FEATURED FLORIDA SOUTH-WEST, FLORIDA STAYS
Vacation Rentals in Florida South-West, Florida
Every property is professionally managed with 24/7 guest support and a best-rate guarantee through RedAwning. Tap a card to check availability and book direct.
Showing 100 of 112 properties
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Marco Island
CONDOMINIUM
Gulf-View Condo with Resort-Style Amenities
2 Bedrooms 2 Bathrooms 6 GuestsMarco Island, FL, Gulf-View Condo with Resort-Style Amenities vacation rental.
Pool Hot Tub -
Marco Island
HOUSE
Sandcastles of Marco Island Waterfront Private Pool
3 Bedrooms 2 Bathrooms 9 GuestsMarco Island, FL, Sandcastles of Marco Island Waterfront Private Pool vacation rental.
Pool -
Longboat Key
CONDOMINIUM
Just Beachy at Beach Castle #16
2 Bedrooms 2 Bathrooms 6 GuestsLongboat Key, FL, Just Beachy at Beach Castle #16 vacation rental.
Pool Hot Tub -
Longboat Key
HOUSE
Decked Out on Marbury
4 Bedrooms 4.5 Bathrooms 10 GuestsLongboat Key, FL, Decked Out on Marbury vacation rental.
Pool Pets OK -
HOLMES BEACH
HOUSE
3706 GULF DR
2 Bedrooms 2 Bathrooms 6 GuestsHOLMES BEACH, FL, 3706 GULF DR vacation rental.
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Marco Island
HOUSE
Lighthouse 1124 Marco Island
3 Bedrooms 2.5 Bathrooms 6 GuestsMarco Island, FL, Lighthouse 1124 Marco Island vacation rental.
Pool -
Siesta Key
CONDOMINIUM
ANC709
2 Bedrooms 2 Bathrooms 6 GuestsSiesta Key, FL, ANC709 vacation rental.
Pool -
Siesta Key
CONDOMINIUM
Sandy Cove Oasis
2 Bedrooms 2 Bathrooms 4 GuestsSiesta Key, FL, Sandy Cove Oasis vacation rental.
Pool Hot Tub -
Siesta Key
CONDOMINIUM
Crescent Siesta Key Charmer
3 Bedrooms 2 Bathrooms 6 GuestsSiesta Key, FL, Crescent Siesta Key Charmer vacation rental.
Pool Hot Tub -
Sarasota
HOUSE
Paradise Palace
4 Bedrooms 2 Bathrooms 10 GuestsSarasota, FL, Paradise Palace vacation rental.
Pool Pets OK -
Siesta Key
HOUSE
The Windward House
3 Bedrooms 2.5 Bathrooms 6 GuestsSiesta Key, FL, The Windward House vacation rental.
Pool Pets OK -
Longboat Key
CONDOMINIUM
Sunset Sanctuary
2 Bedrooms 2 Bathrooms 4 GuestsLongboat Key, FL, Sunset Sanctuary vacation rental.
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Sarasota
HOUSE
Coastal Cottage
2 Bedrooms 2 Bathrooms 6 GuestsSarasota, FL, Coastal Cottage vacation rental.
Pool -
Sarasota
HOUSE
Casa de Flores
4 Bedrooms 3 Bathrooms 9 GuestsSarasota, FL, Casa de Flores vacation rental.
Pool -
Sarasota
CONDOMINIUM
The Beach House
2 Bedrooms 2 Bathrooms 6 GuestsSarasota, FL, The Beach House vacation rental.
Pool -
Sarasota
TOWNHOUSE
Coastal Moderne
2 Bedrooms 2.5 Bathrooms 6 GuestsSarasota, FL, Coastal Moderne vacation rental.
Pets OK -
Siesta Key
