Summerland Key vacation rentals
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Top-rated vacation rentals in Summerland Key
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
Cottage in Cudjoe Key
4.92 out of 5 average rating, 130 reviewsATLANTIS...Ocean Front Cottage Retreat!
ATLANTIS~An ocean front cottage retreat! Completely remodeled, direct ocean-front cottage offers everything you'll need for the perfect getaway. Boat dock (25ft), HD TVs, washer & dryer, S/S appliances & gas cooking! Complimentary kayaks & bikes plus access to all the Venture Out Residential Condominium Community amenities: heated pool, Jacuzzi, kiddie pool, tennis, basketball & bocce courts, ocean bay swimming area, marina w/fuel, boat ramps & wash station, and a convenience market on-site!
Dec 28 – Jan 4
Home in Key West
4.94 out of 5 average rating, 268 reviewsRomantic Retreat - 2 person K Suite, Pvt deck/Spa!
Romantic Retreat is an Historic, free standing cottage which, in the 1800's, was the cistern for the Cigar Maker cottages here. It is decorated in a light Caribbean motif, efficiency kitchen (frig, microwave, hot plate) and a very airy bathroom with tub/shower. King memory foam bed and sleeps 2 persons only. 32” Smart TV (bring your Netflix, Amazon UN/PW's). Bose Bluetooth speaker, Amazon Alexa provided. A private adjacent deck with a 2 person Solana spa/seating. Also handicapped accessible.
Aug 4 – 11
Apartment in Key West
4.98 out of 5 average rating, 441 reviewsBella Vita: 1B/1B Condo for 2 Just Steps off Duval
1B/1B condo located in Old Town less than 1/2 block from Duval St. & a couple blocks from the Southernmost Point, Hemingway House & many other Key West attractions. Bella Vita accommodates 2 adults only and features a large porch with chairs & table, living room with leather sofa, galley kitchen with bar seating, king-size bed with Tempurpedic mattress, desk area, bathroom with large walk-in shower, wi-fi, sound machine, 2 Smart TVs, DVD players & BlueTooth stereo system with CD player & radio.
Mar 16 – 23
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Summerland Key vacation rentals
Other great vacation rentals in Summerland Key
Condo in Key Colony Beach
4.92 out of 5 average rating, 191 reviewsOceanfront Breeze, Stunning Views, Beach/Pool
Feb 4 – 11
Apartment in Key West
4.97 out of 5 average rating, 234 reviewsPoolside Truman Annex 2 Bed | Conch Life Condo
Aug 20 – 27
Home in Summerland Key
4.8 out of 5 average rating, 5 reviewsBungalows at Sugarloaf Beach - Little Hammock
Feb 17 – 24
Tiny home in Big Pine Key
4.8 out of 5 average rating, 88 reviewsBreezy pines 28 foot 5th wheel trailer .
Nov 20 – 27
Home in Cudjoe Key
4.94 out of 5 average rating, 16 reviewsMay Extravaganza - Relax in Paradise!
May 24 – 31
Home in Summerland Key
4.95 out of 5 average rating, 21 reviewsCanal front cottage in Summerland Cove
Jun 12 – 19
Home in Cudjoe Key
4.84 out of 5 average rating, 38 reviewsRelaxing Home in the Keys
Aug 31 – Sep 7
Home in Cudjoe Key
4.85 out of 5 average rating, 39 reviews*Emerald Seas*-Florida Keys Ocean Front Paradise!
Jun 4 – 11
Home in Cudjoe Key
4.84 out of 5 average rating, 45 reviewsSpanish Queen @Venture Out
Dec 11 – 18
Camper/RV in Big Pine Key
4.91 out of 5 average rating, 34 reviewsHaving fun in the lower Keys
Jul 6 – 13
Home in Cudjoe Key
4.83 out of 5 average rating, 24 reviewsKeys Island Villa - Venture Out Home 354
Sep 1 – 8
Home in Cudjoe Key
5.0 out of 5 average rating, 18 reviewsParadise in Cudjoe! Perfect Family Home!
Nov 15 – 22
Other great vacation rentals in Summerland Key
Camper/RV in Big Pine Key
4.94 out of 5 average rating, 34 reviewsDelightful 1 bedroom camper with pool
Jul 9 – 16
Home in Cudjoe Key
4.84 out of 5 average rating, 37 reviewsKeys Cove
Aug 29 – Sep 5
Guest suite in Key Colony Beach
4.99 out of 5 average rating, 81 reviewsTurtle-By-The-Sea: the Best Deal in KCB!
May 3 – 10
Cottage in Cudjoe Key
4.94 out of 5 average rating, 52 reviewsTurtle Cove Views @ Venture Out - Waterfront
Jan 2 – 9
Vacation home in Cudjoe Key
5.0 out of 5 average rating, 30 reviewsBeautiful Cottage & Amenities in Gated Community
Jun 21 – 28
Home in Cudjoe Key
5.0 out of 5 average rating, 5 reviewsVenture Out -Million Dollar Island Resort
Nov 23 – 30
Home in Marathon
4.97 out of 5 average rating, 31 reviewsBeach House, Private Pool & Dock, Gulf Sunset view
Nov 9 – 16
Home in Marathon
4.97 out of 5 average rating, 31 reviewsThe Gulf Cottage at Marathon Key
Jun 8 – 15
Home in Cudjoe Key
4.96 out of 5 average rating, 23 reviewsCozy 2 br/2 bath home in Cudjoe
Oct 22 – 29
Home in Cudjoe Key
5.0 out of 5 average rating, 3 reviewsLatitudes-Ocean Front Pool
Aug 31 – Sep 7
Home in Marathon
5.0 out of 5 average rating, 8 reviewsMillion Dollar View
Oct 12 – 19
Home in Cudjoe Key
4.82 out of 5 average rating, 67 reviewsTree Top Paradise
Nov 5 – 12
Quick stats about vacation rentals in Summerland Key
Total rentals | 210 properties |
---|---|
Rentals with a pool | 140 properties have a pool |
Pet-friendly rentals | 90 properties allow pets |
Family-friendly rentals | 180 properties are a good fit for families |
Total number of reviews | 3.3K reviews |
Nightly prices starting at | G$18,845 GYD before taxes and fees |
Frequently Asked Questions
Are there vacation rentals with a dedicated workspace in Summerland Key?
Yes! Work meets play with ease at over 80 vacation rentals in Summerland Key featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Summerland Key?
Four-legged friends are welcome in Summerland Key. Choose from more than 90 vacation rentals for guests traveling with pets.
How much does it cost to stay in cottage rentals in Summerland Key?
Experience the best of Summerland Key with our cottage rentals, starting at about $170 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Summerland Key have self check-in?
Absolutely! We offer over 30 house rentals with self check-in in Summerland Key. Enjoy a tailored experience with all the comforts you desire.
Are there Summerland Key cottage rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 10 cottage rentals with pools in Summerland Key, available on Airbnb. Make a splash and soak up the sun in style!
Do house rentals in Summerland Key have a bbq area?
Absolutely! We offer over 60 house rentals with a bbq area in Summerland Key. Enjoy a tailored experience with all the comforts you desire.
Do cottage rentals in Summerland Key have wifi?
Absolutely! We offer over 10 cottage rentals with wifi in Summerland Key. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly house rentals in Summerland Key?
Summerland Key has more than 150 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
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