 per night (USD)
VRBO
Coastal Cudjoe Key Home with Excellent Boating
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Escape to the tranquil paradise of Latitudes and Attitudes, a charming 3-bedroom, 2-bathroom home nestled in the picture ...
From $244 per night (USD)
VRBO
$Venture Out 1 bed\/1 bath Cottage on Cudjoe Key$
From $246 per night (USD)
VRBO
Venture Out 1 bed\/1 bath Cottage on Cudjoe Key
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 $246 per night (USD)
VRBO
$Waterfront home with boat\/canal access, screened lanai, & renovated interior$
From $258 per night (USD)
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 ...
From $258 per night (USD)
Expedia
From $347 per night (USD)
VRBO
NEW LISTING - 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 $347 per night (USD)
VRBO
From $360 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 $360 per night (USD)
Expedia
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 $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
From $141 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 $141 per night (USD)
VRBO
From $235 per night (USD)
Expedia
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 $235 per night (USD)
Expedia
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 $568 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 $568 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
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
$Ocean\/Canal Views 21ft Dock - Venture Out #357$
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 $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
From $500 per night (USD)
VRBO
Latitude Adjustment in Cudjoe Key
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Nestled in a serene location in the Florida Keys, this Oceanfront house offers breathtaking open water views that promis ...
From $500 per night (USD)
VRBO
From $212 per night (USD)
Expedia
Cuddie Cottage: 2BR Waterfront Home in Venture Out Resort, Open Water Views, Shared Pool & Hot Tub!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to Cuddie Cottage, your charming haven nestled within the picturesque Venture Out resort on Cudjoe Key. This del ...
From $212 per night (USD)
Expedia
From $395 per night (USD)
VRBO
PEACEFUL PARADISE DEEP WATER CANAL 5 MINUTES TO OCEAN Fishing and Lobster season
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Location Location Location! Welcome to our very special community Summerland Key. Summerland is one of the best fishi ...
From $395 per night (USD)
VRBO
From $235 per night (USD)
Expedia
Paradise in the Fabulous Florida Keys - Fishing and Dive capital of the world.
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Beautiful open water views with gorgeous Sunsets across Cudjoe Bay. Enjoy happy hour overlooking the canal and dock or o ...
From $235 per night (USD)
Expedia
From $325 per night (USD)
VRBO
Tropical Tides in Cudjoe Key
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Enjoy an Oceanfront getaway in this Beautiful home, boasting stunning panoramic ocean views. Featuring 2 bedrooms and 2 ...
From $325 per night (USD)
VRBO
From $385 per night (USD)
Expedia
Tropical Island Getaway - VO196
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 $385 per night (USD)
Expedia
From $265 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 $265 per night (USD)
VRBO
From $260 per night (USD)
Expedia
House, relaxing space,waterfront at Cudjoe Key
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 $260 per night (USD)
Expedia
$Super Nice 2 BR Canal Home in Summerland w\/ Great Boating Access & Private Pool!$
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VRBO
Super Nice 2 BR Canal Home in Summerland w\/ Great Boating Access & Private 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 ...
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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
From $1000 per night (USD)
VRBO
Luxury Retreat in Summerland Key - Book Today!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Stay in this one-of-a-kind home right in the Channal of Summerland Key. Only 25 min from KeyWest in one of the most soug ...
From $1000 per night (USD)
VRBO
From $490 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 $490 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 $363 per night (USD)
VRBO
Beautifully Decorated, Comfortable Cottage with Amenities in Gated Community
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Our comfortable, beautifully decorated two bedroom/two bathroom home with full sized kitchen is located in the Venture O ...
From $363 per night (USD)
VRBO
From $300 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 $300 per night (USD)
Expedia
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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 ...
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VRBO
From $320 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 $320 per night (USD)
Expedia
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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 ...
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VRBO
From $738 per night (USD)
Expedia
Oceanfront Gated Corner lot Amazing Sunsets. 90” BoatDock & 12 person Swim Spa!
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
As featured on the TV Show; Selling Coastal, Vista de Sirenas translates to ‘Mermaid Views’ is a piece of paradise with ...
From $738 per night (USD)
Expedia
From $410 per night (USD)
VRBO
Beautiful Ocean Views 35' Dockage - Venture Out unit 469
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
VO469 Beautiful Ocean Views 35' Dockage 2Bd/2Ba This beautiful home on stilts overlooks the open water for breathtakin ...
From $410 per night (USD)
VRBO
From $285 per night (USD)
Expedia
Panoramic Ocean Front! Venture Out Unit 522
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
VO522 Panoramic Ocean Front! 42' Boat Dockage!Beautiful light and bright vacation rental overlooks the most breathtaking ...
From $285 per night (USD)
Expedia
From $281 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 $281 per night (USD)
VRBO
$REEL ESCAPE - 4 Bedroom \/ 2 Bathroom w\/ Pool & Deep Water Access$
From $563 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 $563 per night (USD)
Expedia
Click For Pricing
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 ...
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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

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Results: 243 Rentals