CONDOMINIUM
Sole Retreat
2 Bedrooms 2 Bathrooms 6 GuestsSiesta Key, FL, Sole Retreat vacation rental.
Pool Hot Tub -
Sarasota
HOUSE
Sunny Urban Escape
3 Bedrooms 2 Bathrooms 6 GuestsSarasota, FL, Sunny Urban Escape vacation rental.
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Siesta Key
CONDOMINIUM
Turtle Beach Bliss
2 Bedrooms 2 Bathrooms 4 GuestsSiesta Key, FL, Turtle Beach Bliss vacation rental.
Pool -
Fort Myers
CONDOMINIUM
Luxurious Waterfront Condo at Alta Mar
2 Bedrooms 2 Bathrooms 4 GuestsFort Myers, FL, Luxurious Waterfront Condo at Alta Mar vacation rental.
Pool Hot Tub Pets OK -
Anna Maria
HOUSE
Once Upon a Tide
4 Bedrooms 3 Bathrooms 8 GuestsAnna Maria, FL, Once Upon a Tide vacation rental.
Pool -
Holmes Beach
HOUSE
Salt Air East
2 Bedrooms 2 Bathrooms 4 GuestsHolmes Beach, FL, Salt Air East vacation rental.
Pool Pets OK -
Sarasota
TOWNHOUSE
Cityscape Retreat
2 Bedrooms 3.5 Bathrooms 6 GuestsSarasota, FL, Cityscape Retreat vacation rental.
Hot Tub Pets OK -
Cape Coral
HOUSE
Waterfront Luxury Micro Resort Heated Salt Pool
4 Bedrooms 2 Bathrooms 10 GuestsCape Coral, FL, Waterfront Luxury Micro Resort Heated Salt Pool vacation rental.
Pool -
Rotonda West
HOUSE
LML80
3 Bedrooms 2 Bathrooms 6 GuestsRotonda West, FL, LML80 vacation rental.
Pool Pets OK -
Englewood
CONDOMINIUM
LD9141-102
2 Bedrooms 1 Bathroom 4 GuestsEnglewood, FL, LD9141-102 vacation rental.
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Siesta Key
CONDOMINIUM
ANC601
2 Bedrooms 2 Bathrooms 6 GuestsSiesta Key, FL, ANC601 vacation rental.
Pool -
Siesta Key
CONDOMINIUM
ANC902
2 Bedrooms 2 Bathrooms 4 GuestsSiesta Key, FL, ANC902 vacation rental.
Pool -
Siesta Key
CONDOMINIUM
ANC304
2 Bedrooms 2 Bathrooms 6 GuestsSiesta Key, FL, ANC304 vacation rental.
Pool -
Holmes Beach
HOUSE
Angel Sea
6 Bedrooms 3.5 Bathrooms 12 GuestsHolmes Beach, FL, Angel Sea vacation rental.
Pool Hot Tub Pets OK -
Siesta Key
CONDOMINIUM
ANC311
3 Bedrooms 2 Bathrooms 8 GuestsSiesta Key, FL, ANC311 vacation rental.
Pool -
Cape Coral
HOUSE
S1A4103
3 Bedrooms 2.5 Bathrooms 6 GuestsCape Coral, FL, S1A4103 vacation rental.
Pool -
Rotonda West
HOUSE
CUT124
3 Bedrooms 2 Bathrooms 6 GuestsRotonda West, FL, CUT124 vacation rental.
Pool -
Siesta Key
CONDOMINIUM
ANC409
2 Bedrooms 2 Bathrooms 6 GuestsSiesta Key, FL, ANC409 vacation rental.
Pool -
Siesta Key
CONDOMINIUM
ANC611
3 Bedrooms 2.5 Bathrooms 6 GuestsSiesta Key, FL, ANC611 vacation rental.
Pool -
Siesta Key
CONDOMINIUM
ANC707
2 Bedrooms 2 Bathrooms 6 GuestsSiesta Key, FL, ANC707 vacation rental.
Pool -
Englewood
HOUSE
E5S831
5 Bedrooms 2.5 Bathrooms 12 GuestsEnglewood, FL, E5S831 vacation rental.
Pool -
Englewood
HOUSE
EBR7483
2 Bedrooms 2 Bathrooms 5 GuestsEnglewood, FL, EBR7483 vacation rental.
Pool Pets OK -
Cape Coral
HOUSE
CC2101
3 Bedrooms 2.5 Bathrooms 8 GuestsCape Coral, FL, CC2101 vacation rental.
Pool Pets OK -
Siesta Key
CONDOMINIUM
ANC805
2 Bedrooms 2 Bathrooms 6 GuestsSiesta Key, FL, ANC805 vacation rental.
Pool -
Holmes Beach
HOUSE
307 65th Street
4 Bedrooms 4 Bathrooms 8 GuestsHolmes Beach, FL, 307 65th Street vacation rental.
Pool Hot Tub -
Sarasota
HOUSE
Paradise Found
3 Bedrooms 3.5 Bathrooms 6 GuestsSarasota, FL, Paradise Found vacation rental.
Pool Pets OK -
Bradenton Beach
BUNGALOW
Beau Soleil Seaside
2 Bedrooms 2 Bathrooms 5 GuestsBradenton Beach, FL, Beau Soleil Seaside vacation rental.
Pets OK -
Nokomis
HOUSE
LRW503
3 Bedrooms 2 Bathrooms 6 GuestsNokomis, FL, LRW503 vacation rental.
Pets OK -
Englewood
TOWNHOUSE
OT1950-1B
2 Bedrooms 2 Bathrooms 6 GuestsEnglewood, FL, OT1950-1B vacation rental.
Pool -
Englewood
HOUSE
MAN8035
4 Bedrooms 3.5 Bathrooms 12 GuestsEnglewood, FL, MAN8035 vacation rental.
Pool Pets OK -
Longboat Key
CONDOMINIUM
Pura Vida at Beach Castle #15
2 Bedrooms 2 Bathrooms 6 GuestsLongboat Key, FL, Pura Vida at Beach Castle #15 vacation rental.
Pool Hot Tub -
Marco Island
CONDOMINIUM
Magnificent Gulf View Condo in Shipp's Landing
2 Bedrooms 2 Bathrooms 6 GuestsMarco Island, FL, Magnificent Gulf View Condo in Shipp's Landing vacation rental.
Pool Hot Tub -
Longboat Key
CONDOMINIUM
Sunshine Cottage at Cedars
2 Bedrooms 2.5 Bathrooms 6 GuestsLongboat Key, FL, Sunshine Cottage at Cedars vacation rental.
Pool -
Cape Coral
HOUSE
Blue Oasis- Saltwater Pool, Dock, Dog-Friendly
3 Bedrooms 3 Bathrooms 8 GuestsCape Coral, FL, Blue Oasis- Saltwater Pool, Dock, Dog-Friendly vacation rental.
Pool Pets OK -
Longboat Key
TOWNHOUSE
Surf and Turf at Cedars East
2 Bedrooms 2.5 Bathrooms 4 GuestsLongboat Key, FL, Surf and Turf at Cedars East vacation rental.
Pool -
Cape Coral
HOUSE
Sleeps 16 plus Central Cape Coral Family Escape
4 Bedrooms 2 Bathrooms 16 GuestsCape Coral, FL, Sleeps 16 plus Central Cape Coral Family Escape vacation rental.
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Fort Myers
APARTMENT
Relaxing 2BR Fort Myers Getaway Near Beaches
2 Bedrooms 2.5 Bathrooms 4 GuestsFort Myers, FL, Relaxing 2BR Fort Myers Getaway Near Beaches vacation rental.
Pool Pets OK -
Longboat Key
TOWNHOUSE
Serenity on Sutton
2 Bedrooms 2 Bathrooms 4 GuestsLongboat Key, FL, Serenity on Sutton vacation rental.
Pool -
Longboat Key
CONDOMINIUM
Buttonwood Bliss
2 Bedrooms 2 Bathrooms 4 GuestsLongboat Key, FL, Buttonwood Bliss vacation rental.
Pool -
Longboat Key
STUDIO
Las Hermanas 1
Studio 1 Bathroom 4 GuestsLongboat Key, FL, Las Hermanas 1 vacation rental.
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Longboat Key
CONDOMINIUM
Las Hermanas 2
1 Bedroom 1 Bathroom 4 GuestsLongboat Key, FL, Las Hermanas 2 vacation rental.
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Sarasota
TOWNHOUSE
Uptown Oasis
3 Bedrooms 3.5 Bathrooms 8 GuestsSarasota, FL, Uptown Oasis vacation rental.
Pets OK -
Sarasota
HOUSE
Sarasota Solitude
3 Bedrooms 2 Bathrooms 6 GuestsSarasota, FL, Sarasota Solitude vacation rental.
Pool Pets OK -
Siesta Key
CONDOMINIUM
White Sands on Siesta
1 Bedroom 1 Bathroom 2 GuestsSiesta Key, FL, White Sands on Siesta vacation rental.
Pool Pets OK -
Siesta Key
CONDOMINIUM
'Bout Time- Turtle Beach, Tennis, Heated Pool, Bay …
2 Bedrooms 2 Bathrooms 7 GuestsSiesta Key, FL, 'Bout Time- Turtle Beach, Tennis, Heated Pool, Bay Views vacation rental.
Pool -
Sarasota
HOUSE
Sunshine Retreat
4 Bedrooms 2 Bathrooms 8 GuestsSarasota, FL, Sunshine Retreat vacation rental.
Pool Hot Tub -
Holmes Beach
HOUSE
Sunshine and Good Times
4 Bedrooms 4.5 Bathrooms 8 GuestsHolmes Beach, FL, Sunshine and Good Times vacation rental.
Pool Hot Tub -
Bradenton Beach
HOUSE
Chasing Sunsets
4 Bedrooms 3 Bathrooms 8 GuestsBradenton Beach, FL, Chasing Sunsets vacation rental.
Pool Hot Tub -
Siesta Key
CONDOMINIUM
ANC605
2 Bedrooms 2 Bathrooms 6 GuestsSiesta Key, FL, ANC605 vacation rental.
Pool -
Rotonda West
HOUSE
BKR249
3 Bedrooms 2 Bathrooms 6 GuestsRotonda West, FL, BKR249 vacation rental.
Pool -
Siesta Key
CONDOMINIUM
ANC608
2 Bedrooms 2 Bathrooms 6 GuestsSiesta Key, FL, ANC608 vacation rental.
Pool -
Siesta Key
CONDOMINIUM
ANC801
2 Bedrooms 2 Bathrooms 6 GuestsSiesta Key, FL, ANC801 vacation rental.
Pool -
Cape Coral
HOUSE
OBS119
4 Bedrooms 2 Bathrooms 8 GuestsCape Coral, FL, OBS119 vacation rental.
Pool -
Manasota Key
CONDOMINIUM
MER50-7
3 Bedrooms 2.5 Bathrooms 8 GuestsManasota Key, FL, MER50-7 vacation rental.
Pool -
Englewood
HOUSE
Englewood Private Vacation Home on Lemon Bay Canal with …
2 Bedrooms 2 Bathrooms 4 GuestsEnglewood, FL, Englewood Private Vacation Home on Lemon Bay Canal with Hot Tub- Only 4 Miles to Gulf Beaches vacation rental.
Hot Tub Pets OK -
Siesta Key
TOWNHOUSE
Siesta Beach Retreat
2 Bedrooms 2 Bathrooms 6 GuestsSiesta Key, FL, Siesta Beach Retreat vacation rental.
Pool -
HOLMES BEACH
CONDOMINIUM
3000 GULF DRIVE UNIT 9
1 Bedroom 1 Bathroom 4 GuestsHOLMES BEACH, FL, 3000 GULF DRIVE UNIT 9 vacation rental.
Pool -
HOLMES BEACH
CONDOMINIUM
2716 GULF DRIVE UNIT 202
2 Bedrooms 2 Bathrooms 4 GuestsHOLMES BEACH, FL, 2716 GULF DRIVE UNIT 202 vacation rental.
Pool -
Sarasota
HOUSE
Sarasota Seascape
4 Bedrooms 2 Bathrooms 7 GuestsSarasota, FL, Sarasota Seascape vacation rental.
Pool Pets OK -
Sarasota
HOUSE
Mauna Loa Hideaway
3 Bedrooms 3 Bathrooms 6 GuestsSarasota, FL, Mauna Loa Hideaway vacation rental.
Pool -
Longboat Key
VILLA
Bayside Hideaway at Beach Castle #27
3 Bedrooms 3 Bathrooms 8 GuestsLongboat Key, FL, Bayside Hideaway at Beach Castle #27 vacation rental.
Pool Hot Tub -
Siesta Key
CONDOMINIUM
Crystal Sands on Siesta
2 Bedrooms 2 Bathrooms 6 GuestsSiesta Key, FL, Crystal Sands on Siesta vacation rental.
Pool -
Sarasota
TOWNHOUSE
Uptown Luxury on Audubon
4 Bedrooms 3.5 Bathrooms 10 GuestsSarasota, FL, Uptown Luxury on Audubon vacation rental.
Hot Tub Pets OK -
Siesta Key
CONDOMINIUM
Hawk's Sea Nest
2 Bedrooms 2 Bathrooms 6 GuestsSiesta Key, FL, Hawk's Sea Nest vacation rental.
Pool -
Siesta Key
CONDOMINIUM
Imperial Sunsets on Siesta
2 Bedrooms 2 Bathrooms 4 GuestsSiesta Key, FL, Imperial Sunsets on Siesta vacation rental.
Pool Hot Tub -
Longboat Key
STUDIO
Las Hermanas 4
Studio 1 Bathroom 2 GuestsLongboat Key, FL, Las Hermanas 4 vacation rental.
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Siesta Key
CONDOMINIUM
Salty Soldi
2 Bedrooms 2 Bathrooms 4 GuestsSiesta Key, FL, Salty Soldi vacation rental.
Pool -
Sarasota
HOUSE
Sarasota Serenity
3 Bedrooms 2 Bathrooms 10 GuestsSarasota, FL, Sarasota Serenity vacation rental.
Pool -
Siesta Key
CONDOMINIUM
Siesta Bayside Bliss
1 Bedroom 2 Bathrooms 4 GuestsSiesta Key, FL, Siesta Bayside Bliss vacation rental.
Pool -
Sarasota
HOUSE
Dream Island
8 Bedrooms 8 Bathrooms 10 GuestsSarasota, FL, Dream Island vacation rental.
Pool Hot Tub Pets OK -
Sarasota
HOUSE
Sapphire Shores
3 Bedrooms 2 Bathrooms 7 GuestsSarasota, FL, Sapphire Shores vacation rental.
Pool Pets OK -
Siesta Key
CONDOMINIUM
My Happy Place
2 Bedrooms 2 Bathrooms 4 GuestsSiesta Key, FL, My Happy Place vacation rental.
Pool -
Sarasota
HOUSE
Urban Nest on 8th
4 Bedrooms 2 Bathrooms 9 GuestsSarasota, FL, Urban Nest on 8th vacation rental.
Pets OK -
Sarasota
HOUSE
Poolside Paradise
3 Bedrooms 3 Bathrooms 8 GuestsSarasota, FL, Poolside Paradise vacation rental.
Pool -
Anna Maria
HOUSE
The TipSea Turtle
4 Bedrooms 4.5 Bathrooms 8 GuestsAnna Maria, FL, The TipSea Turtle vacation rental.
Pool Hot Tub -
Anna Maria
HOUSE
Casa Amiga
4 Bedrooms 4.5 Bathrooms 10 GuestsAnna Maria, FL, Casa Amiga vacation rental.
Pool Hot Tub Pets OK -
Bradenton Beach
TOWNHOUSE
Meant to Bee on AMI
2 Bedrooms 2 Bathrooms 6 GuestsBradenton Beach, FL, Meant to Bee on AMI vacation rental.
Pool -
Siesta Key
CONDOMINIUM
Siesta Pearl
2 Bedrooms 2.5 Bathrooms 6 GuestsSiesta Key, FL, Siesta Pearl vacation rental.
Pool -
Siesta Key
VILLA
Siesta Treasure #3
2 Bedrooms 1 Bathroom 4 GuestsSiesta Key, FL, Siesta Treasure #3 vacation rental.
Pool -
Siesta Key
HOUSE
Siesta Treasure
4 Bedrooms 2 Bathrooms 8 GuestsSiesta Key, FL, Siesta Treasure vacation rental.
Pool -
Englewood
HOUSE
GSR9220
2 Bedrooms 2 Bathrooms 4 GuestsEnglewood, FL, GSR9220 vacation rental.
Hot Tub Pets OK -
Sarasota
HOUSE
Private Cozy Sarasota Home
3 Bedrooms 2 Bathrooms 6 GuestsSarasota, FL, Private Cozy Sarasota Home vacation rental.
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Siesta Key
CONDOMINIUM
ANC506
2 Bedrooms 2 Bathrooms 6 GuestsSiesta Key, FL, ANC506 vacation rental.
Pool -
Longboat Key
CONDOMINIUM
It's a Shore Thing at Beach Castle #14
1 Bedroom 1 Bathroom 4 GuestsLongboat Key, FL, It's a Shore Thing at Beach Castle #14 vacation rental.
Pool Hot Tub